Light-emitting element, polycyclic compound, and electronic device

Abstract

The present disclosure relates to a light-emitting element, a polycyclic compound, and an electronic device. A light-emitting element can include a first electrode, a second electrode over the first electrode, and a light-emitting layer between the first electrode and the second electrode and including a first compound represented by Formula 1. Formula 1

Description

Cross-reference to related applications

[0001] This application claims priority and benefit to Japanese Patent Application No. 2025-021473, filed on February 13, 2025, with the Japan Patent Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] One or more embodiments of this disclosure relate to light-emitting elements, polycyclic compounds used in light-emitting elements, and electronic devices including light-emitting elements. Background Technology

[0003] Organic electroluminescent display devices, including organic electroluminescent elements, have been used as display devices included in electronic devices. An organic electroluminescent display device is a display device that displays images by injecting holes and electrons from a first electrode and a second electrode, respectively, into a light-emitting layer under a driving voltage, and by emitting light from the light-emitting material of the light-emitting layer (light-emitting layer). It includes self-emissive type (type) light-emitting elements.

[0004] When light-emitting elements are applied to display devices, it is desirable or necessary to improve light efficiency and lifespan, and therefore there is a continuous demand or expectation for developing materials for light-emitting elements that can reliably achieve these improvements (e.g., low driving voltage, high luminous efficiency, and long lifespan). Summary of the Invention

[0005] One or more aspects of embodiments of this disclosure relate to light-emitting elements having improved luminous efficiency and lifetime.

[0006] One or more aspects of embodiments of this disclosure relate to polycyclic compounds having improved quantum efficiency and material stability.

[0007] One or more aspects of embodiments of this disclosure relate to electronic devices that have excellent or suitable display quality by including light-emitting elements with improved luminous efficiency and lifetime.

[0008] 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 embodiments presented.

[0009] One or more embodiments of this disclosure provide polycyclic compounds represented by Formula 1.

[0010] Formula 1

[0011] In Equation 1, X1 to X4 can each be independently O, S, or Se, or as represented by Equation 2, Y1 to Y... 16 Each can be CR independently aOr N, and R a It can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0012] Formula 2

[0013] In Equation 2, Y 17 To Y 21 Each can be CR independently b Or N, and R b It can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms. If none of X1 to X4 of Formula 1 is represented by Formula 2 (e.g., when none of X1 to X4 of Formula 1 is represented by Formula 2), then it is selected from Y1 to Y4 of Formula 1. 16 At least one of them can be N, and if at least one of X1 to X4 selected from Equation 1 is represented by Equation 2 (e.g., when at least one of X1 to X4 selected from Equation 1 is represented by Equation 2), then Y1 to Y4 selected from Equation 1 16 Y of formula 2 17 To Y 21 At least one of them can be N.

[0014] In one or more embodiments, Equation 2 may be represented by Equation 2-1, or in Equation 2, the formula may be selected from Y. 17 To Y 21 One of them can be N and the others can be CR. b .

[0015] Equation 2-1

[0016] In Equation 2-1, R b1 To R b5 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0017] In one or more embodiments, one selected from Y1 to Y4, one selected from Y6 to Y8, and one selected from Y... 13 To Y 16One of the choices in Y5 and one of the choices in Y6 can be N, and the others can each be CR independently. a Furthermore, X1 to X4 in Equation 1 can each be O, S or Se independently, or can be represented by Equation 2-1.

[0018] Equation 2-1

[0019] In Equation 2-1, R b1 To R b5 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0020] In one or more embodiments, if Y1 to Y of equation 1 16 Each is CR independently a (For example, when Y1 to Y in Equation 1) 16 Each is CR independently a (When), then at least one of X1 to X4 can be represented by Equation 2, and in Equation 2, the one selected from Y 17 To Y 21 One of them can be N, and the others can each be CR independently. b .

[0021] In one or more embodiments, at least one hydrogen atom in Formula 1 and Formula 2 may be substituted with deuterium.

[0022] The polycyclic compound represented by Formula 1 can be a blue emission dopant.

[0023] The polycyclic compound represented by Formula 1 can be a thermally activated delayed fluorescence material.

[0024] According to one or more embodiments of the present disclosure, the light-emitting element includes: a first electrode; a second electrode disposed on (e.g., on) the first electrode; and a light-emitting layer disposed between (e.g., between) the first electrode and the second electrode and comprising a polycyclic compound of one or more embodiments.

[0025] In one or more embodiments, the light-emitting layer may further include at least one of a second compound represented by formula HT-1 and a third compound represented by formula ET-1.

[0026] HT-1

[0027] In formula HT-1, A1 to A8 can each be N or CR independently. 51L1 can be a directly attached, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, Y a It can be a direct connection, CR 52 R 53 or SiR 54 R 55 Ar1 can be a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and R 51 To R 55 Each of the groups may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, 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 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 cyclic carbon atoms, and / or combined with adjacent groups to form a ring.

[0028] ET-1

[0029] In Equation ET-1, at least one of X1 to X3 can be N, and the rest are CR. 56 R 56 It can be hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 cyclic carbon atoms; b1 to b3 can each be an integer from 0 to 10; Ar2 to Ar4 can each be hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms; and L2 to L4 can each be a directly linked, substituted or unsubstituted arylene with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroarylene with 2 to 30 cyclic carbon atoms.

[0030] In one or more embodiments, the light-emitting layer may further include a fourth compound represented by formula D-1.

[0031] Formula D-1

[0032] In formula D-1, Q1 to Q4 can each be independently C or N, and C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring with 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle with 2 to 30 cyclic carbon atoms, L 11 To L 13 They can be directly connected independently. , , , , a substituted or unsubstituted alkylene group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 cyclic carbon atoms, wherein, " "This can refer to the position to be connected; b11 to b13 can each be 0 or 1 independently, R..." 61 To R 66 Each of the following can be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, 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 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 cyclic carbon atoms, and d1 to d4 can each be independently an integer from 0 to 4.

[0033] The fluorescence lifetime of polycyclic compounds can be about 3.0 microseconds (μs) or less.

[0034] The luminescent layer can emit delayed fluorescence.

[0035] The light-emitting layer can emit blue light.

[0036] According to one or more embodiments of the present disclosure, an electronic device includes a display module comprising a plurality of light-emitting elements, wherein at least one of the plurality of light-emitting elements includes a first electrode, a second electrode disposed on (e.g., disposed on) the first electrode, and a light-emitting layer disposed between (e.g., disposed between) the first electrode and the second electrode and comprising a polycyclic compound of one or more embodiments.

[0037] In one or more embodiments, the electronic device may further include at least one selected from processor, memory, and power module.

[0038] For example, one or more embodiments of this disclosure provide a light-emitting element that achieves high external quantum efficiency, excellent blue purity, and extended operating lifetime by containing a polycyclic compound represented by Formula 1 as a thermally activated delayed fluorescence dopant. The specification further supports variations in heteroatom arrangement, substituent selection, and optional inclusion of host and sensitizer compounds (e.g., Formula HT-1, Formula ET-1, and Formula D-1) to enhance charge balance and energy transfer within the light-emitting layer. These features, together with the disclosed fluorescence lifetime of about 3.0 μs or less and optional deuteration, enable improved material stability and device reliability. Attached Figure Description

[0039] The accompanying drawings are included to provide a further understanding of this disclosure, and these drawings are incorporated in and constitute a part of this disclosure. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain the principles of the disclosure. The above and / or other aspects of this disclosure will become apparent and readily understood from the following description of embodiments taken in conjunction with the accompanying drawings. In the drawings: Figure 1 This is a block diagram of an electronic device according to one or more embodiments of the present disclosure; Figure 2 A schematic diagram of an electronic device according to one or more embodiments of the present disclosure is shown; Figure 3 This is a plan view illustrating a display module according to one or more embodiments of the present disclosure; Figure 4 This illustrates a corresponding embodiment of one or more embodiments according to the present disclosure. Figure 3 A cross-sectional view of the section along line I-I'; Figure 5 This is a schematic cross-sectional view of a light-emitting element according to one or more embodiments of the present disclosure; Figure 6 This is a schematic cross-sectional view of a light-emitting element according to one or more embodiments of the present disclosure; Figure 7 This is a schematic cross-sectional view of a light-emitting element according to one or more embodiments of the present disclosure; Figure 8 This is a schematic cross-sectional view of a light-emitting element according to one or more embodiments of the present disclosure; Figure 9 This is a schematic cross-sectional view of a light-emitting element according to one or more embodiments of the present disclosure; Figure 10 This is a cross-sectional view showing a display module according to one or more embodiments of the present disclosure; Figure 11 This is a cross-sectional view showing a display module according to one or more embodiments of the present disclosure; Figure 12 This is a cross-sectional view showing a display module according to one or more embodiments of the present disclosure; Figure 13 This is a cross-sectional view showing a display module according to one or more embodiments of the present disclosure; Figure 14 This is a perspective view of an electronic device according to one or more embodiments of the present disclosure; Figure 15 This is a perspective view of an electronic device according to one or more embodiments of the present disclosure; and Figure 16 This is a diagram showing the interior of a vehicle in which electronic devices according to one or more embodiments of the present disclosure are arranged. Detailed Implementation

[0040] This disclosure may be modified in one or more suitable ways and may take one or more suitable forms, and specific / exemplary embodiments are shown in the accompanying drawings and will be described in more detail in the text. However, this is not intended to limit this disclosure to the specific form of disclosure, but should be understood to include all modifications, equivalents or substitutions included within the teachings and technical scope of this disclosure.

[0041] In this disclosure, it will be understood that if an element (or region, layer, and / or portion, etc.) is referred to as being "on" another element, "connected to," or "coupled to" another element (e.g., when an element (or region, layer, and / or portion, etc.) is referred to as being "on" another element, "connected to," or "coupled to" another element), then the element may be directly arranged on, directly connected to, or directly coupled to the other element, or one or more other elements may be arranged between the element and the other element. Conversely, "directly on" may mean that there are no additional layers, films, regions, and / or plates, etc., between the element and the other element. For example, "directly on" or "directly below" may mean arranging two layers or two components without utilizing additional components such as adhesive components between the two layers or two components.

[0042] Throughout this disclosure, the same reference numerals or symbols refer to the same elements, and for the sake of brevity, repeated descriptions may be omitted. In the drawings, for the purpose of effectively describing the technical content, the thickness, ratio, and / or dimensions of elements may be exaggerated or reduced. As used herein, the terms "and / or," "or," or " / " can include any and all combinations of one or more of the associated listed elements.

[0043] It will be understood that although the terms “first” and / or “second” may be used herein to describe one or more suitable elements, the elements should not be limited by these terms. These terms are used only to distinguish one element, component, area, layer, or segment from another element, component, area, layer, or segment. For example, a first element, component, area, layer, or segment discussed herein may be named a second element, component, area, layer, or segment without departing from the scope and teachings of this disclosure. Similarly, a second element, component, area, layer, or segment may be named a first element, component, area, layer, or segment. In this disclosure, unless the context clearly indicates otherwise, the singular expressions “a,” “an,” “an,” and “the” are intended to include the plural forms as well. Furthermore, the word “may” is used when describing embodiments of this disclosure to refer to “one or more embodiments of this disclosure.”

[0044] Furthermore, terms such as "below," "under," "on the lower side," "above," "on top," and / or "on the upper side" may be used to describe the relationships between the elements shown in the accompanying drawings. These terms are relative concepts and are described based on the directions indicated in the drawings.

[0045] It will be further understood that if the terms “comprise(s) / comprising,” “include(s) / including,” and / or “has(have) / having” are used in this disclosure (e.g., when the terms “comprise,” “include,” and / or “have” are used in this disclosure), it indicates the presence of the stated features, numbers, steps, operations, elements, components, or combinations thereof, but does not preclude the possibility of the presence or addition of one or more other features, numbers, steps, operations, elements, components, and / or combinations thereof. Furthermore, the terms “comprise,” “include,” “have,” or other similar terms include or support the terms “consisting of” and “substantially consisting of” that indicate the presence of the stated features, numbers, steps, operations, elements, and / or components without or substantially without other features, numbers, steps, operations, elements, components, and / or groups thereof.

[0046] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will also be understood that, unless expressly defined herein, terms (such as those defined in a general dictionary) should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and will not be interpreted in an idealized or overly formalized sense.

[0047] In this disclosure, the term "substituted or unsubstituted" may refer to a substance substituted or unsubstituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boronyl, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heterocyclic groups. Furthermore, each of the substituents shown may be substituted or unsubstituted. For example, biphenyl may be interpreted as aryl or a phenyl group substituted with a phenyl group.

[0048] In this disclosure, the terms "forming a ring via bonding with an adjacent group," "forming a ring by bonding with an adjacent group," and / or "bonding to an adjacent group to form a ring," etc., can refer to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle via bonding with an adjacent group. The hydrocarbon ring may include aliphatic hydrocarbon rings and / or aromatic hydrocarbon rings. The heterocycle may include aliphatic heterocycles and / or aromatic heterocycles. The hydrocarbon ring and the heterocycle may each be monocyclic or polycyclic. In one or more embodiments, the ring formed via bonding with an adjacent group may bond with another ring to form a spirocyclic structure.

[0049] In this disclosure, the term "adjacent group" can refer to a substituent that substitutes for an atom directly bonded to the atom substituted by the corresponding substituent, another substituent that substitutes for the atom substituted by the corresponding substituent, or a substituent located spatially closest to the corresponding substituent. For example, in 1,2-dimethylbenzene, the two methyl groups can be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentane, the two ethyl groups can be interpreted as "adjacent groups" to each other. Furthermore, in 4,5-dimethylphenanthrene, the two methyl groups can be interpreted as "adjacent groups" to each other.

[0050] In this disclosure, halogens can be fluorine, chlorine, bromine, or iodine.

[0051] In this disclosure, the alkyl group can be straight-chain or branched. The number of carbon atoms in the alkyl group can be 1 to 60, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups 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, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecane The group includes, but is not limited to, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecanyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-hexadecyl, 2-hexadecyl, 2-octylhexadecyl, 2-hexadecyl, 2-hexadecyl, and / or triadecyl, etc.

[0052] In this disclosure, cycloalkyl can refer to a ring-type (category) alkyl group. The number of carbon atoms in a cycloalkyl group can be 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, and / or dicycloheptyl.

[0053] In this disclosure, alkenyl refers to a hydrocarbon group comprising one or more carbon-carbon double bonds at the middle or end of an alkyl group having two or more carbon atoms. The alkenyl group can be straight-chain or branched. The number of carbon atoms in the alkenyl group is not specifically limited, and can be, for example, 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups may include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, and / or styrylvinyl.

[0054] In this disclosure, alkynyl refers to a hydrocarbon group comprising one or more carbon-carbon triple bonds at the middle or end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. The number of carbon atoms in the alkynyl group is not specifically limited, and can be, for example, 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups may include, but are not limited to, ethynyl and / or propynyl.

[0055] In this disclosure, cycloalkyl group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The cycloalkyl group can be a saturated cycloalkyl group with 5 to 20 cyclic carbon atoms.

[0056] In this disclosure, aryl refers to any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl can be monocyclic or polycyclic. The number of cyclic carbon atoms in the aryl group can be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrene, benzofluoranthracene, and / or hydroxyl.

[0057] In this disclosure, the fluorene group can be substituted, and two substituents can combine with each other to form a spirocyclic structure. Examples of substituted fluorene groups are given below, but the embodiments of this disclosure are not limited thereto.

[0058]

[0059] In this disclosure, a heterocyclic group refers to any functional group or substituent derived from a ring comprising one or more heteroatoms selected from B, O, N, P, S, Si, and Se. Heterocyclic groups can include aliphatic heterocyclic groups and / or aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Both aliphatic and aromatic heterocyclic groups can be monocyclic or polycyclic.

[0060] In this disclosure, the heterocyclic group may include one or more heteroatoms selected from B, O, N, P, S, Si, and Se. If the heterocyclic group includes two or more heteroatoms (e.g., when the heterocyclic group includes two or more heteroatoms), the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group and has the concept of including a heteroaryl group. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.

[0061] In this disclosure, the aliphatic heterocyclic group may include one or more selected from B, O, N, P, S, Si, and Se as heteroatoms. The number of cyclic carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups may include, but are not limited to, oxirane group, thiirane group, pyrrolyl group, piperidinyl group, tetrahydrofuranyl group, tetrahydrothiophenyl group, thiyl group, tetrahydropyranyl group, and / or 1,4-dioxane group.

[0062] In this disclosure, a heteroaryl group may include one or more heteroatoms selected from B, O, N, P, S, Si, and Se. If the heteroaryl group includes two or more heteroatoms (e.g., when the heteroaryl group includes two or more heteroatoms), the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phthalazinyl, pyridopyridyl, pyridopyrazinyl, pyrazopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, N-arylcarbazoleyl, N-heteroarylcarbazoleyl, N-alkylcarbazoleyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothiaryl and / or dibenzofuranyl.

[0063] In this disclosure, the same description of aryl groups as described above applies to aryl groups, except that arylene groups are divalent. The same description of heteroaryl groups as described above applies to heteroaryl groups, except that heteroaryl groups are divalent.

[0064] In this disclosure, silane includes alkylsilane and / or arylsilane. Examples of silane may include, but are not limited to, trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, and / or phenylsilane.

[0065] In this disclosure, the number of carbon atoms in the carbonyl group is not specifically limited, and may be, for example, 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but the embodiments of this disclosure are not limited thereto.

[0066]

[0067] In this disclosure, the number of carbon atoms in the sulfinyl group or sulfonyl group is not specifically limited, and may be, for example, from 1 to 30. The sulfinyl group may include alkylsulfinyl groups and / or arylsulfinyl groups. The sulfonyl group may include alkylsulfonyl groups and / or arylsulfonyl groups.

[0068] In this disclosure, the thio group may include alkylthio and / or arylthio. The thio group may refer to an alkyl or aryl group defined above bonded to a sulfur atom. Examples of thio groups may include, but are not limited to, methylthio, ethylthio, propanethio, pentanethio, hexanethio, octylthio, dodecanethio, cyclopentanethio, cyclohexanethio, phenylthio, and / or naphthio.

[0069] In this disclosure, an oxygen group can refer to an alkyl or aryl group defined above combined with an oxygen atom. An oxygen group can include alkoxy and / or aryloxy groups. An alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not specifically limited, and can be, for example, from 1 to 20 or from 1 to 10. Examples of oxygen groups can include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, and / or benzyloxy, etc. However, the embodiments of this disclosure are not limited thereto.

[0070] In this disclosure, boryl group can refer to an alkyl or aryl group defined above bonded to a boron atom. Boryl group can include alkylboryl and / or arylboryl. Examples of boryl group can include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl and / or phenylboryl.

[0071] In this disclosure, the number of carbon atoms in an amino group is not specifically limited, and may be, for example, from 1 to 30. Amino groups may include alkylamino and / or arylamino groups. Examples of amino groups may include, but are not limited to, methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, and / or 9-methyl-anthraylamino.

[0072] In this disclosure, the alkyl group in alkylthio, alkylsulfonyl, alkylsulfinyl, alkylaryl, alkoxy, alkylboryl, alkylsilyl, and alkylamino can be the same as the examples of the alkyl groups described above.

[0073] In this disclosure, the aryl group in aryloxy, arylthio, arylsulfonyl, arylsulfinylarylboryl, arylsilyl or arylamino can be the same as the examples of the aryl groups described above.

[0074] In this disclosure, a direct connection can refer to a single key.

[0075] In this disclosure, " "or" "This refers to the position to be connected."

[0076] In the following description, embodiments of the present disclosure will be illustrated with reference to the accompanying drawings.

[0077] Figure 1 This is a block diagram of an electronic device according to one or more embodiments of the present disclosure. (Refer to...) Figure 1 An electronic device EA according to one or more embodiments may include a display module DM, a processor PR, a memory MR, and a power module PM.

[0078] The processor PR may include at least one of a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller.

[0079] The memory MR can store the data information required for the operation of the processor PR and / or the display module DM. When the processor PR executes the application program stored in the memory MR, image data signals and / or input control signals are sent to the display module DM, and the display module DM can process the received signals and output image information through the display screen. The display module DM may include a display panel for displaying images.

[0080] The power module PM may include a power supply module such as a power adapter or battery device, and a power conversion module that converts the power supplied by the power supply module to generate the power desired or required for the operation of the electronic device EA.

[0081] At least one of the components selected from the above-described electronic device EA may be included in a display module according to one or more embodiments described later, or in a display device including a display module in one or more embodiments. In one or more embodiments, some of the individual modules that are functionally included in a single module may be included in the display device, and other modules may be provided separately from the display device. For example, in one or more embodiments, the display device may include a display module DM, and a processor PR, a memory MR, and a power module PM may be provided in the form of other devices within the electronic device EA besides the display device.

[0082] Figure 2 Schematic diagrams of various electronic devices according to one or more embodiments of the present disclosure are shown.

[0083] Reference Figure 2According to one or more embodiments, one or more suitable electronic devices including a display module may include not only electronic devices for displaying images (such as smartphones EA_1a, tablet PCs EA_1b, laptop computers EA_1c, televisions (TVs) EA_1d, and desktop monitors EA_1e), but also wearable electronic devices (such as smart glasses EA_2a, head-mounted displays EA_2b, and smartwatches EA_2c) and vehicle electronic devices EA_3 (such as a vehicle's dashboard, central instrument panel, central information display (CID) arranged on the dashboard, and rearview mirror display).

[0084] Figure 3 This is a plan view illustrating a display module DM according to one or more embodiments of the present disclosure. Figure 4 This is a cross-sectional view of a display module DM according to one or more embodiments of the present disclosure. For example, Figure 4 It shows the corresponding Figure 3 A cross-sectional view of the section along line I-I'.

[0085] Reference Figure 3 and Figure 4 The display module DM may include a plurality of light-emitting elements ED-1, ED-2 and ED-3. In one or more embodiments, the display module DM may further include a display panel DP containing a plurality of light-emitting elements ED-1, ED-2 and ED-3 and an optical layer PP disposed on the display panel DP.

[0086] The display panel DP may include a substrate layer BS, a circuit layer DP-CL and a display element layer DP-ED provided on the substrate layer BS. The display element layer DP-ED may include a pixel defining layer PDL, light-emitting elements ED-1, ED-2 and ED-3 arranged in the pixel defining layer PDL, and an encapsulation layer TFE arranged on the light-emitting elements ED-1, ED-2 and ED-3.

[0087] The substrate layer BS can be a component providing a substrate surface on which the display element layers DP-ED are disposed. The substrate layer BS can be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of this disclosure are not limited thereto, and the substrate layer BS can be an inorganic layer, an organic layer, or a composite material layer.

[0088] In one or more embodiments, the circuit layer DP-CL may be disposed on the substrate layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the plurality of transistors may include a control electrode, an input electrode, and an output electrode. For example, in one or more embodiments, the circuit layer DP-CL may include switching transistors and driving transistors for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.

[0089] Each of the light-emitting elements ED-1, ED-2, and ED-3 can independently have a selection selected from those described later. Figures 5 to 9 The structure of the light-emitting element ED shown is as follows. Each of the light-emitting elements ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, a corresponding light-emitting layer EML-R, EML-G or EML-B, an electron transport region ETR and a second electrode EL2.

[0090] An optical layer PP can be disposed on the display panel DP to control the light reflected from the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. In one or more embodiments, the optical layer PP may not be provided in the display module DM.

[0091] A substrate BL can be disposed on the optical layer PP. The substrate BL can be a component that provides a substrate surface on which the optical layer PP is disposed. The substrate BL can be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer. In one or more embodiments, a substrate BL may not be provided.

[0092] The display module DM according to one or more embodiments may further include a filler layer. The filler layer may be disposed between the display element layer DP-ED and the substrate BL. The filler layer may be an organic layer. The filler layer may include at least one selected from acrylic resins, silicone resins, and epoxy resins.

[0093] exist Figure 4 The illustration shows an embodiment in which the corresponding light-emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are each arranged in an opening OH defined in a pixel-defining layer PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are each provided as a common layer in all light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments disclosed herein are not limited thereto. Figure 4 In one or more embodiments, the hole transport region (HTR) and electron transport region (ETR) can each be patterned and provided in an opening (OH) defined in the pixel defining layer (PDL). For example, in one or more embodiments, the hole transport region (HTR), the corresponding light-emitting layers (EML-R, EML-G, and EML-B), and the electron transport region (ETR) of light-emitting elements ED-1, ED-2, and ED-3 can be patterned and provided by an inkjet printing method.

[0094] The encapsulation layer TFE can cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE can encapsulate the display element layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be a single layer or a stack of multiple layers. The encapsulation layer TFE can include at least one insulating layer. According to one or more embodiments, the encapsulation layer TFE can include at least one inorganic layer (hereinafter, encapsulated inorganic layer). In one or more embodiments, the encapsulation layer TFE can include at least one organic layer (hereinafter, encapsulated organic layer) and at least one encapsulated inorganic layer.

[0095] The encapsulation inorganic layer protects the display element layer (DP-ED) from moisture / oxygen, while the encapsulation organic layer protects the DP-ED from foreign matter such as dust particles. The encapsulation inorganic layer may include, but is not specifically limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium dioxide, and / or aluminum oxide. The encapsulation organic layer may include acrylic compounds and / or epoxy compounds, etc. In one or more embodiments, the encapsulation organic layer may include a photopolymerizable organic material, but is not specifically limited to.

[0096] The encapsulation layer TFE can be placed on the second electrode EL2 and can be placed at the same time as filling the opening OH.

[0097] Reference Figure 3 and Figure 4 The display module DM may include a non-emitting area NPXA and emitting areas PXA-R, PXA-G, and PXA-B. The emitting areas PXA-R, PXA-G, and PXA-B may be areas that emit light generated from corresponding light-emitting elements ED-1, ED-2, and ED-3. The display module DM may include a first emitting area PXA-R, a second emitting area PXA-G, and a third emitting area PXA-B that are spaced apart and / or separated from each other (e.g., spaced apart or separated) on a plane.

[0098] The first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B can be regions separated by a pixel defining layer PDL. The non-light-emitting region NPXA can be the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and can be a region corresponding to the pixel defining layer PDL. In this disclosure, each of the light-emitting regions PXA-R, PXA-G, and PXA-B can correspond to a pixel. The pixel defining layer PDL can divide light-emitting elements ED-1, ED-2, and ED-3. The corresponding light-emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 can be arranged and divided in openings OH defined in the pixel defining layer PDL.

[0099] Based on the color of the light emitted from the light-emitting elements ED-1, ED-2, and ED-3, the emitting regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups. Figure 3 and Figure 4 The display module DM shown according to one or more embodiments illustrates three light-emitting regions PXA-R, PXA-G, and PXA-B that respectively emit red light, green light, and blue light (e.g., blue light). For example, the first light-emitting region PXA-R can be referred to as the red light emitting region (i.e., red light emitting region) PXA-R, the second light-emitting region PXA-G can be referred to as the green light emitting region (i.e., green light emitting region) PXA-G, and the third light-emitting region PXA-B can be referred to as the blue light emitting region (i.e., blue light emitting region) PXA-B.

[0100] In a display module DM according to one or more embodiments, a plurality of light-emitting elements ED-1, ED-2, and ED-3 can emit light with different wavelength ranges. For example, in one or more embodiments, the display module DM may include a first light-emitting element ED-1 that emits red light, a second light-emitting element ED-2 that emits green light, and a third light-emitting element ED-3 that emits blue light. For example, in one or more embodiments, the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B of the display module DM may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0101] However, the embodiments disclosed herein are not limited thereto, and the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may emit light within substantially the same wavelength range, or at least one of the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may emit light within different wavelength ranges. For example, in one or more embodiments, all the first light-emitting elements ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may emit blue light.

[0102] The light-emitting regions PXA-R, PXA-G, and PXA-B in the display module DM according to one or more embodiments can be arranged in a stripe pattern. (Refer to...) Figure 3 Multiple first luminescent regions PXA-R can be arranged relative to each other along the second direction axis DR2, multiple second luminescent regions PXA-G can be arranged relative to each other along the second direction axis DR2, and multiple third luminescent regions PXA-B can be arranged relative to each other along the second direction axis DR2. Furthermore, the first luminescent regions PXA-R, the second luminescent regions PXA-G, and the third luminescent regions PXA-B can be arranged sequentially along the first direction axis DR1.

[0103] exist Figure 3 and Figure 4 In the illustration, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B are similarly shown, but embodiments of this disclosure are not limited thereto. In one or more embodiments, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B may differ from each other depending on the wavelength range of the emitted light. The areas of the luminescent regions PXA-R, PXA-G, and PXA-B may each refer to the area on the plane defined by the first directional axis DR1 and the second directional axis DR2 (e.g., the area in a plan view).

[0104] The arrangement types (categories) of the luminescent regions PXA-R, PXA-G, and PXA-B are not limited to... Figure 3 The configuration shown, and the arrangement order of the first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B, can be provided in one or more suitable combinations, depending on the display quality characteristics desired or required by the display module DM and the display device including the display module DM. For example, in one or more embodiments, the arrangement type (type) of the light-emitting regions PXA-R, PXA-G, and PXA-B can be pentile. ® Arrangement type (type) (e.g., RGBG matrix, RGBG structure, or RGBG matrix structure) or Diamond (Diamond Pixel) ® Arrangement type (type) (e.g., a display with red, blue, and green (RGB) light-emitting areas arranged in a diamond shape (e.g., an organic light-emitting diode (OLED) display)). PENTILE ® Diamond Pixel is an officially registered trademark of Samsung Display Co., Ltd. ® It is an officially registered trademark of Samsung Display Co., Ltd.

[0105] In one or more embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one or more embodiments, the area of ​​the second light-emitting region PXA-G, which is a green light emitting region, may be smaller than the area of ​​the third light-emitting region PXA-B, which is a blue light emitting region, but the embodiments of this disclosure are not limited thereto.

[0106] In the following text, Figures 5 to 9Each of the above schematically illustrates a cross-sectional view of a light-emitting element (ED) according to one or more embodiments of the present disclosure. The light-emitting element (ED) according to one or more embodiments may include a first electrode EL1, a hole transport region HTR, a light-emitting layer EML, an electron transport region ETR, and a second electrode EL2, stacked sequentially (e.g., in the order stated).

[0107] When with Figure 5 In comparison, Figure 6 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) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). Furthermore, when combined with… Figure 5 In comparison, Figure 7 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). When compared with... Figure 5 In comparison, Figure 8 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 a light-emitting auxiliary layer (EAL), and the electron transport region (ETR) includes an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). When compared with... Figure 6 In comparison, Figure 9 A cross-sectional view of a light-emitting element ED including one or more embodiments of a capping layer CPL disposed on a second electrode EL2 is shown.

[0108] The first electrode EL1 is conductive (e.g., a conductor). The first electrode EL1 can be formed using a metallic material, a metal alloy, or a conductive compound. The first electrode EL1 can be an anode or a cathode. However, embodiments of this disclosure are not limited thereto. In one or more embodiments, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive / semi-reflective electrode, or a reflective electrode. The first electrode EL1 can include at least one selected from silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn), zinc (Zn), compounds selected from two or more of these, mixtures selected from two or more of these, and oxides thereof.

[0109] If the first electrode EL1 is a transmission electrode (e.g., when the first electrode EL1 is a transmission electrode), then the first electrode EL1 may include a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO). If the first electrode EL1 is a semi-transmissive / semi-reflective electrode or a reflective electrode (e.g., when the first electrode EL1 is a semi-transmissive / semi-reflective electrode or a reflective electrode), then the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, W, compounds thereof, or mixtures 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 structure comprising multiple layers, said multiple layers including a reflective layer or a semi-transmissive / semi-reflective layer formed using one or more of the materials described above, and a transmission conductive layer formed using ITO, IZO, ZnO, or ITZO. For example, in one or more embodiments, the first electrode EL1 may include a three-layer structure of ITO / Ag / ITO. However, the embodiments of this disclosure are not limited thereto. The first electrode EL1 may include one of the above-described metallic materials, a combination of two or more metallic materials selected from the above-described metallic materials, or an oxide of the above-described metallic materials. The thickness of the first electrode EL1 may be from about 700 angstroms (Å) to about 10,000 Å. For example, in one or more embodiments, the thickness of the first electrode EL1 may be from about 1,000 Å to about 3,000 Å.

[0110] A hole transport region (HTR) can be provided on the first electrode EL1. The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer (EAL), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, from about 50 Å to about 15,000 Å. The light-emitting auxiliary layer (EAL) may also be referred to as a buffer layer.

[0111] The hole transport region (HTR) can have a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure including multiple layers formed using multiple different materials.

[0112] For example, in one or more embodiments, the hole transport region HTR may have a monolayer structure of a hole injection layer HIL or a hole transport layer HTL, and may have a monolayer structure formed using a hole injection material and / or a hole transport material. In one or more embodiments, the hole transport region HTR may have a monolayer structure formed using a variety of different materials, or a structure stacked from the first electrode EL1 consisting of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / light emission auxiliary layer EAL, a hole injection layer HIL / light emission auxiliary layer EAL, a hole transport layer HTL / light emission auxiliary layer EAL, a hole injection layer HIL / hole transport layer HTL / light emission auxiliary layer EAL, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, but is not limited thereto.

[0113] Hole transport regions (HTRs) can be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI) method.

[0114] In one or more embodiments, the hole transport region (HTR) may include a compound represented by formula H-1.

[0115] Formula H-1

[0116] In formula H-1, L1 and L2 can each independently be a directly linked, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. “a” and “b” can each independently be an integer from 0 to 10. If “a” or “b” is an integer of 2 or greater (e.g., when “a” or “b” is an integer of 2 or greater), then multiple L1 and / or multiple L2 can each independently be a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0117] In formula H-1, Ar1 and Ar2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group with 2 to 30 cyclic carbon atoms. Furthermore, in formula H-1, Ar3 can be an aryl group with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted.

[0118] 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 diamine compound wherein at least one of Ar1 to Ar3 includes an amino group as a substituent. In one or more embodiments, the compound represented by formula H-1 may be a carbazole compound wherein at least one of Ar1 and Ar2 includes a substituted or unsubstituted carbazole group, or a fluorene compound wherein at least one of Ar1 and Ar2 includes a substituted or unsubstituted fluorene group.

[0119] The compound represented by formula H-1 can be any of the compounds selected from compound group H. However, the compounds shown 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.

[0120] Compound group H

[0121] In one or more embodiments, the hole transport region (HTR) may include phthalocyanine compounds selected from, for example, copper phthalocyanine, N... 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -Phenyl-N 4 N 4 -di-m-tolylphenyl-1,4-diamine (DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DB) One or more of the following: SA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-bis(1-naphth-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate] and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN).

[0122] In one or more embodiments, the hole transport region (HTR) may include one or more selected from carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), N,N'-bis(1-naphth-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) and / or 1,3-bis(N-carbazolyl)benzene (mCP).

[0123] In one or more embodiments, the hole transport region (HTR) may include one or more selected from 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), and / or 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP).

[0124] One or more compounds may include a hole transport region HTR in at least one of the hole injection layer HIL, hole transport layer HTL, light emission assist layer EAL, and electron blocking layer EBL.

[0125] The thickness of the hole transport region (HTR) can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 5,000 Å. If the hole transport region (HTR) includes a hole injection layer (HIL) (e.g., when the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, from about 30 Å to about 1,000 Å. If the hole transport region (HTR) includes a hole transport layer (HTL) (e.g., when the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be from about 30 Å to about 1,000 Å. For example, if the hole transport region (HTR) includes an electron blocking layer (EBL) (e.g., when the hole transport region (HTR) includes an electron blocking layer (EBL), the thickness of the electron blocking layer (EBL) can be from about 10 Å to about 1,000 Å. If the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL meet the corresponding ranges mentioned above (for example, when the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL meet the corresponding ranges mentioned above), satisfactory hole transport properties can be achieved without significantly increasing the driving voltage.

[0126] In one or more embodiments, in addition to one or more of the materials described above, the hole transport region (HTR) may also include a charge-generating material to increase conductivity (e.g., electrical conductivity). The charge-generating material may be uniformly (e.g., substantially uniformly) or 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, but is not limited to, at least one selected from metal halide compounds, quinone derivatives, metal oxides, and cyano-containing compounds. For example, in one or more embodiments, the p-doper may include, but is not limited to, one or more of the following: metal halide compounds such as CuI and RbI; quinone derivatives such as tetracyanoquinone dimethyl ether (TCNQ) and 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and / or cyano-containing compounds such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN) and 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9).

[0127] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may also include at least one of the luminescent auxiliary layer EAL and the electron blocking layer EBL. The luminescent auxiliary layer EAL can compensate for the resonant distance based on the wavelength of light emitted from the luminescent layer EML, and can improve luminous efficiency by controlling the hole charge balance. Furthermore, the luminescent auxiliary layer EAL can prevent or reduce electron injection into the hole transport region HTR. Materials that can be included in the hole transport region HTR can be used as materials included in the luminescent auxiliary layer EAL. The electron blocking layer EBL is a layer that prevents electrons from being injected from the electron transport region ETR into the hole transport region HTR.

[0128] In one or more embodiments of the light-emitting element (ED), the light-emitting layer (EML) may include a polycyclic compound according to one or more embodiments. In one or more embodiments of the light-emitting element (ED), the EML may include a first compound as a polycyclic compound of one or more embodiments, and at least one compound selected from a second compound and a third compound. Furthermore, in one or more embodiments of the light-emitting element (ED), the EML may also include a fourth compound. The second compound may include a fused ring of three rings containing a nitrogen atom as a cyclic atom. The third compound may include a hexagonal (e.g., 6-membered) cyclic group containing at least one nitrogen atom as a cyclic atom. The fourth compound may include an organometallic complex. The second to fourth compounds will be described in more detail later.

[0129] In this disclosure, the first compound may be referred to as a polycyclic compound of one or more embodiments. The polycyclic compound of one or more embodiments comprises a boron-containing fused ring as a core structure. The polycyclic compound of one or more embodiments as the first compound may include a core structure comprising two boron atoms as cyclic atoms and one or more other heteroatoms as cyclic atoms in addition to the boron atoms. The core structure of the polycyclic compound of one or more embodiments may include a boron-containing heterofused ring structure in the form of fused nine rings. The core structure of the polycyclic compound of one or more embodiments may be represented as comprising a heteroboron backbone comprising two boron atoms as cyclic atoms.

[0130] One or more embodiments of the polycyclic compound may include at least one nitrogen atom in the fused ring constituting the ring without boron as a cyclic atom, or may include a heterocycle containing a nitrogen atom as a cyclic atom as a substituent. For example, one or more embodiments of the polycyclic compound may include a pyridine derivative group as at least one of the rings forming the fused ring, or may include a pyridinyl group as a substituent for an amine forming the core structure.

[0131] The polycyclic compounds of one or more embodiments can exhibit thermally activated delayed fluorescence (TADF) luminescence properties through reverse intersystem crossing.

[0132] Furthermore, the polycyclic compounds of one or more embodiments have structures in which some of the carbon atoms in the heteroboron skeleton are replaced by nitrogen, or structures in which pyridyl groups replace the amino groups forming the heteroboron skeleton, thereby achieving harmony between electron-donating and electron-withdrawing groups, thus exhibiting short delayed fluorescence extinction (e.g., decay) time and excellent or suitable material stability. Therefore, the light-emitting elements of one or more embodiments comprising the polycyclic compounds of one or more embodiments can exhibit high luminous efficiency and long lifetime characteristics.

[0133] One or more light-emitting elements (EDs) may include one or more polycyclic compounds. The polycyclic compounds of one or more embodiments may be represented by Formula 1.

[0134] Formula 1

[0135] In Formula 1, X1 to X4 can each be independently O, S, or Se, or represented by Formula 2. For example, in Formula 1, X1 to X4 can each be independently O, S, Se, or an amino group represented by Formula 2 (e.g., X1 to X4 can each be independently O, S, or Se, or an amino group represented by Formula 2). If X1 to X4 are amino groups represented by Formula 2 (e.g., when X1 to X4 are amino groups represented by Formula 2), then the nitrogen atom of the amino group can be included at the corresponding positions X1 to X4.

[0136] Formula 2

[0137] In the polycyclic compound represented by Formula 1, Y1 to Y... 16 Each can be CR independently a Or N. CR a R in a It can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0138] In the amino group represented by formula 2, Y 17 To Y 21 Each can be CR independently b Or N, and CR b R in b It can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0139] In the polycyclic compound represented by Formula 1, if none of X1 to X4 is represented by Formula 2 (e.g., when none of X1 to X4 is represented by Formula 2), then Y1 to Y4 selected from Formula 1... 16 At least one of them can be N. For example, in a polycyclic compound represented by Formula 1, if X1 to X4 are each independently selected from O, S, or Se (e.g., when X1 to X4 are each independently selected from O, S, or Se), then Formula 1 may have a structure in which one of the cyclic carbon atoms of the core structure of the polycyclic compound represented by Formula 1 is changed to N. In one or more embodiments, in a polycyclic compound represented by Formula 1, if at least one of X1 to X4 is represented by Formula 2 (e.g., when at least one of X1 to X4 is represented by Formula 2), then Y1 to Y4 selected from Formula 1... 16 Y in equation 2 17 To Y 21At least one of them can be N.

[0140] The amino group represented by Formula 2 can be represented by Formula 2-1.

[0141] Equation 2-1

[0142] In one or more embodiments, the amino group represented by Formula 2 can be selected from Y in Formula 2. 17 To Y 21 One of them is N, and the others can each be CR independently. b The pyridyl substitution.

[0143] In Equation 2-1, R b1 To R b5 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0144] In the polycyclic compounds of one or more embodiments, the compounds selected from one of Y1 to Y4, one of Y6 to Y8, and one of Y4 from Formula 1 are... 13 To Y 16 One of them, and one of Y5, can be N, and the others can each be CR independently. a In one or more embodiments, if one of Y1 to Y4, one of Y6 to Y8, or one of Y... from Formula 1... 13 To Y 16 One of them, and one of Y5, can be N, and the others can each be CR independently. a (For example, when choosing one of Y1 to Y4, one of Y6 to Y8, or one of Y from Equation 1) 13 To Y 16 One of them, and one of Y5, can be N, and the others can each be CR independently. a (When), then X1 to X4 can each be O, S or Se independently, or can be represented by Equation 2-1.

[0145] For example, the polycyclic compound of one or more embodiments may be represented by any one of Formula 1-1A to Formula 1-1E.

[0146]

[0147]

[0148]

[0149] In Equation 1-1A, one of Y1 to Y4 can be N, and the others can be CR. a In Equation 1-1C, one of Y6 to Y8 can be N, and the others can be CR. a In Equation 1-1D, Y9 to Y9 are selected. 12 One of them can be N, and the others can be CR. a And in Equation 1-1E, Y is selected from 13 To Y 16 One of them can be N, and the others can be CR. a In Equations 1-1A, 1-1C, 1-1D, and 1-1E, the same content described in Equation 1 can be applied to CR. a R a .

[0150] In equations 1-1A to 1-1E, R a1 To R a16 Each of the following can be independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms. In formulas 1-1A to 1-1E, X1 to X4 can each be independently O, S, or Se, or represented by formula 2-1.

[0151] One or more embodiments of the polycyclic compound can be represented by Formula 1-2. In Formula 1-2, at least one selected from X1 to X4 can be represented by Formula 2, and the remainder can each independently be O, S, or Se. In one or more embodiments, if at least one selected from X1 to X4 is represented by Formula 2 (e.g., when at least one of X1 to X4 is represented by Formula 2), then Y selected from Formula 2... 17 To Y 21 One of them can be N, and the others can be CR. b The same content described in Equation 2 can be applied to R. b .

[0152] Formula 1-2

[0153] Formula 2

[0154] In the polycyclic compounds of one or more embodiments represented by formulas 1-2, R a1 To Ra16 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0155] The polycyclic compound of one or more embodiments may be any one of the compounds selected from compound group 1. The light-emitting element ED according to one or more embodiments may include at least one of the compounds selected from compound group 1 (e.g., any one of the compounds selected from compound group 1). In compound group 1, D is deuterium.

[0156] Compound group 1

[0157] One or more embodiments of the polycyclic compound may include a boron-containing fused ring core comprising two boron atoms as cyclic atoms, and may include N as a core cyclic atom or may include a nitrogen-containing heteroaryl group of N bonded to the included amino group as a core cyclic atom. One or more embodiments of the polycyclic compound may have a core structure in which a fused heterocycle of nine six-membered rings is fused.

[0158] One or more of the polycyclic compounds of the embodiments can be used as delayed fluorescence materials. For example, one or more of the polycyclic compounds of the embodiments can be used as thermally activated delayed fluorescence (TADF) materials. One or more of the polycyclic compounds of the embodiments can exhibit high fluorescence quantum yields. For example, one or more of the polycyclic compounds of the embodiments can exhibit high fluorescence quantum yields in the blue wavelength range having a maximum center wavelength of about 470 nm or less.

[0159] The polycyclic compounds of one or more embodiments can exhibit excellent or suitable material stability by including a core structure comprising a fused ring in which nine six-membered rings are fused and by including N in the core structure, or by including a pyridinyl group as a substituent. Furthermore, the polycyclic compounds of one or more embodiments can exhibit high emission efficiency and excellent or suitable lifetime characteristics in the blue light wavelength range.

[0160] Light-emitting elements (EDs) comprising one or more embodiments of a polycyclic compound according to one or more embodiments can exhibit high efficiency and long lifetime characteristics. EDs comprising one or more embodiments of a polycyclic compound according to one or more embodiments, having excellent or suitable emission efficiency and improved material stability in the light-emitting layer, can exhibit high luminous efficiency and excellent or suitable lifetime characteristics.

[0161] One or more embodiments of the luminescent element (ED), including the polycyclic compound according to one or more embodiments, can exhibit short fluorescence lifetime characteristics. One or more embodiments of the luminescent element (ED) can exhibit fluorescence lifetime characteristics of about 3.0 μs or less. Because one or more embodiments of the luminescent element (ED) have accelerated fluorescence lifetime characteristics of about 3.0 μs or less, one or more embodiments of the luminescent element can exhibit improved lifetime characteristics.

[0162] In a light-emitting element (ED) according to one or more embodiments, the emissive layer (EML) may be a delayed fluorescence emissive layer comprising a host and a dopant. For example, the emissive layer (EML) may emit thermally activated delayed fluorescence. The polycyclic compound of one or more embodiments may be a thermally activated delayed fluorescence dopant.

[0163] The emissive layer (EML) may include one or more polycyclic compounds as dopants. The polycyclic compounds of one or more embodiments may emit blue light. For example, the polycyclic compounds of one or more embodiments may be luminescent materials having a maximum emission wavelength (e.g., peak emission wavelength) in the wavelength range of about 430 nm to about 490 nm. For example, the polycyclic compounds of one or more embodiments may be luminescent materials having a maximum emission wavelength (e.g., peak emission wavelength) in the wavelength range of about 440 nm to about 470 nm.

[0164] In one or more embodiments, the emissive layer EML comprises a polycyclic compound of one or more embodiments, and may further comprise at least one selected from the second to the fourth compound. In one or more embodiments, the emissive layer EML may comprise a second compound represented by formula HT-1. For example, the second compound may be used as a hole transport host material of the emissive layer EML.

[0165] HT-1

[0166] In formula HT-1, A1 to A8 can each be N or CR independently. 51 For example, in one or more embodiments, A1 to A8 may each be a CR. 51 In one or more embodiments, any one of A1 to A8 is N, and the remainder may be CR.51 .

[0167] In formula HT-1, L1 can be a directly linked, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. For example, in one or more embodiments, L1 can be a directly linked, substituted or unsubstituted divalent phenyl, substituted or unsubstituted divalent biphenyl, or substituted or unsubstituted divalent carbazole group, but the embodiments of this disclosure are not limited thereto.

[0168] In equation HT-1, Y a It can be a direct connection, CR 52 R 53 or SiR 54 R 55 For example, in one or more embodiments, the two 6-membered rings (e.g., two benzene rings) connected to the nitrogen atom of formula HT-1 can be connected via direct link, ,or Connection. In equation HT-1, if Y a It is a direct connection (e.g., when Y...) a (When it is a direct connection), the second compound represented by formula HT-1 may include a carbazole moiety.

[0169] In formula HT-1, Ar1 can be a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. For example, in one or more embodiments, Ar1 can be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted biphenyl group, but the embodiments of this disclosure are not limited thereto.

[0170] In equation HT-1, R 51 To R 55 It may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 cyclic carbon atoms. In one or more embodiments, it is selected from R 51 To R 55 One or more of them can independently combine with adjacent groups to form a ring. For example, in one or more embodiments, R 51 To R 55 Each can be either hydrogen or deuterium, independently. In one or more embodiments, R51 To R 55 Each can be an unsubstituted methyl or an unsubstituted phenyl group, which can be independent of each other.

[0171] In one or more embodiments, the second compound represented by formula HT-1 may be any one of the compounds represented in compound group 2. The luminescent layer EML may include at least one of the compounds represented in compound group 2 as a hole transport host material.

[0172] Compound group 2

[0173] In the specific compounds represented in Compound Group 2, "D" refers to deuterium, and "Ph" can refer to a substituted or unsubstituted phenyl group. For example, in the specific compounds represented in Compound Group 2, "Ph" can be an unsubstituted phenyl group.

[0174] In one or more embodiments, the emissive layer EML may include a third compound represented by formula ET-1. For example, the third compound may be used as the electron transport host material of the emissive layer EML.

[0175] ET-1

[0176] In Equation ET-1, at least one of X1 to X3 can be N, and the rest are CR. 56 For example, in one or more embodiments, one of X1 to X3 may be N, and the other two may each be CR independently. 56 In these embodiments, the third compound represented by formula ET-1 may include a pyridine moiety. In one or more embodiments, two of X1 to X3 may be N, and the remaining one is CR. 56 In these embodiments, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In one or more embodiments, all X1 to X3 may be N. In these embodiments, the third compound represented by Formula ET-1 may include a triazine moiety.

[0177] In equation ET-1, R 56 It can be hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms.

[0178] In Equation ET-1, b1 to b3 can each be an integer from 0 to 10 independently.

[0179] In formula ET-1, Ar2 to Ar4 can each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. For example, in one or more embodiments, Ar2 to Ar4 can each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.

[0180] In formula ET-1, L2 to L4 can each be independently a directly linked, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. If b1 to b3 are each an integer of 2 or greater (e.g., when b1 to b3 are each an integer of 2 or greater), then the plurality of L2 to L4 can each be independently a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0181] In one or more embodiments, the third compound may be any one of the compounds selected from compound group 3. The light-emitting element ED in one or more embodiments may include at least one compound selected from compound group 3.

[0182] Compound group 3

[0183] In the specific compounds represented in compound group 3, "D" refers to deuterium and "Ph" refers to unsubstituted phenyl.

[0184] In one or more embodiments, the emissive layer EML comprises a second compound and a third compound, and the second and third compounds can form an exciton complex. In the emissive layer EML, the exciton complex can be formed by a hole transport host and an electron transport host. In this respect, the triplet energy of the exciton complex formed by the hole transport host and the electron transport host can 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.

[0185] For example, in one or more embodiments, the triplet (T1) energy level of the excimer complex formed by the hole transport host and the electron transport host can be from about 2.4 eV to about 3.0 eV. Furthermore, the triplet energy of the excimer complex can be less than the bandgap value of each host material. The excimer complex can have a triplet energy of about 3.0 eV or less, which serves as the bandgap between the hole transport host and the electron transport host.

[0186] In one or more embodiments, in addition to the first to third compounds described above, the emissive layer EML may also include a fourth compound. The fourth compound can be used as a phosphorescent photosensitizer for the emissive layer EML. Energy can be transferred from the fourth compound to the first compound, thereby generating light emission.

[0187] For example, in one or more embodiments, the luminescent layer EML may include an organometallic complex as a fourth compound, the organometallic complex comprising Pt (platinum) as a central metal atom and ligands bonded to the central metal atom. In one or more embodiments of the luminescent element ED, the luminescent layer EML may include a compound represented by formula D-1 as a fourth compound.

[0188] Formula D-1

[0189] In formula D-1, Q1 to Q4 can each be C or N independently. C1 to C4 can each be a substituted or unsubstituted hydrocarbon ring with 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0190] In equation D-1, L 11 To L 13 They can be directly connected independently. , , , substituted or unsubstituted alkylene groups of 1 to 20 carbon atoms, substituted or unsubstituted arylene groups of 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroarylene groups of 2 to 30 cyclic carbon atoms. In L 11 To L 13 middle," "Refers to the part that connects to one of C1 to C4."

[0191] In equation D-1, b11 to b13 can each be 0 or 1 independently. If b11 is 0 (for example, when b11 is 0), then C1 and C2 can be unconnected to each other. If b12 is 0 (for example, when b12 is 0), then C2 and C3 can be unconnected to each other. If b13 is 0 (for example, when b13 is 0), then C3 and C4 can be unconnected to each other.

[0192] In equation D-1, R 61 To R 66 Each of these components may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 cyclic carbon atoms. In one or more embodiments, the components are selected from R. 61 To R 66 One or more of them can independently connect to adjacent groups to form a ring. In one or more embodiments, R 61 To R 66 Each can be independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted tert-butyl group.

[0193] In equation D-1, d1 to d4 can each be an integer from 0 to 4 independently. In equation D-1, if each of d1 to d4 is 0 (e.g., when each of d1 to d4 is 0), then the fourth compound can be respectively not R 61 To R 64 Replace. Where each of d1 to d4 is 4 and R 61 (Multiple Rs) 61 ) to R 64 (Multiple Rs) 64 An embodiment in which each of d1 to d4 is hydrogen can be the same as an embodiment in which each of d1 to d4 is 0. If each of d1 to d4 is an integer of 2 or greater (e.g., when each of d1 to d4 is an integer of 2 or greater), then each of the provided R is represented by a plurality of R. 61 To R 64 Each of them can be identical, or selected from multiple R... 61 (Multiple Rs) 61 ) to R 64 (Multiple Rs) 64 At least one of them can be different.

[0194] In formula D-1, C1 to C4 can each be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle represented by one of C-1 to C-4.

[0195]

[0196] In C-1 to C-4, P1 can be... or CR74 P2 can be or NR 81 P3 can be or NR 82 And P4 can be or CR 88 R 71 To R 88 Each of the groups may be independently substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted aryl groups of 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups of 2 to 30 cyclic carbon atoms, and / or may be independently bonded to adjacent groups to form a ring.

[0197] Furthermore, in C-1 to C-4, " "is the part connected to the central metal atom Pt, and" "Corresponds to the connection to a neighboring ring group (C1 to C4) or a neighboring linker group (L)" 11 To L 13 ( ) part.

[0198] One or more embodiments of the luminescent layer EML may include a first compound as a polycyclic compound and at least one selected from the second to the fourth compound. For example, in one or more embodiments, the luminescent layer EML may include a first compound, a second compound, and a third compound. In the luminescent layer EML, the second and third compounds may form an excimer complex, and energy may be transferred from the excimer complex to the first compound to generate light emission.

[0199] In one or more embodiments, the emissive layer (EML) may include a first compound, a second compound, a third compound, and a fourth compound. In the EML, the second and third compounds may form an exciton complex, and energy can be transferred from the exciton complex to the fourth and first compounds to generate light emission. In one or more embodiments, the fourth compound may be a sensitizer. In one or more embodiments of the light-emitting element (ED), the fourth compound included in the EML can serve as a sensitizer to transfer energy from the host to the first compound, which is a light-emitting dopant. For example, in one or more embodiments, the fourth compound, acting as an auxiliary dopant, can accelerate the energy transfer to the first compound, thereby increasing the luminescence ratio of the first compound. Therefore, the EML of one or more embodiments may have improved emission efficiency. Furthermore, if the energy transferred to the first compound increases (e.g., when the energy transferred to the first compound increases), excitons formed in the EML may not accumulate inside the EML and emit light rapidly, thus reducing the degradation of the light-emitting element. Therefore, the lifetime of the ED of one or more embodiments may be improved.

[0200] One or more embodiments of the light-emitting element (ED) may include all of the first, second, third, and fourth compounds, such that the light-emitting layer (EML) comprises a combination of two host materials and two dopant materials. In one or more embodiments of the light-emitting element (ED), the light-emitting layer (EML) may exhibit excellent or suitable emission efficiency characteristics by concurrently (e.g., simultaneously) including two different hosts as the second and third compounds, a first compound that emits delayed fluorescence, and a fourth compound comprising an organometallic complex.

[0201] In one or more embodiments, the fourth compound represented by formula D-1 may be any one of the compounds represented in compound group 4. The luminescent layer EML may include at least one of the compounds represented in compound group 4 as a sensitizer material.

[0202] Compound group 4

[0203] In the specific compounds represented in compound group 4, "D" refers to deuterium.

[0204] In one or more embodiments of the light-emitting element (ED), if the light-emitting layer (EML) includes all of the first, second, and third compounds described above (e.g., when the EML includes all of the first, second, and third compounds described above), the content (e.g., amount) of the first compound can be from about 0.1 wt% to about 5 wt% based on the total weight of the first, second, and third compounds. However, embodiments of this disclosure are not limited thereto. When the content (e.g., amount) of the first compound satisfies the above ratio, energy transfer from the second and third compounds to the first compound can be increased, and therefore, emission efficiency and element lifetime can be improved.

[0205] The content (e.g., amount) of the second and third compounds in the emissive layer EML can be the remaining weight excluding the weight of the first compound. For example, in one or more embodiments, based on the total weight of the first, second, and third compounds, the sum of the content (e.g., amount) of the second compound and the content (e.g., amount) of the third compound in the emissive layer EML can be from about 65 wt% to about 95 wt%.

[0206] The weight ratio of the second compound to the third compound in the total weight of the second and third compounds can be approximately 3:7 to 7:3.

[0207] When the content (e.g., amount) of the second compound and the content (e.g., amount) of the third compound meet the above ratio, the charge balance characteristics within the emissive layer (EML) can be improved, thereby increasing emission efficiency and device lifetime. When the content (e.g., amount) of the second compound and the content (e.g., amount) of the third compound deviate from the above ratio range, the charge balance within the emissive layer (EML) may be disrupted, potentially reducing emission efficiency and making the device more prone to degradation.

[0208] In one or more embodiments, when the emitting layer EML includes a fourth compound, the content (e.g., amount) of the fourth compound can be from about 10 wt% to about 30 wt% based on the total weight of the first, second, third, and fourth compounds in the emitting layer EML. However, embodiments of this disclosure are not limited thereto. When the content (e.g., amount) of the fourth compound meets the above-mentioned content (e.g., amount) range, energy transfer from the host to the first compound, which is a luminescent dopant, can be increased, thereby improving the luminescence ratio and thus improving the emission efficiency of the emitting layer EML. When the first, second, third, and fourth compounds included in the emitting layer EML meet the above-mentioned content (e.g., amount) ratio range, excellent or suitable emission efficiency and long lifetime can be achieved.

[0209] The luminescent layer (EML) can have a thickness of, for example, from about 100 Å to about 1,000 Å or from about 100 Å to about 300 Å. The luminescent layer (EML) can be a monolayer formed using a single material, a monolayer formed using multiple different materials, or a multilayer structure formed using multiple different materials.

[0210] exist Figures 5 to 9 In each of the light-emitting elements (EDs) shown in the embodiments, the light-emitting layer (EML) may include the polycyclic compound of one or more of the embodiments described above as a dopant. In one or more embodiments, in Figures 5 to 9 In each of the light-emitting elements (EDs) shown in the embodiments, the light-emitting layer (EML) may include at least one of a first compound as a polycyclic compound in one or more embodiments and a second compound represented by formula HT-1 or a third compound represented by formula ET-1. In one or more embodiments, in Figures 5 to 9 In each of the light-emitting elements ED in the embodiments shown, the light-emitting layer EML may include a first compound as a polycyclic compound in one or more embodiments, 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.

[0211] In one or more embodiments of the light-emitting element ED, the light-emitting layer EML may further include at least one selected from anthracene derivatives, pyrene derivatives, fluoranthene derivatives, β-derived derivatives, dihydrobenzanthene derivatives, and benzo[a]phenanthrene derivatives. For example, in one or more embodiments, the light-emitting layer EML may further include anthracene derivatives and / or pyrene derivatives.

[0212] exist Figures 5 to 9 In one or more embodiments of the light-emitting element ED shown, the light-emitting layer EML may include a host and a dopant, and the light-emitting layer EML may also include a compound represented by Formula E-1. The compound represented by Formula E-1 can be used as a fluorescent host material.

[0213] E-1

[0214] In equation E-1, R 31 To R 40 Each of the following can be independently hydrogen, deuterium, halogen, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted alkenyl with 2 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms, and / or combined with adjacent groups to form a ring. In one or more embodiments, selected from R 31 To R40 One or more of them can independently combine with adjacent groups to form saturated hydrocarbon rings, unsaturated hydrocarbon rings, saturated heterocycles, or unsaturated heterocycles.

[0215] In E-1, “c” and “d” can each be an integer from 0 to 5 independently.

[0216] The compound represented by formula E-1 can be any one of compounds E1 to E19.

[0217]

[0218]

[0219]

[0220]

[0221] In one or more embodiments, the emissive layer EML may further comprise a compound represented by formula E-2a or E-2b. The compound represented by formula E-2a or E-2b may be used as a host material in the phosphorescent emissive layer.

[0222] E-2a

[0223] In equation E-2a, "a" can be an integer from 0 to 10, L a It can be a directly linked, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. If "a" is an integer of 2 or greater (e.g., when "a" is an integer of 2 or greater), then multiple L a Each can be an arylene with 6 to 30 cyclic carbon atoms, substituted or unsubstituted, or a heteroarylene with 2 to 30 cyclic carbon atoms, substituted or unsubstituted.

[0224] Furthermore, in E-2a, A1 to A5 can each be N or CR independently. i R a To R iEach of the following groups may independently be hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or may be combined with adjacent groups to form a ring. In one or more embodiments, the group selected from R... a To R i One or more of them can independently combine with adjacent groups to form a hydrocarbon ring or a heterocycle including N, O and / or S as cyclic atoms.

[0225] In one or more embodiments, in formula E-2a, two or three of A1 to A5 may be N, and the remainder is CR. i .

[0226] E-2b

[0227] In formula E-2b, Cbz1 and Cbz2 can each be an unsubstituted carbazole group or a carbazole group substituted with aryl groups of 6 to 30 cyclic carbon atoms. b It can be a directly linked, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. “b” is an integer from 0 to 10, and if “b” is an integer of 2 or greater (e.g., when “b” is an integer of 2 or greater), multiple L… b Each can be an arylene with 6 to 30 cyclic carbon atoms, substituted or unsubstituted, or a heteroarylene with 2 to 30 cyclic carbon atoms, substituted or unsubstituted.

[0228] The compound represented by formula E-2a or E-2b can be any of the compounds selected from compound group E-2. However, the compounds shown in compound group E-2 are merely examples, and the compounds represented by formula E-2a or E-2b are not limited to those represented in compound group E-2.

[0229] Compound group E-2

[0230]

[0231]

[0232]

[0233] In one or more embodiments, the light-emitting layer EML may further comprise a compound represented by the formula Ma. The compound represented by the formula Ma can be used as a phosphorescent dopant material.

[0234] Formula Ma

[0235] In formula Ma, Y1 to Y4 and Z1 to Z4 can each independently be CR1 or N, and R1 to R4 can each independently be hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or can independently combine with adjacent groups to form a ring. In formula Ma, "m" is 0 or 1, and "n" is 2 or 3. In formula Ma, if "m" is 0 (e.g., when "m" is 0), then "n" is 3, and if "m" is 1 (e.g., when "m" is 1), then "n" is 2.

[0236] Compounds represented by the formula Ma can be used as phosphorescent dopants.

[0237] The compound represented by formula Ma can be any one of compounds M-a1 to M-a25. However, compounds M-a1 to M-a25 are merely examples, and the compound represented by formula Ma is not limited to the compounds represented by compounds M-a1 to M-a25.

[0238]

[0239]

[0240]

[0241] In one or more embodiments, the emissive layer EML may further include a compound selected from those represented by formulas Fa to Fc. Compounds represented by formulas Fa to Fc can be used as fluorescent dopant materials.

[0242] Formula Fa

[0243] In formula Fa, the formula is selected from R. a To R j The two of them can be independently... Replace. R a To R j The un-included The remaining substituted elements may be, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0244] exist In this embodiment, Ar1 and Ar2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group with 2 to 30 cyclic carbon atoms. For example, in one or more embodiments, at least one of Ar1 and Ar2 can be a heteroaryl group including O or S as cyclic atoms.

[0245] Formula Fb

[0246] In equation Fb, R a and R b Each of the groups can be independently hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or can be combined with adjacent groups to form a ring. Ar1 to Ar4 can each be independently a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0247] In formula Fb, U and V can each independently be a substituted or unsubstituted hydrocarbon ring of 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 cyclic carbon atoms. In one or more embodiments, at least one selected from Ar1 to Ar4 can be a heteroaryl group including O or S as a cyclic atom.

[0248] In formula Fb, the number of rings represented by U and V can each be 0 or 1 independently. For example, in formula Fb, if the number of U or V is 1 (e.g., when the number of U or V is 1), a ring forms part of the fused ring at the portion specified by U or V, and if the number of U or V is 0 (e.g., when the number of U or V is 0), no ring exists at the portion specified by U or V. For example, if the number of U is 0 and the number of V is 1 (e.g., when 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 (e.g., when the number of U is 1 and the number of V is 0), then the fused ring with a fluorene core in formula Fb can be a cyclic compound with four rings. In one or more embodiments, if both the number of U and V is 0 (e.g., the number of U and V is 0 simultaneously) (e.g., when both the number of U and V is 0 simultaneously), then the fused ring with a fluorene core in formula Fb can be a cyclic compound with three rings. In one or more embodiments, if the quantity of both U and V is 1 (e.g., the quantity of both U and V is 1 at the same time) (e.g., when the quantity of both U and V is 1 at the same time), then the fused ring with a fluorene core of formula Fb can be a cyclic compound with five rings.

[0249] Formula Fc

[0250] In equation Fc, A1 and A2 can each be independently O, S, Se, or NR. m And R m It can be hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. R1 to R 11 Each of the groups can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted oxy, substituted or unsubstituted thio, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms, and / or combined with adjacent groups to form a ring.

[0251] In one or more embodiments, in formula Fc, A1 and A2 can each independently bind to substituents of adjacent rings to form fused rings. For example, if A1 and A2 can each independently be NR m (For example, when A1 and A2 can each be NR independently) mIn one or more embodiments, A1 may be combined with R4 or R5 to form a ring. In one or more embodiments, A2 may be combined with R7 or R8 to form a ring.

[0252] In one or more embodiments, the light-emitting layer EML may include a styrene derivative selected from styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N One or more of the following can be used as suitable dopant materials: 1,4'-phenylaniline (N-BDAVBi) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) and / or pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene and 1,4-bis(N,N-diphenylamino)pyrene).

[0253] In one or more embodiments, the light-emitting layer (EML) may further comprise a suitable phosphorescent dopant material. For example, the phosphorescent dopant may be a metal complex comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). For example, in one or more embodiments, iridium (III) bis(4,6-difluorophenylpyridine-N,C2')pyridinecarboxylate (FIrpic), iridium (III) bis(2,4-difluorophenylpyridine)tetra(1-pyrazolyl)borate (FIr6), or octaethylporphyrin platinum (PtOEP) may be used as the phosphorescent dopant. However, embodiments of this disclosure are not limited thereto.

[0254] In one or more embodiments, the light-emitting layer EML may comprise a quantum dot material (e.g., a quantum dot). In one or more embodiments, the quantum dot comprises a core, and the core of the quantum dot may be selected from group II-VI compounds, group I-II-VI compounds, group II-IV-VI compounds, group I-II-IV-VI compounds, group II-IV-V compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0255] Group II-VI compounds can be selected from the following groups: 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, CdZnSe The group consisting of CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof; mixtures thereof.

[0256] III-VI compounds may include binary compounds such as In2S3 and / or In2Se3, ternary compounds such as InGaS3 and / or InGaSe3, or any combination thereof.

[0257] Group I-III-VI compounds may be selected from ternary compounds and / or quaternary compounds such as AgInGaS2 and / or CuInGaS2, wherein the ternary compounds are selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof.

[0258] Group III-V compounds may be selected from the group consisting of: binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; quaternary compounds selected from GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof; and mixtures thereof. In one or more embodiments, the Group III-V compounds may also include Group II metals. For example, InZnP and other compounds can be selected as III-II-V group compounds.

[0259] Group IV-VI compounds can be selected from the following groups: binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof; and mixtures thereof. Group IV elements can be selected from the group consisting of Si, Ge and mixtures thereof. Group IV compounds can be binary compounds selected from the group consisting of SiC, SiGe and mixtures thereof.

[0260] Each element included in a multi-element compound, such as a binary, ternary, or quaternary compound, can exist in the particles at a substantially uniform or non-uniform concentration. For example, the chemical formula representing a semiconductor compound indicates the type (class) of elements included in the compound, and the ratio of elements in the compound can vary. For example, AgInGaS2 can indicate AgIn x Ga 1-x S2 (x is a real number between 0 and 1).

[0261] Quantum dots can have a single structure with a substantially uniform concentration of each element contained within them, or a core-shell dual structure. For example, the materials contained in the core and the materials contained in the shell can be different from each other.

[0262] The shell of a quantum dot can serve as a protective layer to prevent or reduce chemical deformation of the nucleus to maintain its semiconductor properties and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. The interface between the nucleus and the shell can have a concentration gradient where the concentration of elements present in the shell decreases towards the nucleus.

[0263] Examples of shells for quantum dots may include metal oxides or non-metal oxides, semiconductor compounds, or combinations thereof. For example, metal oxides or non-metal oxides may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO, or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4, but the embodiments of this disclosure are not limited thereto.

[0264] Additionally, suitable semiconductor compounds 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, but the embodiments disclosed herein are not limited thereto.

[0265] Each element included in a binary, ternary, or other multi-element compound may exist in the particles at a substantially homogeneous or non-homogeneous concentration. For example, the chemical formula representing a multi-element compound indicates the type (class) of elements included in the compound, and the element ratios within the compound may vary.

[0266] Quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum (e.g., emission spectrum) of about 45 nm or less, about 40 nm or less, or about 30 nm or less. Within this range, the color purity or color reproducibility of quantum dots can be improved. Furthermore, light emitted via such quantum dots is emitted in all directions, and the optical viewing angle properties can be improved.

[0267] Furthermore, the shape of quantum dots can be any shape commonly used in the art, without specific limitations. For example, shapes such as spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, and / or nanoplate particles can be used.

[0268] Because the band gap of quantum dots can be controlled or selected by controlling the size of the quantum dots and / or the element ratios in the quantum dot compound, light of one or more suitable wavelengths can be obtained from the quantum dot emitting layer. Therefore, by using quantum dots as described above (e.g., using quantum dots of different sizes or with different element ratios in the quantum dot compound), light-emitting elements that emit one or more suitable wavelengths of light can be realized. For example, the size of the quantum dots and / or the element ratios in the quantum dot compound can be selected to emit red, green, and / or blue light. Furthermore, quantum dots can be configured to emit white light by combining one or more suitable colors of light.

[0269] In one or more embodiments of the light-emitting element ED, such as Figures 5 to 9 As shown, the electron transport region (ETR) can be provided on the light-emitting layer (EML). The electron transport region (ETR) may include at least one of the hole blocking layer (HBL), the electron transport layer (ETL), and the electron injection layer (EIL). However, embodiments of this disclosure are not limited thereto.

[0270] The electronic transport region (ETR) can have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure made of multiple different materials.

[0271] For example, in one or more embodiments, the electron transport region (ETR) may have a monolayer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or a monolayer structure formed using an electron injection material and / or an electron transport material. In one or more embodiments, the ETR may have a monolayer structure formed using a variety of different materials, or a structure of an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) stacked from the emitting layer (EML), but is not limited thereto. The thickness of the ETR may be, for example, from about 1,000 Å to about 1,500 Å.

[0272] The electron transport region (ETR) can be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI) method.

[0273] In one or more embodiments, the electron transport region (ETR) may include a compound represented by the formula ET-2.

[0274] ET-2

[0275] In Equation ET-2, at least one of X1 to X3 can be N, and the rest are CR. a R a Ar1 to Ar3 can be hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. Ar1 to Ar3 can each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0276] In Formula ET-2, "a" through "c" can each be an integer from 0 to 10 independently. In Formula ET-2, L1 through L3 can each be an arylene group with 6 to 30 cyclic carbon atoms that is directly connected, substituted, or unsubstituted, or a heteroarylene group with 2 to 30 cyclic carbon atoms that is substituted or unsubstituted. In one or more embodiments, if "a" through "c" is an integer of 2 or greater (e.g., when "a" through "c" is an integer of 2 or greater), then a plurality of L1 through L3 can each be an arylene group with 6 to 30 cyclic carbon atoms that is substituted or unsubstituted, or a heteroarylene group with 2 to 30 cyclic carbon atoms that is substituted or unsubstituted.

[0277] In one or more embodiments, the electron transport region (ETR) may include anthracene compounds. However, embodiments of this disclosure are not limited thereto; for example, in one or more embodiments, the ETR may include, for example, a compound selected from tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridyl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazolyl-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazolyl-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(biphenyl)-2-yl)-phenyl ... Benzene-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphth-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-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(10-hydroxybenzoquinoline)beryllium (Bebq2), 9,10-bis(naphth-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), and mixtures thereof, but not limited thereto.

[0278] In one or more embodiments, the electron transport region (ETR) may include at least one selected from compounds ET1 to ET36.

[0279]

[0280] In one or more embodiments, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI, lanthanides such as Yb, or co-deposited materials of metal halides and lanthanides. For example, in one or more embodiments, the ETR may include KI:Yb, RbI:Yb, and / or LiF:Yb as co-deposited materials. In one or more embodiments, the ETR may use metal oxides such as Li₂O and / or BaO, or lithium 8-hydroxyquinoline (Liq). However, embodiments of this disclosure are not limited thereto. In one or more embodiments, the ETR may also be formed using a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material having a band gap of about 4 eV or greater. For example, the organometallic salt may include one or more selected from, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and metal stearates.

[0281] In one or more embodiments, in addition to one or more of the foregoing materials, the electron transport region (ETR) may 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). However, embodiments of this disclosure are not limited thereto.

[0282] The electron transport region (ETR) may be one or more compounds selected from at least one of the electron injection layer (EIL), electron transport layer (ETL), and hole blocking layer (HBL) that include the electron transport region.

[0283] If the electron transport region (ETR) includes an electron transport layer (ETL) (e.g., when the ETR includes an ETL), the thickness of the ETL can be from about 100 Å to about 1,000 Å, for example, from about 150 Å to about 500 Å. If the thickness of the ETL meets the above range (e.g., when the ETL meets the above range), satisfactory electron transport properties can be obtained without a significant increase in the driving voltage. If the ETR includes an electron injection layer (EIL) (e.g., when the ETR includes an EIL), the thickness of the EIL can be from about 1 Å to about 100 Å, for example, from about 3 Å to about 90 Å. If the thickness of the EIL meets the above range (e.g., when the EIL meets the above range), satisfactory electron injection properties can be obtained without causing a significant increase in the driving voltage.

[0284] The second electrode EL2 can be provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiments of this disclosure are not limited thereto. For example, if the first electrode EL1 is an anode (e.g., when the first electrode EL1 is an anode), then the second electrode EL2 can be a cathode, and if the first electrode EL1 is a cathode (e.g., when the first electrode EL1 is a cathode), then the second electrode EL2 can be an anode.

[0285] The second electrode EL2 can be a transmission electrode, a semi-transmission / semi-reflection electrode, or a reflection electrode. If the second electrode EL2 is a transmission electrode (e.g., when the second electrode EL2 is a transmission electrode), then the second electrode EL2 can 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), etc.

[0286] If the second electrode EL2 is a semi-transmissive / semi-reflective electrode or a reflective electrode (e.g., when the second electrode EL2 is a semi-transmissive / semi-reflective electrode or a reflective electrode), then the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, Yb, W, or compounds or mixtures thereof (e.g., AgMg, AgYb, or MgYb), or a multilayer structure material such as LiF / Ca or LiF / Al. In one or more embodiments, the second electrode EL2 may have a multilayer structure, the multilayer structure including a reflective layer or a semi-transmissive / semi-reflective layer formed using one or more of the above materials, and a transparent conductive layer formed using ITO, IZO, ZnO, and / or ITZO, etc. For example, in one or more embodiments, the second electrode EL2 may include one of the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or an oxide of the aforementioned metallic materials.

[0287] In one or more embodiments, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode (e.g., when the second electrode EL2 is connected to the auxiliary electrode), the resistance of the second electrode EL2 may be reduced.

[0288] A capping layer CPL may be further disposed on the second electrode EL2 in one or more embodiments of the light-emitting element ED. The capping layer CPL may include multiple layers or a single layer.

[0289] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, if the capping layer CPL comprises an inorganic material (e.g., when the capping layer CPL comprises an inorganic material), the inorganic material may include alkali metal compounds such as LiF, alkaline earth metal compounds such as MgF2, SiON, SiN. x and / or SiO y wait.

[0290] In one or more embodiments, if the capping layer CPL comprises an organic material (e.g., when the capping layer CPL comprises an organic material), the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15) and / or 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), or may include epoxy resins and / or acrylates such as methacrylates. In one or more embodiments, the capping layer CPL may include at least one selected from compounds P1 to P5, but the embodiments of this disclosure are not limited thereto.

[0291]

[0292] The refractive index of the capping layer CPL can be about 1.6 or greater. For example, the refractive index of the capping layer CPL for light in the wavelength range of about 550 nm to about 660 nm can be about 1.6 or greater.

[0293] Figures 10 to 13 Each of the above is a cross-sectional view illustrating a display module DM-a, DM-TD, DM-b, and DM-c according to one or more embodiments of the present disclosure. (Refer to...) Figures 10 to 13 In the description of the display modules DM-a, DM-TD, DM-b, and DM-c according to one or more embodiments, references to... Figures 1 to 9 The overlapping parts of the description will be explained, and the different features will be the main focus.

[0294] Reference Figure 10 According to one or more embodiments, the display module DM-a may include a display panel DP containing a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. Figure 10 In one or more embodiments shown, the display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display element layer DP-ED, and the display element layer DP-ED may include a light-emitting element ED.

[0295] The light-emitting element (ED) may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, a light-emitting layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the light-emitting layer EML, and a second electrode EL2 disposed on the electron transport region ETR. Figures 5 to 9 The same structure in each of the light-emitting elements (EDs) can be equivalently applied to Figure 10 The structure of the light-emitting element ED shown is illustrated. Figure 10 The light-emitting element (ED) shown may comprise one or more polycyclic compounds according to one or more embodiments. Therefore, the ED can exhibit high efficiency and long lifetime characteristics. Furthermore, the ED of one or more embodiments can exhibit high luminous efficiency and long lifetime characteristics in the blue light emission range.

[0296] Reference Figure 10 The emissive layer EML can be disposed in an opening OH defined in the pixel defining layer PDL. For example, an emissive layer EML divided by the pixel defining layer PDL and correspondingly provided to each of the emissive regions PXA-R, PXA-G, and PXA-B can emit light within substantially the same wavelength range. In the display module DM-a according to one or more embodiments, the emissive layer EML can emit blue light. In one or more embodiments, the emissive layer EML can be provided as a common layer for all emissive regions PXA-R, PXA-G, and PXA-B.

[0297] The light control layer (CCL) can be placed on the display panel (DP). Although in Figure 10 The light control layer (CCL) is shown disposed above the display element layer (DP-ED), but embodiments of this disclosure are not limited thereto; for example, the light control layer (CCL) may be disposed below the display element layer (DP-ED). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor. The light converter can convert the wavelength of the provided light and then emit the wavelength-converted light. For example, the light control layer (CCL) may be a layer comprising quantum dots or a layer comprising phosphors.

[0298] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be separate from each other.

[0299] Reference Figure 10 The separator pattern BMP can be arranged between the separate optical control units CCP1, CCP2, and CCP3, but the embodiments disclosed herein are not limited thereto. Figure 10In the diagram, the separator pattern BMP is shown as not overlapping with the light control units CCP1, CCP2 and CCP3, but in one or more embodiments, at least a portion of the edge of each of the light control units CCP1, CCP2 and CCP3 may overlap with the separator pattern BMP.

[0300] In one or more embodiments, the light control layer CCL may include: a first light control unit CCP1 including a first quantum dot QD1 that converts first color light provided by the light-emitting element ED into second color light; a second light control unit CCP2 including a second quantum dot QD2 that converts first color light into third color light; and a third light control unit CCP3 that transmits first color light.

[0301] In one or more embodiments, the first light control unit CCP1 can provide red light as a second color light, and the second light control unit CCP2 can provide green light as a third color light. The third light control unit CCP3 can transmit and provide blue light as the first color light provided from the light-emitting element ED. For example, the first quantum dot QD1 can be a red quantum dot for emitting red light, and the second quantum dot QD2 can be a green quantum dot for emitting green light. The same principles applied to quantum dots QD1 and QD2 can be applied.

[0302] In one or more embodiments, the light control layer CCL may further include a scatterer SP. The first light control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control unit CCP3 may not include (e.g., may exclude) quantum dots (e.g., any quantum dot) but includes the scatterer SP.

[0303] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one selected from TiO2, ZnO, Al2O3, and SiO2 (e.g., hollow silica). The scatterer SP can include at least one selected from TiO2, ZnO, Al2O3, and SiO2 (e.g., hollow silica), or it can be a mixture of two or more materials selected from TiO2, ZnO, Al2O3, and SiO2 (e.g., hollow silica).

[0304] The first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 may each include matrix resins BR1, BR2, and BR3, respectively, which disperse quantum dots QD1 and QD2 and scatterers SP accordingly. In one or more embodiments, the first light control unit CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in the first matrix resin BR1, the second light control unit CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in the second matrix resin BR2, and the third light control unit CCP3 may include the scatterer SP dispersed in the third matrix resin BR3.

[0305] The matrix resins BR1, BR2, and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are correspondingly dispersed, and can be composed of one or more suitable resin compositions, generally referred to as binders. For example, matrix resins BR1, BR2, and BR3 can each be independently selected from acrylic resins, urethane resins, silicone resins, and / or epoxy resins, etc. Matrix resins BR1, BR2, and BR3 can each be a transparent resin. 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 as or different from each other.

[0306] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 serves to block the penetration of moisture and / or oxygen (hereinafter referred to as "humidity / oxygen"). The barrier layer BFL1 may be disposed on the light control units CCP1, CCP2, and CCP3, and may prevent the light control units CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. The barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. In one or more embodiments, the color filter layer CFL, which will be described later, may include a barrier layer BFL2 disposed on the light control units CCP1, CCP2, and CCP3.

[0307] Barrier layers BFL1 and BFL2 may each comprise at least one inorganic layer. For example, in one or more embodiments, barrier layers BFL1 and BFL2 may be formed by comprising inorganic materials. For example, barrier layers BFL1 and BFL2 may each be independently formed by comprising silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and / or silicon oxynitride or a metal thin film that ensures light transmittance. Barrier layers BFL1 and BFL2 may also each independently comprise an organic film. Barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.

[0308] In the display module DM-a according to one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL. For example, in one or more 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.

[0309] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 that transmits a second color of light, a second filter CF2 that transmits a third color of light, and a third filter CF3 that transmits a first color of light. For example, in one or more 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. Each of filters CF1, CF2, and CF3 may include a polymeric photosensitive resin and pigments and / or dyes. For example, in one or more embodiments, the first filter CF1 may include red pigments and / or red dyes, the second filter CF2 may include green pigments and / or green dyes, and the third filter CF3 may include blue pigments and / or blue dyes.

[0310] However, embodiments of this disclosure are not limited thereto. For example, in one or more embodiments, the third filter CF3 may not include (e.g., may exclude) any pigments or dyes. The third filter CF3 may include a polymeric photosensitive resin and may not include pigments or dyes. The third filter CF3 may be transparent. In one or more embodiments, the third filter CF3 may be formed using a transparent photosensitive resin.

[0311] Furthermore, in one or more embodiments, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may be provided integrally without distinction.

[0312] In one or more embodiments, the color filter layer CFL may further include a light-blocking portion. The light-blocking portion may be a black matrix. The light-blocking portion may be formed using organic and / or inorganic light-blocking materials, each comprising a black pigment and / or a black dye. The light-blocking portion can prevent or reduce light leakage and demarcates filters CF1, CF2, and CF3 at the boundaries between adjacent filters CF1, CF2, and CF3. Furthermore, in one or more embodiments, the light-blocking portion may be formed as a blue filter.

[0313] The first filter CF1, the second filter CF2, and the third filter CF3 can be arranged to correspond to the first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B, respectively.

[0314] A substrate BL may be disposed on the color filter layer CFL. The substrate BL may be a component providing a substrate surface on which the color filter layer CFL and / or light control layer CCL, etc., are disposed. The substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In one or more embodiments, the substrate BL may not be provided.

[0315] Figure 11 This is a cross-sectional view illustrating a portion of a display module according to one or more embodiments of the present disclosure. In the display module DM-TD according to one or more embodiments, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. At least one of the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 may include a polycyclic compound of one or more embodiments. Therefore, the light-emitting element ED-BT can exhibit high efficiency and long lifetime characteristics. Furthermore, the light-emitting element ED-BT of one or more embodiments can exhibit high luminous efficiency and long lifetime characteristics in the blue light emission range.

[0316] The light-emitting element (ED-BT) may include a first electrode EL1 and a second electrode EL2 arranged opposite to each other, and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 are stacked sequentially in the thickness direction and provided between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a light-emitting layer (EML). Figure 5 ) and hole transport region HTR ( Figure 5 ) and Electronic Transfer Zone (ETR) Figure 5 ), and the light-emitting layer EML ( Figure 5 The light-emitting element ED-BT is arranged between the hole transport region HTR and the electron transport region ETR. For example, the light-emitting element ED-BT included in the display module DM-TD according to one or more embodiments may be a light-emitting element with a series structure comprising multiple light-emitting layers.

[0317] exist Figure 11 In one or more embodiments shown, the light emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 can all be blue light. However, the embodiments of this disclosure are not limited thereto. For example, in one or more embodiments, the wavelength ranges of the light emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 can be different from each other. For example, in one or more embodiments, a light-emitting element ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 emitting light in different wavelength ranges can emit white light.

[0318] Charge generation layers CGL1 and CGL2 can be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3, respectively. Figure 11 In one or more embodiments shown, charge generation layers CGL1 and CGL2 may include a first charge generation layer CGL1 disposed between a first light-emitting structure OL-B1 and a second light-emitting structure OL-B2, and a second charge generation layer CGL2 disposed between a second light-emitting structure OL-B2 and a third light-emitting structure OL-B3. The first charge generation layer CGL1 and the second charge generation layer CGL2 may each independently include a p-type (category) charge generation layer and / or an n-type (category) charge generation layer.

[0319] Reference Figure 12 The display module DM-b according to one or more embodiments may include light-emitting elements ED-1, ED-2, and ED-3, with two light-emitting layers stacked in each of the light-emitting elements ED-1, ED-2, and ED-3. At least one of the light-emitting elements ED-1, ED-2, and ED-3 may include a polycyclic compound of one or more embodiments. Therefore, the light-emitting elements ED-1, ED-2, and ED-3 can exhibit high efficiency and long lifetime characteristics. Furthermore, the display module DM-b according to one or more embodiments can exhibit high luminous efficiency and long lifetime characteristics in the blue light emission range.

[0320] and Figure 3 and Figure 4 Compared to the display module DM of one or more embodiments shown, Figure 12 The difference in the illustrated embodiment is that the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 each include two light-emitting layers stacked in the thickness direction. In each of the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, the two light-emitting layers can emit light within substantially the same wavelength range.

[0321] According to one or more embodiments, the first light-emitting element ED-1 may include a first red light-emitting layer EML-R1 and a second red light-emitting layer EML-R2. The second light-emitting element ED-2 may include a first green light-emitting layer EML-G1 and a second green light-emitting layer EML-G2. Furthermore, the third light-emitting element ED-3 may include a first blue light-emitting layer EML-B1 and a second blue light-emitting layer EML-B2. A light-emitting auxiliary part OG may be disposed between the first red light-emitting layer EML-R1 and the second red light-emitting layer EML-R2, between the first green light-emitting layer EML-G1 and the second green light-emitting layer EML-G2, and between the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2. In this regard, at least one of the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2 may include a polycyclic compound from the embodiments.

[0322] The light-emitting auxiliary region (OG) may comprise a single layer or multiple layers. The OG may include a charge generation layer. For example, the OG may include an electron transport region, a charge generation layer, and a hole transport region stacked sequentially. The OG may be provided as a common layer across all first light-emitting elements ED-1, second light-emitting elements ED-2, and third light-emitting elements ED-3. However, embodiments of this disclosure are not limited thereto; for example, in one or more embodiments, the OG may be patterned and provided in an opening OH defined in a pixel defining layer PDL.

[0323] The first red emitting layer EML-R1, the first green emitting layer EML-G1, and the first blue emitting layer EML-B1 can each be arranged between the light-emitting auxiliary section OG and the electron transport region ETR. The second red emitting layer EML-R2, the second green emitting layer EML-G2, and the second blue emitting layer EML-B2 can each be arranged between the hole transport region HTR and the light-emitting auxiliary section OG.

[0324] For example, in one or more embodiments, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red light emitting layer EML-R2, a light-emitting auxiliary part OG, a first red light emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2, stacked sequentially. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green light emitting layer EML-G2, a light-emitting auxiliary part OG, a first green light emitting layer EML-G1, an electron transport region ETR, and a second electrode EL2, stacked sequentially. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue light emitting layer EML-B2, a light-emitting auxiliary part OG, a first blue light emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2, stacked sequentially.

[0325] An optical auxiliary layer PL can be disposed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL can be disposed on the display panel DP and can control the reflected light at the display panel DP caused by external light. In one or more embodiments, the optical auxiliary layer PL may not be provided in the display module DM-b.

[0326] and Figure 11 and Figure 12 different, Figure 13 The display module DM-c shown according to one or more embodiments is illustrated as including four light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 arranged opposite each other, and first light-emitting structures OL-B1, second light-emitting structures OL-B2, third light-emitting structures OL-B3, and fourth light-emitting structures OL-C1 stacked sequentially in the thickness direction between the first electrode EL1 and the second electrode EL2. At least one of the first light-emitting structures OL-B1, second light-emitting structures OL-B2, third light-emitting structures OL-B3, and fourth light-emitting structures OL-C1 may include a polycyclic compound from one or more embodiments. Therefore, the light-emitting element ED-CT can exhibit high efficiency and long lifetime characteristics. Furthermore, the light-emitting element ED-CT of one or more embodiments can exhibit high luminous efficiency and long lifetime characteristics in the blue light emission range.

[0327] Charge generation layers CGL3, CGL2, and CGL1 can be arranged between adjacent first light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1, respectively. In one or more embodiments, among the four light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1, the first light-emitting structure OL-B1, the second light-emitting structure OL-B2, and the third light-emitting structure OL-B3 emit blue light, and the fourth light-emitting structure OL-C1 can emit green light. However, the embodiments of this disclosure are not limited to this; for example, in one or more embodiments, the first light-emitting structure OL-B1, the second light-emitting structure OL-B2, the third light-emitting structure OL-B3, and the fourth light-emitting structure OL-C1 can emit light of different wavelengths. The charge generation layers CGL3, CGL2, and CGL1 arranged between adjacent light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 can each include a p-type (type) charge generation layer and / or an n-type (type) charge generation layer.

[0328] In one or more embodiments, the electronic device may include a display device comprising a plurality of light-emitting elements and a control unit for controlling the display device. In one or more embodiments, in the electronic device, at least one of the plurality of light-emitting elements may include a polycyclic compound of one or more embodiments described above in the light-emitting layer.

[0329] One or more embodiments of the electronic device may be a device activated according to an electrical signal. One or more embodiments of the electronic device may include one or more display devices, said one or more display devices including a reference... Figure 3 and / or Figures 10 to 13 The display modules DM, DM-a, DM-TD, DM-b, and DM-c described according to one or more embodiments. For example, electronic devices may include large display devices such as televisions, monitors, and external billboards, and / or small and medium-sized display devices such as personal computers, laptops, personal digital terminals, display devices for automobiles, game consoles, portable electronic devices, and cameras.

[0330] An electronic device according to one or more embodiments may include a display module comprising a polycyclic compound according to one or more embodiments, and may exhibit high efficiency and long lifespan characteristics. An electronic device according to one or more embodiments may have improved display efficiency and display lifespan, and may exhibit excellent or suitable display quality.

[0331] Figure 14 A tablet terminal is illustrated as an embodiment of an electronic device EA. One or more embodiments of the electronic device EA may include a display module DM according to one or more embodiments. For example, electronic modules, camera modules, and / or power modules mounted on a motherboard may be arranged together with the display module DM in a bracket / housing HAU to configure the tablet terminal.

[0332] Figure 14 The electronic device EA of one or more embodiments shown may include references Figure 3 and / or Figures 10 to 13 The display modules DM, DM-a, DM-TD, DM-b, and DM-c of one or more embodiments described above.

[0333] In one or more embodiments, such as Figure 14As shown, the electronic device EA including the display module DM can have a flat display surface, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, the electronic device EA can also include a curved display surface or a three-dimensional display surface. For example, a three-dimensional display surface can include multiple display areas pointing in different directions, and can also include a bent display surface. The electronic device EA according to these embodiments can be a flexible electronic device. A flexible electronic device can be a foldable electronic device.

[0334] like Figure 14 As shown, the display surface EA-IS may include an active area AA on which an image is displayed and a border area NAA adjacent to the active area AA. The border area NAA is the area where no image is displayed. Figure 14 An example of an icon image is shown. The active area AA can be referred to as the display area of ​​the display module DM, and the border area NAA can be referred to as the non-display area of ​​the display module DM.

[0335] Figure 15 A portable terminal is shown as an embodiment of the electronic device EA-M according to one or more embodiments. (See also...) Figure 15 The electronic device EA-M according to one or more embodiments may include a plurality of display surfaces. The electronic device EA-M according to one or more embodiments may include display surfaces IS-M, IS-S1, IS-S2, IS-S3 and IS-S4 with different main display orientations.

[0336] In one or more embodiments, the electronic device EA-M may be a three-dimensional display device including an upper display surface IS-M and a plurality of side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4. Each of the plurality of side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may be a display surface extending from one side of the upper display surface IS-M. In one or more embodiments, the electronic device EA-M may include a main display surface that provides images primarily in one direction and a plurality of sub-display surfaces that provide images in directions different from said one direction. Figure 15 In the embodiment of the electronic device EA-M shown, the main display surface may be the upper display surface IS-M, and the sub-display surfaces may be the side display surfaces IS-S1, IS-S2, IS-S3 and IS-S4.

[0337] Side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may each have a display surface that is not parallel to the upper display surface IS-M. The multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may each be a display area that is bent and extends from one side of the upper display surface IS-M, and for example, the multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may be bent display areas.

[0338] Figure 15 The electronic device EA-M shown may include reference Figure 3 and / or Figures 10 to 13 The display modules DM, DM-a, DM-TD, DM-b and DM-c described according to one or more embodiments.

[0339] Figure 16 This is a diagram showing a vehicle AM ​​in which a first electronic device EA-A1, a second electronic device EA-A2, a third electronic device EA-A3, and a fourth electronic device EA-A4 are arranged. At least one of the first electronic device EA-A1, the second electronic device EA-A2, the third electronic device EA-A3, and the fourth electronic device EA-A4 may include reference... Figure 3 and Figures 10 to 13 The described embodiments are display modules DM, DM-a, DM-TD, DM-b, and DM-c.

[0340] exist Figure 16 In this example, the car is shown as vehicle AM, but this is just an example, and the first electronic device EA-A1, the second electronic device EA-A2, the third electronic device EA-A3 and the fourth electronic device EA-A4 can be arranged on other transportation equipment such as bicycles, motorcycles, trains, ships and airplanes.

[0341] At least one of the first electronic device EA-A1, the second electronic device EA-A2, the third electronic device EA-A3, and the fourth electronic device EA-A4 may include reference to Figures 5 to 9The described embodiments include a light-emitting element (ED). At least one of the first electronic devices EA-A1, the second electronic device EA-A2, the third electronic device EA-A3, and the fourth electronic device EA-A4 may include the polycyclic compound of one or more embodiments. Therefore, the first electronic device EA-A1, the second electronic device EA-A2, the third electronic device EA-A3, and the fourth electronic device EA-A4 including the polycyclic compound of one or more embodiments can have improved display efficiency and display lifespan. Furthermore, the first electronic device EA-A1, the second electronic device EA-A2, the third electronic device EA-A3, and the fourth electronic device EA-A4 including the polycyclic compound of one or more embodiments can exhibit excellent or suitable display quality.

[0342] Reference Figure 16 The vehicle AM ​​may include a steering wheel HA and a gear GR for motion control, and may include a front window GL arranged in front of the vehicle AM ​​(e.g., facing the driver).

[0343] The first electronic device EA-A1 can be a digital instrument cluster displaying first information about the vehicle's engine (AM). This first information may include a first scale indicating the vehicle's speed, a second scale indicating engine speed in revolutions per minute (RPM), and an image indicating fuel status. The first and second scales can be displayed as digital images. Figure 16 In one or more embodiments shown, the first electronic device EA-A1 may be arranged in a first region overlapping with the steering wheel HA. However, embodiments of this disclosure are not limited thereto, and the first electronic device EA-A1 may be arranged on the entire dashboard, or may be arranged separately in a portion opposite to the driver's seat (e.g., facing the driver's seat) and a portion opposite to the passenger seat (e.g., facing the passenger seat).

[0344] The second electronic device EA-A2 may be disposed in a second area between the driver's seat and the windshield GL. For example, the second electronic device EA-A2 may be a head-up display (HUD) showing second information about the vehicle's AM (Autonomous Vehicle). In one or more embodiments, the second electronic device EA-A2 may be optically transparent. The second information may include a digital number indicating the vehicle's AM speed, and may also include information such as the current time. In one or more embodiments, the second information of the second electronic device EA-A2 may be projected and displayed on the windshield GL. The display surface of the second electronic device EA-A2 may face the driver's seat. In one or more embodiments, the second electronic device EA-A2 may provide an image in the direction of the windshield GL.

[0345] The third electronic device EA-A3 can be located in a third area adjacent to the gearshift GR. For example, the third electronic device EA-A3 can be a vehicle information guidance display (central information display (CID)) located between the driver's seat and the passenger seat and displaying third information. The passenger seat can be a seat spaced apart from the driver's seat with the gearshift GR located between the passenger seat and the driver's seat. The third information may include information about road conditions (e.g., navigation information), music or radio playback, video playback, and / or the temperature inside the vehicle's AM system.

[0346] The fourth electronic device EA-A4 can be located in a fourth area, separate from the steering wheel HA and gearshift GR, and adjacent to one side of the vehicle AM. For example, the fourth electronic device EA-A4 can be a digital side mirror displaying fourth information. The fourth electronic device EA-A4 can display an image of the exterior of the vehicle AM ​​captured by a camera module CM located outside the vehicle AM. The fourth information may include the image of the exterior of the vehicle AM.

[0347] The first to fourth information described above are embodiments, and the first electronic device EA-A1, the second electronic device EA-A2, the third electronic device EA-A3, and the fourth electronic device EA-A4 can also display information about the interior and exterior of the vehicle. The first to fourth information may include information that is different from each other. However, embodiments of this disclosure are not limited thereto; for example, some of the information in the first to fourth information may include the same information.

[0348] Figures 14 to 16 The embodiments of the electronic device presented or including embodiments of the electronic device, and without departing from the concept and teachings of this disclosure, a display module including a light-emitting element comprising one or more embodiments of a polycyclic compound can be used in other electronic devices.

[0349] In the following, polycyclic compounds and light-emitting elements according to one or more embodiments of the present disclosure will be specifically described with reference to examples and comparative examples. However, the examples shown herein are for the purpose of aiding in understanding the present disclosure, and the scope of the present disclosure is not limited thereto.

[0350] Example 1. Synthesis of the polycyclic compounds in the examples The synthesis methods of polycyclic compounds according to one or more embodiments will be specifically described by illustrating synthetic methods for (polycyclic) compounds 1, 2, 3, 21, 31, 36, 51, 61, 69, 71, 86, 113, and 126. Furthermore, the synthetic methods of polycyclic compounds described below are merely examples, and the synthetic methods of polycyclic compounds according to one or more embodiments of this disclosure are not limited to the examples provided herein.

[0351] (1) Synthesis of compound 1 The polycyclic compound 1 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 1.

[0352] Reaction Scheme 1

[0353] Synthesis of intermediate 1C Under an argon (Ar) atmosphere, 2,6-dichloropyridine (1A) (20 g), carbazole (1B) (23 g), Cs₂CO₃ (66 g), and 1-methyl-2-pyrrolidone (270 mL) were added to a 1000 mL three-necked flask and stirred and heated at approximately 150 °C for about 16 hours. After cooling to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 19.6 g (52% yield) of intermediate 1C. The mass number of intermediate 1C, measured by rapid atomic impact mass spectrometry (FAB-MS), was 279.

[0354] Synthesis of intermediate 1E Under an argon atmosphere, intermediate 1C (19.6 g), 2-aminobiphenyl (1D) (18 g), bis(dibenzylacetone)palladium (0) (Pd(dba)2, 1.2 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 1.7 g), sodium tert-butoxide (NaOtBu, 10 g), and toluene (350 mL) were added to a 1000 mL three-necked flask and heated and stirred at approximately 70 °C for about 24 hours. After cooling to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 18.2 g (63% yield) of intermediate 1E. The mass number of intermediate 1E, as measured by FAB-MS, was 412.

[0355] Synthesis of intermediate 1H Under an argon atmosphere, 30 g of 1,3-difluoro-5-iodobenzene (1F), 30 g of phenol (1G), 52 g of K₂CO₃, and 400 mL of 1-methyl-2-pyrrolidone were added to a 1000 mL three-necked flask and heated and stirred at approximately 160 °C for about 32 hours. After cooling to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 35 g (70% yield) of intermediate 1H. The mass number of intermediate 1H, measured by FAB-MS, was 404.

[0356] Synthesis of intermediate 1J Under an argon atmosphere, intermediate 1H (35 g), [1,1':3',1''-terphenyl]-2'-amine (1I) (26 g), bis(dibenzylacetone)palladium (0) (Pd(dba)2, 0.52 g), tri-tert-butylphosphine tetrafluoroborate (0.52 g), sodium tert-butoxide (NaOtBu, 13 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at approximately 100 °C for about 6 hours. After cooling to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 41 g (90% yield) of intermediate 1J. The mass number of intermediate 1J, measured by FAB-MS, was 506.

[0357] Synthesis of intermediate 1L Under an argon atmosphere, intermediate 1J (41 g), 1,3-dibromo-5-tert-butylbenzene (1K) (71 g), CuI (15.4 g), and K₂CO₃ (34 g) were added to a 500 mL three-necked flask and heated and stirred at approximately 230 °C for about 32 hours. After cooling to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 20.3 g (35% yield) of intermediate 1L was obtained. The mass number of intermediate 1L, measured by FAB-MS, was 717.

[0358] Synthesis of intermediate 1M Under an argon atmosphere, intermediate 1L (6 g), intermediate 1E (4.1 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.096 g), tri-tert-butylphosphine tetrafluoroborate (0.097 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 300 mL three-necked flask and heated and stirred at approximately 100 °C for about 6 hours. After cooling to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.2 g (82% yield) of intermediate 1M. The mass number of intermediate 1M, measured by FAB-MS, was 1047.

[0359] Synthesis of Compound 1 Under an argon atmosphere, intermediate 1M (7.2 g) was added to a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL), and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 16 g) and pyridine (4.9 g) were then added, and the mixture was heated and stirred at approximately 190 °C for about 3 hours, cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.1 g (15% yield) of compound 1. The molecular weight of compound 1, measured by FAB-MS, was 1063.

[0360] (2) Synthesis of compound 2 The polycyclic compound 2 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 2.

[0361] Reaction Scheme 2

[0362] Synthesis of intermediate 2C Under an argon atmosphere, 2-bromoaniline (2A) (10 g), 3,5-di-tert-butylboronic acid (2B) (27 g), tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4, 0.67 g), K2CO3 (16 g), and toluene / ethanol / H2O (150 / 60 / 30 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 80 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 13.6 g (83% yield) of intermediate 2C. The mass number of intermediate 2C, as measured by FAB-MS, was 281.

[0363] Synthesis of intermediate 2D Under an argon atmosphere, intermediate 2C (13.6 g), intermediate 1C (9 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.56 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.8 g), sodium tert-butoxide (NaOtBu, 4.7 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 70 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 11.3 g (67% yield) of intermediate 2D. The mass number of intermediate 2D, measured by FAB-MS, was 524.

[0364] Synthesis of intermediate 2F Under an argon atmosphere, intermediate 1F (10 g), 4-phenylphenol (2E) (17 g), Cs₂CO₃ (54 g), and 1-methyl-2-pyrrolidone (300 mL) were added to a 1000 mL three-necked flask and heated and stirred at approximately 160 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 18.5 g (82% yield) of intermediate 2F. The mass number of intermediate 2F, measured by FAB-MS, was 540.

[0365] Synthesis of intermediate 2G Under an argon atmosphere, intermediate 2F (18.5 g), intermediate 1I (10.1 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.2 g), tri-tert-butylphosphine tetrafluoroborate (0.2 g), sodium tert-butoxide (NaOtBu, 4.9 g), and toluene (200 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 19.8 g (yield 88%) of intermediate 2G was obtained. The mass number of intermediate 2G, measured by FAB-MS, was 658.

[0366] Synthesis of intermediate 2H Under an argon atmosphere, intermediate 2G (19.8 g), intermediate 1K (26 g), CuI (5.7 g), and K₂CO₃ (12.5 g) were added to a 300 mL three-necked flask and heated and stirred at approximately 230 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.8 g (30% yield) of intermediate 2H. The mass number of intermediate 2H, measured by FAB-MS, was 869.

[0367] Synthesis of intermediate 2I Under an argon atmosphere, intermediate 2H (7.8 g), intermediate 2D (5.6 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.10 g), tri-tert-butylphosphine tetrafluoroborate (0.10 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (100 mL) were added to a 300 mL three-necked flask and stirred and heated at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 9.4 g (80% yield) of intermediate 2I. The mass number of intermediate 2I, measured by FAB-MS, was 1311.

[0368] Synthesis of Compound 2 Under an argon atmosphere, intermediate 2I (9.4 g) was added to a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL). The mixture was cooled to approximately 0 °C in an ice bath, and boron triiodide (BI3, 17 g) and pyridine (5.1 g) were added. The mixture was stirred and heated at approximately 190 °C for about 3 hours. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.7 g (yield 18%) of compound 2. The molecular weight of compound 2, measured by FAB-MS, was 1327.

[0369] (3) Synthesis of compound 3 The polycyclic compound 3 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 3.

[0370] Reaction scheme 3

[0371] Synthesis of intermediate 3B Under an argon atmosphere, 20 g of 1-bromo-3-chloro-5-fluorobenzene (3A), 13.4 g of intermediate 1G, 62 g of Cs₂CO₃, and 300 mL of 1-methyl-2-pyrrolidone were added to a 1000 mL three-necked flask and stirred and heated at approximately 140 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 23.3 g (86% yield) of intermediate 3B was obtained. The mass number of intermediate 3B, measured by FAB-MS, was 284.

[0372] Synthesis of intermediate 3D Under an argon atmosphere, intermediate 3B (10 g), diphenylamine (3 C) (9 g), palladium(II) acetate (Pd(OAc)2, 0.24 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthanium (Xantphos, 0.61 g), sodium tert-butoxide (NaOtBu, 5.1 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 110 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 12 g (92% yield) of intermediate 3D. The mass number of intermediate 3D, as measured by FAB-MS, was 372.

[0373] Synthesis of intermediate 3E Under an argon atmosphere, intermediate 3D (12 g), intermediate 1I (9.5 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.19 g), tri-tert-butylphosphine tetrafluoroborate (0.19 g), sodium tert-butoxide (NaOtBu, 4.6 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 110 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 16.1 g (yield 86%) of intermediate 3E was obtained. The mass number of intermediate 3E, measured by FAB-MS, was 581.

[0374] Synthesis of intermediate 3F Under an argon atmosphere, intermediates 3E (16.1 g), 1K (24 g), CuI (5.3 g), and K₂CO₃ (11.5 g) were added to a 300 mL three-necked flask and heated and stirred at approximately 230 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.9 g (36% yield) of intermediate 3F. The mass number of intermediate 3F, measured by FAB-MS, was 792.

[0375] Synthesis of intermediate 3G Under an argon atmosphere, intermediates 3F (7.9 g), 1E (4.9 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.057 g), tri-tert-butylphosphine tetrafluoroborate (0.057 g), sodium tert-butoxide (NaOtBu, 1.5 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain intermediate 3G (10 g, 90% yield). The mass number of intermediate 3G, as determined by FAB-MS, was 1122.

[0376] Synthesis of Compound 3 Under an Ar atmosphere, intermediate 3G (10 g) was dissolved in o-dichlorobenzene (ODCB, 200 mL) in a 500 mL three-necked flask and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 21 g) and pyridine (5.3 g) were added, and the mixture was stirred and heated at approximately 190 °C for approximately 3 hours. The resulting product was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.4 g (yield 14%) of compound 3. The molecular weight of compound 3, as measured by FAB-MS, was 1138.

[0377] (4) Synthesis of compound 21 The polycyclic compound 21 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 4.

[0378] Reaction scheme 4

[0379] Synthesis of intermediate 21B Under an argon atmosphere, 1-bromo-3-iodobenzene (21A) (30 g), carbazole (1B) (17.7 g), palladium(II) acetate (Pd(OAc)2, 0.71 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthanium (Xantphos, 1.8 g), sodium tert-butoxide (NaOtBu, 13 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and stirred and heated at approximately 100 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 27.2 g (80% yield) of intermediate 21B was obtained. The mass number of intermediate 21B, measured by FAB-MS, was 322.

[0380] Synthesis of intermediate 21D Under an argon atmosphere, intermediate 21B (27.3 g), intermediate 21C (20 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.98 g), (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (2.1 g), sodium tert-butoxide (NaOtBu, 12.2 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and stirred and heated at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 29.2 g (84% yield) of intermediate 21D. The mass number of intermediate 21D, as measured by FAB-MS, was 412.

[0381] Synthesis of intermediate 21E Under an argon atmosphere, intermediate 21D (4.1 g), intermediate 1L (6 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.048 g), tri-tert-butylphosphine tetrafluoroborate (0.049 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 200 mL three-necked flask and stirred and heated at approximately 100 °C for approximately 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography was performed to obtain 7.7 g (82% yield) of intermediate 21E. The mass number of intermediate 21E, measured by FAB-MS, was 1122.

[0382] Synthesis of Compound 21 Under an argon atmosphere, intermediate 21E (7.7 g) was dissolved in o-dichlorobenzene (ODCB, 200 mL) in a 500 mL three-necked flask and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 17 g) and pyridine (5.2 g) were then added, and the mixture was heated and stirred at approximately 190 °C for about 3 hours. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.2 g (yield 14%) of compound 21. The molecular weight of compound 21, measured by FAB-MS, was 1063.

[0383] (5) Synthesis of compound 31 The polycyclic compound 31 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 5.

[0384] Reaction scheme 5

[0385] Synthesis of intermediate 31B Under an argon atmosphere, intermediate 21B (10 g), intermediate 31A (7.4 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.36 g), (±)-BINAP (0.77 g), sodium tert-butoxide (NaOtBu, 4.4 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 100 °C for approximately 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 10 g (81% yield) of intermediate 31B. The mass number of intermediate 31B, as measured by FAB-MS, was 412.

[0386] Synthesis of intermediate 31C Under an argon atmosphere, intermediate 31B (4.1 g), intermediate 1L (6 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.48 g), tri-tert-butylphosphine tetrafluoroborate (0.49 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 8 g (85% yield) of intermediate 31C. The mass number of intermediate 31C, measured by FAB-MS, was 1122.

[0387] Synthesis of Compound 31 Under an argon atmosphere, intermediate 31C (8 g) was dissolved in o-dichlorobenzene (ODCB, 200 mL) in a 500 mL three-necked flask and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 18 g) and pyridine (5.4 g) were then added, and the mixture was heated and stirred at approximately 190 °C for about 3 hours. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.3 g (16% yield) of compound 31. The molecular weight of compound 31, measured by FAB-MS, was 1063.

[0388] (6) Synthesis of compound 36 The polycyclic compound 36 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 6.

[0389] Reaction scheme 6

[0390] Synthesis of intermediate 36A Under an argon atmosphere, intermediate 1H (6 g), intermediate 1D (3.7 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.18 g), (±)-BINAP (0.39 g), sodium tert-butoxide (NaOtBu, 2.2 g), and toluene (100 mL) were added to a 300 mL three-necked flask and stirred and heated at approximately 100 °C for approximately 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 6.1 g (92% yield) of intermediate 36A. The mass number of intermediate 36A, as measured by FAB-MS, was 430.

[0391] Synthesis of intermediate 36C Under an argon atmosphere, intermediate 36B (6 g), intermediate 3C (7.5 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.38 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.54 g), sodium tert-butoxide (NaOtBu, 6.4 g), and toluene (200 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 60 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 6.1 g (62% yield) of intermediate 36C. The mass number of intermediate 36C, measured by FAB-MS, was 448.

[0392] Synthesis of intermediate 36D Under an argon atmosphere, intermediates 36C (5 g), 36A (5.7 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.06 g), tri-tert-butylphosphine tetrafluoroborate (0.06 g), sodium tert-butoxide (NaOtBu, 1.6 g), and toluene (80 mL) were added to a 200 mL three-necked flask and stirred and heated at approximately 110 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 8.1 g (86% yield) of intermediate 36D. The mass number of intermediate 36D measured by FAB-MS was 841.

[0393] Synthesis of Compound 36 Under an argon atmosphere, intermediate 36D (8.1 g) was dissolved in o-dichlorobenzene (ODCB, 200 mL) in a 500 mL three-necked flask and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 22.6 g) and pyridine (6.8 g) were then added, and the mixture was stirred and heated at approximately 190 °C for about 3 hours. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 35 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.2 g (15% yield) of compound 36. The molecular weight of compound 36, measured by FAB-MS, was 857.

[0394] (7) Synthesis of compound 51 The polycyclic compound 51 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 7.

[0395] Reaction Scheme 7

[0396] Synthesis of intermediate 51A Under an argon atmosphere, intermediate 1H (5 g), intermediate 21C (3.1 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.15 g), (±)-BINAP (0.32 g), sodium tert-butoxide (NaOtBu, 1.9 g), and toluene (80 mL) were added to a 200 mL three-necked flask and stirred and heated at approximately 100 °C for approximately 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4.8 g (86% yield) of intermediate 51A. The mass number of intermediate 51A, as measured by FAB-MS, was 431.

[0397] Synthesis of intermediate 51C Under an argon atmosphere, bromobenzene (51B) (15 g), intermediate 1I (26 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.54 g), tri-tert-butylphosphine tetrafluoroborate (0.55 g), sodium tert-butoxide (NaOtBu, 13 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and stirred and heated at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 27.6 g (90% yield) of intermediate 51C. The mass number of intermediate 51C, measured by FAB-MS, was 321.

[0398] Synthesis of intermediate 51D Under an argon atmosphere, intermediates 51C (27.6 g), 1K (75 g), CuI (16.3 g), and K₂CO₃ (36 g) were added to a 500 mL three-necked flask and heated and stirred at approximately 230 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 14.6 g (32% yield) of intermediate 51D was obtained. The mass number of intermediate 51D, measured by FAB-MS, was 533.

[0399] Synthesis of intermediate 51E Under an argon atmosphere, intermediates 51D (5 g), 51A (4.8 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.054 g), tri-tert-butylphosphine tetrafluoroborate (0.055 g), sodium tert-butoxide (NaOtBu, 1.3 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7 g (85% yield) of intermediate 51E. The mass number of intermediate 51E, measured by FAB-MS, was 882.

[0400] Synthesis of Compound 51 Under an argon atmosphere, intermediate 51E (7 g) was dissolved in o-dichlorobenzene (ODCB, 200 mL) in a 500 mL three-necked flask and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 18.6 g) and pyridine (5.6 g) were then added, and the mixture was stirred and heated at approximately 190 °C for about 3 hours. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.3 g (18% yield) of compound 51. The molecular weight of compound 51, measured by FAB-MS, was 898.

[0401] (8) Synthesis of compound 61 The polycyclic compound 61 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 8.

[0402] Reaction Scheme 8

[0403] Synthesis of intermediate 61A Under an argon atmosphere, intermediate 1H (5 g), intermediate 31A (3.1 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.15 g), (±)-BINAP (0.32 g), sodium tert-butoxide (NaOtBu, 1.9 g), and toluene (80 mL) were added to a 200 mL three-necked flask and stirred and heated at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4.5 g (82% yield) of intermediate 61A. The mass number of intermediate 61A, measured by FAB-MS, was 431.

[0404] Synthesis of intermediate 61B Under an argon atmosphere, intermediates 61A (4.5 g), 51D (4.6 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.05 g), tri-tert-butylphosphine tetrafluoroborate (0.05 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 200 mL three-necked flask and stirred and heated at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 5.9 g (78% yield) of intermediate 61B. The mass number of intermediate 61B, measured by FAB-MS, was 882.

[0405] Synthesis of Compound 61 Under an argon atmosphere, intermediate 61B (5.9 g) was added to a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL). The mixture was cooled to approximately 0 °C in an ice bath, and boron triiodide (BI3, 15.7 g) and pyridine (4.8 g) were added. The mixture was stirred and heated at approximately 190 °C for about 3 hours. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 25 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 0.9 g (15% yield) of compound 61. The molecular weight of compound 61, measured by FAB-MS, was 898.

[0406] (9) Synthesis of compound 69 The polycyclic compound 69 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 9.

[0407] Reaction scheme 9

[0408] Synthesis of intermediate 69B Under an argon atmosphere, intermediate 69A (50 g), intermediate 3C (12.9 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 2.6 g), tri-tert-butylphosphine tetrafluoroborate (2.6 g), sodium tert-butoxide (NaOtBu, 15 g), and toluene (400 mL) were added to a 1 L three-necked flask and heated and stirred at approximately 80 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was dried completely over anhydrous MgSO4 in a single pass, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 22.2 g (70% yield) of intermediate 69B. The mass number of intermediate 69B, measured by FAB-MS, was 417.

[0409] Synthesis of intermediate 69D Under an argon atmosphere, intermediates 69B (22.2 g), 69C (9.5 g), CuBr (0.76 g), 1,2,3,4-tetrahydro-8-quinolinol (0.71 g), Cs₂CO₃ (26 g), and dimethylformamide (200 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 130 °C for approximately 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was dried completely over anhydrous MgSO₄ in a single pass, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 22.3 g (82% yield) of intermediate 69D. The mass number of intermediate 69D, measured by FAB-MS, was 515.

[0410] Synthesis of intermediate 69F Under an argon atmosphere, intermediates 69D (22.3 g), 69E (14 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.50 g), tri-tert-butylphosphine tetrafluoroborate (0.50 g), sodium tert-butoxide (NaOtBu, 6.2 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 110 °C for approximately 12 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was dried over anhydrous MgSO4 in a single pass, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 12 g (35% yield) of intermediate 69F. The mass number of intermediate 69F, measured by FAB-MS, was 800.

[0411] Synthesis of intermediate 69H Under an argon atmosphere, intermediate 69F (12 g), phenylboronic acid (69G) (3.8 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride (PdCl2(Amphos)2, 0.11 g), K2CO3 (4.1 g), and toluene / ethanol / H2O (100 / 40 / 20 mL) were added to a 200 mL three-necked flask and stirred and heated at approximately 80 °C for approximately 24 hours. After returning to room temperature, water was added, the product was extracted with toluene, and the organic layer was dried completely over anhydrous MgSO4 in a single pass, followed by distillation off the solvent under reduced pressure. Purification was performed by silica gel column chromatography, yielding 10.5 g (83% yield) of intermediate 69H. The mass number of intermediate 69H, measured by FAB-MS, was 842.

[0412] Synthesis of Compound 69 Under an argon atmosphere, intermediate 69H (10.5 g) was added to a 1 L three-necked flask and dissolved in o-dichlorobenzene (ODCB, 300 mL). The mixture was cooled to approximately 0 °C in an ice bath, and boron triiodide (BI3, 29 g) and pyridine (8.8 g) were added. The mixture was stirred and heated at approximately 190 °C for approximately 3 hours, and then cooled to approximately 0 °C in an ice bath. N,N-diisopropylethylamine (DIPEA, 45 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.3 g (12% yield) of compound 69. The molecular weight of compound 69, as measured by FAB-MS, was 858.

[0413] (10) Synthesis of compound 71 The polycyclic compound 71 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 10.

[0414] Reaction Scheme 10

[0415] Synthesis of intermediate 71A Under an argon atmosphere, intermediates 3B (10 g), 21D (17.4 g), palladium(II) acetate (Pd(OAc)2, 0.23 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthanium (Xantphos, 0.61 g), sodium tert-butoxide (NaOtBu, 5 g), and toluene (200 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 110 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 18 g (83% yield) of intermediate 71A. The mass number of intermediate 71A, measured by FAB-MS, was 614.

[0416] Synthesis of intermediate 71B Under an argon atmosphere, intermediate 71A (18 g), intermediate 1I (8.6 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.16 g), tri-tert-butylphosphine tetrafluoroborate (0.17 g), sodium tert-butoxide (NaOtBu, 4.2 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 110 °C for approximately 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 19.3 g (80% yield) of intermediate 71B. The mass number of intermediate 71B, measured by FAB-MS, was 823.

[0417] Synthesis of intermediate 71C Under an argon atmosphere, intermediates 71B (19.3 g), 51D (18.7 g), CuI (4.4 g), and K₂CO₃ (10 g) were added to a 300 mL three-necked flask and stirred and heated at approximately 230 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 6 g (20% yield) of intermediate 71C was obtained. The mass number of intermediate 71C, measured by FAB-MS, was 1275.

[0418] Synthesis of Compound 71 Under an argon atmosphere, intermediate 71C (6 g) was dissolved in o-dichlorobenzene (ODCB, 200 mL) in a 300 mL three-necked flask and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 11 g) and pyridine (3.3 g) were then added, and the mixture was stirred and heated at approximately 190 °C for about 3 hours. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 20 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1 g (yield 16%) of compound 71. The molecular weight of compound 71, measured by FAB-MS, was 1290.

[0419] (11) Synthesis of compound 86 The polycyclic compound 86 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 11.

[0420] Reaction Scheme 11

[0421] Synthesis of intermediate 86B Under an argon atmosphere, intermediate 3A (15 g), 3-phenylphenol (86A) (14.6 g), Cs₂CO₃ (47 g), and 1-methyl-2-pyrrolidone (300 mL) were added to a 1000 mL three-necked flask and stirred and heated at approximately 140 °C for about 16 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 21.6 g (84% yield) of intermediate 86B was obtained. The mass number of intermediate 86B, measured by FAB-MS, was 360.

[0422] Synthesis of intermediate 86C Under an argon atmosphere, intermediates 86B (15 g), 1E (18.5 g), palladium(II) acetate (Pd(OAc)2, 0.25 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthanium (Xantphos, 0.65 g), sodium tert-butoxide (NaOtBu, 5.1 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 110 °C for approximately 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 22.3 g (86% yield) of intermediate 86C. The mass number of intermediate 86C, measured by FAB-MS, was 690.

[0423] Synthesis of intermediate 86D Under an argon atmosphere, intermediate 86C (22.3 g), intermediate 1I (8.7 g), bis(dibenzylacetone)palladium(0) (Pd(dba)2, 0.19 g), tri-tert-butylphosphine tetrafluoroborate (0.19 g), sodium tert-butoxide (NaOtBu, 4.3 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 110 °C for approximately 12 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was collected, dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography was performed to obtain 24.4 g (84% yield) of intermediate 86D. The mass number of intermediate 86D, measured by FAB-MS, was 899.

[0424] Synthesis of intermediate 86E Under an argon atmosphere, intermediates 86D (24.4 g), 51D (21.7 g), CuI (5.2 g), and K₂CO₃ (11 g) were added to a 300 mL three-necked flask and heated and stirred at approximately 230 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was collected, dried over anhydrous MgSO₄, and the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography was performed to obtain 6.6 g (yield 18%) of intermediate 86E. The mass number of intermediate 86E, measured by FAB-MS, was 1351.

[0425] Synthesis of Compound 86 Under an argon atmosphere, intermediate 86E (6.6 g) was added to a 300 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL). The mixture was cooled to approximately 0 °C in an ice bath, and boron triiodide (BI3, 11.5 g) and pyridine (3.5 g) were added. The mixture was heated at approximately 190 °C for approximately 3 hours with stirring. The reaction solution was then cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 20 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1.1 g (17% yield) of compound 86. The molecular weight of compound 86, measured by FAB-MS, was 1366.

[0426] (12) Synthesis of compound 113 The polycyclic compound 113 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 12.

[0427] Reaction Scheme 12

[0428] Synthesis of intermediate 113B Under an argon atmosphere, intermediate 113A (25 g), intermediate 3C (6.4 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 1.3 g), tri-tert-butylphosphine tetrafluoroborate (1.3 g), sodium tert-butoxide (NaOtBu, 7.3 g), and toluene (150 mL) were added to a 500 mL three-necked flask and stirred and heated at approximately 80 °C for approximately 8 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was dried completely over anhydrous MgSO4 in a single pass, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.9 g (50% yield) of intermediate 113B. The mass number of intermediate 113B, measured by FAB-MS, was 417.

[0429] Synthesis of intermediate 113D Under an argon atmosphere, intermediates 113B (7.9 g), 113C (2.4 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.22 g), (±)-BINAP (0.47 g), sodium tert-butoxide (NaOtBu, 2.7 g), and toluene (80 mL) were added to a 200 mL three-necked flask and stirred and heated at approximately 110 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was dried over anhydrous MgSO4 in one pass, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.1 g (87% yield) of intermediate 113D. The mass number of intermediate 113D, measured by FAB-MS, was 412.

[0430] Synthesis of intermediate 113E Under an argon atmosphere, intermediate 1K (10 g), intermediate 3C (5.8 g), palladium(II) acetate (Pd(OAc)2, 0.23 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthanium (Xantphos, 0.59 g), sodium tert-butoxide (NaOtBu, 5 g), and toluene (130 mL) were added to a 300 mL three-necked flask and heated and stirred at approximately 110 °C for about 24 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was dried over anhydrous MgSO4 in a single pass, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 9.4 g (72% yield) of intermediate 113E. The mass number of intermediate 113E, measured by FAB-MS, was 380.

[0431] Synthesis of intermediate 113F Under an argon atmosphere, intermediates 113D (7 g), 113E (6.2 g), bis(dibenzylacetone)palladium(O) (Pd(dba)2, 0.19 g), tri-tert-butylphosphine tetrafluoroborate (0.19 g), sodium tert-butoxide (NaOtBu, 2.4 g), and toluene (100 mL) were added to a 300 mL three-necked flask and stirred and heated at approximately 100 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with toluene. The organic layer was dried over anhydrous MgSO4 in a single pass, and the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography was performed to obtain 9.6 g (81% yield) of intermediate 113F. The mass number of intermediate 113F, measured by FAB-MS, was 729.

[0432] Synthesis of Compound 113 Under an argon atmosphere, intermediate 113F (9.6 g) was added to a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 250 mL). The mixture was cooled to approximately 0 °C in an ice bath, and boron triiodide (BI3, 31 g) and pyridine (9.4 g) were added. The mixture was heated and stirred at approximately 190 °C for about 3 hours. The reaction solution was cooled to approximately 0 °C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 45 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 1 g (10% yield) of compound 113. The molecular weight of compound 113, as measured by FAB-MS, was 745.

[0433] (13) Synthesis of compound 126 The polycyclic compound 126 according to one or more embodiments can be synthesized according to, for example, the steps of reaction scheme 13.

[0434] Reaction Scheme 13

[0435] Synthesis of intermediate 126B Under an argon atmosphere, intermediate 1K (60 g), intermediate 126A (32 g), potassium tert-butoxide (KOtBu, 35 g), and dimethyl sulfoxide (DMSO) were added to a 500 mL three-necked flask and stirred and heated at approximately 80 °C for about 6 hours. After returning to room temperature, water was added, and the product was extracted with CH2Cl2. The organic layer was dried completely over anhydrous MgSO4 in a single pass, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 25.8 g (68% yield) of intermediate 126B was obtained. The mass number of intermediate 126B, measured by FAB-MS, was 368.

[0436] Synthesis of intermediate 126C Under an argon atmosphere, intermediates 126B (25.8 g), 86D (30 g), CuI (6.4 g), and K₂CO₃ (14 g) were added to a 300 mL three-necked flask and heated and stirred at approximately 230 °C for about 32 hours. After returning to room temperature, water was added, and the product was extracted with CH₂Cl₂. The organic layer was dried completely over anhydrous MgSO₄ in a single pass, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography, 8.3 g (yield 21%) of intermediate 126C was obtained. The mass number of intermediate 126C, measured by FAB-MS, was 1186.

[0437] Synthesis of Compound 126 Under an argon atmosphere, intermediate 126C (8.3 g) was dissolved in o-dichlorobenzene (ODCB, 200 mL) in a 500 mL three-necked flask and cooled to approximately 0 °C in an ice bath. Boron triiodide (BI3, 16.4 g) and pyridine (5 g) were added, and the mixture was heated and stirred at approximately 190 °C for about 3 hours, then cooled to approximately 0 °C in an ice bath. N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 0.78 g (9% yield) of compound 126. The molecular weight of compound 126, as measured by FAB-MS, was 1202.

[0438] 2. Manufacturing and evaluation of light-emitting elements (1) Manufacturing of light-emitting elements The light-emitting elements comprising the polycyclic compounds of the embodiments or the comparative compounds in the light-emitting layer are each manufactured by the methods provided herein. The polycyclic compounds of the embodiments are used as dopant materials for the light-emitting layer to manufacture light-emitting elements of Examples 1 to 13. Comparative Examples 1 to 9 are manufactured using comparative compounds X-1 to X-9 as dopant materials for the light-emitting layer.

[0439] The glass substrate, with ITO patterned to a thickness of approximately 150 nm as the first electrode, was ultrasonically cleaned with isopropanol and then with pure water for approximately 5 minutes each. After ultrasonic cleaning, UV irradiation was performed for approximately 30 minutes, followed by ozone treatment. Subsequently, HAT-CN was sequentially deposited to a thickness of approximately 10 nm, α-NPD was deposited to a thickness of approximately 80 nm, and mCP was deposited to a thickness of approximately 5 nm to form the hole transport region.

[0440] The example or comparative compound is then co-deposited with mCBP to form an emissive layer with a thickness of approximately 20 nm. The example or comparative compound and mCBP are co-deposited at a weight ratio of approximately 1:99. In the fabrication of the light-emitting element, the example or comparative compound is used as a dopant material.

[0441] Subsequently, TPBi was sequentially deposited to a thickness of approximately 30 nm and LiF was deposited to a thickness of approximately 0.5 nm to form an electron transport region.

[0442] Then, Al is deposited to a thickness of about 100 nm to form the second electrode.

[0443] In this embodiment, the hole transport region, the light-emitting layer, the electron transport region, and the second electrode are each formed using a vacuum deposition apparatus.

[0444] The compounds used in the corresponding luminescent layers of Examples 1 to 13 and Comparative Examples 1 to 9 are shown in Table 1.

[0445] Table 1

[0446] In addition, other compounds used in the manufacture of light-emitting elements are as follows.

[0447] Materials used in the manufacture of light-emitting elements

[0448] (2) Evaluation of light-emitting elements Table 2 shows the evaluation results of the light-emitting elements of Examples 1 to 13 and Comparative Examples 1 to 9. Table 2 also shows the relative element lifetime (LT50) and maximum external quantum yield (EQE) for each of the light-emitting elements of Examples 1 to 13 and Comparative Examples 1 to 9. max ) and fluorescence lifetime (τ).

[0449] Relative component lifetime (LT50) is expressed as half-life, which is approximately 900 cd / m² when continuously driven. 2 The time taken for the initial brightness to degrade to approximately 50% of its original value was compared, with the value for Comparison Example 9 set to 1.0. Voltage and current density in each organic electroluminescent device were measured using a source meter (Keithley Instrument, 2400 series), and brightness and external quantum efficiency were measured using an external quantum efficiency measurement device C9920-12 from Hamamatsu Photonics. Fluorescence lifetime was measured using a fluorescence lifetime measurement device from Hamamatsu Photonics.

[0450] Table 2

[0451] Referring to the results in Table 2, compared with the light-emitting elements of Comparative Examples 1 to 9, the light-emitting elements of Examples 1 to 13 each exhibit increased relative element lifetime characteristics and higher maximum external quantum yield (EQE). maxFurthermore, compared to the light-emitting elements of Comparative Examples 1 to 9, the light-emitting elements of Examples 1 to 13 each exhibit shorter fluorescence lifetime characteristics. For example, it can be confirmed that, compared to the light-emitting elements of Comparative Examples 1 to 9, the light-emitting elements of Examples 1 to 13 each exhibit longer element lifetime and higher efficiency characteristics. In the case of the comparative compounds used in Comparative Examples 1 to 5, the difference lies in that although the comparative compounds have a framework including the heteroboron core structure in the examples, a carbon in the heteroboron core framework is not converted to nitrogen, or a pyridyl group is not substituted for an amino group in the heteroboron framework. Therefore, Comparative Examples 1 to 5 show that both element lifetime and luminous efficiency are reduced (e.g., simultaneously) compared to Examples 1 to 13.

[0452] Compared to the example compounds, the difference in the comparative compounds used in Comparative Examples 6 to 8 lies in the position and / or total number of oxaboron skeletons fused to the heteroboron core structure. The difference in the comparative compounds used in Comparative Examples 7 and 8 lies in the additional fusion of two dioxaboron skeletons onto the heteroboron core structure skeleton included in the comparative compounds. Compared to Examples 1 to 13, Comparative Examples 6 to 8 exhibit significantly reduced device lifetime characteristics. Without being bound by any theory, it is believed that the reduced device lifetime characteristics of Comparative Examples 6 to 8 are because the comparative compounds X-6 to X-8 used in Comparative Examples 6 to 8, respectively, have relatively larger acceptor characteristics compared to the example compounds, thereby accelerating electron capture in the comparative example devices.

[0453] The difference between the comparative compound X-9 used in Comparative Example 9 and the comparative compound X-9 is that it has a modified DABNA core structure, which differs from the heteroboron core structure included in the example compounds. Without being bound by any theory, it is considered that the light-emitting element of Comparative Example 9 exhibits reduced element lifetime characteristics because the fluorescence lifetime of the light-emitting element is extended due to the properties of the comparative compound X-9, which has a different core structure.

[0454] One or more embodiments of the polycyclic compound include a boron-containing fused ring core comprising two boron atoms, a structure in which a carbon in the fused ring core backbone is converted to nitrogen, or a structure in which a pyridyl group replaces an amino group forming the boron-containing fused ring core backbone. One or more embodiments of the polycyclic compound may have a fused ring core structure comprising nitrogen as a cyclizing atom or comprising an amino group substituted with a pyridyl group as a core backbone, and may have a short fluorescence lifetime due to increased absorbance. Therefore, one or more embodiments of the polycyclic compound may exhibit improved lifetime characteristics and excellent or suitable luminous efficiency characteristics. Furthermore, one or more embodiments of the polycyclic compound may be used as a thermally activated delayed fluorescence material. One or more embodiments of the luminescent element comprising one or more embodiments of the polycyclic compound in the luminescent layer may exhibit excellent or suitable emission efficiency characteristics in the blue light emission range and may exhibit long lifetime characteristics.

[0455] Electronic devices comprising light-emitting elements of polycyclic compounds including one or more embodiments may exhibit excellent or suitable reliability characteristics due to the long lifespan of the light-emitting element. Furthermore, electronic devices comprising one or more embodiments of light-emitting elements of polycyclic compounds having improved emission efficiency may exhibit improved characteristics in terms of brightness and display quality.

[0456] One or more embodiments of the light-emitting element can exhibit high efficiency and long lifetime characteristics by including one or more polycyclic compounds of the same embodiment in the light-emitting layer.

[0457] One or more embodiments of the polycyclic compound can help improve the luminous efficiency and lifespan of light-emitting elements.

[0458] The electronic devices of one or more embodiments may exhibit excellent or suitable display quality and improved reliability properties.

[0459] The foregoing descriptions and examples should collectively demonstrate that the disclosed polycyclic compounds, when incorporated as dopants into the luminescent layer, can thermally activate delayed fluorescence in the blue emission range with short fluorescence lifetimes (≤3.0 μs) and high external quantum efficiency. The examples should further confirm that structural changes (such as heteroatom substitution, pyridyl incorporation, and optional deuteration) contribute to improved material stability and device lifetime. Combined with the host and sensitizer systems described herein, these compounds provide balanced charge transport and efficient energy transfer, resulting in enhanced brightness and extended operating lifetime for luminescent elements and electronic devices.

[0460] In this disclosure, expressions such as “at least one of…”, “one of…”, and “selected from…” modify the entire list of elements when placed before / after the list of elements, but do not modify individual elements in that list. For example, “at least one of a, b, and c”, “selected from a, b, and c”, and / or “selected from a to c” can indicate only a, only b, only c, both a and b (e.g., both a and b at the same time), both a and c (e.g., both a and c at the same time), both b and c (e.g., both b and c at the same time), all a, b, and c, or variations thereof. The “ / ” used herein may be interpreted as “and” or “or” depending on the context.

[0461] As used herein, the terms “approximately,” “about,” or similar terms are used as approximations rather than terms of degree and are intended to account for inherent biases in measured or calculated values ​​as would be recognized by a person skilled in the art. Taking into account the measurements discussed and the errors associated with the measurement of a particular quantity (i.e., limitations of the measurement system), as used herein, “about” includes the stated value and means within an acceptable range of deviation from the stated value as determined by a person skilled in the art. For example, “about” may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value. Furthermore, it should be understood that even if the terms “about,” “approximately,” or “approximately” are not explicitly stated in a given element (e.g., a claim element), the scope of such an element is intended to include non-substantial variations or variations as understood by a person skilled in the art. For example, the numerical values ​​and ranges provided herein are intended to include tolerances and measurement uncertainties as would be recognized by a person skilled in the art, and elements (e.g., claim elements) should be interpreted accordingly to cover such equivalents.

[0462] In the context of this application and unless otherwise defined, the term “use” may be considered synonymous with the term “utilize”.

[0463] Any numerical range described herein is intended to include all subranges with the same numerical precision contained within the described range. For example, the range “1.0 to 10.0” is intended to include all subranges between (and including) the described minimum value of 1.0 and the described maximum value of 10.0, i.e., 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 incorporated herein, and any minimum numerical limit described herein is intended to include all higher numerical limits incorporated herein. Therefore, the applicant reserves the right to modify this disclosure, including the claims, to expressly describe any subranges falling within the expressly described range herein.

[0464] The light-emitting elements, display modules, display devices, electronic devices, means for manufacturing light-emitting elements, or any other related devices / devices or components according to embodiments of the present disclosure described herein can be implemented using any suitable hardware, firmware (e.g., application-specific integrated circuits), software, or a combination of software, firmware, and hardware. For example, various components of the device can be formed on an integrated circuit (IC) chip or on a separate IC chip. Furthermore, various components of the device can be implemented on a flexible printed circuit film, a tape-on-a-chip (TCP), a printed circuit board (PCB), or formed on a substrate. Additionally, various components of the device can be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact with other system components for performing the various functions described herein. The computer program instructions are stored in memory, which can be implemented in a computing device using standard memory devices, such as random access memory (RAM). The computer program instructions can also be stored on other non-transitory computer-readable media, such as, for example, a CD-ROM or a flash drive. Furthermore, those skilled in the art should recognize that, without departing from the scope of the embodiments of this 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 across one or more other computing devices.

[0465] In this disclosure, each suitable feature of the various embodiments of the disclosure may be combined in part or in whole or in combination with one another, and may be technically interlocked and operated in a variety of suitable ways, and unless otherwise stated or implied, each embodiment may be implemented independently or in combination with one another in any suitable manner.

[0466] In the foregoing, one or more embodiments of the present disclosure have been described with reference to them. However, those skilled in the art or those of ordinary skill in the art will understand that one or more suitable modifications and changes may be made to the present disclosure without departing from the spirit and technical scope of the present disclosure as set forth in the appended claims.

[0467] Therefore, the technical scope of this disclosure is not limited to what is set forth in the detailed description herein, but should be determined by the claims and their equivalents.

Claims

1. A light-emitting element, wherein, The light-emitting element includes: First electrode; A second electrode, on top of the first electrode; and A light-emitting layer, located between the first electrode and the second electrode, comprises a first compound represented by Formula 1: Formula 1 In Equation 1, X1 to X4 are each independently O, S, or Se, or can be represented by Equation 2. Y1 to Y 16 Each is CR independently a Or N, and R a It is hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms. Formula 2 In Equation 2, Y 17 To Y 21 Each is CR independently b Or N, and R b It is hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms. When none of X1 to X4 in Equation 1 is represented by Equation 2, then Y1 to Y4 selected from Equation 1... 16 At least one of them is N, and When at least one of X1 to X4 selected from Equation 1 is represented by Equation 2, Y1 to Y4 selected from Equation 1 16 Y of formula 2 17 To Y 21 At least one of them is N.

2. The light-emitting element according to claim 1, wherein, The luminescent layer further includes at least one of a second compound represented by formula HT-1 and a third compound represented by formula ET-1: HT-1 In formula HT-1, A1 through A8 are each independently either N or CR. 51 , L1 is a directly attached, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. Y a It is a direct connection, CR 52 R 53 or SiR 54 R 55 , Ar1 is an aryl group with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group with 2 to 30 cyclic carbon atoms, and R 51 To R 55 Each of the following groups is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 60 cyclic carbon atoms, and / or combined with adjacent groups to form a ring. ET-1 ,and In Equation ET-1, At least one of X1 to X3 is N, and the rest are CR. 56 , R 56 It is hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms. b1 to b3 are each an independent integer from 0 to 10. Ar2 to Ar4 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and L2 to L4 are each independently an arylene group with 6 to 30 cyclic carbon atoms directly attached, substituted or unsubstituted, or a heteroarylene group with 2 to 30 cyclic carbon atoms attached, substituted or unsubstituted.

3. The light-emitting element according to claim 2, wherein, The light-emitting layer also includes a fourth compound represented by formula D-1: Formula D-1 ,and In equation D-1, Q1 through Q4 are each independently either C or N. Each of the C1 to C4 atoms is independently a hydrocarbon ring with 5 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heterocycle with 2 to 30 cyclic carbon atoms, either substituted or unsubstituted. L 11 To L 13 Each is directly connected independently. , , , , a substituted or unsubstituted alkylene group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 cyclic carbon atoms, wherein, "Refers to the position to be connected." b11 to b13 are each independently 0 or 1. R 61 To R 66 Each of these elements is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 60 cyclic carbon atoms. d1 to d4 are each an independent integer from 0 to 4.

4. The light-emitting element according to claim 1, wherein, The fluorescence lifetime of the first compound is 3.0 μs or less.

5. The light-emitting element according to claim 1, wherein, The luminescent layer emits delayed fluorescence.

6. The light-emitting element according to claim 1, wherein, The light-emitting layer emits blue light.

7. The light-emitting element according to claim 1, wherein, From Equation 1, one selected from Y1 to Y4, one selected from Y6 to Y8, and one selected from Y... 13 To Y 16 One of them, and one of them chosen from Y5, is N, and the rest are each independently CR. a , In Equation 1, X1 to X4 are each independently O, S, or Se, or can be represented by Equation 2-1: Equation 2-1 In Equation 2-1, R b1 To R b5 Each of the following is independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

8. The light-emitting element according to claim 1, wherein, From Y1 to Y 16 Each is CR independently a In the first compound of formula 1, At least one of X1 to X4 selected from Equation 1 is represented by Equation 2, and Y selected from Equation 2 17 To Y 21 One of them is N, and the others are each independently CR. b .

9. The light-emitting element according to claim 1, wherein, At least one hydrogen atom in the first compound is replaced by deuterium.

10. The light-emitting element according to claim 1, wherein, The first compound includes at least one compound selected from group 1: Compound group 1 In compound group 1, D is deuterium.

11. A polycyclic compound, represented by Formula 1: Formula 1 in, In Equation 1, X1 to X4 are each independently O, S, or Se, or can be represented by Equation 2. Y1 to Y 16 Each is CR independently a Or N, and R a It is hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms: Formula 2 ,and In Equation 2, Y 17 To Y 21 Each is CR independently b Or N, and R b It is hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms. When none of X1 to X4 in Equation 1 is represented by Equation 2, then Y1 to Y4 selected from Equation 1... 16 At least one of them is N, and When at least one of X1 to X4 selected from Equation 1 is represented by Equation 2, Y1 to Y4 selected from Equation 1 16 Y of formula 2 17 To Y 21 At least one of them is N.

12. The polycyclic compound according to claim 11, wherein, Equation 2 is represented by Equation 2-1, or in Equation 2, the terms are selected from Y. 17 To Y 21 One of them is N, and the others are each independently CR. b : Equation 2-1 In Equation 2-1, R b1 To R b5 Each of the following is independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

13. The polycyclic compound according to claim 11, wherein... From Equation 1, one selected from Y1 to Y4, one selected from Y6 to Y8, and one selected from Y... 13 To Y 16 One of them, and one of them chosen from Y5, is N, and the rest are each independently CR. a , In Equation 1, X1 to X4 are each independently O, S, or Se, or can be represented by Equation 2-1: Equation 2-1 In Equation 2-1, R b1 To R b5 Each of the following is independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

14. The polycyclic compound according to claim 11, wherein, When Y1 to Y in equation 1 16 Each is CR independently a When, at least one of X1 to X4 is represented by Equation 2, and In Equation 2, Y is selected 17 To Y 21 One of them is N, and the others are each independently CR. b .

15. The polycyclic compound according to claim 11, wherein, At least one hydrogen atom in Formulas 1 and 2 is replaced by deuterium.

16. The polycyclic compound according to claim 11, wherein, The polycyclic compound is a blue emission dopant.

17. The polycyclic compound according to claim 11, wherein, The polycyclic compound is a thermally activated delayed fluorescence material.

18. The polycyclic compound according to claim 11, wherein, The polycyclic compound is selected from any of the compounds in compound group 1: Compound group 1 In compound group 1, D is deuterium.

19. An electronic device, wherein, The electronic device includes a display module comprising multiple light-emitting elements, wherein, At least one of the plurality of light-emitting elements includes a first electrode, a second electrode on the first electrode, and a light-emitting layer between the first electrode and the second electrode, comprising a polycyclic compound represented by Formula 1: Formula 1 In Equation 1, X1 to X4 are each independently O, S, or Se, or can be represented by Equation 2. Y1 to Y 16 Each is CR independently a Or N, and R a It is hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms: Formula 2 ,and In Equation 2, Y 17 To Y 21 Each is CR independently b Or N, and R b It is hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms. When none of X1 to X4 in Equation 1 is represented by Equation 2, then Y1 to Y4 selected from Equation 1... 16 At least one of them is N, and When at least one of X1 to X4 selected from Equation 1 is represented by Equation 2, then Y1 to Y4 selected from Equation 1 16 Y of formula 2 17 To Y 21 At least one of them is N.

20. The electronic device according to claim 19, wherein, The electronic device further includes at least one selected from processor, memory, and power module.

Images