Fused polycyclic compound and light-emitting element including same

Abstract

The invention relates to a fused polycyclic compound and a light-emitting element including the same. There is provided a light emitting element including a first electrode, a second electrode facing the first electrode, and at least one functional layer provided between the first electrode and the second electrode. The at least one functional layer includes a fused polycyclic compound represented by Formula 1, which may be used as a dopant material. The fused ring core includes three aromatic rings attached to three heteroatoms, and includes a first linker attached to at least two substituents, such as a first substituent and a second substituent. Formula 1 # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0101265 filed in the Korean Intellectual Property Office on August 2, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure herein relates to fused polycyclic compounds and light-emitting elements including the same. Background Art

[0004] Recently, development of organic electroluminescent display devices as image display devices is being actively carried out. Unlike liquid crystal display devices and the like, organic electroluminescent display devices are so-called "self-luminous" display devices in which holes and electrons injected from the first electrode and the second electrode, respectively, are recombined in the emission layer of the display device. Subsequently, the light-emitting material including an organic compound in the emission layer (e.g., light-emitting layer) emits light to implement display (e.g., image display).

[0005] Implementing an organic electroluminescent element as a display device requires (or there is a need or expectation) an organic electroluminescent element with a relatively low driving voltage, a relatively high luminous efficiency and a relatively long service life. Therefore, there is a need or expectation to focus on the continuous research and development of materials for organic electroluminescent elements that can stably obtain such (e.g., desired) characteristics.

[0006] In recent years, in particular, in order to implement high-efficiency organic electroluminescent elements, technologies focusing on phosphorescence emission (e.g., using triplet energy levels) and / or delayed fluorescence emission (e.g., using triplet-triplet annihilation (TTA), in which singlet excitons are generated by collision of triplet excitons) are being developed. In addition, technologies focusing on thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon are being developed or pursued. Summary of the invention

[0007] One or more aspects of embodiments of the present disclosure provide a light emitting element in which light emitting efficiency and lifetime are improved.

[0008] One or more aspects of the embodiments of the present disclosure also provide a condensed polycyclic compound capable of improving the luminous efficiency and lifetime of a light-emitting element.

[0009] One or more aspects of embodiments of the present disclosure also provide a display device including a light emitting element in which light emitting efficiency and lifetime are improved, thereby having excellent or appropriate display quality.

[0010] One or more embodiments of the present disclosure provide a light-emitting element including a first electrode, a second electrode provided on the first electrode, and at least one functional layer, wherein the at least one functional layer is provided between the first electrode and the second electrode and includes a first compound, wherein the first compound is a fused polycyclic compound represented by Formula 1.

[0011] Formula 1

[0012]

[0013] In formula 1, R a1 To R a11 and R 1 To R 5 may be each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, selected from R 1 To R 5 At least one of them is cyano, and at least another one (e.g., selected from R 1 To R 5 The remaining one of the above) is a substituent represented by Formula 2, and Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0014] Formula 2

[0015]

[0016] In formula 2, X 1 and X 2 Each of them can be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, n1 and n2 can be independently an integer selected from 0 to 4, and *- is a position connected to Formula 1.

[0017] In one or more embodiments, at least one functional layer may include an emission layer, a hole transport region provided between the first electrode and the emission layer, and an electron transport region provided between the emission layer and the second electrode, and the emission layer may include a first compound. The first compound is a fused polycyclic compound represented by Formula 1.

[0018] In one or more embodiments, the emission layer may emit (eg, be configured to emit) delayed fluorescence having a light emission center wavelength in a wavelength region of about 430 nanometers (nm) to about 490 nm.

[0019] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:

[0020] Formula 1-1

[0021]

[0022] Formula 1-2

[0023]

[0024] In formula 1-1 and formula 1-2, R c1 To R c6 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, m1, m3, m4 and m6 may each independently be an integer selected from 0 to 5, m2 and m5 may each independently be an integer selected from 0 to 3, and R a1 To R a11 and R 1 To R 5 may be independently defined as in Formula 1.

[0025] In one or more embodiments, R c1 To R c6 They may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0026] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-3.

[0027] Formula 1-3

[0028]

[0029] In formula 1-3, R 6 To R 10 may be each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, selected from R 6 To R 10 At least one of them may be a cyano group, and at least another one (e.g., selected from R 6 To R 10 The remaining one of the above) may be a substituent represented by Formula 2, and R a1 To R a11 and R1 To R 5 may be independently defined as in Formula 1.

[0030] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from Formula 1-4 to Formula 1-6.

[0031] Formula 1-4

[0032]

[0033] Formula 1-5

[0034]

[0035] Formula 1-6

[0036]

[0037] In Formula 1-4 to Formula 1-6, X 11 To X 16 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, x1 to x6 may each independently be an integer selected from 0 to 4, and R a1 To R a11 and Ar may each independently be as defined in Formula 1.

[0038] In one or more embodiments, X 11 To X 16 They may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0039] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from Formula 1-7 to Formula 1-9.

[0040] Formula 1-7

[0041]

[0042] Formula 1-8

[0043]

[0044] Formula 1-9

[0045]

[0046] In Formula 1-7 to Formula 1-9, Y 1 To Y3 may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, k1 may be an integer selected from 0 to 5, k2 and k3 may each independently be an integer selected from 0 to 4, and R a1 To R a8 , R 1 To R 5 and Ar may each independently be as defined in Formula 1.

[0047] In one or more embodiments, in Formula 1, R a2 , R a3 , R a6 and R a7 Each may independently be a hydrogen atom, a deuterium atom or a substituent represented by any one selected from Formula 3-1 to Formula 3-7.

[0048] Formula 3-1

[0049]

[0050] Formula 3-2

[0051]

[0052] Formula 3-3

[0053]

[0054] Formula 3-4

[0055]

[0056] Formula 3-5

[0057]

[0058] Formula 3-6

[0059]

[0060] Formula 3-7

[0061]

[0062] In Formula 3-1 to Formula 3-7, *- may be a position connected to Formula 1.

[0063] In one or more embodiments of the present disclosure, the fused polycyclic compound may be represented by Formula 1.

[0064] In one or more embodiments of the present disclosure, the display device may include a substrate layer, a circuit layer provided on the substrate layer, and a display device layer provided on the circuit layer and including a light-emitting element. In one or more embodiments, the light-emitting element may include a first electrode, a second electrode provided on the first electrode, and an emission layer provided between the first electrode and the second electrode and including a first compound according to one or more embodiments described herein. BRIEF DESCRIPTION OF THE DRAWINGS

[0065] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of this specification. The drawings illustrate example embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure. In the drawings:

[0066] Figure 1 is a plan view of a display device according to one or more embodiments of the present disclosure;

[0067] Figure 2 is a cross-sectional view of a display device according to an embodiment of the present disclosure;

[0068] Figure 3 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0069] Figure 4 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0070] Figure 5 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0071] Figure 6 A cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0072] Figure 7 and Figure 8 Each is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;

[0073] Fig. 9 A cross-sectional view for explaining a display device according to one or more embodiments of the present disclosure;

[0074] Fig.10 A cross-sectional view for explaining a display device according to one or more embodiments of the present disclosure; and

[0075] Fig.11 A view for explaining a vehicle in which a display device is provided according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0076] The present disclosure may be modified in one or more suitable ways and have a variety of forms, and therefore specific embodiments will be illustrated in the accompanying drawings and described in more detail in the detailed description of the present disclosure. However, it should be understood that it is not intended to limit the present disclosure to the specific form disclosed, but is intended to cover all modifications, equivalents and alternatives that fall within the spirit and scope of the present disclosure.

[0077] When explaining each of the accompanying drawings, the same reference numerals are used to refer to the same elements. In the attached drawings, the size of each structure is exaggerated for clarity of the present disclosure. It will be understood that although the terms "first" and / or "second" and the like may be used herein to describe one or more appropriate components, these components should not be limited by these terms. These terms are only used to distinguish one component from another component. For example, without departing from the scope of the example embodiments of the present disclosure, a first component may be referred to as a second component, and similarly, a second component may be referred to as a first component.

[0078] As used herein, the singular forms “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0079] As used herein, the term "and / or" includes any and all combinations that the relevant configurations can define.

[0080] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.

[0081] As used herein, expressions such as “at least one of,” “one of,” “selected from,” and “selected from” when preceding / following a list of elements modify the entire list of elements and do not modify the individual elements of the list. For example, the expressions “at least one of a through c” and “at least one of a, b, and c” may indicate only a, only b, only c, both a and b (e.g., a and b simultaneously), both a and c (e.g., a and c simultaneously), both b and c (e.g., b and c simultaneously), all of a, b, and c, or variations thereof.

[0082] In the present application, it will be understood that the terms “include,” “includes,” “including,” “comprise,” “comprises,” “comprising,” “has,” “having” and / or “have” and the like specify the presence of features, numbers, steps, operations, components, parts, or a combination thereof disclosed in the specification, but do not exclude the possibility of the presence or addition of one or more other features, numbers, steps, operations, components, parts, or a combination thereof.

[0083] In the present application, when a layer, film, region or plate is referred to as being "on" another layer, film, region or plate or "in the upper part" of another layer, film, region or plate, it may not only be "directly on" the layer, film, region or plate, but also there may be intervening layers, films, regions or plates. In contrast, when a layer, film, region or plate is referred to as being "under" another layer, film, region or plate or "in the lower part" of another layer, film, region or plate, it may not only be directly under the layer, film, region or plate, but also there may be intervening layers, films, regions or plates. In some embodiments, it will be understood that when a component is referred to as being "on" another component, it may be provided above the other component, or it may also be provided below the other component. The preceding comparative terms are relative concepts and are described based on the directions indicated in the accompanying drawings. It will be understood that the terms have relative concepts and are described based on the orientations depicted in the accompanying drawings. It will be understood that spatially relative terms are intended to encompass different orientations of the device in use or operation other than the orientations depicted in the accompanying drawings. For example, if the device in the figures is turned over, elements described as "below" other elements or features would then be oriented "above" or "over" the other elements or features. Thus, the term "below" can encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations) and the spatially relative descriptors used herein interpreted accordingly.

[0084] As used herein, the term "may" will be understood to refer to "one or more embodiments of the present disclosure," some of which include the described elements, while some of which exclude the elements and / or include alternative elements. Similarly, alternative language such as "or" refers to "one or more embodiments of the present disclosure," each of which includes the corresponding enumerated items.

[0085] Unless otherwise defined, all terms used herein (including chemical, technical and scientific terms) have the same meaning as those commonly understood by those of ordinary skill in the art to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and will not be interpreted as an ideal or overly formal meaning unless expressly so defined herein.

[0086] As used herein, the phrase "consisting essentially of" means that any additional components will not substantially affect the chemical, physical, optical or electrical properties of the target moiety.

[0087] As used herein, the phrase “on a plane” or “plan view” means observing a target portion from the top, and the phrase “in cross section” means observing a cross section formed by vertically cutting the target portion from the side.

[0088] In the present disclosure, "not including one or any 'component'", "excluding one or any 'component'" and / or "free of component" etc. means that the "component" is not added, selected or used as a component in the composition / structure, but due to other impurities and / or external factors, less than an appropriate amount of the "component" may still be included.

[0089] definition

[0090] In the specification, the term "substituted or unsubstituted" may refer to being substituted or unsubstituted by at least one substituent selected from the group consisting of: deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, amido groups, silyl groups, oxy groups, sulfenyl groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. In some embodiments, each of the substituents illustrated herein may be substituted or unsubstituted. For example, biphenyl groups may be interpreted as aryl groups or phenyl groups substituted with phenyl groups.

[0091] In the specification, the phrase "bonded to an adjacent group to form a ring" may refer to a group bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. In some embodiments, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.

[0092] In the specification, the term "adjacent group" may refer to a substituent substituted for an atom directly connected to the atom substituted by the corresponding substituent, another substituent substituted for the atom substituted by the corresponding substituent, or a substituent located closest to the corresponding substituent in space. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. In some embodiments, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.

[0093] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0094] In the specification, the alkyl group may be linear or branched. The number of carbons in the alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-Dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heonicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl and / or n-triacontyl, etc., but embodiments of the present disclosure are not limited thereto.

[0095] In the specification, cycloalkyl may refer to a cyclic alkyl. The number of carbons in the cycloalkyl is 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl and / or bicycloheptyl, but embodiments of the present disclosure are not limited thereto.

[0096] In the specification, alkenyl refers to a hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of an alkyl group having two or more carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not specifically limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl and / or styrylvinyl, etc., but embodiments of the present disclosure are not limited thereto.

[0097] In the specification, alkynyl refers to a hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having two or more carbon atoms. The alkynyl group may be straight chain or branched. Although the number of carbon atoms in the alkynyl group is not specifically limited, it is 2 to 30, 2 to 20 or 2 to 10. Specific examples of the alkynyl group may include ethynyl and / or propynyl, etc., but are not limited thereto.

[0098] In the specification, the hydrocarbon ring group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.

[0099] In the specification, aryl refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl may be a monocyclic aryl or a polycyclic aryl. The number of ring carbon atoms in the aryl may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrenyl, benzofluoranthenyl and / or 1,2-triphenylenyl, etc., but embodiments of the present disclosure are not limited thereto.

[0100] In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the substituted fluorenyl group are as follows. However, the embodiments of the present disclosure are not limited thereto.

[0101]

[0102] The heterocyclic group herein refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, S and Se as a heteroatom. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

[0103] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si, S and Se as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and includes a heteroaryl group. The number of ring carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.

[0104] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, an oxirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thiol group, a tetrahydropyranyl group and / or a 1,4-dioxanyl group, etc., but embodiments of the present disclosure are not limited thereto.

[0105] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si, S and Se as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothirolyl and / or dibenzofuranyl, but embodiments of the present disclosure are not limited thereto.

[0106] In the specification, the description of an aryl group may be applied to an arylene group, except that the arylene group is a divalent group. The description of a heteroaryl group may be applied to a heteroarylene group, except that the heteroarylene group is a divalent group.

[0107] In the specification, silyl includes alkylsilyl and arylsilyl. The alkyl in the alkylsilyl may be linear, branched or cyclic. The number of carbon atoms in the alkylsilyl is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylsilyl is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of silyl may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and / or phenylsilyl, etc., but embodiments of the present disclosure are not limited thereto.

[0108] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but embodiments of the present disclosure are not limited thereto.

[0109]

[0110] In the specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 to 30. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group.

[0111] In the specification, the thio group may include an alkylthio group and an arylthio group. The thio group may refer to a sulfur atom bonded to an alkyl group or an aryl group as defined herein. The alkyl group in the alkylthio group may be linear, branched or cyclic. The number of carbon atoms in the alkylthio group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylthio group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of thio groups may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio and / or naphthylthio, etc., but embodiments of the present disclosure are not limited thereto.

[0112] In the specification, an oxy group may refer to an oxygen atom bonded to an alkyl or aryl group as defined herein. The oxy group may include an alkoxy group and an aryloxy group. The alkoxy group may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms in the alkoxy group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryloxy group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy and / or benzyloxy, etc., but embodiments of the present disclosure are not limited thereto.

[0113] The boryl group herein may refer to a boron atom bonded to an alkyl or aryl group as defined herein. Boryl groups include alkyl boryl groups and aryl boryl groups. The alkyl group in the alkyl boryl group may be linear, branched or cyclic. The number of carbon atoms in the alkyl boryl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryl boryl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of boryl groups may include dimethyl boryl, tert-butyl methyl boryl, diphenyl boryl and / or phenyl boryl, etc., but embodiments of the present disclosure are not limited thereto.

[0114] In the specification, the amine group may include an alkylamine group and an arylamine group. The alkyl group in the alkylamine group may be linear, branched or cyclic. The number of carbon atoms in the alkylamine group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylamine group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of the amine group may include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group and / or a 9-methyl-anthrylamine group, etc., but the embodiments of the present disclosure are not limited thereto.

[0115] In the specification, the phosphine oxide group may mean an alkyl group or an aryl group defined above combined with -P(=O)-. The number of carbon atoms of the phosphine oxide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine oxide group may include an alkyl phosphine oxide group and an aryl phosphine oxide group. For example, the phosphine oxide group may have the following structure, but is not limited thereto.

[0116]

[0117] In the specification, the phosphinosulfide group may mean an alkyl group or an aryl group defined above combined with -P(=S)-. The number of carbon atoms of the phosphinosulfide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphinosulfide group may include an alkylphosphinosulfide group and an arylphosphinosulfide group. For example, the phosphinosulfide group may have the following structure, but is not limited thereto.

[0118]

[0119] In the specification, the alkyl group in the alkoxy group, the alkylthio group, the alkylsulfonyl group, the alkylaryl group, the alkylamino group, the alkylboryl group, the alkylsilyl group, and the alkylamine group is the same as the examples of the alkyl group described herein.

[0120] In the specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfonyl group, the arylamino group, the arylboryl group, the arylsilyl group, and the arylamine group is the same as the examples of the aryl group described herein.

[0121] In the specification, a direct connection may refer to a single bond.

[0122] In some embodiments, in the description, and "-*" indicate where to link.

[0123] Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.

[0124] Display device

[0125] Figure 1 A plan view of a display device DD for explaining one or more embodiments. Figure 2 is a cross-sectional view of a display device DD according to an embodiment. Figure 2 To explain along Figure 1 A cross-sectional view of a portion taken along line II'.

[0126] The display device DD may include a display panel DP and an optical layer PP provided on the display panel DP. The display panel DP includes light emitting elements ED-1, ED-2, and ED-3. The display device DD may include a plurality of light emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be provided on the display panel DP to control light reflected by external light at the display panel DP. The optical layer PP may include, for example, a polarizing layer or a color filter layer. In some embodiments, unlike the configuration illustrated in the drawings, the display device DD of one or more embodiments may not provide (e.g., exclude) the optical layer PP.

[0127] The base substrate BL may be provided on the optical layer PP. The base substrate BL may be a member that provides a base surface on which the optical layer PP is provided. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the configuration illustrated in the drawings, in one or more embodiments, the base substrate BL may not be provided (e.g., excluded).

[0128] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be provided between the display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of acrylic resin, silicone resin, and epoxy resin (for example, at least one selected from acrylic resin, silicone resin, and epoxy resin).

[0129] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light emitting elements ED-1, ED-2, and ED-3 provided between the pixel defining films PDL, and an encapsulation layer TFE provided on the light emitting elements ED-1, ED-2, and ED-3.

[0130] The base layer BS may be a member providing a base surface on which the display device layer DP-ED is provided. The base layer BS may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

[0131] In one or more embodiments, the circuit layer DP-CL is provided on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0132] Each of the light emitting elements ED-1, ED-2, and ED-3 may have a configuration according to Figures 3 to 6 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 layer selected from emission layers EML-R, EML-G and EML-B, an electron transport region ETR, and a second electrode EL2.

[0133] Figure 2 One or more embodiments are explained in which the emission layers EML-R, EML-G, and EML-B of the light emitting elements ED-1, ED-2, and ED-3 are provided in the opening OH defined by the pixel defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as common layers in the entire light emitting elements ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and are not limited to the embodiments of the present disclosure. Figure 2 Different from the configuration explained in the embodiment, the hole transport region HTR and the electron transport region ETR in one or more embodiments may be provided by patterning in the opening OH defined by the pixel definition film PDL. For example, the hole transport region HTR, the emission layers EML-R, EML-G and EML-B, and the electron transport region ETR of the light-emitting elements ED-1, ED-2 and ED-3 in one or more embodiments may be provided by patterning in an inkjet printing method.

[0134] The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the light emitting elements ED-1, ED-2 and ED-3 in the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one or more layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to one or more embodiments may include at least one inorganic film (hereinafter, encapsulation inorganic film). The encapsulation layer TFE according to one or more embodiments may also include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.

[0135] The encapsulated inorganic film protects the display device layer DP-ED from moisture and / or oxygen, and the encapsulated organic film protects the display device layer DP-ED from foreign substances (such as dust particles). The encapsulated inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide and / or aluminum oxide, etc., but the embodiments of the present disclosure are not particularly limited thereto. The encapsulated organic film may include acrylic compounds and / or epoxy compounds, etc. The encapsulated organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.

[0136] An encapsulation layer TFE may be provided on the second electrode EL2 and may be provided to fill the opening OH.

[0137] See also Figure 1 and Figure 2 , the display device DD may include one or more non-light emitting areas NPXA and also include light emitting areas PXA-R, PXA-G, and PXA-B. The light emitting areas PXA-R, PXA-G, and PXA-B may be areas in which light generated by the respective light emitting elements ED-1, ED-2, and ED-3 is emitted. The light emitting areas PXA-R, PXA-G, and PXA-B may be spaced and / or separated from each other on a plane.

[0138] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B may be an area divided by a pixel-defining film PDL. The non-light-emitting area NPXA may be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, and the non-light-emitting area NPXA corresponds to the pixel-defining film PDL. In some embodiments, in the specification, the light-emitting areas PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel-defining film PDL may divide the light-emitting elements ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be provided in the opening OH defined by the pixel-defining film PDL and separated from each other.

[0139] The light emitting areas PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of light generated from the light emitting elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of one or more embodiments explained in , three light emitting areas PXA-R, PXA-G and PXA-B that emit red light, green light and blue light respectively are explained by way of example. For example, the display device DD of one or more embodiments may include a red light emitting area PXA-R, a green light emitting area PXA-G and a blue light emitting area PXA-B that are separated from each other.

[0140] In the display device DD according to one or more embodiments, a plurality of light emitting elements ED-1, ED-2, and ED-3 may emit light beams having different wavelengths from each other. For example, in one or more embodiments, the display device DD may include a first light emitting element ED-1 emitting red light, a second light emitting element ED-2 emitting green light, and a third light emitting element ED-3 emitting blue light. For example, a red light emitting region PXA-R, a green light emitting region PXA-G, and a blue light emitting region PXA-B of the display device DD may correspond to the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element ED-3, respectively.

[0141] However, the embodiments of the present disclosure are not limited thereto, and the first to third light emitting elements ED-1, ED-2, and ED-3 may emit light beams in substantially the same wavelength range or at least one light emitting element may emit light beams in a wavelength range different from that of other light emitting elements. For example, the first to third light emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

[0142] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to one or more embodiments may be arranged in a stripe form. Figure 1 , a plurality of red light emitting areas PXA-R may be arranged along the second direction axis DR2, a plurality of green light emitting areas PXA-G may be arranged along the second direction axis DR2, and a plurality of blue light emitting areas PXA-B may be arranged along the second direction axis DR2. In some embodiments, the red light emitting areas PXA-R, the green light emitting areas PXA-G, and the blue light emitting areas PXA-B may be alternately arranged in this order along the first direction axis DR1.

[0143] Figure 1 and Figure 2 It is explained that all the light-emitting regions PXA-R, PXA-G, and PXA-B have substantially the same area, but the embodiments of the present disclosure are not limited thereto. Therefore, the light-emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other according to the wavelength range of the emitted light. In this case, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may refer to the areas when observed on a plane defined by the first direction axis DR1 and the second direction axis DR2 (for example, in a plan view). The third direction axis DR3 may be perpendicular to the plane defined by the first direction axis DR1 and the second direction axis DR2.

[0144] In some embodiments, the arrangement of the light-emitting areas PXA-R, PXA-G, and PXA-B is not limited to Figure 1The arrangement of the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B can be provided in one or more appropriate combinations according to the characteristics of the display quality required in the display device DD. For example, the arrangement form of the light emitting areas PXA-R, PXA-G and PXA-B can be a honeycomb. Layout or diamond )Layout( and Diamond is a registered trademark owned by Samsung Display Co., Ltd.).

[0145] In some embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one or more embodiments, the area of ​​the green light-emitting region PXA-G may be smaller than the area of ​​the blue light-emitting region PXA-B, but the embodiments of the present disclosure are not limited thereto.

[0146] Below, Figures 3 to 6 The light emitting element ED of one or more embodiments may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 stacked in sequence.

[0147] and Figure 3 compared to, Figure 4 A cross-sectional view of a light emitting element ED according to one or more embodiments is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5 A cross-sectional view of a light emitting element ED according to one or more embodiments is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 compared to, Figure 6 A cross-sectional view of a light emitting element ED according to one or more embodiments including a capping layer CPL provided on the second electrode EL2 is illustrated.

[0148] The first electrode EL1 has conductivity (e.g., is a conductor). The first electrode EL1 may include a metal material, a metal alloy, or a conductive compound (e.g., formed of a metal material, a metal alloy, or a conductive compound). The first electrode EL1 may be an anode or a cathode. However, the embodiments of the present disclosure are not limited thereto. In some embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound selected from two or more of these, a mixture selected from two or more of these, or an oxide thereof.

[0149] When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, and W, a compound or mixture thereof (e.g., a mixture of Ag and Mg), or a material having a multilayer structure such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film of a material described herein (e.g., formed of a material described herein), and a transparent conductive film including ITO, IZO, ZnO and / or ITZO, etc. (e.g., formed of ITO, IZO, ZnO and / or ITZO, etc.). For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto. In some embodiments, the first electrode EL1 may include a metal material described herein, a combination of at least two metal materials of the metal materials described herein, and / or an oxide of the metal material described herein, etc. The thickness of the first electrode EL1 may be about 100 Å. to about For example, the thickness of the first electrode EL1 may be about to about

[0150] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer, an emission auxiliary layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about

[0151] The hole transport region HTR may have a single layer including (eg, formed of) a single material, a single layer including (eg, formed of) a plurality of different materials, or a multilayer structure including (eg, formed of) a plurality of layers including (eg, formed of) a plurality of different materials.

[0152] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure including a hole injection material and a hole transport material (e.g., formed of a hole injection material and a hole transport material). In some embodiments, the hole transport region HTR may have a single-layer structure including a plurality of different materials (e.g., formed of a plurality of different materials), or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer, hole injection layer HIL / buffer layer, hole transport layer HTL / buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in sequence from the first electrode EL1, but embodiments of the present disclosure are not limited thereto.

[0153] The hole transport region HTR may be formed using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brokett (LB), inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).

[0154] The hole transport region HTR may include a compound represented by Formula H-1:

[0155] Formula H-1

[0156]

[0157] In the formula H-1 herein, L 1 and L 2 Each of the L groups may be independently a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. The variables a and b may be independently an integer selected from 0 to 10. In some embodiments, when a or b is an integer of 2 or more, multiple L 1 and multiple L 2 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0158] In formula H-1, Ar 1 and Ar 2and Ar may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 3 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0159] The compound represented by Formula H-1 herein may be a monoamine compound. In some embodiments, the compound represented by Formula H-1 herein may be a compound selected from Ar 1 To Ar 3 In some embodiments, the compound represented by formula H-1 herein may be a diamine compound in which Ar 1 and Ar 2 A carbazole compound comprising a substituted or unsubstituted carbazole group in at least one of Ar 1 and Ar 2 A fluorene compound in which at least one of the compounds includes a substituted or unsubstituted fluorenyl group.

[0160] The compound represented by formula H-1 may be represented by any one (e.g., one) of the compounds selected from compound group H. However, the compounds listed in compound group H are examples, and the compound represented by formula H-1 is not limited to those represented by compound group H:

[0161] Compound Group H

[0162]

[0163] The hole transport region HTR may include a phthalocyanine compound such as copper phthalocyanine, N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PAN I / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate] and / or dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.

[0164] The hole transport region HTR may include: carbazole derivatives (such as N-phenylcarbazole or polyvinylcarbazole), fluorene derivatives and / or triphenylamine derivatives (for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD) or 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl]aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(carbazole-9-yl)benzene (mCP)), etc.

[0165] In some embodiments, the hole transport region HTR may include 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), etc.

[0166] The hole transport region HTR may include the compound described herein in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0167] The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about 100 nm. to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the ranges described herein, satisfactory hole transport properties may be achieved without significantly increasing the driving voltage.

[0168] In addition to the materials described herein, the hole transport region HTR may further include a charge generation material to increase conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide, a quinone derivative, a metal oxide, and a cyano compound, but the embodiments of the present disclosure are not limited thereto. For example, the p-dopant may include a metal halide such as CuI or RbI, a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ), a metal oxide such as tungsten oxide or molybdenum oxide, and / or a cyano compound such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9), etc., but the embodiments of the present disclosure are not limited thereto.

[0169] As described herein, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer and an electron blocking layer EBL. The buffer layer may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, and thus may increase the light emission efficiency. As the material to be included in the buffer layer, a material that may be included in the hole transport region HTR may be used. The electron blocking layer EBL is a layer for preventing or reducing electrons from being injected from the electron transport region ETR to the hole transport region HTR.

[0170] The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have, for example, about to about or about to about The emission layer EML may have a single layer including a single material (eg, formed of a single material), a single layer including a plurality of different materials (eg, formed of a plurality of different materials), or a multilayer structure having a plurality of layers including a plurality of different materials (eg, formed of a plurality of different materials).

[0171] The emission layer EML may be formed using one or more appropriate methods, such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Brokett (LB) method, an inkjet printing method, a laser printing method, or a laser induced thermal imaging (LITI) method.

[0172] The light-emitting element ED of one or more embodiments may include a fused polycyclic compound represented by Formula 1 in at least one functional layer provided between the first electrode EL1 and the second electrode EL2. At least one functional layer of the light-emitting element ED includes an emission layer EML. The emission layer EML in the light-emitting element ED according to one or more embodiments may include a fused polycyclic compound represented by Formula 1 of one or more embodiments. In one or more embodiments, the emission layer EML may include a fused polycyclic compound represented by Formula 1 of one or more embodiments as a dopant. The fused polycyclic compound represented by Formula 1 of one or more embodiments may be a dopant material of the emission layer EML. In some embodiments, in the specification, the fused polycyclic compound represented by Formula 1 of one or more embodiments to be described later may be referred to as a first compound.

[0173] The condensed polycyclic compound represented by Formula 1

[0174] One or more embodiments of the fused polycyclic compound represented by Formula 1 may include a structure in which three aromatic rings are fused via a boron atom and two heteroatoms. For example, one or more embodiments of the fused polycyclic compound represented by Formula 1 may include a structure in which the first to third aromatic rings are fused via a boron atom, a first nitrogen atom, and a second nitrogen atom. The first to third aromatic rings may each be connected to a boron atom, the first aromatic ring and the third aromatic ring may be connected to each other via a first nitrogen atom, and the second aromatic ring and the third aromatic ring may be connected to each other via a second nitrogen atom. In one or more embodiments, the first to third aromatic rings may be six-membered aromatic hydrocarbon rings. For example, the first to third aromatic rings may be benzene rings. In some embodiments, in this specification, the boron atom, the first nitrogen atom, and the second nitrogen atom, and the first to third aromatic rings fused via a boron atom, a first nitrogen atom, and a second nitrogen atom may be referred to as "condensed ring cores".

[0175] One or more embodiments of the fused polycyclic compound represented by Formula 1 may include a first linker connected to the first nitrogen atom of the fused ring core. The first linker may include a benzene moiety connected to the first nitrogen atom of the fused ring core. The first linker may be a substituted or unsubstituted phenylene linker.

[0176] The fused polycyclic compound represented by Formula 1 of one or more embodiments may include a first substituent and a second substituent connected to a first linker. The first substituent may include a carbazole moiety, and the second substituent may include a nitrile moiety. The first substituent may be a substituted or unsubstituted carbazole group, and the second substituent may be a cyano group. The first substituent may be connected to the carbon atom in the meta position relative to the carbon atom connected to the first nitrogen atom in the carbon atom constituting the first linker. The second substituent may be connected to the carbon atom in the ortho position or para position relative to the carbon atom connected to the first nitrogen atom in the carbon atom constituting the first linker. Among the carbon atoms constituting the first linker, the carbon atom to which the first substituent is connected may be in an ortho position or para position relationship with the carbon atom to which the second substituent is connected.

[0177] Therefore, the fused polycyclic compound represented by Formula 1 of one or more embodiments may have an increased multiple resonance effect because the first substituent and the second substituent are connected to the fused ring core via the first linker. Therefore, the fused polycyclic compound represented by Formula 1 of one or more embodiments may achieve high luminous efficiency and long service life when applied to a light-emitting element.

[0178] The fused polycyclic compound of one or more embodiments may be represented by Formula 1:

[0179] Formula 1

[0180]

[0181] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a structure in which three aromatic rings are fused via one boron atom, a first nitrogen atom, and a second nitrogen atom.

[0182] In formula 1, R a1 To R a11 and R 1 To R 5 Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 5 At least one of the R 1 To R 5 One of the above) may be a substituent represented by Formula 2. For example, R a1 To R a11 can each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.2 It may be a substituent represented by Formula 2, selected from R 1 , R 3 and R 5 Any one of may be cyano, and the others (e.g., selected from any of the remaining R 1 To R 5 ) may be a hydrogen atom or a deuterium atom.

[0183] In Formula 1, Ar may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, Ar may be a substituted or unsubstituted biphenyl group or a substituted or unsubstituted tert-phenyl group. When Ar is a substituted biphenyl group, the substituent may be a deuterium atom, a cyano group or a carbazolyl group. When Ar is a substituted tert-phenyl group, the substituent may be a deuterium atom, an unsubstituted aryl group having 6 to 12 carbon atoms or an unsubstituted tert-butyl group.

[0184] In some embodiments, in this specification, in Formula 1, represented by R a1 To R a4 The benzene ring substituted with a substituent represented by may correspond to the aforementioned first aromatic ring, which is represented by R a5 To R a8 The benzene ring substituted with a substituent represented by may correspond to the aforementioned second aromatic ring and is represented by R a9 To R a11 The benzene ring substituted with the substituent represented by may correspond to the aforementioned third aromatic ring. As described herein, the two N atoms in Formula 1 may correspond to the first nitrogen atom and the second nitrogen atom, respectively. In Formula 1, the substituent represented by R 1 To R 5 The benzene portion substituted by the substituent represented by may correspond to the aforementioned first linker. In Formula 1, R 1 To R 5 The substituent corresponding to the cyano group may correspond to the aforementioned second substituent.

[0185] In Formula 1, R 1 To R 5 At least one of may be a substituent represented by Formula 2:

[0186] Formula 2

[0187]

[0188] In formula 2, X 1 and X 2Each of X and X may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 and X 2 They may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0189] In Formula 2, n1 and n2 may each independently be an integer selected from 0 to 4. When each of n1 and n2 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be replaced by X. 1 and X 2 Each of n1 and n2 is 4 and X 1 and X 2 The case where each of n1 and n2 is a hydrogen atom may be the same as the case where each of n1 and n2 is 0. When each of n1 and n2 is an integer of 2 or more, a plurality of X 1 and multiple X 2 Can be the same or selected from multiple X 1 and multiple X 2 At least one of the X 1 and X 2 ).

[0190] In Formula 2, *- is the position of connection to Formula 1 herein.

[0191] In some embodiments, in the present specification, Formula 2 may correspond to the aforementioned first substituent.

[0192] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:

[0193] Formula 1-1

[0194]

[0195] Formula 1-2

[0196]

[0197] Formula 1-1 and Formula 1-2 each represent a case where the type (kind) of the substituent represented by Ar is specified in Formula 1.

[0198] In formula 1-1 and formula 1-2, R c1 To R c6and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. c1 To R c6 They may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0199] In Formula 1-1, m1 and m3 may each independently be an integer selected from 0 to 4. When each of m1 and m3 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be R c1 and R c3 Each of m1 and m3 is 4 and R c1 and R c3 The case where each of m1 and m3 is a hydrogen atom may be the same as the case where each of m1 and m3 is 0. When each of m1 and m3 is an integer of 2 or more, a plurality of R c1 and multiple R c3 Can be the same as each other, or selected from multiple R c1 and multiple R c3 At least one of the R c1 and R c3 ).

[0200] In Formula 1-1, m2 is an integer selected from 0 to 3. When m2 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be R c2 Where m2 is 3 and R c2 The case where each is a hydrogen atom may be the same as the case where m2 is 0. When m2 is an integer of 2 or more, a plurality of R c2 Can be the same as each other, or selected from multiple R c2 At least one of the R c2 ).

[0201] In Formula 1-2, m4 and m6 may each independently be an integer selected from 0 to 5. When each of m4 and m6 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be R c4 and R c6 Each of m4 and m6 is 5 and R c4 and R c6 The case where each of m4 and m6 is a hydrogen atom may be the same as the case where each of m4 and m6 is 0. When each of m4 and m6 is an integer of 2 or more, a plurality of R c4 and multiple Rc6 Can be the same as each other, or selected from multiple R c4 and multiple R c6 At least one of the R c4 and R c6 ).

[0202] In Formula 1-2, m5 may be an integer selected from 0 to 3. When m5 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be R c5 Where m5 is 3 and R c5 The case where each is a hydrogen atom may be the same as the case where m5 is 0. When m5 is an integer of 2 or more, a plurality of R c5 Can be the same as each other, or selected from multiple R c5 At least one of the R c5 ).

[0203] In some embodiments, in Formula 1-1 and Formula 1-2, the definitions described herein in Formula 1 may be applied to R a1 To R a11 and R 1 To R 5 .

[0204] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-3:

[0205] Formula 1-3

[0206]

[0207] Formula 1-3 represents a case where the type or kind of the substituent represented by Ar is specified in Formula 1.

[0208] In formula 1-3, R 6 To R 10 Each of them can be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 6 To R 10 When R 7 It can be a substituent represented by Formula 2 herein, selected from R 6 , R 8 and R 10 Any one of may be cyano, and the others (e.g., selected from any of the remaining R 6 To R 10 ) may be a hydrogen atom or a deuterium atom.

[0209] In some embodiments, in Formulas 1-3, the definitions described herein in Formula 1 may apply to R a1 To R a11 and R 1 To R 5 .

[0210] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from Formula 1-4 to Formula 1-6:

[0211] Formula 1-4

[0212]

[0213] Formula 1-5

[0214]

[0215] Formula 1-6

[0216]

[0217] Formula 1-4 to Formula 1-6 represent the following: 1 To R 5 The type (kind) of the substituent represented is the case where it is specified in Formula 1.

[0218] In Formula 1-4 to Formula 1-6, X 11 To X 16 Each of X and X may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 11 To X 16 They may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0219] In Formulae 1-4 to 1-6, x1 to x6 may each independently be an integer selected from 0 to 4. When each of x1 to x6 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be replaced by X. 11 To X 16 Each of x1 to x6 is 4 and X 11 To X 16 The case where each of x1 to x6 is a hydrogen atom may be the same as the case where each of x1 to x6 is 0. When each of x1 to x6 is an integer of 2 or more, a plurality of X 11 Up to multiple X 16 Can be the same or selected from multiple X11 Up to multiple X 16 At least one of the X 11 To X 16 ).

[0220] In some embodiments, in Formula 1-4 to Formula 1-6, the definitions described herein in Formula 1 may apply to R a1 To R a11 and Ar.

[0221] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be a compound represented by any one selected from Formula 1-7 to Formula 1-9:

[0222] Formula 1-7

[0223]

[0224] Formula 1-8

[0225]

[0226] Formula 1-9

[0227]

[0228] Formula 1-7 to Formula 1-9 represent the following: a9 To R a11 The type (kind) of the substituent represented is the case where it is specified in Formula 1.

[0229] In Formula 1-8 and Formula 1-9, Y 1 To Y 3 Each of them independently may be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Y 3 They may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0230] In Formula 1-8, k1 is an integer selected from 0 to 5. When k1 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be 1 Where k1 is 5 and Y 1 The case where each is a hydrogen atom may be the same as the case where k1 is 0. When k1 is an integer of 2 or more, a plurality of Y 1 Can be the same or selected from multiple Y 1At least one of the Y 1 ).

[0231] In Formula 1-9, k2 and k3 may each independently be an integer selected from 0 to 4. When each of k2 and k3 is 0, the fused polycyclic compound represented by Formula 1 of one or more embodiments may not be 2 and Y 3 Each of k2 and k3 is 4 and Y 2 and Y 3 The case where each of k2 and k3 is a hydrogen atom may be the same as the case where each of k2 and k3 is 0. When each of k2 and k3 is an integer of 2 or more, the plurality of Y 2 and multiple Y 3 Can be the same or multiple Y 2 and multiple Y 3 At least one of the Y 2 and Y 3 ).

[0232] In some embodiments, in Formula 1-7 to Formula 1-9, the definitions described herein in Formula 1 may apply to R a1 To R a8 , R 1 To R 5 and Ar.

[0233] In one or more embodiments of the fused polycyclic compound represented by Formula 1, R a2 , R a3 , R a6 and R a7 Each independently may be a hydrogen atom, a deuterium atom or a substituent represented by any one selected from Formula 3-1 to Formula 3-7:

[0234] Formula 3-1

[0235]

[0236] Formula 3-2

[0237]

[0238] Formula 3-3

[0239]

[0240] Formula 3-4

[0241]

[0242] Formula 3-5

[0243]

[0244] Formula 3-6

[0245]

[0246] Formula 3-7

[0247]

[0248] In Formula 3-1 to Formula 3-7 herein, *- may be a position for connection to Formula 1 herein.

[0249] The condensed polycyclic compound represented by Formula 1 of one or more embodiments may be any one (e.g., one) selected from the compounds represented by Compound Group 1. The light emitting element ED of one or more embodiments may include at least one (e.g., one or more) condensed polycyclic compound selected from the compounds represented by Compound Group 1 in the emission layer EML.

[0250] Compound Group 1

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301] In compound group 1 herein, "D" is a deuterium atom.

[0302] The condensed polycyclic compound represented by Formula 1 according to one or more embodiments may have a structure in which a first substituent and a second substituent connected to a first linker are introduced (eg, included), and thus may achieve improved luminous efficiency and long lifetime.

[0303] The fused polycyclic compound represented by Formula 1 of one or more embodiments may have a structure including a fused ring core in which the first to third aromatic rings are fused via a boron atom, a first nitrogen atom, and a second nitrogen atom, and a first linker is connected to the first nitrogen atom and a first substituent and a second substituent are connected to the first linker. The first linker includes a benzene portion connected to the first nitrogen atom. The first substituent includes a carbazole portion, and the second substituent includes a nitrile portion.

[0304] In the case of the fused polycyclic compound represented by Formula 1 of one or more embodiments, the first substituent and the second substituent are introduced (for example, including), and thus the empty p orbital of the boron atom can be protected due to the steric effect caused by the first substituent and the second substituent, and the triangular planar structure of the boron atom can be effectively maintained. Accordingly, the fused polycyclic compound represented by Formula 1 of one or more embodiments may have improved material stability. The fused polycyclic compound represented by Formula 1 of one or more embodiments may include the first substituent and the second substituent, and thus the intermolecular interaction may be suppressed or reduced. Accordingly, the fused polycyclic compound represented by Formula 1 of one or more embodiments may reduce phenomena as side effects of intermolecular interactions, such as aggregation, the formation of excited molecules between molecules, and / or the formation of excited complexes between molecules. Because the first substituent and the second substituent may be introduced (for example, included) in the fused polycyclic compound represented by Formula 1 of one or more embodiments, the distance between the molecules is relatively increased to suppress or reduce Dexter energy transfer and / or reduce quenching phenomena such as triplet-triplet annihilation (TTA) caused by an increase in triplet concentration. Accordingly, the condensed polycyclic compound represented by Formula 1 according to one or more embodiments may achieve the effects of improving luminous efficiency and lifespan characteristics.

[0305] In the case of the fused polycyclic compound represented by Formula 1 of one or more embodiments, the first substituent may be connected to the first linker, and thus the spatial overlap of the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level may be minimized or reduced, thereby improving the multiple resonance effect. Accordingly, the fused polycyclic compound represented by Formula 1 of one or more embodiments may have improved material stability. The fused polycyclic compound represented by Formula 1 of one or more embodiments may have improved intramolecular rigidity by connecting the second substituent to the first linker. Accordingly, intramolecular movement (e.g., intramolecular vibration) may be suppressed or reduced, and the Stokes shift is reduced so that the photoluminescence quantum yield (PLQY) and fluorescence resonance energy transfer (FRET) between molecules may be increased. The term "Stokes shift" as used herein may refer to the difference between the maximum wavelength when energy is absorbed by or absorbed in a compound and the maximum wavelength when energy is emitted by or emitted from a compound. Accordingly, the fused polycyclic compound represented by Formula 1 of one or more embodiments may achieve blue emission with high color purity.

[0306] In one or more embodiments of the fused polycyclic compound represented by Formula 1, the first nitrogen atom and the first substituent of the fused ring core may be connected to the position of the carbon atom having electron-withdrawing properties among the carbon atoms included in (e.g., constituting) the first linker. Referring to Formula S1, the carbon atom at the "a" position in the first linker may have electron-withdrawing properties. In some embodiments, the cyano group connected to the first linker in Formula S1 refers to a second substituent.

[0307] Formula S1

[0308]

[0309] In the fused polycyclic compound represented by Formula 1 of one or more embodiments, the first nitrogen atom and the first substituent of the fused ring core can each be connected to the "a" position of the first linker having electron-withdrawing properties. Accordingly, the HOMO energy level and the LUMO energy level can be effectively separated, and thus it is expected to improve the multiple resonance effect. Therefore, the fused polycyclic compound represented by Formula 1 of one or more embodiments in which (e.g., including) the first substituent and the second substituent are introduced can exhibit high luminous efficiency.

[0310] The fused polycyclic compound represented by Formula 1 according to one or more embodiments of the present disclosure may include a first substituent and a second substituent, and thus the material stability may be improved, and blue emission with high color purity may be achieved. In the case of introducing (e.g., including) the fused polycyclic compound represented by Formula 1 according to one or more embodiments of the present disclosure as a dopant for the emission layer, the service life, luminous efficiency, and color purity may be improved.

[0311] The emission spectrum of the fused polycyclic compound represented by Formula 1 of one or more embodiments has a full width at half maximum (FWHM) of about 10 nanometers (nm) to about 50nm or about 20nm to about 40nm. The emission spectrum of the fused polycyclic compound represented by Formula 1 of one or more embodiments has the described FWHM range, thereby improving the luminous efficiency when applied to the element. In some embodiments, when the fused polycyclic compound represented by Formula 1 of one or more embodiments is used as a blue light-emitting element material for a light-emitting element, the service life can be improved.

[0312] In some embodiments, the fused polycyclic compound represented by Formula 1 of one or more embodiments may be included in the emission layer EML. The fused polycyclic compound represented by Formula 1 of one or more embodiments may be included in the emission layer EML as a dopant material. The fused polycyclic compound represented by Formula 1 of one or more embodiments may be a thermally activated delayed fluorescent material. The fused polycyclic compound represented by Formula 1 of one or more embodiments may be used as a thermally activated delayed fluorescent dopant. For example, in the light-emitting element ED of one or more embodiments, the emission layer EML may include at least one of the fused polycyclic compounds represented by compound group 1 as described herein as a thermally activated delayed fluorescent dopant. However, the use of the fused polycyclic compound represented by Formula 1 of one or more embodiments is not limited thereto.

[0313] The fused polycyclic compound represented by Formula 1 of one or more embodiments may be a thermally activated delayed fluorescence emitting material. In some embodiments, the fused polycyclic compound represented by Formula 1 of one or more embodiments may be a luminescent material having a luminescent center wavelength in a wavelength region of about 430 nm to about 490 nm. For example, the fused polycyclic compound represented by Formula 1 of one or more embodiments may be a blue thermally activated delayed fluorescence (TADF) dopant. However, the embodiments of the present disclosure are not limited thereto, and when the fused polycyclic compound represented by Formula 1 of one or more embodiments is used as a luminescent material, it may be used as a dopant material that emits light in one or more appropriate wavelength regions, such as a red light emitting dopant and a green light emitting dopant.

[0314] The emission layer EML in the light emitting element ED of one or more embodiments may emit delayed fluorescence. For example, the emission layer EML may emit thermally activated delayed fluorescence (TADF).

[0315] In some embodiments, the emission layer EML of the light emitting element ED may emit blue light. For example, the emission layer EML of the light emitting element ED of one or more embodiments may emit blue light in a wavelength region of about 490 nm or less. However, the embodiments of the present disclosure are not limited thereto, and the emission layer EML may emit green light or red light.

[0316] In one or more embodiments, the emission layer EML may include a first compound represented by Formula 1, and may further include at least one selected from a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1, each of which is described in more detail herein.

[0317] In one or more embodiments, the second compound may be used as a hole transport host material of the emission layer EML.

[0318] Formula HT-1

[0319]

[0320] In formula HT-1, A 1 To A 8 Can be N or CR independently 51 For example, all A 1 To A 8 Can be CR 51 In some embodiments, selected from A 1 To A 8 At least (e.g., any) one of may be N, and the rest (e.g., any remaining A 1 To A 8 ) can be CR 51 .

[0321] In formula HT-1, L 1 It may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 It may be a direct connection, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, and / or a substituted or unsubstituted divalent carbazole group, etc., but the embodiments of the present disclosure are not limited thereto.

[0322] In formula HT-1, Y a Can be direct connection, CR 52 R 53 or SiR 54 R 55 For example, it may refer to the two benzene rings connected to the nitrogen atom in formula HT-1 being directly connected, In formula HT-1, when Y a In case of direct connection, the second compound represented by Formula HT-1 may include a carbazole moiety.

[0323] In formula HT-1, Ar 1 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 It may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and / or a substituted or unsubstituted biphenyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0324] In formula HT-1, R 51 To R 55Each of R and R may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. In some embodiments, R 51 To R 55 Each of R may be bonded to an adjacent group to form a ring. 51 To R 55 R may be independently a hydrogen atom or a deuterium atom. 51 To R 55 Each independently may be an unsubstituted methyl group or an unsubstituted phenyl group.

[0325] In one or more embodiments, the second compound represented by Formula HT-1 may be represented by any one (eg, one) selected from the compounds represented by Compound Group 2. The emission layer EML may include at least one (eg, one or more) selected from the compounds represented by Compound Group 2 as a hole transport host material.

[0326] Compound Group 2

[0327]

[0328]

[0329] In the embodiment compounds presented in compound group 2, "D" may refer to a deuterium atom, and "Ph" may refer to a substituted or unsubstituted phenyl group. For example, in the embodiment compounds presented in compound group 2, "Ph" may refer to an unsubstituted phenyl group.

[0330] In one or more embodiments, the emission layer EML may include a third compound represented by Formula ET-1. For example, the third compound may be used as an electron transport host material for the emission layer EML.

[0331] Formula ET-1

[0332]

[0333] In formula ET-1, selected from X 1 To X 3 At least one of them is N, and the rest are CR 56 For example, select X 1 To X 3Any one of may be N, and the rest (e.g., any remaining X 1 To X 3 ) can be independently CR 56 In this case, the third compound represented by Formula ET-1 may include a pyridine moiety. In some embodiments, the compound selected from X 1 To X 3 Two of them may be N, and the rest (eg, the remaining (eg, selected from) X 1 To X 3 ) can be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In some embodiments, X 1 To X 3 All may be N. In this case, the third compound represented by Formula ET-1 may include a triazine moiety.

[0334] In formula ET-1, R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.

[0335] In Formula ET-1, b1 to b3 may each independently be an integer selected from 0 to 10.

[0336] In formula ET-1, Ar 2 To Ar 4 and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 2 To Ar 4 Each independently may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.

[0337] In formula ET-1, L 2 To L 4 Each of them may be independently a directly connected, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when b1 to b3 are integers of 2 or more, L 2 To L 4 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0338] In one or more embodiments, the third compound may be represented by any one (eg, one) of the compounds selected from Compound Group 3. The light emitting element ED of one or more embodiments may include at least one (eg, one or more) of the compounds selected from Compound Group 3.

[0339] Compound Group 3

[0340]

[0341] In embodiments of compounds presented in Compound Group 3, "D" refers to a deuterium atom and "Ph" refers to an unsubstituted phenyl group.

[0342] The emission layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, the exciplex may be formed by a hole transport host and an electron transport host. In this case, the triplet energy level of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.

[0343] For example, the absolute value of the triplet energy level (T1) of the excited complex formed by the hole transport host and the electron transport host may be about 2.4 electron volts (eV) to about 3.0 eV. In some embodiments, the triplet energy level of the excited complex may be a value less than the energy gap of each host material. The excited complex may have a triplet energy level of about 3.0 eV or less, which is the energy gap between the hole transport host and the electron transport host.

[0344] In one or more embodiments, the emission layer EML may include a fourth compound in addition to the first to third compounds described herein. The fourth compound may be used as a sensitizer of the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.

[0345] For example, the emission layer EML may include an organic metal complex containing platinum (Pt) as a central metal atom and a ligand connected to the central metal atom as the fourth compound. The emission layer EML in the light emitting element ED of one or more embodiments may include a compound represented by Formula D-1 as the fourth compound:

[0346] Formula D-1

[0347]

[0348] In formula D-1, Q 1 To Q 4 They may each independently be C or N.

[0349] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.

[0350] In formula D-1, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 11 To L 13 In the above, “-*” refers to the portion connected to C1 to C4.

[0351] In Formula D-1, b1 to b3 may each independently be 0 or 1. When b1 is 0, C1 and C2 may not be connected to each other. When b2 is 0, C2 and C3 may not be connected to each other. When b3 is 0, C3 and C4 may not be connected to each other.

[0352] In formula D-1, R 61 To R 66 Each of R and R may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. In some embodiments, R 61 To R 66 Each of R may be bonded to an adjacent group to form a ring. 61 To R 66 Each independently may be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.

[0353] In Formula D-1, d1 to d4 may each independently be an integer selected from 0 to 4. In Formula D-1, when each of d1 to d4 is 0, the fourth compound may not be R 61 To R 64 Each of d1 to d4 is 4 and R 61 To R 64 The case where each of d1 to d4 is 0 may be the same as the case where each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or more, a plurality of R 61 To multiple R 64 Can be the same or selected from multiple R 61 To multiple R 64 At least one of may be different from the others.

[0354] In formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group or a substituted or unsubstituted heterocyclic group represented by any one selected from C-1 to C-4:

[0355]

[0356]

[0357] In C-1 to C-4, P 1 Can be C-* or CR 74 , P 2 Can be N-* or NR 81 , P 3 Can be N-* or NR 82 , and P 4 Can be C-* or CR 88 . R 71 To R 88 Each may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may bond with an adjacent group to form a ring.

[0358] In some embodiments, among C-1 to C-4, corresponds to the moiety connected to Pt as the central metal atom, and “-*” corresponds to the moiety connected to the adjacent cyclic group (C1 to C4) or the linker (L 11 To L 13 ) part.

[0359] The emission layer EML of one or more embodiments may include a first compound that is a fused polycyclic compound and at least one of the second compound to the fourth compound. For example, the emission layer EML may include a first compound, a second compound, and a third compound. In the emission layer EML, the second compound and the third compound may form an excited complex, and energy may be transferred from the excited complex to the first compound, thereby emitting light.

[0360] In some embodiments, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In one or more embodiments, the fourth compound may be a sensitizer. The fourth compound in the emission layer EML included in the light-emitting element ED of one or more embodiments may be used as a sensitizer to transfer energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound used as a sensitizer accelerates the energy transfer to the first compound as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emission layer EML of one or more embodiments may improve the luminous efficiency. In some embodiments, when the energy delivered to the first compound increases, the excitons formed in the emission layer EML are not accumulated inside the emission layer EML and emit light quickly, thereby reducing the degradation of the element. Therefore, the service life of the light-emitting element ED of one or more embodiments may be increased.

[0361] The light-emitting element ED of one or more embodiments may include (e.g., all of) the first compound, the second compound, the third compound, and the fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light-emitting element ED of one or more embodiments, the emission layer EML may simultaneously (e.g., synchronously) include the second compound and the third compound as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound being an organic metal complex, thereby exhibiting excellent or appropriate luminous efficiency characteristics.

[0362] In one or more embodiments, the fourth compound represented by Formula D-1 may represent any one (eg, one) selected from the compounds represented by Compound Group 4. The emission layer EML may include at least one (eg, one or more) selected from the compounds represented by Compound Group 4 as a sensitizer.

[0363] Compound Group 4

[0364]

[0365] In the embodiment compounds presented in compound group 4, "D" refers to a deuterium atom.

[0366] In some embodiments, the light-emitting element ED of one or more embodiments may include a plurality of emission layers EML. A plurality of emission layers EML may be stacked and provided in sequence, and, for example, the light-emitting element ED including a plurality of emission layers EML may emit white light. The light-emitting element including a plurality of emission layers EML may be a light-emitting element having a series structure. When the light-emitting element ED includes a plurality of emission layers EML, at least one emission layer EML may include the first compound represented by Formula 1 of one or more embodiments. In some embodiments, when the light-emitting element ED includes a plurality of emission layers EML, at least one emission layer EML may include the first compound, the second compound, the third compound, and the fourth compound described herein (e.g., all).

[0367] When the emission layer EML in the light-emitting element ED of one or more embodiments includes (e.g., all) the first compound, the second compound, and the third compound, the content (e.g., amount) of the first compound may be about 0.1 wt% to about 5 wt% relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the first compound satisfies the ratio described herein, the energy transfer from the second compound, the third compound, and the fourth compound to the first compound may be increased, thereby increasing the luminous efficiency and the service life.

[0368] The content of the second compound and the third compound in the emission layer EML may be the remaining content except the weight of the first compound and the fourth compound (e.g., the balance of the total weight of the first compound, the second compound, the third compound, and the fourth compound). For example, the total content (e.g., amount) of the second compound, the third compound, and the fourth compound in the emission layer EML may be about 65 wt % to about 95 wt % relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound.

[0369] A weight ratio of the second compound to the third compound may be about 3:7 to about 7:3 in the total weight of the second compound and the third compound.

[0370] When the content (e.g., amount) of the second compound and / or the third compound satisfies the ratio described in this article, at least one charge balance characteristic in the emission layer EML can be improved, and thus the luminous efficiency and the service life can be increased. When the content (e.g., amount) of the second compound and / or the third compound deviates from the ratio range described in this article, the charge balance in the emission layer EML can be broken, and thus the luminous efficiency can be reduced and the element can be easily degraded.

[0371] When the emission layer EML includes the fourth compound, the content (e.g., amount) of the fourth compound in the emission layer EML may be about 10 wt% to about 30 wt% relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the fourth compound satisfies the content (e.g., amount) described herein, the energy transfer from the host to the first compound as a light-emitting dopant can be increased, thereby improving the luminous efficiency, and thus improving the luminous efficiency of the emission layer EML. When the first compound, the second compound, the third compound, and the fourth compound included in the emission layer EML meet the content (e.g., amount) ratio range described herein, excellent or appropriate luminous efficiency and long service life can be achieved.

[0372] In the light emitting element ED of one or more embodiments, the emission layer EML may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-triphenylene derivatives, dihydrobenzanthracene derivatives and / or triphenylene derivatives. For example, the emission layer EML may include anthracene derivatives or pyrene derivatives.

[0373] exist Figures 3 to 6 In each light-emitting element ED of one or more embodiments explained in the present invention, the emission layer EML may further include a suitable host and a dopant in addition to (e.g., in addition to) the host and the dopant described herein, and for example, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.

[0374] Formula E-1

[0375]

[0376] In formula E-1, R 31 To R 40 Each of R and R may be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be bonded to an adjacent group to form a ring. In some embodiments, R 31 To R 40 It may bond with an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.

[0377] In Formula E-1, c and d may be an integer selected from 0 to 5, each independently.

[0378] Formula E-1 can be represented by any one (for example, one) selected from Compound E1 to Compound E19:

[0379]

[0380]

[0381] In one or more embodiments, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.

[0382] Formula E-2a

[0383]

[0384] In Formula E-2a, a may be an integer selected from 0 to 10, and L a It may be a directly connected, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when a is an integer of 2 or more, multiple L a Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0385] In some embodiments, in Formula E-2a, A 1 To A 5 Can be N or CR independently i . R a To R i Each of the R groups may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be bonded to an adjacent group to form a ring. In an embodiment, R a To R i It may be bonded with an adjacent group to form a hydrocarbon ring group or a heterocyclic group including (eg, containing) N, O and / or S etc. as ring-constituting atoms.

[0386] In some embodiments, in Formula E-2a, selected from A 1 To A 5 Two or three of them may be N, and the rest (e.g., any remaining A 1 To A 5 ) can be CRi .

[0387] Formula E-2b

[0388]

[0389] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group, or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. b It may be a directly connected, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, b may be an integer selected from 0 to 10, and when b is an integer of 2 or more, multiple L b Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0390] The compound represented by formula E-2a or formula E-2b can be represented by any one (e.g., one) of the compounds selected from compound group E-2. However, the compounds listed in compound group E-2 are only examples, and the compounds represented by formula E-2a or formula E-2b are not limited to those represented in compound group E-2.

[0391] Compound Group E-2

[0392]

[0393] The emission layer EML may further include a general material appropriate in the art as a host material. For example, the emission layer EML may include at least one of bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, embodiments of the present disclosure are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq 3), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO 3 ) and / or octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.

[0394] The emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.

[0395] Formula Ma

[0396]

[0397] In the formula Ma in this paper, Y 1 To Y 4 and Z 1 To Z 4 Can be independently CR 1 or N, R 1 To R 4 Each independently may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be bonded to an adjacent group to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

[0398] The compound represented by the formula Ma may be used as a phosphorescent dopant.

[0399] The compound represented by formula Ma can be represented by any one (e.g., one) selected from compound M-a1 to compound M-a25. However, compound M-a1 to compound M-a25 are only examples, and the compound represented by formula Ma is not limited to those represented by compound M-a1 to compound M-a25.

[0400]

[0401] The emission layer EML may include a compound represented by at least (eg, any) one selected from Formula Fa to Formula Fc. The compounds represented by Formula Fa to Formula Fc may be used as a fluorescent dopant material.

[0402] Formula

[0403]

[0404] In this article Fa, selected from R a To R j The two of them can be independently *-NAr 1 Ar 2 Replace. a To R j Not *-NAr 1 Ar 2 Other groups substituted (for example, R a To R j The remaining groups in (in) may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0405] In *-NAr 1 Ar 2 in Ar 1 and Ar 2 and Ar may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of the may be a heteroaryl group containing O or S as a ring-forming atom.

[0406] Formula Fb

[0407]

[0408] In the formula Fb herein, R a and R b Each of them may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring. Ar 1 To Ar 4Each may independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0409] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of may be a heteroaryl group including (eg, containing) O or S as a ring-forming atom.

[0410] In formula Fb, the number of rings represented by U and V may be 0 or 1 independently of each other. For example, in formula Fb, it means that when the number of U or V is 1, a ring may be (for example, constitute) a condensed ring in the portion indicated by U or V, and when the number of U or V is 0, the ring indicated by U or V may not exist. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the condensed ring with a fluorene core in formula Fb may be a cyclic compound with four rings. In some embodiments, when the respective numbers of U and V are 0, the condensed ring with a fluorene core in formula Fb may be a cyclic compound with three rings. In some embodiments, when the respective numbers of U and V are 1, the condensed ring with a fluorene core in formula Fb may be a cyclic compound with five rings.

[0411] Formula Fc

[0412]

[0413] In Formula Fc, A 1 and A 2 can be independently O, S, Se or NR m , and R m R may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 11 They may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may bond with an adjacent group to form a ring.

[0414] In Formula Fc, A 1 and A2 Each of A and B may independently bond to a substituent of an adjacent ring to form a condensed ring. 1 and A 2 Each independently is NR m When A 1 Can be used with R 4 or R 5 In some embodiments, A 2 Can be used with R 7 or R 8 bonded to form a ring.

[0415] In one or more embodiments, the emission layer EML may further include a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)benzene As suitable dopant materials, perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) and / or pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene) can be used.

[0416] The emission layer EML may further include a suitable phosphorescent dopant material. For example, a metal complex including (e.g., containing) iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and / or thulium (Tm) may be used as a phosphorescent dopant. For example, bis(4,6-difluorophenylpyridyl-N,C2) pyridinecarboxylate iridium (III) (FIrpic), bis(2,4-difluorophenylpyridyl)-tetra(1-pyrazolyl) borate iridium (III) (FIr6) and / or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, embodiments of the present disclosure are not limited thereto.

[0417] The emission layer EML may include a quantum dot material. The core of the quantum dot may be selected from a group consisting of a II-VI compound, a III-VI compound, a I-III-VI compound, a III-V compound, a III-II-V compound, a IV-VI compound, a group IV element, a group IV compound, and / or a combination thereof.

[0418] The II-VI Group compounds may be selected from the group consisting of: binary compounds selected from the group consisting of: CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and mixtures thereof; ternary compounds selected from the group consisting of: CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, C CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof, and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof.

[0419] Group III-VI compounds may include binary compounds such as In 2 S 3 or In 2 Se 3 , ternary compounds such as InGaS 3 or InGaSe 3 , or any combination thereof.

[0420] The Group I-III-VI compound may be selected from: a ternary compound selected from the group consisting of: AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof, and / or quaternary compounds such as AgInGaS 2 、CuInGaS 2 and mixtures thereof.

[0421] The III-V compounds may be selected from the group consisting of: binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof, ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and mixtures thereof, and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb and mixtures thereof. In some embodiments, the Group III-V compound may further include a Group II metal. For example, InZnP or the like may be selected as the Group III-II-V compound.

[0422] The IV-VI group compound may be selected from the group consisting of: a binary compound selected from the group consisting of: SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof, a ternary compound selected from the group consisting of: SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof, and a quaternary compound selected from the group consisting of: SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof. The IV group element may be selected from the group consisting of: Si, Ge and mixtures thereof. The IV group compound may be a binary compound selected from the group consisting of: SiC, SiGe and mixtures thereof.

[0423] Each element included in a multi-element (e.g., multi-element) compound such as a binary compound, a ternary compound, or a quaternary compound may be present in the particle in a substantially uniform or substantially non-uniform concentration distribution. For example, the general formula may refer to the type (species) of elements included in the compound, and the ratios of the elements in the compound may be similar or different. For example, AgInGaS 2 Can refer to AgIn x Ga 1-x S 2 (where 0 <x<1)。

[0424] In some embodiments, the quantum dot may have a single structure or a dual structure (eg, a core-shell structure) in which the concentration of each element included in the quantum dot is substantially uniform. For example, the material included in the core may be different from the material included in the shell.

[0425] The shell of the quantum dot can be used as a protective layer to prevent or reduce the chemical denaturation of the core to maintain the semiconductor properties, and / or a charging layer to give the quantum dot electrophoretic properties. The shell can be a single layer or can include multiple layers. The interface between the core and the shell can have a concentration gradient, wherein the concentration of the element present in the shell becomes lower towards the center of the core.

[0426] In some embodiments, the quantum dot may have a core-shell structure as described herein, which includes a core containing nanocrystals and a shell surrounding (eg, enclosing) the core. Examples of the shell of the quantum dot may include metal or non-metal oxides, semiconductor compounds, or combinations thereof.

[0427] For example, the metal or non-metal oxide may be a binary compound such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 or NiO, or ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 or CoMn 2 O 4 , but the embodiments of the present disclosure are not limited thereto.

[0428] Moreover, examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP and / or AlSb, etc., but embodiments of the present disclosure are not limited thereto.

[0429] The quantum dots may have a full width at half maximum (FWHM) of a light emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less, and may improve color purity or color reproducibility within the described range. In some embodiments, light emitted by such quantum dots is emitted in all directions so that a wide viewing angle may be improved.

[0430] In some embodiments, although the form of quantum dots is not specifically limited, as long as it is a form commonly used in the art, for example, quantum dots in the form of spherical, pyramidal, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers and / or nanoplates can be used.

[0431] As the size of the quantum dots is adjusted and / or the ratio of elements in the quantum dot compound is adjusted, the band gap can be controlled, and thus one or more appropriate wavelength ranges of light can be obtained in the quantum dot emission layer. Therefore, using the described quantum dots (using quantum dots of different sizes or quantum dot compounds of different element ratios), a light-emitting element that emits light of one or more appropriate wavelength ranges can be realized. For example, the size of the quantum dots or the ratio of elements in the quantum dot compound can be selected to emit red light, green light, and / or blue light. In some embodiments, the quantum dots can be configured to emit white light by combining one or more appropriate colors of light.

[0432] exist Figures 3 to 6 In each of the light emitting elements ED of the embodiments illustrated in , an electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiments of the present disclosure are not limited thereto.

[0433] The electron transport region ETR may have a single layer including (eg, formed of) a single material, a single layer including (eg, formed of) a plurality of different materials, or a multilayer structure including (eg, formed of) a plurality of layers including (eg, formed of) a plurality of different materials.

[0434] For example, the electron transport region ETR may have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single-layer structure formed of an electron injection material and an electron transport material. In some embodiments, the electron transport region ETR may have a single-layer structure including a plurality of different materials (e.g., formed of a plurality of different materials), or may have a structure in which an electron transport layer ETL / electron injection layer EIL, a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked in sequence from the emission layer EML, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, about to about Thickness.

[0435] The electron transport region ETR may be formed using one or more appropriate methods, such as vacuum deposition, spin coating, casting, Langmuir-Brokett (LB) method, inkjet printing, laser printing and / or laser induced thermal imaging (LITI) method.

[0436] The electron transport region ETR may include a compound represented by Formula ET-2:

[0437] Formula ET-2

[0438]

[0439] In formula ET-2, selected from X 1 To X 3 At least one of them is N, and the rest (e.g., any remaining X 1 To X 3 ) is CR a . R a Ar may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 3 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0440] In Formula ET-2, a to c may each independently be an integer selected from 0 to 10. In Formula ET-2, L 1 To L 3 and L may be each independently a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when a to c may each independently be an integer of 2 or more, L 1 To L 3 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0441] The electron transport region ETR may include an anthracene compound. However, one or more embodiments of the present disclosure are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl 1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) and / or mixtures thereof.

[0442] The electron transport region ETR may include at least one selected from the group consisting of compounds ET1 to ET36:

[0443]

[0444]

[0445] In some embodiments, the electron transport region ETR may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI and KI, lanthanide metals such as Yb and / or co-deposited materials of metal halides and lanthanide metals. For example, the electron transport region ETR may include KI:Yb, RbI:Yb and / or LiF:Yb as co-deposited materials. In some embodiments, the electron transport region ETR may use metal oxides such as Li 2 O or BaO, and / or 8-hydroxy-quinoline lithium (Liq), etc., but one or more embodiments of the present disclosure are not limited thereto. The electron transport region ETR may also be formed by a mixture material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt may be a material with an energy band gap of about 4 eV or greater. For example, the insulating organic metal salt may include, for example, a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate and / or a metal stearate.

[0446] In addition to the materials described herein, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but embodiments of the present disclosure are not limited thereto.

[0447] The electron transport region ETR may include the compound described herein for the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0448] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about to about For example, about to about When the thickness of the electron transport layer ETL satisfies the aforementioned range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about to about For example, about to about When the thickness of the electron injection layer EIL satisfies the range described herein, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0449] The second electrode EL2 may be provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiments of the present disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. The second electrode may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn and Zn, a compound selected from two or more of these, a mixture selected from two or more of these, or an oxide thereof.

[0450] The second electrode EL2 may be a transmissive electrode, a transflective electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may 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. (e.g., formed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) and / or indium tin zinc oxide (ITZO), etc.).

[0451] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb and W, or a compound or mixture thereof (e.g., AgMg, AgYb or MgYb), or a material having a multilayer structure such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of a material described herein, and a transparent conductive film formed of ITO, IZO, ZnO and / or ITZO, etc. For example, the second electrode EL2 may include a metal material described herein, a combination of at least two of the metal materials described herein, and / or an oxide of a metal material described herein, etc.

[0452] In some embodiments, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0453] In some embodiments, a capping layer CPL may be further provided on the second electrode EL2 of the light emitting element ED of one or more embodiments. The capping layer CPL may include a multi-layer or a single layer.

[0454] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, when the capping layer CPL contains an inorganic material, the inorganic material may include an alkali metal compound (e.g., LiF), an alkaline earth metal compound (e.g., MgF 2 )、SiON、SiN x and / or SiO y wait.

[0455] For example, when the capping layer CPL includes an organic material, the organic material may include N,N'-bis(1-naphthyl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine (α-NPD), NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15) and / or 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc., or epoxy resin or acrylate (such as methacrylate). However, the embodiments of the present disclosure are not limited thereto, and the capping layer CPL may include at least one selected from compounds P1 to P5:

[0456]

[0457]

[0458] In some embodiments, the capping layer CPL may have a refractive index of about 1.6 or more. For example, the capping layer CPL may have a refractive index of about 1.6 or more with respect to light in a wavelength range of about 550 nm to about 660 nm.

[0459] Figures 7 to 10 Each of them is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. Figures 7 to 10 In the display device of the embodiment of Figures 1 to 6 Instead of repeating features already described in , we will focus on describing their differences.

[0460] See also Figure 7 According to one or more embodiments, a display device DD-a may include a display panel DP including a display device layer DP-ED, a light control layer CCL provided on the display panel DP, and a color filter layer CFL. Figure 7 In one or more embodiments explained in the accompanying drawings, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light emitting element ED.

[0461] The light emitting element ED may include a first electrode EL1, a hole transport region HTR provided on the first electrode EL1, an emission layer EML provided on the hole transport region HTR, an electron transport region ETR provided on the emission layer EML, and a second electrode EL2 provided on the electron transport region ETR. Figures 3 to 6 The structure of the light emitting element can also be applied to Figure 7 The structure of the light-emitting element ED explained in FIG.

[0462] The emission layer EML of the light emitting element ED included in the display device DD according to one or more embodiments may include the condensed polycyclic compound represented by Formula 1 according to one or more embodiments described herein.

[0463] See also Figure 7, the emission layer EML may be provided in the opening OH defined by the pixel defining film PDL. For example, the emission layer EML divided by the pixel defining film PDL and provided corresponding to each light emitting area PXA-R, PXA-G and PXA-B may emit light in substantially the same wavelength range. In the display device DD-a of one or more embodiments, the emission layer EML may emit blue light. In some embodiments, unlike the configuration illustrated in the drawings, in one or more embodiments, the emission layer EML may be provided as a common layer in the entire light emitting areas PXA-R, PXA-G and PXA-B.

[0464] The light control layer CCL may be provided on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot and / or a phosphor, etc. The light converter may emit the provided light by converting the wavelength of the provided light. For example, the light control layer CCL may include a layer containing quantum dots or a layer containing phosphors.

[0465] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced apart and / or separated from each other.

[0466] See also Figure 7 , the divided pattern BMP may be provided between the light control parts CCP1 , CCP2 , and CCP3 that are spaced apart and / or separated from each other, but the embodiments of the present disclosure are not limited thereto. Figure 7 It is illustrated that the divided pattern BMP does not overlap with the light control parts CCP1 , CCP2 , and CCP3 , however, at least a portion of the edges of the light control parts CCP1 , CCP2 , and CCP3 may overlap with the divided pattern BMP.

[0467] The light control layer CCL may include a first light control component CCP1 containing a first quantum dot QD1 (which converts the first color light provided from the light emitting element ED into a second color light), a second light control component CCP2 containing a second quantum dot QD2 (which converts the first color light into a third color light), and a third light control component CCP3 (which transmits the first color light).

[0468] In one or more embodiments, the first light control component CCP1 may provide red light as the second color light, and the second light control component CCP2 may provide green light as the third color light. The third light control component CCP3 may provide blue light by transmitting blue light as the first color light provided from the light emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same contents described herein may apply to quantum dots QD1 and QD2.

[0469] In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control component CCP3 may not include (e.g., may exclude) any quantum dot, but include a scatterer SP.

[0470] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica. The scatterer SP may include a member selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica, or may be selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and a mixture of at least two of the materials selected from hollow spherical silica.

[0471] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may each include base resins BR1, BR2, and BR3, respectively, in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In one or more embodiments, the first light control component CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control component CCP3 may include scatterers SP dispersed in the third base resin BR3.

[0472] The base resins BR1, BR2 and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may include one or more suitable resin compositions (e.g., formed by one or more suitable resin compositions), which may be generally referred to as adhesives. For example, the base resins BR1, BR2 and BR3 may be acrylic resins, urethane resins, silicone resins and / or epoxy resins, etc. The base resins BR1, BR2 and BR3 may be transparent resins. In one or more embodiments, the first base resin BR1, the second base resin BR2 and the third base resin BR3 may be the same or different from each other.

[0473] The light control layer CCL may include an isolation layer BFL1. The isolation layer BFL1 may be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The isolation layer BFL1 may block or reduce the exposure of the light control components CCP1, CCP2, and CCP3 to moisture / oxygen. In some embodiments, the isolation layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In some embodiments, the isolation layer BFL2 may be provided between the light control components CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3.

[0474] The isolation layers BFL1 and BFL2 may include at least one inorganic layer. For example, the isolation layers BFL1 and BFL2 may include an inorganic material. For example, the isolation layers BFL1 and BFL2 may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, and / or a metal film that ensures light transmittance, etc. In some embodiments, the isolation layers BFL1 and BFL2 may further include an organic layer. The isolation layers BFL1 and BFL2 may be formed of a single layer or a plurality of layers.

[0475] In the display device DD-a of one or more embodiments, the color filter layer CFL may be provided on the light control layer CCL. For example, the color filter layer CFL may be directly provided on the light control layer CCL. In this case, the isolation layer BFL2 may not be provided.

[0476] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit a second color light, a second filter CF2 configured to transmit a third color light, and a third filter CF3 configured to transmit the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The filters CF1, CF2, and CF3 may each include a polymerized photosensitive resin and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye.

[0477] In some embodiments, the embodiments of the present disclosure are not limited thereto, and the third filter CF3 may not include (e.g., may exclude) a pigment or a dye. The third filter CF3 may include a polymerized photosensitive resin and may not include (e.g., may exclude) a pigment or a dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

[0478] In addition, 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 not be separated but provided as one filter.

[0479] In one or more embodiments, the color filter layer CFL may further include a light shielding member. The light shielding member may be a black matrix. The light shielding member may include an organic light shielding material or an inorganic light shielding material containing a black pigment or dye. The light shielding member may prevent or reduce light leakage and may separate adjacent filters CF1, CF2, and CF3.

[0480] The first to third filters CF1, CF2, and CF3 may be provided to correspond to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.

[0481] The base substrate BL may be provided on the color filter layer CFL. The base substrate BL may be a member providing a base surface on which the color filter layer CFL and / or the light control layer CCL, etc. are provided. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the configuration illustrated in the drawings, in one or more embodiments, the base substrate BL may not be provided.

[0482] Figure 8 A cross-sectional view of a portion of a display device according to one or more embodiments is provided to explain the display device according to one or more embodiments. In the display device DD-TD of 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. The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 sequentially stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light emitting structures OL-B1, OL-B2, and OL-B3 may include an emission layer EML ( Figure 7 ) and a hole transport region HTR ( Figure 7 ) and the electron transport region ETR ( Figure 7 ).

[0483] For example, the light emitting elements ED-BT included in the display devices DD-TD of one or more embodiments may be light emitting elements having a tandem structure and including a plurality of emission layers.

[0484] exist Figure 8In one or more embodiments explained in, all light beams emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may be blue light. However, the embodiments of the present disclosure are not limited thereto, and the light beams emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may have wavelength ranges different from each other. For example, the light emitting element ED-BT including a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 emitting light beams having wavelength ranges different from each other may emit white light.

[0485] Charge generation layers CGL1 and CGL2 may be provided between two of the adjacent light emitting structures OL-B1, OL-B2, and OL-B3, respectively. The charge generation layers CGL1 and CGL2 may include p-type or p-like charge generation layers and / or n-type or n-like charge generation layers.

[0486] At least one selected from the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display devices DD-TD of one or more embodiments may contain the condensed polycyclic compound represented by Formula 1 of one or more embodiments described herein. For example, at least one selected from the plurality of emission layers included in the light emitting elements ED-BT may include the condensed polycyclic compound represented by Formula 1 of one or more embodiments.

[0487] Fig. 9 A cross-sectional view illustrating a display device DD-b according to one or more embodiments of the present disclosure. Fig.10 Illustrated is a cross-sectional view of a display device DD-c according to one or more embodiments of the present disclosure.

[0488] See also Fig. 9 , the display device DD-b according to one or more embodiments may include light emitting elements ED-1, ED-2, and ED-3 in which two emission layers are stacked. Figure 2 Compared to the display device DD of one or more embodiments described in Fig. 9 The one or more embodiments explained in are different in that the first to third light-emitting elements ED-1, ED-2, and ED-3 each include two emission layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2, and ED-3, the two emission layers may emit light in substantially the same wavelength range.

[0489] The first light-emitting element ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting element ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. In some embodiments, the third light-emitting element ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary component OG may be provided between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.

[0490] The emission auxiliary component OG may include a single layer or a multilayer. The emission auxiliary component OG may include a charge generation layer. More specifically, the emission auxiliary component OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown) stacked in sequence. The emission auxiliary component OG may be provided as a common layer in the entire first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and the emission auxiliary component OG may be provided by being patterned in an opening OH defined by a pixel defining film PDL.

[0491] The first red emission layer EML-R1, the first green emission layer EML-G1 and the first blue emission layer EML-B1 may be provided between the emission auxiliary component OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2 and the second blue emission layer EML-B2 may be provided between the hole transport region HTR and the emission auxiliary component OG.

[0492] For example, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary component OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in sequence. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary component OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in sequence. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary component OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in sequence.

[0493] In some embodiments, an optical auxiliary layer PL may be provided on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be provided on the display panel DP and controls reflected light at the display panel DP due to external light. Unlike the configuration illustrated in the drawings, the optical auxiliary layer PL in the display device according to one or more embodiments may not be provided.

[0494] Included in Fig. 9 At least one emission layer in the display device DD-b of one or more embodiments explained in the specification may include the fused polycyclic compound represented by Formula 1 of one or more embodiments described herein. For example, in one or more embodiments, at least one of the first blue emission layer EML-B1 and the second blue emission layer EML-B2 may include the fused polycyclic compound represented by Formula 1 of one or more embodiments.

[0495] and Figure 8 and Fig. 9 different, Fig.10 It is explained that the display device DD-c includes four light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1. The light emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 sequentially stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. The light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3 are sequentially stacked, and a charge generation layer CGL1 is disposed between the light emitting structures OL-B1 and OL-C1, a charge generation layer CGL2 is disposed between the light emitting structures OL-B1 and OL-B2, and a charge generation layer CGL3 is disposed between the light emitting structures OL-B2 and OL-B3. Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2 and OL-B3 may emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, the embodiments of the present disclosure are not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light beams within different wavelength ranges.

[0496] The charge generation layers CGL1, CGL2 and CGL3 provided between adjacent light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3 may include p-type or p-like charge generation layers (e.g., p-charge generation layers) and / or n-type or n-like charge generation layers (e.g., n-charge generation layers).

[0497] At least one selected from the light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-c of one or more embodiments may include (e.g., contain) the condensed polycyclic compound represented by Formula 1 of one or more embodiments described herein. For example, in one or more embodiments, at least one selected from the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may include the condensed polycyclic compound represented by Formula 1 of one or more embodiments described.

[0498] The light-emitting element ED according to one or more embodiments of the present disclosure may include the fused polycyclic compound represented by Formula 1 of the described one or more embodiments in at least one functional layer provided between the first electrode EL1 and the second electrode EL2, thereby exhibiting excellent or appropriate luminous efficiency and improved service life characteristics. For example, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may be included in the emission layer EML of the light-emitting element ED of one or more embodiments, and the light-emitting element of one or more embodiments may exhibit long service life characteristics.

[0499] In one or more embodiments, the electronic device may include: a display device including a plurality of light emitting elements and a control component for controlling the display device. The electronic device of one or more embodiments may be a device activated according to an electrical signal. The electronic device may include a display device of one or more appropriate embodiments. For example, the electronic device may include not only large-sized electronic devices such as televisions, monitors, or outdoor billboards, but also small-sized and medium-sized electronic devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, and / or cameras.

[0500] Fig.11 To explain the view of the vehicle AM ​​in which the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 are provided. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may include the reference Figure 1 and Figure 2 as well as Figures 7 to 10 The described display devices DD, DD-TD, DD-a, DD-b and DD-c have the same configuration.

[0501] Fig.11The vehicle AM ​​is explained, but this is only an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be provided in another means of transportation such as a bicycle, a motorcycle, a train, a ship, and / or an airplane. In some embodiments, at least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 including the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one or more embodiments may be used in a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, and / or an outdoor billboard, etc. In some embodiments, these are provided only as example embodiments, and thus may be used in other electronic devices unless departing from the present disclosure.

[0502] At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may include as shown in reference Figures 3 to 6 The light-emitting element ED of one or more embodiments described. The light-emitting element ED of one or more embodiments may include the fused polycyclic compound represented by Formula 1 of one or more embodiments. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a light-emitting element ED including the fused polycyclic compound represented by Formula 1 of one or more embodiments, thereby improving display life.

[0503] refer to Fig.11 , the vehicle AM ​​may include a steering wheel HA and a gearshift GR for driving the vehicle AM. In some embodiments, the vehicle AM ​​may include a front window GL provided so as to face the driver.

[0504] The first display device DD-1 may be provided in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital instrument cluster displaying first information of the vehicle AM. The first information may include a first scale indicating the driving speed of the vehicle AM, a second scale indicating the engine speed (i.e., revolutions per minute (RPM)), and / or an image indicating the fuel status, etc. The first scale and the second scale may be indicated as digital images.

[0505] The second display device DD-2 may be provided in a second area facing the driver's seat and overlapping the front window GL. The driver's seat may be a seat in which a steering wheel HA is provided. For example, the second display device DD-2 may be a head-up display (HUD) that displays the second information of the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include a number indicating the driving speed, and may further include information such as the current time. Different from the configuration illustrated in the accompanying drawings, the second information of the second display device DD-2 may be projected onto the front window GL to be displayed.

[0506] The third display device DD-3 may be provided in a third area adjacent to the gear GR. For example, the third display device DD-3 may be provided between the driver's seat and the passenger seat and may be a central information display (CID) of the vehicle AM ​​for displaying the third information. The passenger seat may be a seat spaced and / or separated from the driver's seat, and the gear GR is provided between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), playing music or radio or video (or images), and / or the temperature inside the vehicle AM, etc.

[0507] The fourth display device DD-4 may be spaced and / or separated from the steering wheel HA and the gearshift GR, and may be provided in a fourth area adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an image outside the vehicle AM ​​captured by a camera module CM provided outside the vehicle AM. The fourth information may include an image outside the vehicle AM.

[0508] The first to fourth information described in this article may be an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the inside and outside of the vehicle AM. The first to fourth information may include information different from that described in this article. However, the embodiments of the present disclosure are not limited thereto, and a portion of the first to fourth information may include the same information as each other.

[0509] Terms such as "substantially," "about," and "approximately" are used as relative terms and not as terms of degree, and are intended to take into account the inherent deviations in measurements or calculations that one of ordinary skill in the art will recognize. They may include deviations from the stated value and an acceptable range determined by one of ordinary skill in the art, taking into account the limitations and errors associated with the measurement of that quantity. For example, "about" may refer to one or more standard deviations of the stated value, or ±30%, ±20%, ±10%, or ±5% of the stated value.

[0510] Numerical ranges disclosed herein include and are intended to disclose all subranges of the same numerical precision. For example, a range of "1.0 to 10.0" includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Applicants therefore reserve the right to amend this specification (including the claims) to expressly set forth any subranges contained within the ranges expressly set forth herein.

[0511] The display device, light emitting element and / or any other related device or component according to the embodiment of the present disclosure described herein may be implemented using any appropriate hardware, firmware (e.g., a dedicated integrated circuit), software, or a combination of software, firmware, and hardware. For example, various components of the display device and / or light emitting element may be formed on an integrated circuit (IC) chip or on a separate IC chip. Further, various components of the display device and / or light emitting element may be implemented on a flexible printed circuit film, a tape carrier package (TCP), or a printed circuit board (PCB), or formed on a substrate. Further, various components of the display device and / or light emitting element may be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions and interacting with other system components for performing various functions described herein. Computer program instructions are stored in a memory, which may be implemented in a computing device using a standard storage device, such as, for example, a random access memory (RAM). Computer program instructions may also be stored in other non-temporary computer-readable media, such as, for example, a CD-ROM or a flash drive, etc. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a dedicated computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.

[0512] Hereinafter, with reference to examples and comparative examples, the fused polycyclic compound represented by Formula 1 according to one or more embodiments of the present disclosure and the light-emitting element of one or more embodiments of the present disclosure will be described in more detail. In some embodiments, the described examples are only explained to help the understanding of the present disclosure, and the scope of the present disclosure is not limited thereto.

[0513] Example

[0514] 1. Synthesis of fused polycyclic compounds

[0515] First, the synthesis method of the fused polycyclic compound represented by Formula 1 according to one or more embodiments will be explained in detail by referring to the synthesis methods of Compound 40, Compound 156, Compound 171, Compound 242, Compound 248, Compound 324, Compound 397, Compound 443, and Compound 489. It will be understood that the synthesis method of the fused polycyclic compound described is only an example, and the synthesis method of the fused polycyclic compound represented by Formula 1 according to one or more embodiments of the present disclosure is not limited to the following examples.

[0516] (1) Synthesis of Compound 40

[0517] Synthesis of Intermediate 40-1

[0518]

[0519] 1,3-dibromo-5-(tert-butyl)benzene (1 eq), 2-(([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5 )amino)-4-(9H-carbazole-9-yl)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), 2,2'-binaphthalene (BINAP, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100°C for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 40-1. (Yield: 69%)

[0520] Synthesis of Intermediate 40-2

[0521]

[0522] Intermediate 40-1 (1 eq), 5'-(tert-butyl)-N-(3-chlorophenyl)-[1,1':3',1"-terphenyl]-2'-amine (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a high-pressure reactor at about 150°C for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 40-2. (Yield: 62%)

[0523] Synthesis of Intermediate 40-3

[0524]

[0525] Intermediate 40-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added.3 (5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by silica filtration, and then purified again by recrystallization in dichloromethane: n-hexane (MC / Hex) to obtain intermediate 40-3. Thereafter, intermediate 40-3 was finally purified by column chromatography (dichloromethane: n-hexane). (Yield: 8%)

[0526] Synthesis of compound 40

[0527]

[0528] Intermediate 40-3 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 40 (yield: 72%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 40 by ESI-LCMS (electrospray-liquid chromatography mass spectrometry). ESI-LCMS: [M] +: C 89 H 73 D 5 BN 5 ,1233.9

[0529] Synthesis of Intermediate 156-1

[0530]

[0531] 3,5-dibromo-3'-(tert-butyl)-1,1'-biphenyl-2',4',5',6'-d 4 (1 eq), 2-(9H-carbazole-9-yl)-4-((3-chlorophenyl)amino)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2(dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 90° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 156-1. (Yield: 71%)

[0532] Synthesis of Intermediate 156-2

[0533]

[0534] Intermediate 156-1 (1 eq), 5'-(tert-butyl)-N-(3-fluorophenyl)-[1,1':3',1"-terphenyl]-2'-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a high-pressure reactor in a nitrogen atmosphere at about 120°C for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 156-2. (Yield: 60%)

[0535] Synthesis of Intermediate 156-3

[0536]

[0537] Intermediate 156-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3(5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by silica filtration and then purified again by recrystallization in MC / Hex to obtain intermediate 156-3. Thereafter, intermediate 156-3 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 9%)

[0538] Synthesis of Intermediate 156-4

[0539]

[0540] Intermediate 156-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d 8 (1.2eq) and tripotassium phosphate (K 3 PO 4 , 3eq) was dissolved in N,N-dimethylformamide (DMF), and then the resulting mixture was stirred for 24 hours after the temperature was raised to about 150°C. After cooling, the resulting mixture was dried under reduced pressure and DMF was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 156-4. (Yield: 56%)

[0541] Synthesis of compound 156

[0542]

[0543] Intermediate 156-4 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 156 (yield: 70%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 156 by ESI-LCMS. ESI-LCMS: [M] +: C 101 H 73 D 12 BN 6 , 1406.1

[0544] (3) Synthesis of Compound 171

[0545] Synthesis of Intermediate 171-1

[0546]

[0547] 3,5-dibromo-3',5'-di-tert-butyl-1,1'-biphenyl (1 eq), 2-(([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5 )amino)-6-(9H-carbazole-9-yl)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 90° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 171-1. (Yield: 76%)

[0548] Synthesis of Intermediate 171-2

[0549]

[0550] Intermediate 171-1 (1 eq), N-(3-chlorophenyl)-4-(methyl-d 3 )-[1,1':3',1"-terphenyl]-5'-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 171-2. (Yield: 68%)

[0551] Synthesis of Intermediate 171-3

[0552]

[0553] Intermediate 171-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3 (5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by silica filtration, and then purified again by recrystallization in MC / Hex to obtain intermediate 171-3. Thereafter, intermediate 171-3 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 13%)

[0554] Synthesis of compound 171

[0555]

[0556] Intermediate 171-3 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 171 (yield: 70%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 171 by ESI-LCMS. ESI-LCMS: [M] +: C 96 H 76 D 8 BN 5 , 1327.0

[0557] (4) Synthesis of Compound 242

[0558] Synthesis of Intermediate 242-1

[0559]

[0560] 1,3-Dibromo-5-fluorobenzene (1 eq), 2-((3-chlorophenyl)amino)-4-(3-phenyl-9H-carbazole-9-yl)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 242-1. (Yield: 73%)

[0561] Synthesis of Intermediate 242-2

[0562]

[0563] Intermediate 242-1 (1 eq), 5'-(tert-butyl)-N-(3-fluorophenyl)-[1,1':3',1"-terphenyl]-2'-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3, 0.05eq), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a high-pressure reactor in a nitrogen atmosphere at about 120°C for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 242-2. (Yield: 58%)

[0564] Synthesis of Intermediate 242-3

[0565]

[0566] Intermediate 242-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3 (5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by silica filtration, and then purified again by recrystallization in MC / Hex to obtain intermediate 242-3. Thereafter, intermediate 242-3 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 10%)

[0567] Synthesis of Intermediate 242-4

[0568]

[0569] Intermediate 242-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d 8 (1.2eq) and tripotassium phosphate (K 3 PO 4 , 3eq) was dissolved in N,N-dimethylformamide (DMF), and then the resulting mixture was stirred for 24 hours after the temperature was raised to about 150°C. After cooling, the resulting mixture was dried under reduced pressure and DMF was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 242-4. (Yield: 55%)

[0570] Synthesis of compound 242

[0571]

[0572] Intermediate 242-4 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 The product was purified by column chromatography and recrystallized (dichloromethane: n-hexane) to obtain compound 242 (yield: 61%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 242 by ESI-LCMS. ESI-LCMS: [M] +: C 109 H 68 D 16 BN 7 ,1519.2

[0573] (5) Synthesis of Compound 248

[0574] Synthesis of Intermediate 248-1

[0575]

[0576] 1,3-Dibromo-5-chlorobenzene (1 eq), 2-(9H-carbazole-9-yl)-6-((3',5'-di-tert-butyl-[1,1'-biphenyl]-3-yl)amino)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 248-1. (Yield: 77%)

[0577] Synthesis of Intermediate 248-2

[0578]

[0579] Intermediate 248-1 (1 eq), 5'-(tert-butyl)-N-(3-chlorophenyl)-[1,1':3',1"-terphenyl]-2'-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a high-pressure reactor in a nitrogen atmosphere at about 120°C for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 248-2. (Yield: 61%)

[0580] Synthesis of Intermediate 248-3

[0581]

[0582] Intermediate 248-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3(5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by filtration with silica, and then purified again by recrystallization in MC / Hex to obtain intermediate 248-3. Thereafter, intermediate 248-3 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 11%)

[0583] Synthesis of compound 248

[0584]

[0585] Intermediate 248-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d 8 (2.4 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.1 eq), tri-tert-butylphosphine (PtBu 3 , 0.2eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 The product was purified by column chromatography and recrystallized (dichloromethane: n-hexane) to obtain compound 248 (yield: 57%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 248 by ESI-LCMS. ESI-LCMS: [M] +: C 97 H 61 D 16 BN 6 , 1354.0

[0586] (6) Synthesis of Compound 324

[0587] Synthesis of Intermediate 324-1

[0588]

[0589] 1,3-Dibromo-5-fluorobenzene (1 eq), 4-((3-chlorophenyl)amino)-2-(2,7-di-tert-butyl-9H-carbazole-9-yl)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 324-1. (Yield: 75%)

[0590] Synthesis of Intermediate 324-2

[0591]

[0592] Intermediate 324-1 (1 eq), N-([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5 )-5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a high-pressure reactor in a nitrogen atmosphere at about 120°C for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 324-2. (Yield: 58%)

[0593] Synthesis of Intermediate 324-3

[0594]

[0595] Intermediate 324-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3(5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by silica filtration and then purified again by recrystallization in MC / Hex to obtain intermediate 324-3. Thereafter, intermediate 324-3 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 12%)

[0596] Synthesis of Intermediate 324-4

[0597]

[0598] Intermediate 324-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d 8 (1.2eq) and tripotassium phosphate (K 3 PO 4 , 3eq) was dissolved in N,N-dimethylformamide (DMF), and then the resulting mixture was stirred for 24 hours after the temperature was raised to about 150°C. After cooling, the resulting mixture was dried under reduced pressure and DMF was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 324-4. (Yield: 57%)

[0599] Synthesis of compound 324

[0600]

[0601] Intermediate 324-4 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4The obtained product was purified and recrystallized by column chromatography (dichloromethane: n-hexane) to obtain compound 324 (yield: 64%). Then, the obtained product was further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 324 by ESI-LCM. ESI-LCMS: [M] +: C 105 H 80 D 13 BN 6 , 1463.2

[0602] (7) Synthesis of Compound 397

[0603] Synthesis of Intermediate 397-1

[0604]

[0605] 1,3-Dibromo-5-chlorobenzene (1 eq), 4-(9H-carbazole-9-yl)-2-((3',5'-di-tert-butyl-[1,1'-biphenyl]-3-yl)amino)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 90° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 397-1. (Yield: 70%)

[0606] Synthesis of Intermediate 397-2

[0607]

[0608] Intermediate 397-1 (1 eq), N-(3',5'-di-tert-butyl-[1,1'-biphenyl]-3-yl)-[1,1':2',1":3",1"'-quadrphenyl]-2,3,4,5,6-d 5 -5"-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3, 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 90° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 397-2. (Yield: 68%)

[0609] Synthesis of Intermediate 397-3

[0610]

[0611] Intermediate 397-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0° C. in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3 (5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by filtration with silica, and then purified again by recrystallization in MC / Hex to obtain intermediate 397-3. Thereafter, intermediate 397-3 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 10%)

[0612] Synthesis of compound 397

[0613]

[0614] Intermediate 397-3 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4The product was purified by column chromatography and recrystallized (dichloromethane:n-hexane) to obtain compound 397 (yield: 62%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 397 by ESI-LCMS. ESI-LCMS: [M] +: C 109 H 97 D 5 BN 5 , 1498.3

[0615] (8) Synthesis of Compound 443

[0616] Synthesis of Intermediate 443-1

[0617]

[0618] 1,3-dibromo-5-(tert-butyl)benzene (1 eq), 2-(9H-carbazole-9-yl-d 8 )-4-((3-chlorophenyl)amino)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0)(Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 443-1. (Yield: 69%)

[0619] Synthesis of Intermediate 443-2

[0620]

[0621] Intermediate 443-1 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0°C in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3(5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by filtration with silica, and then purified again by recrystallization in MC / Hex to obtain intermediate 443-2. ​​Thereafter, intermediate 443-2 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 12%)

[0622] Synthesis of compound 443

[0623]

[0624] Intermediate 443-3 (1 eq), 9H-carbazole-1,2,3,4,5,6,7,8-d 8 (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 443 (yield: 66%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 443 by ESI-LCMS. ESI-LCMS: [M] +: C 84 H 23 D 32 BN 8 ,1219.8

[0625] (9) Synthesis of Compound 489

[0626] Synthesis of Intermediate 489-1

[0627]

[0628] 3,5-dibromo-3',5'-di-tert-butyl-1,1'-biphenyl (1 eq), 4-(([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5)amino)-2-(9H-carbazole-9-yl)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dry, and then dry under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 489-1. (Yield: 74%)

[0629] Synthesis of Intermediate 489-2

[0630]

[0631] Intermediate 489-1 (1 eq), 4-(9H-carbazole-9-yl)-2-((3-chlorophenyl)amino)benzonitrile (1 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 100° C. for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 Dried, and then dried under reduced pressure. The resulting product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 489-2.

[0632] (Yield: 76%)

[0633] Synthesis of Intermediate 489-3

[0634]

[0635] Intermediate 489-2 (1 eq) was dissolved in o-dichlorobenzene (oDCB), and the flask was cooled to about 0°C in a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was added. 3(5eq) was slowly injected therein. After the addition was completed, the temperature was raised to about 190°C and the mixture was stirred for 24 hours. After the resulting mixture was cooled to about 0°C, triethylamine was slowly dripped into the flask until heating was stopped to terminate the reaction, and then n-hexane and methanol were added to the flask to precipitate a solid. The precipitated solid was obtained by filtration. The obtained solid was purified by silica filtration, and then purified again by recrystallization in MC / Hex to obtain intermediate 489-3. Thereafter, intermediate 489-3 was finally purified by column chromatography (dichloromethane:n-hexane). (Yield: 11%)

[0636] Synthesis of compound 489

[0637]

[0638] Intermediate 489-3 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05eq), tri-tert-butylphosphine (PtBu 3 , 0.10eq) and sodium tert-butoxide (NaOtBu, 3eq) were dissolved in o-xylene, and the resulting mixture was then stirred in a nitrogen atmosphere at about 150° C. for about 24 hours. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed three times with water and ethyl acetate to obtain an organic layer. The obtained organic layer was washed with MgSO 4 The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 489 (yield: 65%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 489 by ESI-LCMS. ESI-LCMS: [M] +: C 96 H 75 D 5 BN 7 , 1348.0

[0639] 1. Manufacturing and evaluation of light-emitting components

[0640] The light-emitting element of the embodiment including the fused polycyclic compound of the embodiment in the emission layer was manufactured as follows. The fused polycyclic compounds of Compound 40, Compound 156, Compound 171, Compound 242, Compound 248, Compound 324, Compound 397, Compound 443 and Compound 489, which are the embodiment compounds described herein, were used as dopant materials for the emission layer to manufacture the light-emitting elements of Embodiments 1 to 9. Comparative Examples 1 to 4 correspond to light-emitting elements manufactured by using Comparative Example Compounds C1 to C4 as dopant materials for the emission layer, respectively.

[0641] Example compounds

[0642]

[0643] Comparative Example Compounds

[0644]

[0645] Manufacturing of light-emitting components

[0646] In the light-emitting elements of the embodiment and the comparative example, a 15 ohm per square centimeter (Ω / cm 2 )(About 1200 Angstroms A glass substrate (manufactured by Corning) with an ITO electrode as an anode was cut into a size of about 50 millimeters (mm) × 50 millimeters × 0.7 millimeters, cleaned by ultrasonic waves using isopropyl alcohol and pure water for about 5 minutes, and then irradiated with ultraviolet rays for about 30 minutes and exposed to ozone and cleaned. The glass substrate was mounted on a vacuum deposition device.

[0647] NPD is deposited on the upper portion of the anode to form Then H-1-1 is deposited on the upper portion of the hole injection layer to form A thick hole transport layer is formed, and CzSi is deposited on the upper portion of the hole transport layer to form Thick emission assist layer.

[0648] Then, a host mixture in which the second compound and the third compound according to one or more embodiments are mixed at a weight ratio of about 6:4, a fourth compound, and an example compound or a comparative example compound as the first compound are co-deposited at a weight ratio of about 85:14:1 to form A thick emission layer is formed, and TSPO1 is deposited on the upper portion of the emission layer to form Then, TPBi is deposited on the upper portion of the hole blocking layer to form A thick electron transport layer is formed, and then LiF is deposited on the upper portion of the electron transport layer to form Next, Al is deposited on the electron injection layer to form Thick cathode, thereby manufacturing light-emitting element. Each layer is formed by vacuum deposition method. HT2 in the compound of compound group 2 as described in this article is used as the second compound, and ETH66 in the compound of compound group 3 as described in this article is used as the third compound, and AD-37 in the compound of compound group 4 as described in this article is used as the fourth compound.

[0649] Compounds used for manufacturing light-emitting elements of Examples and Comparative Examples are disclosed herein. The materials shown were used for manufacturing elements by sublimation purification of commercial products.

[0650]

[0651]

[0652] Evaluation of light-emitting element characteristics

[0653] The luminous efficiency and service life of each of the light-emitting elements manufactured using Example Compound 40, Example Compound 156, Example Compound 171, Example Compound 242, Example Compound 248, Example Compound 324, Example Compound 397, Example Compound 443, and Example Compound 489 and Comparative Example Compound C1 to Comparative Example Compound C4 described herein were evaluated. The evaluation results of the light-emitting elements of Examples 1 to 9 and Comparative Examples 1 to 4 are listed in Table 1. In order to evaluate the characteristics of the light-emitting elements manufactured in Examples 1 to 9 and Comparative Examples 1 to 4, the luminance of each of the light-emitting elements was measured at 10 mA / cm2 by using Keithley MU 236 and a luminance meter PR650. 2 ) at a current density of , the driving voltage (V), the maximum luminous efficiency (cd / A) and the emission color, and the time taken to reach 95% brightness relative to the initial brightness was measured as the service life (T95), and the relative service life was calculated based on the light-emitting element of Comparative Example 4, and the results are listed in Table 1.

[0654] Table 1

[0655]

[0656] With reference to the results of Table 1, it can be confirmed that, compared with the light-emitting element of the comparative example, the light-emitting element of the embodiment using the fused polycyclic compound according to the embodiment of the present disclosure as the light-emitting material has a relatively high luminous efficiency and a low driving voltage, as well as improved service life characteristics. The embodiment compound includes a fused ring core in which three aromatic rings are fused via a boron atom, a first nitrogen atom, and a second nitrogen atom, and has a structure in which a first substituent and a second substituent are substituted via a first linker connected to a first nitrogen atom of the fused ring core, and thus high luminous efficiency and long service life can be achieved. The embodiment compound includes a fused ring core in which the first to third aromatic rings are fused around a boron atom, a first nitrogen atom, and a second nitrogen atom, and the first substituent and the second substituent are connected to the first nitrogen atom via a first linker. The first linker includes a benzene portion connected to the first nitrogen atom. The first substituent and the second substituent are connected to the first linker, the first substituent includes a carbazole portion, and the second substituent includes a nitrile portion. By using the example compound including the first substituent and the second substituent as a dopant for a thermally activated delayed fluorescence (TADF) light-emitting element, high element characteristics with increased luminous efficiency and long lifetime can be achieved in a short wavelength region, particularly a blue wavelength region.

[0657] It can be confirmed that the comparative example compound C1, the comparative example compound C2 and the comparative example compound C4 include a planar skeleton structure centered on a boron atom and two nitrogen atoms, but do not include the first substituent and the second substituent proposed in the present disclosure, and therefore, compared with the embodiment, the comparative example 1, the comparative example 2 and the comparative example 4 including the comparative example compound C1, the comparative example compound C2 and the comparative example compound C4 may have a relatively high driving voltage value and degradation of luminous efficiency and service life. The comparative example compound C1 and the comparative example compound C2 each include a carbazole portion and a nitrile portion. However, the described portion is not connected to the first nitrogen atom of the condensed ring core via the first linker proposed in the present disclosure. Accordingly, it is believed that the light-emitting elements of comparative examples 1 and 2 have degradation of luminous efficiency and service life. Because the comparative example compound C4 does not include a substituent such as a carbazole portion proposed in the present disclosure, it is believed that the light-emitting element of comparative example 4 has degradation of luminous efficiency and service life.

[0658] It can be confirmed that the comparative example compound C3 includes a planar skeleton structure centered on a boron atom, an N atom, and an O atom, but does not include the first substituent and the second substituent proposed in the present disclosure, and therefore, compared with the embodiment, the comparative example 3 including the comparative example compound C3 has a relatively high driving voltage value and degradation of luminous efficiency and service life. The comparative example compound C3 includes a carbazole portion and a nitrile portion, but the described portion is not connected to the first nitrogen atom of the condensed ring core by the first linker proposed in the present disclosure. Accordingly, it is believed that the light-emitting element of the comparative example 3 has degradation of luminous efficiency and service life.

[0659] The light-emitting element of one or more embodiments may exhibit improved element characteristics with high light-emitting efficiency and long lifetime.

[0660] The condensed polycyclic compound represented by Formula 1 according to one or more embodiments may be included in an emission layer of a light emitting element to contribute to high light emission efficiency and long lifetime of the light emitting element.

[0661] Although the present disclosure has been described with reference to preferred embodiments thereof, it will be understood that the present disclosure should not be limited to these preferred embodiments, but one or more suitable changes and modifications may be made by one skilled in the art without departing from the spirit and scope of the present disclosure.

[0662] Accordingly, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the detailed description of the specification, but is intended to be defined by the appended claims and their equivalents.

Claims

1. A fused polycyclic compound represented by Formula 1: Formula 1 In formula 1, R a1 To R a11 and R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, At least one selected from R1 to R5 is a cyano group, and at least the remaining one selected from R1 to R5 is a substituent represented by Formula 2, and Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, Formula 2 In formula 2, X1 and X2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n1 and n2 are each independently an integer selected from 0 to 4, and *—is the position connected to formula 1.

2. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 In formula 1-1 and formula 1-2, R c1 To R c6 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, m1, m3, m4 and m6 are each independently an integer selected from 0 to 5, m2 and m5 are each independently an integer selected from 0 to 3, and R a1 To R a11 and R1 to R5 are each as defined in Formula 1.

3. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 1-3: Formula 1-3 In formula 1-3, R6 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, Selected from R6 to R 10 At least one of them is cyano, and is selected from R6 to R 10 At least one of the remaining is a substituent represented by Formula 2, and R a1 To R a11 and R1 to R5 are each as defined in Formula 1.

4. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by any one selected from Formula 1-4 to Formula 1-6: Formula 1-4 Formula 1-5 Formula 1-6 In Formula 1-4 to Formula 1-6, X 11 To X 16 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, x1 to x6 are each independently an integer selected from 0 to 4, and R a1 To R a11 and Ar are each as defined in Formula 1.

5. The fused polycyclic compound according to claim 4, wherein X 11 To X 16 Each is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted tert-butyl group or a substituted or unsubstituted phenyl group.

6. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by any one selected from Formula 1-7 to Formula 1-9: Formula 1-7 Formula 1-8 Formula 1-9 In Formula 1-7 to Formula 1-9, Y1 to Y3 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, k1 is an integer selected from 0 to 5, k2 and k3 are each independently an integer selected from 0 to 4, and R a1 To R a8 , R1 to R5 and Ar are each as defined in Formula 1.

7. The fused polycyclic compound according to claim 1, wherein R a2 , R a3 , R a6 and R a7 Each is independently a hydrogen atom, a deuterium atom or a substituent represented by any one selected from Formula 3-1 to Formula 3-7: Formula 3-1 Formula 3-2 Formula 3-3 Formula 3-4 Formula 3-5 Formula 3-6 Formula 3-7 In Formula 3-1 to Formula 3-7, *—is the position connected to formula 1.

8. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is any one selected from the compounds represented by Compound Group 1: Compound Group 1 9. A light emitting element, comprising: a first electrode; a second electrode facing the first electrode; as well as at least one functional layer between the first electrode and the second electrode, wherein the at least one functional layer comprises an emitting layer, The emissive layer may include a first compound, The first compound is a condensed polycyclic compound according to any one of claims 1 to 8. 10 . The light-emitting element according to claim 9 , wherein the emission layer is configured to emit delayed fluorescence having a light emission center wavelength in a wavelength region of 430 nanometers to 490 nanometers.

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