Light-emitting element, polycyclic compound for light-emitting element, and display device including light-emitting element
By using polycyclic compounds of indolenocarbazole cores in the light emitting layer of the light emitting element, combining cyano or triazine group as electron-absorbing group and carbazole group as electron-donating group, the problem of insufficient light efficiency and lifetime of the existing light emitting element is solved, and efficient light emission and material stability are achieved.
Patent Information
- Application Number
- CN202411358604.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-04
- Filing Date
- 2024-09-27
- Publication Date
- 2025-04-08
AI Technical Summary
There is room for improvement in existing light emitting elements in terms of light efficiency and lifetime, especially in terms of efficient light emission and material stability.
The polycyclic compounds represented by Formula 1 are used as the main components of the light emitting layer, including indolenocarbazole cores, and the luminescence efficiency and material stability are improved by combining cyano or triazine groups as electron withdrawing groups and carbazole groups as electron donor groups.
The improvement of luminous efficiency and material stability are achieved, the life of the light emitting element is extended, and the display quality of the display device is improved.
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Figure CN119775282A_ABST
Abstract
Description
Technical Field
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0131495 filed in the Korean Intellectual Property Office on October 4, 2023, the entire contents of which are incorporated herein by reference. Background Art
[0002] The present disclosure herein relates to a light emitting element, a polycyclic compound for a light emitting element, and a display device including the light emitting element.
[0003] Recently, as image display devices, organic electroluminescent display devices and the like have been actively developed. The organic electroluminescent display device and the like are display devices including so-called self-luminous light-emitting elements, which realize display by combining holes and electrons injected from a first electrode and a second electrode in a light-emitting layer to emit light from a light-emitting material of the light-emitting layer.
[0004] When a light-emitting element is applied to a display device, improvement in light efficiency and / or improvement in life, etc. is desired or required, and development of materials for light-emitting elements that can stably achieve (eg, obtain) the above characteristics is continuously needed or sought.
[0005] For example, in recent years, in order to realize high-efficiency light-emitting elements, technologies for phosphorescent emission utilizing triplet energy or delayed fluorescence emission utilizing triplet-triplet annihilation (TTA) in which singlet excitons are generated by collision of triplet excitons are being developed, and development of thermally activated delayed fluorescence (TADF) materials utilizing delayed fluorescence is underway. Summary of the invention
[0006] Aspects according to embodiments of the present disclosure relate to a light emitting element having improved light emitting efficiency and lifetime.
[0007] Aspects according to embodiments of the present disclosure relate to polycyclic compounds having improved quantum efficiency and material stability.
[0008] Aspects of embodiments according to the present disclosure are directed to a display device having excellent or desired display quality by including a light emitting element having improved light emitting efficiency and lifetime.
[0009] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments of the disclosure.
[0010] According to some embodiments of the present disclosure, the polycyclic compound is represented by Formula 1.
[0011] Formula 1
[0012]
[0013] In Formula 1, R 1 To R 11 At least one of them may be a cyano group or a first substituent of a substituted or unsubstituted triazine group, and is selected from R 1 To R 11 Among them, two or more except the at least one as the first substituent may be independently a second substituent, the second substituent is a substituted or unsubstituted carbazolyl group that is fully bonded to any ring selected from Ar1 to Ar3, and the rest (remainder) of any ring among Ar1 to Ar3 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 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. That is, R 1 To R 11 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 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 11 At least one of them may be a first substituent, the first substituent being selected from cyano or substituted or unsubstituted triazine, and selected from R 1 To R 11 The remaining part (e.g., the remaining R 1 To R 11 ) may each independently be a second substituent, which is a substituted or unsubstituted carbazolyl group.
[0014] In one or more embodiments, the above Formula 1 may be represented by any one selected from Formula 1-1 to Formula 1-3.
[0015] Formula 1-1
[0016]
[0017] Formula 1-2
[0018]
[0019] Formula 1-3
[0020]
[0021] In the above formulas 1-1 to 1-3, Sb1 may be a cyano group or represented by formula 2, and Sb2 may be represented by formula 3, and Ra to Rc may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. n1 may be 1, n2 may be an integer of 1 to 3 (e.g., selected from 1 to 3), and n3 may be an integer of 1 to 4, m1 may be 2 or 3, and m2 may be an integer of 2 to 4, p1 may be 0 or 1, p2 may be an integer of 0 to 2, q may be an integer of 0 to 2, and r may be an integer of 0 to 3, and R 5 To R 11 and may each independently be the same as defined in Formula 1 above.
[0022] Formula 2
[0023]
[0024] Formula 3
[0025]
[0026] In equations 2 and 3, W 1 , W 2 and R 21 To R 28 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and Each may represent a position of bonding to a corresponding ring among Ar1 to Ar3.
[0027] In one or more embodiments, the above Formula 1-1 may be represented by Formula 1-1a.
[0028] Formula 1-1a
[0029]
[0030] In Formula 1-1a, Sb1 and Sb2 may be independently the same as defined in Formula 1-1, and R 5 To R 11 and may be independently the same as defined in Formula 1.
[0031] In one or more embodiments, the above Formula 1-2 may be represented by Formula 1-2a.
[0032] Formula 1-2a
[0033]
[0034] In Formula 1-2a, Sb1, Sb2 and Rb may be independently the same as defined in Formula 1-2, and R 8 To R 11 and may be independently the same as defined in Formula 1.
[0035] In one or more embodiments, R is selected from Formula 1 1 To R 11 At least one of them can be deuterium or R 1 To R 11 At least one hydrogen atom in may be replaced by a deuterium atom.
[0036] In one or more embodiments, the polycyclic compound represented by Formula 1 may be a blue light emitting dopant.
[0037] In one or more embodiments, the polycyclic compound represented by Formula 1 may be a thermally activated delayed fluorescent material.
[0038] In one or more embodiments of the present disclosure, a light-emitting element includes: a first electrode; a second electrode on the first electrode; and a light-emitting layer between the first electrode and the second electrode, and includes the above-mentioned polycyclic compound of one or more embodiments as a first compound.
[0039] In one or more embodiments, the light emitting layer may further include at least one selected from the second compound represented by Formula HT-1 and the third compound represented by Formula ET-1.
[0040] Formula HT-1
[0041]
[0042] In formula HT-1, A 1 To A 8 can be independently N or CR 51 , L 1 It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 , and Ar 1It 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. 51 To R 55 They may each independently be 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and may be optionally bonded to an adjacent group to form a ring.
[0043] Formula ET-1
[0044]
[0045] In formula ET-1, X 1 To X 3 At least one of them can be N, and X 1 To X 3 The rest of the CR 56 , 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, and b1 to b3 may each independently be an integer of 0 to 10. Ar 2 To Ar 4 and L 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, and L 2 To L 4 Each of them may independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0046] In one or more embodiments, the light emitting layer may further include a fourth compound represented by Formula D-1.
[0047] Formula D-1
[0048]
[0049] In formula D-1, Q 1 To Q 4may be each independently C or N, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms, and L 11 To L 13 Can be independently connected to the key, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. b11 to b13 may all independently be 0 or 1, and R 61 To R 66 Each of d1 to d4 may independently be 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and d1 to d4 may independently be an integer from 0 to 4.
[0050] In one or more embodiments, the light emitting layer may include a first compound, a second compound, a third compound, and a fourth compound.
[0051] In one or more embodiments, the light emitting layer may emit delayed fluorescence.
[0052] In one or more embodiments, the light emitting layer can emit blue light.
[0053] In one or more embodiments of the present disclosure, a display device includes a base layer, a circuit layer on the base layer, and a display element layer on the circuit layer, and the display element layer includes a light-emitting element, wherein the light-emitting element includes a first electrode, a second electrode opposite to the first electrode, and a light-emitting layer between the first electrode and the second electrode, and the light-emitting layer includes the above-mentioned polycyclic compound of one or more embodiments.
[0054] In one or more embodiments, the light emitting element may emit blue light.
[0055] In one or more embodiments, the display device may further include a light control layer including quantum dots. BRIEF DESCRIPTION OF THE DRAWINGS
[0056] 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 accompanying drawings illustrate embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure. In the drawings:
[0057] Figure 1 is a plan view showing a display device according to one or more embodiments of the present disclosure;
[0058] Figure 2 is shown corresponding to Figure 1 A cross-sectional view of a portion of line II';
[0059] Figure 3 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0060] Figure 4 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0061] Figure 5 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0062] Figure 6 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0063] Figure 7 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0064] Figure 8 is a cross-sectional view showing a display device according to one or more embodiments;
[0065] Fig. 9 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure;
[0066] Fig.10 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure;
[0067] Fig.11 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure; and
[0068] Fig.12 is a view showing the interior of a vehicle in which the display device of one or more embodiments of the present disclosure is arranged. DETAILED DESCRIPTION
[0069] The present disclosure can be modified in one or more suitable ways and has many forms, so specific embodiments will be shown in the drawings and described in more detail in the detailed description of the present disclosure. However, it should be understood that it is not intended to limit the present disclosure to the specific forms disclosed, but is intended to cover all modifications, equivalents and substitutes falling within the spirit and scope of the present disclosure.
[0070] When explaining each of the accompanying drawings, the same reference numerals are used to refer to the same elements. In the accompanying drawings, for the sake of clarity of the present disclosure, the size of each structure may be exaggeratedly shown. It will be understood that, although the terms "first" and / or "second" etc. can be used herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only used to distinguish one component from another component. For example, without departing from the scope of the exemplary embodiments of the present disclosure, the first component may be referred to as the second component, and similarly, the second component may be referred to as the first component. As used herein, unless the context clearly indicates otherwise, the singular forms "one", "one (kind / person)" and "the (described)" are also intended to include plural forms.
[0071] In the present application, it will be understood that the terms "including" and / or "having" and the like indicate the presence of the features, quantities, steps, operations, components, parts and / or their (e.g., any suitable) combinations disclosed in the specification, but do not exclude the possibility of the presence or addition of one or more other features, quantities, steps, operations, components, parts and / or their (e.g., any suitable) combinations.
[0072] In the present application, if a layer, film, region or plate is referred to as being "on" another layer, film, region or plate or "in the upper part of" another layer, film, region or plate, the layer, film, region or plate may not only be "directly on" the layer, film, region or plate, but there may also be intervening layers, films, regions or plates (for example, when a layer, film, region or plate is referred to as being "on" another layer, film, region or plate or "in the upper part of" another layer, film, region or plate, the layer, film, region or plate may not only be "directly on" the layer, film, region or plate, but there may also be intervening layers, films, regions or plates). In contrast, if a layer, film, region or plate is referred to as being "below" or "in the "lower portion" of another layer, film, region or plate, the layer, film, region or plate may not only be directly below the layer, film, region or plate, but there may also be intervening layers, films, regions or plates (for example, when a layer, film, region or plate is referred to as being "below" or "in the "lower portion" of another layer, film, region or plate, the layer, film, region or plate may not only be directly below the layer, film, region or plate, but there may also be intervening layers, films, regions or plates). In addition, it will be understood that if a part is referred to as being "on" another part, the part may be arranged above the other part, or may also be arranged below the other part (for example, when a part is referred to as being "on" another part, the part may be arranged above the other part, or may also be arranged below the other part).
[0073] In the specification, the term "substituted or unsubstituted" may refer to a functional group that is unsubstituted or substituted with at least one substituent selected from the group including deuterium atoms, halogen atoms, cyano groups, nitro groups, amino (or 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 (e.g., composed of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino (or 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 addition, each of the above exemplary substituents may be substituted or unsubstituted. For example, biphenyl groups may be interpreted as aryl groups or phenyl groups substituted with phenyl groups.
[0074] In the specification, the phrase "bonds 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 addition, a ring formed by combining with an adjacent group may be connected to another ring to form a spiro structure.
[0075] In the specification, the term "adjacent group" may refer to a substituent that replaces an atom directly connected to an atom substituted with a corresponding substituent, another substituent that replaces an atom substituted with a corresponding substituent, or a substituent that is spatially located at the nearest position of the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. In addition, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.
[0076] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
[0077] In the specification, the alkyl group may be linear or branched. The number of carbons in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, alkyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heonicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl and / or n-triacontyl, etc., but the present disclosure is not limited thereto.
[0078] In the specification, cycloalkyl may refer to a cyclic alkyl. The carbon number in the cycloalkyl may be 3 to 50, 3 to 30, 3 to 20 or 3 to 10. Examples of cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl and / or bicycloheptyl, but the disclosure is not limited thereto.
[0079] In the specification, alkenyl refers to a hydrocarbon group including at least one carbon-carbon double bond in the middle and / or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but may be 2 to 30, 2 to 20 or 2 to 10. Examples of alkenyl groups may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl and / or styryl vinyl, etc., but the present disclosure is not limited thereto.
[0080] In the specification, alkynyl refers to a hydrocarbon group including at least one carbon-carbon triple bond in the middle and / or at the end of an alkyl group having 2 or more carbon atoms. The alkynyl group may be straight chain or branched. The number of carbon atoms in the alkynyl group is not particularly limited, and it may be 2 to 30, 2 to 20, or 2 to 10. Specific examples of alkynyl groups may include ethynyl and / or propynyl, etc., but are not limited thereto.
[0081] 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.
[0082] In the specification, aryl refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, and / or Base, etc., but the present disclosure is not limited thereto.
[0083] In the specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. Examples of the substituted fluorenyl group are as follows. However, the present disclosure is not limited thereto.
[0084]
[0085] As used herein, the term "heterocyclic group" refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, S and Se as a ring-forming heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic heterocyclic rings and aromatic heterocyclic rings can be monocyclic or polycyclic.
[0086] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si, Se and S as a ring-forming heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and may include a heteroaryl group. The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.
[0087] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, Se and S as a ring-forming 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 thiocyclopentane group, a tetrahydropyranyl group and / or a dioxanyl group, but the present disclosure is not limited thereto.
[0088] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si, Se and S as a ring-forming heteroatom. If 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-forming carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furanyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, 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, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothirolyl and / or dibenzofuranyl, but the present disclosure is not limited thereto.
[0089] In the specification, the above description of the aryl group may be applied to the arylene group except that the arylene group is a divalent group. The above description of the heteroaryl group may be applied to the heteroarylene group except that the heteroarylene group is a divalent group.
[0090] In the specification, silyl includes alkylsilyl and arylsilyl. Examples of silyl may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and / or phenylsilyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0091] 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 the present disclosure is not limited thereto.
[0092]
[0093] 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.
[0094] 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 above. Examples of the thio group may include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, and a naphthylthio group, but the present disclosure is not limited thereto.
[0095] In the specification, oxy group may refer to an oxygen atom bonded to an alkyl or aryl group as defined above. Oxy group may include alkoxy and aryloxy. Alkoxy group may be linear, branched or cyclic (e.g., cyclic) chain. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy and / or benzyloxy, etc., but embodiments of the present disclosure are not limited thereto.
[0096] The term "boryl" as used herein may refer to a boron atom bonded to an alkyl or aryl group as defined above. Boryl groups include alkylboryl groups and arylboryl groups. Examples of boryl groups may include dimethylboryl, tert-butylmethylboryl, diphenylboryl and / or phenylboryl, etc., but embodiments of the present disclosure are not limited thereto.
[0097] In the specification, the number of carbon atoms in the amine group is not particularly limited, but may be 1 to 30. The amine group may include an alkylamine group and an arylamine group. Examples of the amine group may include a methylamine group, a dimethylamine group, an aniline group, a diphenylamine group, a naphthylamine group and / or a 9-methyl-anthrylamine group, but the present disclosure is not limited thereto.
[0098] In the specification, the alkyl group among the alkoxy group, the alkylthio group, the alkylsulfonyl group, the alkylsulfinyl group, the alkylaryl group, the alkylamino group, the alkylboryl group, the alkylsilyl group, and the alkylamino group may be the same as the examples of the alkyl group described above.
[0099] In the specification, the aryl group among the aryloxy group, the arylthio group, the arylsulfonyl group, the arylsulfinyl group, the arylamino group, the arylboryl group, the arylsilyl group, and the arylamine group may be the same as the examples of the aryl group described above.
[0100] In the specification, a direct key may refer to a single key.
[0101] In one or more embodiments, in the specification, and "-*" both refer to the location to be linked.
[0102] Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.
[0103] Figure 1 is a plan view showing a display device DD according to one or more embodiments. Figure 2 is a cross-sectional view of a display device DD according to the embodiment. Figure 2 It is shown along Figure 1 A cross-sectional view of a portion taken along line II'.
[0104] The display device DD may include a display panel DP and an optical layer PP arranged 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 arranged on the display panel DP to control reflection of external light in the display panel DP. The optical layer PP may include, for example, a polarizing layer and / or a color filter layer. In one or more embodiments, unlike the configuration shown in the drawings, the optical layer PP may not be provided in the display device DD of one or more embodiments.
[0105] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member that provides a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the present disclosure is 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 shown in the drawings, the base substrate BL may not be provided.
[0106] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be arranged between the display element layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic resin, a (poly)siloxane resin, and an epoxy resin.
[0107] The display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display device layer DP-ED. The display element layer DP-ED may include a pixel defining layer PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between portions of the pixel defining layer PDL, and an encapsulation layer TFE disposed on the light emitting elements ED-1, ED-2, and ED-3.
[0108] The base layer BS may be a member that provides a base surface on which the display element layer DP-ED is arranged. The base layer BS may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the present disclosure is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
[0109] In one or more embodiments, the circuit layer DP-CL is arranged on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, 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 element layer DP-ED.
[0110] Each of the light emitting elements ED-1, ED-2, and ED-3 may have a configuration according to the embodiment described in more detail later. Figures 3 to 7 Each of the light-emitting elements ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, light-emitting layers EML-R, EML-G, and EML-B (e.g., a corresponding one of the light-emitting layers EML-R, EML-G, and EML-B), an electron transport region ETR, and a second electrode EL2.
[0111] Figure 2 One or more embodiments are shown, in which the light-emitting layers EML-R, EML-G and EML-B of the light-emitting elements ED-1, ED-2 and ED-3 are arranged in the opening OH defined in the pixel defining layer PDL, and the hole transport region HTR, the electron transport region ETR and the second electrode EL2 are provided as a common layer in the entire light-emitting elements ED-1, ED-2 and ED-3. However, the present disclosure is not limited thereto, and is not limited to the embodiment described in Figure 2Different from the configuration shown in FIG. 1 , in one or more embodiments, the hole transport region HTR and the electron transport region ETR may be provided by patterning inside the opening OH defined in the pixel defining layer PDL. For example, in one or more embodiments, the hole transport region HTR, the light emitting 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 may be provided by patterning in an inkjet printing method.
[0112] 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. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be one layer or multiple layers stacked. 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.
[0113] The encapsulated inorganic film protects the light-emitting elements ED-1, ED-2 and ED-3 from moisture / oxygen, and the encapsulated organic film protects the light-emitting elements ED-1, ED-2 and ED-3 from foreign matter such as dust particles. The encapsulated inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide and / or aluminum oxide, etc., but one or more 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 one or more embodiments of the present disclosure are not particularly limited thereto.
[0114] The encapsulation layer TFE may be disposed on the second electrode EL2 , and may be disposed to fill the opening OH.
[0115] Reference Figure 1 and Figure 2 , the display device DD may include a non-light emitting area NPXA and light emitting areas PXA-R, PXA-G, and PXA-B. The light emitting areas PXA-R, PXA-G, and PXA-B may be areas in which light generated by the 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 spaced apart (e.g., spaced apart or separated) from each other on a plane.
[0116] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a region divided by a pixel defining layer PDL. The non-light-emitting region NPXA may be a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, which corresponds to the pixel defining layer PDL. In one or more embodiments, in the specification, the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel defining layer PDL may divide the light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be arranged in the opening OH defined in the pixel defining layer PDL and separated from each other.
[0117] The light emitting regions PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of the lights generated from the light emitting elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of one or more embodiments shown in , three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red light, green light, and blue light, respectively, are exemplarily shown. For example, the display device DD of one or more embodiments may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are separated from each other.
[0118] 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 (e.g., light beams) having wavelengths different from each other. For example, in one or more embodiments, the display device DD may include a first light emitting element ED-1 that emits red light, a second light emitting element ED-2 that emits green light, and a third light emitting element ED-3 that emits blue light. For example, 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.
[0119] However, the present disclosure is not limited thereto, and the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may emit light (e.g., light beam) in substantially the same wavelength range, or at least one light-emitting element may emit light (e.g., light beam) in a wavelength range different from the wavelength range of light (e.g., light beam) emitted by other light-emitting elements. For example, the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may all emit blue light.
[0120] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to one or more embodiments may be arranged in a stripe form. Figure 1 , a plurality of red light emitting regions PXA-R may be arranged along the second direction axis DR2, a plurality of green light emitting regions PXA-G may be arranged along the second direction axis DR2, and a plurality of blue light emitting regions PXA-B may be arranged along the second direction axis DR2. In some embodiments, the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B may be alternately arranged along the first direction axis DR1 in the order stated.
[0121] Figure 1 and Figure 2 It is shown that all the light-emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but the present disclosure is not limited thereto. Therefore, the light-emitting regions PXA-R, PXA-G, and PXA-B may have areas different 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 an area as viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2 intersecting the third direction axis DR3 (e.g., in a plan view) (e.g., an area when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2 intersecting the third direction axis DR3 (e.g., in a plan view)).
[0122] In one or more embodiments, the arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B is not limited to Figure 1 , and the order in which the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B are arranged can be set in one or more appropriate combinations according to the characteristics of the display quality desired or 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 pentile Layout or diamond )Layout form. and Diamond is a registered trademark of Samsung Display Co., Ltd.
[0123] 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 present disclosure is not limited thereto.
[0124] In the following, Figures 3 to 7is a cross-sectional view schematically showing a light emitting element ED according to one or more embodiments. Each of the light emitting elements ED according to one or more embodiments may include a first electrode EL1, a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, and a second electrode EL2 sequentially stacked.
[0125] and Figure 3 compared to, Figure 4 A cross-sectional view of a light emitting element ED of one or more embodiments in which 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 is shown. Figure 3 compared to, Figure 5 A cross-sectional view of a light emitting element ED of one or more embodiments in which 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 is shown. Figure 3 compared to, Figure 6 A cross-sectional view of a light emitting element ED of one or more embodiments in which a hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and a light emitting auxiliary layer EAL and an electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL is shown. Figure 4 compared to, Figure 7 A cross-sectional view of a light emitting element ED including one or more embodiments of a cap layer CPL disposed on the second electrode EL2 is shown.
[0126] The first electrode EL1 has conductivity (for example, is a conductor). The first electrode EL1 may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the present disclosure is 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 thereof, a mixture selected from two or more thereof, or an oxide thereof.
[0127] If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). If the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg) or a material having a multilayer structure including two or more selected therefrom (e.g., LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al)). In one or more embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the above materials and a transparent conductive film formed of ITO, IZO, ZnO, and / or ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the present disclosure is not limited thereto. In some embodiments, the first electrode EL1 may include the above metal material, a combination of at least two of the above metal materials, and / or an oxide of the above metal material, etc. The thickness of the first electrode EL1 may be about 1000 Å. to about For example, the thickness of the first electrode EL1 may be about to about
[0128] The hole transport region HTR is disposed on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a light emitting auxiliary layer EAL, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about
[0129] The hole transport region HTR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure including a plurality of layers formed of a plurality of different materials.
[0130] 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 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 formed of a plurality of different materials, or a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / luminescence auxiliary layer EAL, a hole injection layer HIL / luminescence auxiliary layer EAL, a hole transport layer HTL / luminescence auxiliary layer EAL, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in the corresponding stated order from the first electrode EL1, but the present disclosure is not limited thereto.
[0131] The hole transport region HTR may be formed using one or more suitable methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser induced thermal imaging (LITI) method.
[0132] The hole transport region HTR may include a compound represented by Formula H-1:
[0133] Formula H-1
[0134]
[0135] In the above formula H-1, L 1 and L 2 L and L may be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b may be independently an integer from 0 to 10. In one or more embodiments, if a and b are integers of 2 or more, the plurality of L 1 and multiple L 2 L and L may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms (for example, when a and b are integers of 2 or more, multiple L 1 and multiple L 2 Each of them 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).
[0136] In formula H-1, Ar 1 and Ar 2and Ar may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 3 The aryl group may be substituted or unsubstituted and has 6 to 30 ring carbon atoms.
[0137] The compound represented by the above formula H-1 may be a monoamine compound (eg, a compound including a single amine group). In one or more embodiments, the compound represented by the above formula H-1 may be a compound selected from Ar 1 To Ar 3 In some embodiments, the compound represented by the above formula H-1 may be a diamine compound in which Ar 1 and Ar 2 A carbazole compound containing a substituted or unsubstituted carbazole group in at least one of the 1 and Ar 2 A fluorene compound in which at least one of the compounds contains a substituted or unsubstituted fluorenyl group.
[0138] The compound represented by Formula H-1 may be represented by any one selected from the compounds in Compound Group H. However, the compounds listed in Compound Group H are merely examples. The compound represented by Formula H-1 is not limited to the compounds listed in Compound Group H.
[0139] Compound Group H
[0140]
[0141]
[0142] The hole transport region HTR may also 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-di-m-tolylbenzene-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 (PA NI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate] and / or dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN), etc.
[0143] The hole transport region HTR may also include carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives, triphenylamine derivatives (such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD) and / or 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthalene-1-yl)-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) and / or 1,3-bis(N-carbazolyl)benzene (mCP), etc.
[0144] In some embodiments, the hole transport region HTR may further 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) and the like.
[0145] The hole transport region HTR may include the above-described compound of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, the emission auxiliary layer EAL, and the electron blocking layer EBL.
[0146] 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 thickness of the hole injection layer HIL may be, for example, about 100 Å. to about When the hole transport region HTR includes the hole transport layer HTL, the thickness of the hole transport layer HTL may be about 100 Å. to about When the hole transport region HTR includes the electron blocking layer EBL, the thickness of the electron blocking layer EBL may be about 100 Å. 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 above ranges, satisfactory hole transport properties may be obtained without significantly increasing driving voltage.
[0147] In addition to the above materials, the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, and a cyano compound, but the present disclosure is not limited thereto. For example, the p-dopant may include (e.g., may be) a halogenated metal compound (such as CuI and / or RbI), a quinone derivative (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 -TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide), cyano compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the present disclosure is not limited thereto.
[0148] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a light-emitting auxiliary layer EAL and an electron blocking layer EBL. The light-emitting auxiliary layer EAL may increase the luminous efficiency by compensating the resonance distance according to the wavelength of the light emitted from the light-emitting layer EML and controlling the hole charge balance. In some embodiments, the light-emitting auxiliary layer EAL may also be used to prevent or reduce the injection of electrons into the hole transport region HTR. The light-emitting auxiliary layer EAL may include a material that may be included in the hole transport region HTR. The electron blocking layer EBL is a layer for preventing or reducing the injection of electrons from the electron transport region ETR into the hole transport region HTR.
[0149] In the light-emitting element ED of one or more embodiments, the light-emitting layer EML may include a polycyclic compound according to one or more embodiments. In the light-emitting element ED of one or more embodiments, the light-emitting layer EML may include a first compound that is a polycyclic compound of one or more embodiments and at least one compound selected from the second compound and the third compound. In addition, in the light-emitting element ED of one or more embodiments, the light-emitting layer EML may further include a fourth compound. The second compound may include a fused ring of three rings including nitrogen atoms as ring atoms. The third compound may include a hexagonal ring group including at least one nitrogen atom as a ring atom. The fourth compound may include an organic metal complex. The second compound to the fourth compound will be discussed in more detail later.
[0150] In this specification, the first compound may be referred to as a polycyclic compound of one or more embodiments. The polycyclic compound of one or more embodiments includes a condensed ring of indole and carbazole as a central structure. For example, the polycyclic compound of one or more embodiments as the first compound includes indole (3,2,1-jk) carbazole as a core structure. The polycyclic compound of one or more embodiments includes at least one electron withdrawing group and a plurality of electron donating groups bonded to the core structure of indole and carbazole. In some embodiments, all of the plurality of electron donating groups may be bonded to an aromatic ring among the aromatic rings constituting (e.g., forming) the indole and carbazole core.
[0151] In one or more embodiments, the electron withdrawing group may be a cyano group or a substituted or unsubstituted triazine group. A cyano group or a substituted or unsubstituted triazine group directly bonded to the indole and carbazole core may be referred to as a first substituent (or a first substituent group, used interchangeably herein). In some embodiments, an electron donating group may be a substituted or unsubstituted carbazole group. Multiple substituted or unsubstituted carbazole groups directly bonded to one benzene ring (among all benzene rings) forming the indole and carbazole core may be referred to as a second substituent (or a second substituent group, used interchangeably herein).
[0152] The polycyclic compound of one or more embodiments includes indole and carbazole as a central structure, and includes (for example, simultaneously) both electron withdrawing groups and electron donating groups directly bonded to a core (for indole and carbazole), therefore, thermally activated delayed fluorescence (TADF) luminescent properties can be exhibited. In addition, due to the above binding structure, the polycyclic compound of one or more embodiments can emit light in a blue wavelength region. In one or more embodiments, the polycyclic compound of one or more embodiments has multiple electron donating groups that are all bonded to a ring of indole and carbazole, therefore, excellent or suitable material stability can be exhibited. Therefore, the light-emitting element of one or more embodiments of the polycyclic compound including one or more embodiments can exhibit high luminous efficiency and long life properties.
[0153] The light emitting element ED of one or more embodiments may include the polycyclic compound of one or more embodiments. The polycyclic compound of one or more embodiments may be represented by Formula 1.
[0154] Formula 1
[0155]
[0156] In Formula 1, R 1 To R 11 At least one of them may be a first substituent, the first substituent being a cyano group or a substituted or unsubstituted triazine group, and is selected from R 1 To R 11 The two or more remaining substituents (excluding the at least one as the first substituent or in addition to the at least one as the first substituent) may each independently be a second substituent, the second substituent being a substituted or unsubstituted carbazolyl group selected from R 1 To R 11 All of the two or more remaining substituents (excluding the at least one as the first substituent or in addition to the at least one as the first substituent) in Ar1 to Ar3 may be bonded to any one ring (e.g., a single ring) selected from Ar1 to Ar3. Here, each of Ar1 to Ar3 refers to a benzene ring.
[0157] R 1 To R 11 The remaining parts except for the first substituent and the second substituent or excluding the first substituent and the second substituent can all independently be hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted silyl groups, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms.
[0158] In one or more embodiments, two or more selected from a plurality of substituted or unsubstituted carbazole groups may all be bonded to any one ring selected from Ar1 to Ar3. For example, there may be three or more second substituents, which are substituted or unsubstituted carbazole groups directly bonded to any one ring selected from Ar1 to Ar3.
[0159] In the polycyclic compound represented by Formula 1, at least one selected from hydrogen atoms may be substituted with a deuterium atom. 1 To R 11 At least one of the remaining parts except for the first substituent and the second substituent or excluding the first substituent and the second substituent may be a deuterium atom, or at least one of the hydrogen atoms in the first substituent and the second substituent may be substituted with a deuterium atom.
[0160] The polycyclic compound of one or more embodiments represented by Formula 1 may be represented by any one selected from Formula 1-1 to Formula 1-3. In Formula 1-1 to Formula 1-3, Sb1 corresponds to a first substituent and Sb2 corresponds to a second substituent.
[0161] Formula 1-1 shows a case where the first substituent and the second substituent are all bonded to one aromatic ring (eg, a benzene ring), and Formula 1-2 and Formula 1-3 respectively show cases where the first substituent and the second substituent are bonded to different aromatic rings.
[0162] Formula 1-1
[0163]
[0164] Formula 1-2
[0165]
[0166] Formula 1-3
[0167]
[0168] In Formulae 1-1 to 1-3, Sb1 may be a cyano group or a substituted or unsubstituted triazine group represented by Formula 2. In addition, in Formulae 1-1 to 1-3, Sb2 may be a substituted or unsubstituted carbazole group represented by Formula 3.
[0169] In Formulae 1-1 to 1-3, Ra to Rc may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0170] In Formula 1-1 to Formula 1-3, the same contents as those described with reference to Formula 1 may be applied to R 5 To R 11 .
[0171] In Formula 1-1, n1 may be 1, m1 may be 2 or 3, and p1 may be 0 or 1. For example, in the polycyclic compound of one or more embodiments represented by Formula 1-1, n1 may be 1, m1 may be 3, and p1 may be 0. In one or more embodiments, the plurality of Sb2 may all be the same or at least one of the plurality of Sb2 may be different from the rest of the plurality of Sb2.
[0172] In Formula 1-2, n2 may be an integer from 1 to 3, m2 may be an integer from 2 to 4, p2 may be an integer from 0 to 2, and q may be an integer from 0 to 2. For example, in the polycyclic compound of one or more embodiments represented by Formula 1-2, n2 may be 1, m2 may be 4, p2 may be 0, and q may be 2. In one or more embodiments, the plurality of Sb2 may all be the same or at least one of the plurality of Sb2 may be different from the rest of the plurality of Sb2. In some embodiments, if p2 is 2, the plurality of Ra may be the same or different from each other, and if q is 2, the plurality of Rb may be the same or different from each other.
[0173] In Formula 1-3, n3 may be an integer from 1 to 4, m2 may be an integer from 2 to 4, p2 may be an integer from 0 to 2, and r may be an integer from 0 to 3. For example, in the polycyclic compound of one or more embodiments represented by Formula 1-3, n3 may be 1, m2 may be 4, p2 may be 0, and r may be 3. In one or more embodiments, the plurality of Sb2 may all be the same or at least one of the plurality of Sb2 may be different from the rest of the plurality of Sb2. In some embodiments, if p2 is 2, the plurality of Ra may be the same or different from each other, and if r is 2 or greater, the plurality of Rc may be the same or different from each other.
[0174] The triazine group as the first substituent may be represented by Formula 2.
[0175] Formula 2
[0176]
[0177] In the above formula 2, W 1 and W 2W 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 alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more embodiments, W 1 and W 2 Can be the same as each other. For example, in one or more embodiments, W 1 and W 2 It may be a substituted or unsubstituted phenyl group. However, the present disclosure is not limited thereto. In Formula 2, The moiety corresponds to a portion of the indolocarbazole core of Formula 1, which is bound to the rings of Ar1 to Ar3.
[0178] The carbazole group as the second substituent may be represented by Formula 3.
[0179] Formula 3
[0180]
[0181] In formula 3, R 21 To R 28 Each of them 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 alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In Formula 3, the "-*" portion corresponds to a portion of the indolocarbazole nucleus of Formula 1, which is bonded to the rings of Ar1 to Ar3.
[0182] In one or more embodiments, Formula 1-1 may be represented by Formula 1-1a.
[0183] Formula 1-1a
[0184]
[0185] In Formula 1-1a, Sb1 may be a cyano group or a substituted or unsubstituted triazine group, and Sb2 may be a substituted or unsubstituted carbazole group. All of the three Sb2 may be the same as each other or any one of the three Sb2 may be different from the other two of the three Sb2. In Formula 1-1a, the same contents as those described with reference to Formula 1 may apply to R 5 To R 11 .
[0186] In one or more embodiments, Formula 1-2 may be represented by Formula 1-2a.
[0187] Formula 1-2a
[0188]
[0189] In Formula 1-2a, Sb1 may be a cyano group or a substituted or unsubstituted triazine group, and Sb2 may be a substituted or unsubstituted carbazole group. All of the four Sb2 may be the same as each other or at least one of the four Sb2 may be different from the rest of the four Sb2. In Formula 1-2a, the same contents as those described with reference to Formula 1 may apply to R 8 To R 11 .
[0190] The polycyclic compound of one or more embodiments may be represented by any one selected from the compounds in compound group 1. The light emitting element ED according to one or more embodiments may include at least one selected from the compounds in compound group 1. In compound group 1, d represents a deuterium atom.
[0191] Compound Group 1
[0192]
[0193]
[0194]
[0195]
[0196]
[0197] The polycyclic compound of one or more embodiments includes an indole and carbazole core, a first substituent (which is a cyano or triazine group directly bonded to the indole and carbazole core) and a second substituent (which is a carbazole group directly bonded to the indole and carbazole core), and can be used as a delayed fluorescence material. For example, the polycyclic compound of one or more embodiments can be used as a thermally activated delayed fluorescence (TADF) material. The polycyclic compound of one or more embodiments can exhibit a high fluorescence quantum yield.
[0198] In some embodiments, the polycyclic compound of one or more embodiments includes multiple second substituents, wherein the carbazolyl groups as multiple second substituents are bonded to an aromatic (e.g., benzene) ring of the condensed ring constituting the indole and carbazole core, so that the carbazolyl groups can prevent or reduce the rotational motion of each other, thereby exhibiting excellent or suitable material stability. In some embodiments, the polycyclic compound of one or more embodiments includes an indole and carbazole core, a cyano or triazine group directly bonded to the indole and carbazole core, and multiple carbazolyl groups directly bonded to an aromatic (e.g., benzene) ring in the indole and carbazole core, and can therefore be used as a luminescent material emitting light in the blue light wavelength region. The polycyclic compound of one or more embodiments can exhibit high luminous efficiency in the blue light wavelength region, and can emit light so as to have a narrow half-maximum full width, thereby exhibiting excellent or suitable luminescent properties of excellent or suitable color purity.
[0199] The light-emitting element ED of one or more embodiments including the polycyclic compound according to one or more embodiments can exhibit high efficiency and long life properties. The light-emitting element ED including the polycyclic compound of one or more embodiments having excellent or suitable luminous efficiency and improved material stability in the light-emitting layer can exhibit high luminous efficiency and excellent or suitable life properties.
[0200] In the light emitting element ED according to one or more embodiments, the light emitting layer EML may be a delayed fluorescence light emitting layer including a host and a dopant. For example, the light emitting layer EML may emit thermally activated delayed fluorescence (TADF). The polycyclic compound of one or more embodiments may be a thermally activated delayed fluorescence dopant.
[0201] The light-emitting layer EML may include the polycyclic compound of one or more embodiments as a dopant. The polycyclic compound of one or more embodiments may emit blue light. For example, the polycyclic compound of one or more embodiments may be a light-emitting material having a maximum light-emitting wavelength in a wavelength region of about 430 nm to about 490 nm. For example, the polycyclic compound of one or more embodiments may be a light-emitting material having a maximum light-emitting wavelength in a wavelength region of about 440 nm to about 470 nm.
[0202] In one or more embodiments, the light-emitting layer EML includes the polycyclic compound of one or more embodiments, and may include at least one selected from the second compound to the fourth compound. In one or more embodiments, the light-emitting layer EML may include a second compound represented by Formula HT-1. For example, the second compound may be used as a hole transport host material of the light-emitting layer EML.
[0203] Formula HT-1
[0204]
[0205] In formula HT-1, A 1 To A 8 can be independently N or CR 51 For example, A 1 To A 8 All can be CR 51 In one or more embodiments, selected from A 1 To A 8 Any one of them can be N, and A 1 To A 8 The rest of them can be independently CR 51 .
[0206] In formula HT-1, L 1 It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 It may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group and / or a substituted or unsubstituted divalent carbazolyl group, but the present disclosure is not limited thereto.
[0207] In formula HT-1, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 For example, the two benzene rings of formula HT-1 connected to the nitrogen atom can be connected by a direct bond, In formula HT-1, if Y a is a direct bond, the second compound represented by Formula HT-1 may include a carbazole moiety.
[0208] 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, but the present disclosure is not limited thereto.
[0209] In formula HT-1, R 51 To R 55R and R are independently hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted silyl groups, substituted or unsubstituted sulfenyl groups, substituted or unsubstituted oxy groups, substituted or unsubstituted amine groups, substituted or unsubstituted boron groups, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 ring carbon atoms. In one or more embodiments, R 51 To R 55 In one or more embodiments, R 51 To R 55 In one or more embodiments, R 51 To R 55 Each may independently be an unsubstituted methyl group or an unsubstituted phenyl group.
[0210] In one or more embodiments, the second compound represented by Formula HT-1 may be represented by any one selected from among the compounds shown in Compound Group 2. The light emitting layer EML may include at least one selected from among the compounds shown in Compound Group 2.
[0211] Compound Group 2
[0212]
[0213]
[0214]
[0215] In the exemplary compounds presented in Compound Group 2, "D" may represent a deuterium atom, and "Ph" may represent a substituted or unsubstituted phenyl group. For example, in the exemplary compounds presented in Compound Group 2, "Ph" may be an unsubstituted phenyl group.
[0216] In one or more embodiments, the light emitting 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 of the light emitting layer EML.
[0217] Formula ET-1
[0218]
[0219] In formula ET-1, X 1 To X 3 At least one of them can be N, and X 1 To X 3 The rest of the CR56 For example, selected from X 1 To X 3 Any one of them can be N, and X 1 To X 3 The other two can be CR independently. 56 In this case, the third compound represented by Formula ET-1 may include a pyridine moiety. In one or more embodiments, the compound selected from X 1 To X 3 Two of them can be N, and X 1 To X 3 Another one of them can be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In one or more 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.
[0220] 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.
[0221] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.
[0222] In formula ET-1, Ar 2 To Ar 4 and R and R are independently hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 2 To Ar 4 Each of them independently may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.
[0223] In formula ET-1, L 2 To L 4 and L may be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, if b1 to b3 are integers of 2 or more, then L 2 To L 4Each 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.
[0224] In one or more embodiments, the third compound may be represented by any one of the compounds selected from the compound group 3. The light emitting element ED of one or more embodiments may include at least one of the compounds selected from the compound group 3.
[0225] Compound Group 3
[0226]
[0227]
[0228]
[0229]
[0230]
[0231]
[0232]
[0233] In the example compounds presented in Compound Group 3, "D" may represent a deuterium atom, and "Ph" may represent an unsubstituted phenyl group.
[0234] In some embodiments, the light-emitting layer EML includes a second compound and a third compound, wherein the second compound and the third compound may form an exciplex. In the light-emitting layer EML, a hole transport host and an electron transport host may form an exciplex. The triplet energy of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.
[0235] For example, the absolute value of the triplet energy level (T1) of the exciplex formed by the hole transport host and the electron transport host can be about 2.4 eV to about 3.0 eV. In some embodiments, the triplet energy level of the exciplex can have a value smaller than the energy gap of each host material. The exciplex can have a triplet energy level of 3.0 eV or less, which is the energy gap between the hole transport host and the electron transport host.
[0236] In one or more embodiments, in addition to the first to third compounds described above, the light emitting layer EML may further include a fourth compound. The fourth compound may be used as a phosphorescence sensitizer for the light emitting layer EML. Energy may be transferred from the fourth compound to the first compound to emit light.
[0237] For example, the light emitting layer EML may include platinum (Pt) as a central metal atom and may include an organic metal complex including a ligand bonded to the central metal atom as a fourth compound. In the light emitting element ED of one or more embodiments, the light emitting layer EML may include a compound represented by Formula D-1 as a fourth compound.
[0238] Formula D-1
[0239]
[0240] In formula D-1, Q 1 To Q 4 Each of C1 to C4 may independently be C or N. Each of C1 to C4 may independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.
[0241] In formula D-1, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 11 To L 13 In the figure, “-*” indicates the part connected to C1 to C4.
[0242] In formula D-1, b11 to b13 may be independently 0 or 1. If b11 is 0, C1 and C2 may not be connected to each other. If b12 is 0, C2 and C3 may not be connected to each other. If b13 is 0, C3 and C4 may not be connected to each other.
[0243] In formula D-1, R 61 To R 66R and R are independently hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted silyl groups, substituted or unsubstituted sulfenyl groups, substituted or unsubstituted oxy groups, substituted or unsubstituted amine groups, substituted or unsubstituted boron groups, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 60 ring carbon atoms. In one or more embodiments, R 61 To R 66 In one or more embodiments, R 61 To R 66 Each may independently be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.
[0244] In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. In Formula D-1, if each of d1 to d4 is 0, the fourth compound may not be R 61 To R 64 If each of d1 to d4 is 4, and R 61 To R 64 If each of d1 to d4 is a hydrogen atom, it may be the same as the case where each of d1 to d4 is 0. If each of d1 to d4 is an integer of 2 or more, then R 61 To R 64 Each of the R 61 To R 64 At least one of may be different.
[0245] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring represented by any one selected from C-1 to C-4.
[0246]
[0247] 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 88Each may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and may optionally form a ring by bonding to an adjacent group (bonding to an adjacent group to form a ring).
[0248] In some embodiments, in C-1 to C-4, corresponds to a portion connected to Pt as the central metal atom, and "-*" corresponds to a portion connected to the adjacent ring groups C1 to C4 or the linking group L 11 To L 13 part of.
[0249] The light-emitting layer EML of one or more embodiments may include a first compound that is a polycyclic compound and at least one selected from the second compound to the fourth compound. For example, the light-emitting layer EML may include a first compound, a second compound, and a third compound. In the light-emitting layer EML, the second compound and the third compound form an exciplex, and energy may be transferred from the exciplex to the first compound to emit light.
[0250] In some embodiments, the light-emitting layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the light-emitting layer EML, the second compound and the third compound form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound to emit light. In one or more embodiments, the fourth compound may be a sensitizer. In the light-emitting element ED of one or more embodiments, the fourth compound included in the light-emitting layer EML may act as a sensitizer for transferring energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound used as an auxiliary dopant may accelerate the energy transfer to the first compound as a light-emitting dopant to increase the luminescence rate (e.g., efficiency) of the first compound. Therefore, the light-emitting layer EML of one or more embodiments may have improved or high luminous efficiency. In some embodiments, if the energy transfer to the first compound increases, the excitons formed in the light-emitting layer EML may emit (e.g., quickly emit) light without accumulating inside the light-emitting layer EML, so that the degradation of the light-emitting element ED may be reduced. Therefore, the light-emitting element ED of one or more embodiments may have an improved or high lifespan.
[0251] The light-emitting element ED of one or more embodiments includes all of the first compound, the second compound, the third compound, and the fourth compound, so that the light-emitting 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 light-emitting layer EML may concurrently (e.g., simultaneously) include the second compound and the third compound as two different hosts from each other, the first compound emitting delayed fluorescence, and the fourth compound including an organic metal complex, and thus may exhibit excellent or desired luminous efficiency properties.
[0252] In one or more embodiments, the fourth compound represented by Formula D-1 may be represented by any one selected from the compounds shown in Compound Group 4. The light emitting layer EML may include at least one selected from the compounds shown in Compound Group 4 as a sensitizing material.
[0253] Compound Group 4
[0254]
[0255]
[0256] In the specific example compounds presented in Compound Group 4, "D" represents a deuterium atom.
[0257] In the light-emitting element ED of one or more embodiments, if the light-emitting layer EML includes all the first compound, the second compound, and the third compound described above, 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, and the third compound. However, the present disclosure is not limited thereto. If the content (e.g., amount) of the first compound satisfies the above ratio, the energy transfer from the second compound and the third compound to the first compound can be increased, and thus the luminous efficiency and the element life can be increased.
[0258] In the light-emitting layer EML, the content (e.g., amount) of the second compound and the third compound may be a residual amount excluding the weight of the first compound described above. For example, in the light-emitting layer EML, the content (e.g., total content, total amount) of the second compound and the third compound may be about 95 wt % to about 99.9 wt % relative to the total weight of the first compound, the second compound, and the third compound.
[0259] A weight ratio of the second compound to the third compound in the total weight of the second compound and the third compound may be about 3:7 to about 7:3.
[0260] If the content (e.g., amount) of the second compound and the third compound satisfies the above ratio, the charge balance property in the light-emitting layer EML can be improved, so that the luminous efficiency and the element life can be increased. If the content (e.g., amount) of the second compound and the third compound is outside the above ratio range, the charge balance in the light-emitting layer EML may be destroyed, so that the luminous efficiency may be degraded and the element may be easily degraded.
[0261] If the light-emitting layer EML includes the fourth compound, the content (e.g., amount) of the fourth compound 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 in the light-emitting layer EML. However, the present disclosure is not limited thereto. If the content (e.g., amount) of the fourth compound satisfies the above content (e.g., amount), energy transfer from the host to the first compound as a light-emitting dopant may be increased, so that the luminescence ratio may be improved, and thus the luminous efficiency of the light-emitting layer EML may be improved. If the first compound, the second compound, the third compound, and the fourth compound included in the light-emitting layer EML satisfy the above content (e.g., amount) ratio range, excellent or appropriate luminous efficiency and long life may be achieved.
[0262] The light emitting layer EML may have a to about or about to about The light emitting layer EML may have a single-layer structure including a single layer formed of a single material, a single-layer structure including a single layer formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.
[0263] exist Figures 3 to 7 In the light emitting element ED of one or more embodiments shown in FIG. 1 , the light emitting layer EML may include the polycyclic compound of one or more embodiments as a dopant. Figures 3 to 7 In the light-emitting element ED of one or more embodiments shown in FIG. 1 , the light-emitting layer EML may include a first compound (which is a polycyclic compound of one or more embodiments), a second compound represented by formula HT-1, and a third compound represented by formula ET-1. Figures 3 to 7 In the light-emitting element ED of one or more embodiments shown in the figure, the light-emitting layer EML may include a first compound (which is a polycyclic compound of one or more embodiments), a second compound represented by formula HT-1, a third compound represented by formula ET-1, and a fourth compound represented by formula D-1.
[0264] In the light emitting element ED of one or more embodiments, the light emitting layer EML may further include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, Derivatives, dihydrobenzanthracene derivatives and / or benzo[9,10]phenanthrene derivatives. For example, the light emitting layer EML may further include anthracene derivatives or pyrene derivatives.
[0265] exist Figures 3 to 7 In the light emitting element ED of one or more embodiments shown in , the light emitting layer EML may include a host and a dopant, and the light emitting layer EML may further include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.
[0266] Formula E-1
[0267]
[0268] In formula E-1, R 31 To R 40 Each of them 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 may optionally form a ring by bonding to an adjacent group (bonding to an adjacent group to form a ring). In one or more embodiments, R 31 To R 40 It may be bonded to an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.
[0269] In Formula E-1, c and d may each independently be an integer of 0 to 5.
[0270] Formula E-1 may be represented by any one of Compound E1 to Compound E19.
[0271]
[0272]
[0273] In one or more embodiments, the light emitting layer EML may further 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.
[0274] Formula E-2a
[0275]
[0276] In Formula E-2a, a may be an integer from 0 to 10, and L aIt may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, if a is an integer of 2 or more, then the plurality of L a L and L may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms (for example, when a is an integer of 2 or more, a plurality of L a Each of them 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).
[0277] In some embodiments, in Formula E-2a, A 1 To A 5 can be independently N or CR i . R a To R i Each may independently 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 10 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 may optionally form a ring by bonding to an adjacent group (bonding to an adjacent group to form a ring). R a To R i It may be bonded to an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O and / or S etc. as ring-constituting atoms.
[0278] In one or more embodiments, in formula E-2a, selected from A 1 To A 5 Two or three of them can be N, and A 1 To A 5 The rest of the 1 To A 5 Any remaining part of the i .
[0279] Formula E-2b
[0280]
[0281] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aromatic group having 6 to 30 ring carbon atoms. bIt may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. b may be an integer from 0 to 10, and if b is an integer of 2 or more, multiple L b L and L may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms (for example, when b is an integer of 2 or more, a plurality of L b Each of them 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).
[0282] The compound represented by formula E-2a or formula E-2b can be represented by any one of the compounds selected from compound group E-2. However, the compounds listed in compound group E-2 are only examples. The compound represented by formula E-2a or formula E-2b is not limited to the compounds listed in compound group E-2.
[0283] Compound Group E-2
[0284]
[0285]
[0286] The light emitting layer EML may further include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.
[0287] Formula Ma
[0288]
[0289] In the above formula, Y 1 To Y 4 and Z 1 To Z 4 Can be independently CR 1 or N, and R 1 To R 4Can be each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted sulfenyl 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 can optionally form a ring by bonding to an adjacent group (bonding to an adjacent group to form a ring). In formula Ma, m can be 0 or 1, and n can be 2 or 3. In formula Ma, if m is 0, n is 3 (e.g., when m is 0, n is 3), and if m is 1, n is 2 (e.g., when m is 1, n is 2).
[0290] The compound represented by the formula Ma may be used as a phosphorescent dopant.
[0291] The compound represented by formula Ma can be represented by any one selected from compound M-a1 to compound M-a25. However, compound M-a1 to compound M-a25 are only examples. The compound represented by formula Ma is not limited to the compounds represented by compound M-a1 to compound M-a25.
[0292]
[0293]
[0294]
[0295] The light emitting layer EML may further include a compound represented by any one selected from Formula Fa to Formula Fc. The compound represented by Formula Fa to Formula Fc may be used as a fluorescent dopant material.
[0296] Formula
[0297]
[0298] In the formula Fa, R a To R j Two of them can be independently *-NAr 1 Ar 2 Replace. a To R j Unrecognized*-NAr 1 Ar 2 The rest of the substitution (e.g., R a To R j Unrecognized*-NAr 1 Ar 2The remaining parts of the above-mentioned groups (including any remaining parts of the above-mentioned groups) 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.
[0299] In *-NAr 1 Ar 2 in Ar 1 and Ar 2 and Ar may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of may be a heteroaryl group containing O or S as a ring-forming atom.
[0300] Formula Fb
[0301]
[0302] In the above formula Fb, 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and may optionally form a ring by bonding to an adjacent group (bonding to an adjacent group to form a ring). Ar 1 To Ar 4 Each may independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0303] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of may be a heteroaryl group containing O or S as a ring-forming atom.
[0304] In Formula Fb, the number of rings represented by U and V may each independently be 0 or 1. For example, in Formula Fb, if the number of U or V is 1, one ring at the portion indicated by U or V forms a condensed ring at the designated portion (e.g., when the number of U or V is 1, one ring at the portion indicated by U or V forms a condensed ring at the designated portion), and if the number of U or V is 0, no ring exists at the portion indicated by U or V (e.g., when the number of U or V is 0, no ring exists at the portion indicated by U or V). For example, if the number of U is 0 and the number of V is 1, or the number of U is 1 and the number of V is 0, the condensed ring of the fluorene core having Formula Fb may be a tetracyclic compound (e.g., a ring compound having four rings) (e.g., when the number of U is 0 and the number of V is 1, or the number of U is 1 and the number of V is 0, the condensed ring of the fluorene core having Formula Fb may be a tetracyclic compound (e.g., a ring compound having four rings)). In some embodiments, if the number of U and the number of V are all 0, the condensed ring of the fluorene core of formula Fb can be a tricyclic compound (e.g., a ring compound having three rings) (e.g., when the number of U and the number of V are all 0, the condensed ring of the fluorene core of formula Fb can be a tricyclic compound (e.g., a ring compound having three rings)). In some embodiments, if the number of U and the number of V are all 1, the condensed ring of the fluorene core of formula Fb can be a pentacyclic compound (e.g., a ring compound having five rings) (e.g., when the number of U and the number of V are all 1, the condensed ring of the fluorene core of formula Fb can be a pentacyclic compound (e.g., a ring compound having five rings)).
[0305] Formula Fc
[0306]
[0307] 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 11Each may 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 may optionally form a ring by bonding to an adjacent group (bonding to an adjacent group to form a ring).
[0308] In Formula Fc, A 1 and A 2 can each independently bind to a substituent of an adjacent ring to form a condensed ring. 1 and A 2 can be independently NR m , then A 1 Can be combined with R 4 or R 5 To form a ring (for example, when A 1 and A 2 can be independently NR m When A 1 Can be combined with R 4 or R 5 In some embodiments, A 2 Can be combined with R 7 or R 8 to form a ring.
[0309] In one or more embodiments, the light-emitting layer EML may also 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) and / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)-N-phenyl As suitable dopant materials (e.g., known in the art), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) and / or pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and / or 1,4-bis(N,N-diphenylamino)pyrene) can be used.
[0310] The light-emitting layer EML may further include a suitable phosphorescent dopant material (e.g., known in the art). For example, metal complexes including 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 phosphorescent dopants. For example, bis(4,6-difluorophenylpyridine-N,C2)picolinic acid iridium (III) (FIrpic), bis(2,4-difluorophenylpyridine)-tetrakis(1-pyrazolyl)borate iridium (III) (FIrpic), 6 ) and / or platinum octaethylporphyrin (PtOEP) may be used as the phosphorescent dopant. However, the present disclosure is not limited thereto.
[0311] The light-emitting layer EML may include a quantum dot material. The core of the quantum dot may be selected from a II-VI group compound, an I-II-VI group compound, a II-IV-VI group compound, an I-II-IV-VI group compound, a II-IV-V group compound, a III-VI group compound, an I-III-VI group compound, a III-V group compound, a III-II-V group compound, a IV-VI group compound, a group IV element, a group IV compound, and / or (e.g., any suitable) combination thereof.
[0312] The II-VI compound can 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 their (e.g., any suitable) mixtures (combinations)), ternary compounds (selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnS e, 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 (e.g., any suitable)).
[0313] III-VI compounds may include: binary compounds (such as In 2 S 3 and / or In 2 Se 3 ); ternary compounds (such as InGaS 3 and / or InGaSe 3); or any combination thereof.
[0314] The I-III-VI group compound can be selected from ternary compounds (selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and their (eg, any suitable) mixtures) or quaternary compounds (such as AgInGaS 2 or CuInGaS 2 ) among.
[0315] The III-V compound can 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 their (e.g., any suitable) mixtures), ternary compounds (selected from the group consisting of GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and their (e.g., any suitable) mixtures) and quaternary compounds (selected from the group consisting of GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb and their (e.g., any suitable) mixtures). In one or more embodiments, the III-V group compound may further include a II group metal. For example, InZnP or the like may be selected as the III-II-V group compound.
[0316] 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 (e.g., any suitable) mixture thereof), a ternary compound (selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and (e.g., any suitable) mixture thereof) and a quaternary compound (selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and (e.g., any suitable) mixture thereof). The IV group element may be selected from the group consisting of Si, Ge and (e.g., any suitable) mixture thereof. The IV group compound may be a binary compound selected from the group consisting of SiC, SiGe and (e.g., any suitable) mixture thereof.
[0317] Each element included in the multi-element compound (such as a binary compound, a ternary compound, and / or a quaternary compound) may be present in the particle in a substantially uniform or non-uniform concentration distribution. For example, the chemical formula represents the type (species) of the element included in the compound, and the ratio of the elements in the compound may be different. For example, AgInGaS 2 Can refer to AgIn x Ga 1-x S 2 (where x is a real number between 0 and 1).
[0318] In one or more embodiments, the quantum dot may have a single layer structure in which the concentration of each element included in the quantum dot is substantially uniform. Alternatively, the quantum dot may have a core-shell structure in which the material included in the core may be different from the material included in the shell.
[0319] The shell of the quantum dot can be used as a protective layer to prevent or reduce chemical deformation of the core to maintain semiconductor properties and / or as a charged layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.
[0320] Examples of quantum dot shells may include metal or non-metal oxides, semiconductor compounds, and / or (e.g., any suitable) combinations thereof. 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 and / or NiO); or ternary compounds (such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and / or CoMn 2 O 4 ), but the present disclosure is not limited thereto.
[0321] In addition, 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 the present disclosure is not limited thereto.
[0322] Each element included in a multi-component compound (such as a binary compound or a ternary compound) may be present in the particle in a substantially uniform or non-uniform concentration distribution. For example, a chemical formula refers to the type (species) of elements included in the compound, and the ratio of elements in the compound may be different.
[0323] The quantum dots can 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 can improve color purity or color reproducibility within the above range. In some embodiments, the light emitted by such quantum dots is emitted in all directions, and therefore, a wide viewing angle can be improved.
[0324] In some embodiments, the form of quantum dots is not particularly 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 nanosheets, etc. can be used.
[0325] When adjusting the size of the quantum dots or adjusting the ratio of elements in the quantum dot compound, the energy band gap can be controlled, so that light within one or more suitable wavelength ranges can be obtained in the quantum dot light-emitting layer. Therefore, when using the quantum dots described above (using different sizes of quantum dots or different ratios of elements in quantum dot compounds), a light-emitting element that emits light of one or more suitable wavelengths can be realized. For example, the size of the quantum dots or the adjustment of 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, quantum dots can be configured to emit white light by combining one or more suitable colors of light.
[0326] exist Figures 3 to 7 In each of the light emitting elements ED of the embodiment shown in , the electron transport region ETR is disposed on the light emitting 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 present disclosure is not limited thereto.
[0327] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure including a plurality of layers formed of a plurality of different materials.
[0328] 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 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 the corresponding order of description from the light-emitting layer EML, but the present disclosure is not limited thereto. The electron transport region ETR may have, for example, about to about Thickness.
[0329] The electron transport region ETR may be formed using one or more suitable methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser induced thermal imaging (LITI) method.
[0330] The electron transport region ETR may include a compound represented by Formula ET-2.
[0331] Formula ET-2
[0332]
[0333] In formula ET-2, selected from X 1 To X3 At least one of them may be N, and the rest (X 1 To X 3 Any remaining part of ) may be independently CR a . R a 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 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.
[0334] In Formula ET-2, a to c may each independently be an integer from 0 to 10. In Formula ET-2, L 1 To L 3 and L are independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, if a to c are independently an integer of 2 or more, then L 1 To L 3 may be each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms (for example, when a to c may each independently be an integer of 2 or more, L 1 To L 3 Each of them 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).
[0335] The electron transport region ETR may include an anthracene compound. However, the present disclosure is 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 (Bp hen), 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 (tBu-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 (e.g., any suitable) mixtures thereof.
[0336] The electron transport region ETR may include at least one selected from compounds ET1 to ET36.
[0337]
[0338]
[0339]
[0340] In some embodiments, the electron transport region ETR may include: a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI and / or KI; a lanthanide metal such as Yb; or a co-deposited material of a metal halide and a lanthanide metal. For example, the electron transport region ETR may include KI:Yb, RbI:Yb and / or LiF:Yb as a co-deposited material. In one or more embodiments, the electron transport region ETR may utilize a metal halide such as Li 2 The electron transport region ETR may be formed by a mixed material of an electron transport material and an insulating organic metal salt. The organic metal salt may be a material having a band gap of about 4 eV or more. For example, the organic metal salt may include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate and / or a metal stearate.
[0341] In addition to the above materials, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1) and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the present disclosure is not limited thereto.
[0342] The electron transport region ETR may include one or more selected from the above-described compounds in 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.
[0343] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about 100 Å. to about (For example, about to about ) thickness. If the thickness of the electron transport layer ETL satisfies the above range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about to about (For example, about to about If the thickness of the electron injection layer EIL satisfies the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0344] The second electrode EL2 is disposed on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the present disclosure is not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode EL2 may be a cathode (for example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode), and if the first electrode EL1 is a cathode, the second electrode EL2 may be an anode (for example, when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode).
[0345] The second electrode EL2 may be a transmissive electrode, a transflective electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) and / or indium tin zinc oxide (ITZO), etc.).
[0346] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W or a compound thereof or a mixture thereof (e.g., AgMg, AgYb or MgYb) or a material having a multilayer structure including two or more selected therefrom (such as LiF / Ca or LiF / Al). In one or more embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the above materials and a transparent conductive film formed of ITO, IZO, ZnO and / or ITZO, etc. For example, the second electrode EL2 may include one or more selected from the above metal materials, a combination of at least two of the above metal materials, and an oxide of the above metal materials, etc.
[0347] In some embodiments, the second electrode EL2 may be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
[0348] In one or more embodiments, the cap layer CPL may be further disposed on the second electrode EL2 of the light emitting element ED of one or more embodiments. The cap layer CPL may include a plurality of layers or a single layer.
[0349] In one or more embodiments, the cap layer CPL may be an organic layer or an inorganic layer. For example, if the cap layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (eg, LiF), an alkaline earth metal compound (eg, MgF 2 )、SiON、SiN x and / or SiO y etc. (For example, when the cap layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (for example, LiF), an alkaline earth metal compound (for example, MgF 2 )、SiON、SiN x and / or SiO y wait).
[0350] For example, if the cap layer CPL includes an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), epoxy resin and / or acrylate such as methacrylate, etc. (for example, when the cap layer CPL includes an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), epoxy resin and / or acrylate such as methacrylate, etc.). However, the present disclosure is not limited thereto, and the cap layer CPL may include at least one selected from compounds P1 to P5.
[0351]
[0352] In one or more embodiments, the refractive index of the cap layer CPL may be about 1.6 or greater. For example, with respect to light in a wavelength range of about 550 nm to about 660 nm, the refractive index of the cap layer CPL may be about 1.6 or greater.
[0353] Figures 8 to 11 Each of them is a cross-sectional view of a display device according to one or more embodiments disclosed. Figures 8 to 11 When describing the display device of the embodiment, the description of the display device already described is omitted. Figures 1 to 7 Instead of repeating the features described in , we will focus on describing their differences.
[0354] Reference Figure 8 , the display device DD-a according to one or more embodiments may include a display panel DP including a display element layer DP-ED, a light control layer CCL and a color filter layer CFL arranged on the display panel DP. Figure 8 In one or more embodiments shown in , the display panel DP may include a base layer BS, a circuit layer DP-CL and a display element layer DP-ED disposed on the base layer BS, and the display device layer DP-ED may include a light emitting element ED.
[0355] The light emitting element ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, a light emitting layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the light emitting layer EML, and a second electrode EL2 disposed on the electron transport region ETR. In one or more embodiments, the above-described Figures 3 to 7 The structure of the light emitting element ED can also be applied to Figure 8 The structure of the light emitting element ED shown in FIG. Figure 8The light emitting element ED shown in the embodiment may include the polycyclic compound of one or more embodiments. Therefore, the light emitting element ED can exhibit high luminous efficiency and long life properties. In some embodiments, the light emitting element ED of one or more embodiments can exhibit high luminous efficiency properties and high color purity. The light emitting element ED of one or more embodiments can exhibit high luminous efficiency properties in the blue light emission region.
[0356] Reference Figure 8 , the light-emitting layer EML may be arranged in the opening OH defined in the pixel defining layer PDL. For example, the light-emitting layer EML divided by the pixel defining layer PDL and arranged corresponding to each light-emitting region 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 light-emitting layer EML may emit blue light. In one or more embodiments, unlike the configuration shown in the drawings, in one or more embodiments, the light-emitting layer EML may be arranged as a common layer in the entire light-emitting regions PXA-R, PXA-G, and PXA-B.
[0357] The light control layer CCL may be arranged on the display panel DP. Although the light control layer CCL is shown as being arranged above the display element layer DP-ED, the present disclosure is not limited thereto, and the light control layer CCL may be arranged below the display element layer DP-ED. The light control layer CCL may include a light converter. The light converter may be a quantum dot and / or a phosphor, etc. The light converter may convert the wavelength of the provided light and then emit light (e.g., emit light of different colors). For example, the light control layer CCL may be a layer containing quantum dots or a layer containing phosphors.
[0358] 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 spaced apart (eg, spaced apart or separated) from each other.
[0359] Reference Figure 8 , the partition pattern BMP may be disposed between the light-controlling portions CCP1 , CCP2 , and CCP3 that are spaced apart and / or separated (eg, spaced apart or separated) from each other, but the present disclosure is not limited thereto. Figure 8 It is shown that the partition pattern BMP does not overlap the light-controlling portions CCP1 , CCP2 , and CCP3 , but in some embodiments, at least a portion of the edges of the light-controlling portions CCP1 , CCP2 , and CCP3 may overlap the partition pattern BMP.
[0360] The light control layer CCL may include a first light control part CCP1, a second light control part CCP2 and a third light control part CCP3, the first light control part CCP1 includes a first quantum dot QD1 that converts a first color light provided from the light emitting element ED into a second color light, the second light control part CCP2 includes a second quantum dot QD2 that converts the first color light into a third color light, and the third light control part CCP3 transmits the first color light.
[0361] In one or more embodiments, the first light control part CCP1 may provide red light as the second color light, and the second light control part CCP2 may provide green light as the third color light. The third light control part 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. With respect to the quantum dots QD1 and QD2, the same as described above may apply.
[0362] In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control portion CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control portion CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control portion CCP3 may not include (e.g., may exclude) any quantum dot but may include a scatterer SP.
[0363] 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 A mixture of at least two materials selected from the group consisting of quartz and hollow spherical silica.
[0364] The first light control part CCP1, the second light control part CCP2 and the third light control part CCP3 may each include base resins BR1, BR2 and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In one or more embodiments, the first light control part CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control part CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control part CCP3 may include scatterers SP dispersed in the third base resin BR3.
[0365] The matrix resins BR1, BR2 and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and can be formed by one or more suitable resin components that can generally be referred to as adhesives. For example, the matrix resins BR1, BR2 and BR3 can be one or more acrylic resins, urethane resins, (poly)siloxane resins and / or epoxy resins, etc. The matrix resins BR1, BR2 and BR3 can be transparent resins. In one or more embodiments, the first matrix resin BR1, the second matrix resin BR2 and the third matrix resin BR3 can be the same as or different from each other.
[0366] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter, referred to as moisture / oxygen). The barrier layer BFL1 may block or reduce the exposure of the light control parts CCP1, CCP2, and CCP3 to moisture / oxygen. In one or more embodiments, the barrier layer BFL1 may cover the light control parts CCP1, CCP2, and CCP3. In some embodiments, the barrier layer BFL2 may be disposed between the light control parts CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3.
[0367] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 may include an inorganic material. For example, the barrier layers BFL1 and BFL2 may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride and / or a metal film ensuring transmittance, etc. In one or more embodiments, the barrier layers BFL1 and BFL2 may also include an organic film. The barrier layers BFL1 and BFL2 may be formed of a single layer or a plurality of layers.
[0368] In the display device DD-a of one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be directly disposed on the light control layer CCL. In this case, the blocking layer BFL2 may not be provided.
[0369] 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 and / or a dye. The first filter CF1 may include a red pigment and / or a red dye, the second filter CF2 may include a green pigment and / or a green dye, and the third filter CF3 may include a blue pigment and / or a blue dye.
[0370] In one or more embodiments, the present disclosure is not limited thereto, and the third filter CF3 may not include (e.g., may exclude) (e.g., any) pigment and / or dye. The third filter CF3 may include a polymerized photosensitive resin, and may not include (e.g., may exclude (e.g., any)) pigment and / or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.
[0371] Furthermore, in one or more embodiments, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may not be separated but provided as one filter.
[0372] In some embodiments, the color filter layer CFL may further include a light shielding portion. The light shielding portion may be a black matrix. The light shielding portion may include an organic light shielding material or an inorganic light shielding material containing a black pigment and / or dye. The light shielding portion may prevent or reduce light leakage and may separate the boundaries between adjacent filters CF1, CF2, and CF3. In addition, in one or more embodiments, the light shielding portion may be formed by a blue filter.
[0373] The first filter CF1, the second filter CF2, and the third filter CF3 may be arranged corresponding to the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B, respectively.
[0374] The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member that provides a base surface on which the color filter layer CFL and / or the light control layer CCL, etc. are disposed. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the present disclosure is 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 shown in the drawings, the base substrate BL may not be provided.
[0375] Fig. 9 is a cross-sectional view showing a portion of a display device DD-TD according to one or more embodiments. In the display device DD-TD according to one or more embodiments, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. At least one selected from the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 may include a polycyclic compound of one or more embodiments. Therefore, the light-emitting element ED-BT may exhibit high efficiency and long life properties. In some embodiments, the light-emitting element ED-BT of one or more embodiments may exhibit high luminous efficiency properties and high color purity, and for example, the light-emitting element ED-BT of one or more embodiments may exhibit high luminous efficiency properties in a blue light emission region.
[0376] 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 between the first electrode EL1 and the second electrode EL2 in a thickness direction. The light emitting structures OL-B1, OL-B2 and OL-B3 may each include a light emitting layer EML ( Figure 8 ) and the hole transport region HTR ( Figure 8 ) and the electron transport region ETR ( Figure 8 ) and the light emitting layer EML is located between the hole transport region HTR and the electron transport region ETR. For example, the light emitting element ED-BT included in the display device DD-TD of one or more embodiments may be a light emitting element having a tandem structure and including a plurality of light emitting layers.
[0377] exist Fig. 9 In one or more embodiments shown in , all lights (e.g., light beams) emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may be blue light. However, the present disclosure is not limited thereto, and the lights (e.g., 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, a 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.
[0378] The charge generation layers CGL1 and CGL2 may be disposed between adjacent light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may include a p-type or similar charge generation layer and / or an n-type or similar charge generation layer.
[0379] Reference Fig.10 , 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 light-emitting layers are stacked. At least one of the light-emitting elements ED-1, ED-2 and ED-3 may include the polycyclic compound of one or more embodiments. Therefore, the light-emitting elements ED-1, ED-2 and ED-3 may exhibit high luminous efficiency and long life properties. In some embodiments, the light-emitting elements ED-1, ED-2 and ED-3 of one or more embodiments may exhibit high light efficiency properties with high color purity. For example, the light-emitting element ED-3 of one or more embodiments may exhibit high luminous efficiency properties in the blue light emission region.
[0380] and Figure 2 Compared with the display device DD of one or more embodiments shown in FIG. Fig.10 The display device DD-b shown in FIG. 1 is different in that the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 each include two light-emitting layers stacked in the thickness direction. In each of the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, the two light-emitting layers can emit light in substantially the same wavelength region.
[0381] The first light-emitting element ED-1 may include a first red light-emitting layer EML-R1 and a second red light-emitting layer EML-R2. The second light-emitting element ED-2 may include a first green light-emitting layer EML-G1 and a second green light-emitting layer EML-G2. In some embodiments, the third light-emitting element ED-3 may include a first blue light-emitting layer EML-B1 and a second blue light-emitting layer EML-B2. The emission auxiliary part OG may be arranged between the first red light-emitting layer EML-R1 and the second red light-emitting layer EML-R2, between the first green light-emitting layer EML-G1 and the second green light-emitting layer EML-G2, and between the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2.
[0382] The emission auxiliary part OG may include a single layer or multiple layers. The emission auxiliary part OG may include a charge generation layer. For example, the emission auxiliary part OG may include an electron transport region, a charge generation layer, and a hole transport region stacked in sequence. The emission auxiliary part OG may be set as a common layer in the entire first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3. However, the present disclosure is not limited thereto, and the emission auxiliary part OG may be set by patterning within an opening OH defined in the pixel defining layer PDL.
[0383] The first red light emitting layer EML-R1, the first green light emitting layer EML-G1, and the first blue light emitting layer EML-B1 may be disposed between the electron transport region ETR and the emission auxiliary portion OG. The second red light emitting layer EML-R2, the second green light emitting layer EML-G2, and the second blue light emitting layer EML-B2 may be disposed between the emission auxiliary portion OG and the hole transport region HTR.
[0384] For example, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red light-emitting layer EML-R2, an emission auxiliary portion OG, a first red light-emitting 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 light-emitting layer EML-G2, an emission auxiliary portion OG, a first green light-emitting 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 light-emitting layer EML-B2, an emission auxiliary portion OG, a first blue light-emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in sequence.
[0385] In one or more embodiments, the optical auxiliary layer PL may be arranged on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be arranged on the display panel DP and control light reflected in the display panel DP due to external light. Unlike the configuration shown in the drawings, the optical auxiliary layer PL in the display device DD-b according to one or more embodiments may not be provided.
[0386] and Fig. 9 and Fig.10 different, Fig.11The display device DD-c is shown to include 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 opposite to each other and a first light emitting structure OL-C1, a second light emitting structure OL-B1, a third light emitting structure OL-B2 and a fourth light emitting structure OL-B3 sequentially stacked between the first electrode EL1 and the second electrode EL2 in the thickness direction. At least one selected from the first light emitting structure OL-C1, the second light emitting structure OL-B1, the third light emitting structure OL-B2 and the fourth light emitting structure OL-B3 may include a polycyclic compound of one or more embodiments. Therefore, the light emitting element ED-CT may exhibit high luminous efficiency and long life properties. In some embodiments, the light emitting element ED-CT of one or more embodiments may exhibit high luminous efficiency properties and high color purity. For example, the light emitting element ED-CT of one or more embodiments may exhibit high luminous efficiency properties in a blue light emission region.
[0387] The charge generation layers CGL1, CGL2, and CGL3 may be disposed between the first light emitting structure OL-C1, the second light emitting structure OL-B1, the third light emitting structure OL-B2, and the fourth light emitting structure OL-B3. Among the four light emitting structures, the second light emitting structure OL-B1, the third light emitting structure OL-B2, and the fourth light emitting structure OL-B3 may emit blue light, and the first light emitting structure OL-C1 may emit green light. However, the present disclosure is not limited thereto, and the first light emitting structure OL-C1, the second light emitting structure OL-B1, the third light emitting structure OL-B2, and the fourth light emitting structure OL-B3 may emit light beams in different wavelength regions. The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include p-type or p-type charge generation layers and / or n-type or n-type charge generation layers.
[0388] In one or more embodiments, the electronic device may include a display device including a plurality of light emitting elements and a control portion for controlling the display device. The electronic device of one or more embodiments may be a device activated according to an electrical signal. The electronic device may include a display device of one or more suitable embodiments. For example, the electronic device may include not only large electronic devices such as televisions, monitors, and / or outdoor billboards, but also small and medium-sized electronic devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, and / or cameras.
[0389] Fig.12is a view showing a vehicle AM in which a first display device DD-1, a second display device DD-2, a third display device DD-3, and a fourth display device DD-4 are arranged. At least one selected from among the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may include a reference Figure 1 , Figure 2 , Figures 8 to 11 The same configuration of the display devices DD, DD-a, DD-TD, DD-b, and DD-c according to one or more embodiments described (for example, the same configuration as that of the reference Figure 1 , Figure 2 , Figures 8 to 11 The configurations of the display devices DD, DD-a, DD-TD, DD-b, and DD-c described according to one or more embodiments are the same configuration).
[0390] Fig.12 A vehicle AM is shown, but this is an example, and the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may be arranged in another means of transport such as a bicycle, a motorcycle, a train, a ship, and an airplane. In some embodiments, at least one of the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 selected from the display devices DD, DD-TD, DD-a, DD-b, and DD-c including the same construction as 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 embodiments, and therefore may be used in other electronic devices unless departing from the present disclosure.
[0391] At least one selected from the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may include a reference Figures 3 to 7 The light-emitting element ED described. At least one selected from the first display device DD-1, the second display device DD-2, the third display device DD-3 and the fourth display device DD-4 may include the polycyclic compound of one or more embodiments. Therefore, the first display device DD-1, the second display device DD-2, the third display device DD-3 and the fourth display device DD-4 including the polycyclic compound of one or more embodiments may have improved display efficiency and display life. In some embodiments, the first display device DD-1, the second display device DD-2, the third display device DD-3 and the fourth display device DD-4 including the polycyclic compound of one or more embodiments may exhibit excellent or suitable display quality.
[0392] Reference Fig.12 , the vehicle AM may include a steering wheel HA and a gear GR for driving the vehicle AM. In some embodiments, the vehicle AM may include a front window GL arranged to face the driver.
[0393] The first display device DD-1 may be arranged in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital cluster that displays first information of the vehicle AM. The first information may include a first scale indicating the driving speed of the vehicle AM, a second scale indicating the engine speed (i.e., revolutions per minute (RPM)), and / or an image indicating the fuel status, etc. The first scale and the second scale may be indicated as digital images.
[0394] The second display device DD-2 can be arranged in a second area opposite to the driver's seat and superimposed with the front window GL. The driver's seat can be a seat where a steering wheel HA is arranged. For example, the second display device DD-2 can be a head-up display (HUD) that displays the second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a number indicating the driving speed, and can also include information such as the current time. In some embodiments, unlike the configuration shown in the accompanying drawings, the second information of the second display device DD-2 can be projected onto the front window GL to be displayed.
[0395] The third display device DD-3 may be arranged in a third area adjacent to the vehicle GR. For example, the third display device DD-3 may be arranged between the driver's seat and the passenger seat, and may be a central information display (CID) for the vehicle for displaying the third information. The passenger seat may be a seat that is spaced and / or separated (e.g., spaced or separated) from the driver's seat and the vehicle GR is arranged between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), playing music or wireless broadcasting or video (or images), and / or the temperature inside the vehicle AM, etc.
[0396] The fourth display device DD-4 may be spaced and / or separated (e.g., spaced or separated) from the steering wheel HA and the gear GR, and may be arranged in a fourth area adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an image of the outside of the vehicle AM taken by a camera module CM arranged outside the vehicle AM. The fourth information may include an image of the outside of the vehicle AM.
[0397] The above-mentioned first to fourth information may be examples, and the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may also display information about the interior and exterior of the vehicle AM. The first to fourth information may include different information. However, the present disclosure is not limited thereto, and part of the first to fourth information may include the same information as each other.
[0398] Hereinafter, with reference to examples and comparative examples, the polycyclic compound according to one or more embodiments of the present disclosure and the light-emitting element of one or more embodiments will be described in more detail. In addition, the examples shown below are only for illustrative purposes, so as to understand the present disclosure, and therefore, the scope of the present disclosure is not limited thereto.
[0399] Example
[0400] 1. Synthesis of polycyclic compounds of the embodiments
[0401] The method for synthesizing the polycyclic compound according to the present embodiment will be described in more detail with reference to the method for synthesizing compounds 25, 26, 29, 30, 41, 44, 57, and 61. In addition, the method for synthesizing the polycyclic compound described in more detail below is only an example, and the method for synthesizing the compound according to one or more embodiments of the present disclosure is not limited to the following example.
[0402] (1) Method for synthesizing intermediates
[0403] Methods for synthesizing intermediates utilized in the synthesis examples of polycyclic compounds according to one or more embodiments will be described with reference to Reaction Formulas M1 to M14.
[0404] Synthesis of intermediate M1
[0405] Intermediate M1 can be synthesized through the steps of reaction formula M1.
[0406] Reaction M1
[0407]
[0408] 10 g of 1-bromocarbazole, 13 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 8.8 g of potassium acetate (KOAc) and 1.2 g of Pd(dppf)Cl 2Put into 500mL three-necked flask, and the inside of flask is replaced (for example, filled) with argon (Ar). After that, 200mL of dioxane is added to the flask, and stirred at 80°C for 5 hours. The reaction solution obtained after the reaction is concentrated by evaporator, and then organic matter is dissolved by toluene to remove inorganic matter by silica gel pad. After that, the crude product is concentrated by evaporator, and purified by silica gel column (ethyl acetate / hexane=1 / 3 volume ratio) to obtain 11g of white solid. The obtained solid is measured by FAB-MS and confirmed to be 293m / z, so it is confirmed as the intermediate M1 as the target (for example, expected product).
[0409] Synthesis of intermediate M2
[0410] Intermediate M2 can be synthesized through the steps of reaction formula M2.
[0411] Reaction M2
[0412]
[0413] 10 g of 1-bromo-3,6-di-tert-butylcarbazole, 9.2 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 6.0 g of potassium acetate (KOAc) and 0.82 g of Pd(dppf)Cl 2 Add to 500mL three-necked flask, and the inside of flask is replaced with argon (Ar). After that, add 140mL of dioxane thereto, and stir for 5 hours at 80 ℃. Utilize evaporator to concentrate the reaction solution obtained after the reaction, and then utilize toluene to dissolve organic matter to utilize silica gel pad to remove inorganic matter. After that, utilize evaporator to concentrate crude product, and utilize silica gel column (ethyl acetate / hexane=1 / 3 volume ratio) to purify to obtain 11g of white solid. Obtained solid is measured by FAB-MS and confirmed as 405m / z, therefore confirmed as intermediate M2 as target.
[0414] Synthesis of intermediate M3
[0415] Intermediate M3 can be synthesized through the steps of reaction formula M3.
[0416] Reactive M3
[0417]
[0418] 10 g of intermediate M1, 10 g of 4-bromo-2,3,5,6-tetrafluorocyanobenzene, and 16 g of potassium carbonate (K 2 CO 3 ) and 4.5 g of Pd(PPh 3 ) 4Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar).After this, add 200mL of tetrahydrofuran (THF) and 100mL of water and stir 5 hours while heating and refluxing.Utilize toluene to extract organic layer from the reaction solution obtained, wash with water, and utilize anhydrous magnesium sulfate drying to filter out (for example, obtain) solid, utilize evaporator to concentrate the organic layer.After this, utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) to purify crude product to obtain 8g of light yellow solid.Measure the solid obtained by FAB-MS and confirm as 340m / z, thus confirm as target intermediate M3.
[0419] Synthesis of intermediate M4
[0420] Intermediate M4 can be synthesized through the steps of reaction formula M4.
[0421] Reactive M4
[0422]
[0423] 9.2 g of intermediate M1, 8.0 g of 1,3-dibromo-2,4,5,6-tetrafluorobenzene, and 13 g of potassium carbonate (K 2 CO 3 ) and 3.8 g of Pd(PPh 3 ) 4 Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar).After this, add 160mL of THF and 80mL of water and stir 5 hours while heating and refluxing.Utilize toluene to extract organic layer from the reaction solution obtained, wash with water, and then utilize anhydrous magnesium sulfate drying to filter out solid, utilize evaporator to concentrate the organic layer.After this, utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) to purify crude product to obtain 10g of white solid.Measure the solid obtained by FAB-MS and confirm as 394m / z, thus confirm as target intermediate M4.
[0424] Synthesis of intermediate M5
[0425] Intermediate M5 can be synthesized through the steps of reaction formula M5.
[0426] Reactive M5
[0427]
[0428] 11 g of intermediate M2, 7.0 g of 4-bromo-2,3,5,6-tetrafluorocyanobenzene, 11 g of potassium carbonate (K 2 CO 3 ) and 3.2 g of Pd(PPh 3 )4 Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar).After this, add 140mL of THF and 70mL of water and stir 5 hours while heating and refluxing.Utilize toluene to extract organic layer from the reaction solution obtained, wash with water, and then utilize anhydrous magnesium sulfate drying to filter out solid, utilize evaporator to concentrate the organic layer.After this, utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) to purify crude product to obtain the light yellow solid of 10g.Measure the solid obtained by FAB-MS and confirm as 453m / z, thus confirm as target intermediate M5.
[0429] Synthesis of intermediate M6
[0430] Intermediate M6 can be synthesized through the steps of reaction formula M6.
[0431] Reactive M6
[0432]
[0433] 6.4 g of intermediate M1, 10 g of 2-(4-bromo-2,3,5,6-tetrafluorophenyl)-4,6-diphenyl-1,3,5-triazine, 9.0 g of potassium carbonate (K 2 CO 3 ) and 2.5 g of Pd(PPh 3 ) 4 Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar).After this, add 100mL of THF and 50mL of water and stir 5 hours while heating and refluxing.Utilize toluene to extract organic layer from the reaction solution obtained, wash with water, and then utilize anhydrous magnesium sulfate drying to filter out solid, utilize evaporator to concentrate the organic layer.After this, utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) to purify crude product to obtain the light yellow solid of 10g.Measure the solid obtained by FAB-MS and confirm as 547m / z, thus confirm as target intermediate M6.
[0434] Synthesis of intermediate M7
[0435] Intermediate M7 can be synthesized through the steps of reaction formula M7.
[0436] Reactive M7
[0437]
[0438] 10 g of intermediate M4, 8.4 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 5.5 g of potassium acetate (KOAc) and 0.74 g of Pd(dppf)Cl 2 Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar). After that, 130mL of dioxane is added thereto, and stirred at 80 ℃ for 5 hours. The reaction solution obtained is concentrated by evaporator, and then organic matter is dissolved by toluene to remove inorganic matter by silica gel pad. After that, the crude product is concentrated by evaporator, and purified by silica gel column (ethyl acetate / hexane=1 / 3 volume ratio) to obtain 11g of white solid. The solid obtained is measured by FAB-MS and confirmed to be 441m / z, thereby confirming the intermediate M7 as the target.
[0439] Synthesis of intermediate M8
[0440] Intermediate M8 can be synthesized through the steps of reaction formula M8.
[0441] Reactive M8
[0442]
[0443] 11 g of intermediate M7, 6.5 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 10 g of potassium carbonate (K 2 CO 3 ) and 2.8 g of Pd(PPh 3 ) 4 Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar).After this, add 120mL of THF and 60mL of water and stir 5 hours while heating and refluxing.Utilize toluene to extract organic layer from the reaction solution obtained, wash with water, and then utilize anhydrous magnesium sulfate drying to filter out solid, utilize evaporator to concentrate the organic layer.After this, utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) purification crude product to obtain 11g of light yellow solid.Measure the solid obtained by FAB-MS and confirm as 547m / z, thus confirm as target intermediate M8.
[0444] Synthesis of intermediate M9
[0445] Intermediate M9 can be synthesized through the steps of reaction formula M9.
[0446] Reactive M9
[0447]
[0448] 10 g of 1-bromo-3-chlorocarbazole, 12 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 7.7 g of potassium acetate (KOAc) and 1.0 g of Pd(dppf)Cl 2 Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar). After that, 180mL of dioxane is added thereto, and stirred at 80 ℃ for 5 hours. Utilize evaporator to concentrate the reaction solution obtained, and then utilize toluene to dissolve organic matter to utilize silica gel pad to remove inorganic matter. Utilize evaporator to concentrate the corresponding crude product, and utilize silica gel column (ethyl acetate / hexane=1 / 3 volume ratio) to purify to obtain 7.9g of white solid. Measure the obtained solid by FAB-MS and confirm as 328m / z, thereby confirm as the intermediate M9 of target.
[0449] Synthesis of intermediate M10
[0450] Intermediate M10 can be synthesized through the steps of reaction formula M10.
[0451] Reactive M10
[0452]
[0453] 5.0 g of 1-bromo-2,3,4,5,6-pentafluorobenzene, 6.6 g of intermediate M9, 8.4 g of potassium carbonate (K 2 CO 3 ) and 2.3 g of Pd(PPh 3 ) 4 Put into 300mL three-necked flask, and the inside of flask is replaced with argon (Ar).After this, add 100mL of THF and 50mL of water to it and stir 5 hours while heating and refluxing.Utilize toluene to extract organic layer from the reaction solution obtained, wash with water, and then utilize anhydrous magnesium sulfate drying.The solid obtained is filtered and then concentrated using evaporator.Utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) to purify the corresponding crude product to obtain 7.1g of light yellow solid.Measure the solid obtained by FAB-MS and confirm as 452m / z, thus confirm as target intermediate M10.
[0454] Synthesis of intermediate M11
[0455] Intermediate M11 can be synthesized through the steps of reaction formula M11.
[0456] Reactive M11
[0457]
[0458] 7.1 g of intermediate M10 and 40 mL of N-methylpyrrolidone (NMP) were added to a 100 mL three-necked flask, and then 12 g of K 3 PO 4 , and the mixture was stirred for 4 hours while being heated at 160°C. The obtained reaction solution was cooled to room temperature, water was added, and then stirred for 10 minutes, and a saline solution and dichloromethane were added thereto. Thereafter, the organic layer was extracted with dichloromethane, washed with water, and dried with anhydrous magnesium sulfate. The obtained solid was filtered and then concentrated with an evaporator. Thereafter, the crude product was recrystallized with toluene and ethanol to obtain 4.3g of a white solid. The obtained solid was confirmed to be 348m / z by FAB-MS measurement, thereby confirming the intermediate M11 as the target.
[0459] Synthesis of intermediate M12
[0460] Intermediate M12 can be synthesized through the steps of reaction formula M12.
[0461] Reactive M12
[0462]
[0463] 2.0 g of intermediate M11, 8.5 g of K 4 [Fe(CN) 6 ], 9.8 g of sodium carbonate and 0.4 g of Pd(amphos) 2 Cl 2 Put into 100mL three-necked flask, and the inside of flask is replaced with argon (Ar).After that, add 60mL of dimethylacetamide (DMA) to it and stir 5 hours while heating at 140 ℃.Utilize dichloromethane to extract organic layer from the reaction solution obtained, wash with water, and then utilize anhydrous magnesium sulfate drying to filter out solid, utilize evaporator to concentrate the organic layer.Utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) to filter the corresponding crude product to obtain 1.4g of light yellow solid.Confirm that the solid obtained is 338m / z by FAB-MS measurement, thus confirm as the target intermediate M12.
[0464] Synthesis of intermediate M13
[0465] Intermediate M13 can be synthesized through the steps of reaction formula M13.
[0466] Reactive M13
[0467]
[0468] 2.0 g of intermediate M11, 1.9 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.2 g of potassium acetate (KOAc), 52 mg of Pd(OAc) 2 0.21g of XPhos was put into a 100mL three-necked flask, and the interior of the flask was replaced with argon (Ar). Thereafter, 30mL of dioxane was added thereto and stirred at 120°C for 5 hours. The reaction solution obtained was concentrated using an evaporator, and then organic matter was dissolved using toluene to remove inorganic matter using a silica gel pad. The corresponding crude product was concentrated using an evaporator, and filtered using a silica gel column (ethyl acetate / hexane=1 / 3 volume ratio) to obtain 1.7g of a white solid. The solid obtained was confirmed to be 439m / z by FAB-MS measurement, thereby confirming the intermediate M13 as the target.
[0469] Synthesis of intermediate M14
[0470] Intermediate M14 can be synthesized through the steps of reaction formula M14.
[0471] Reactive M14
[0472]
[0473] 1.6 g of intermediate M13, 1.0 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.5 g of potassium carbonate (K 2 CO 3 ) and 0.43 g of Pd(PPh 3 ) 4 Put into 500mL three-necked flask, and the inside of flask is replaced with argon (Ar), and 20mL of THF and 10mL of water are added thereto and stirred for 5 hours while heating and refluxing. Utilize toluene to extract organic layer from the reaction solution obtained, wash with water, and then utilize anhydrous magnesium sulfate drying to filter out solid, utilize evaporator to concentrate the organic layer. Utilize silica gel column (ethyl acetate / hexane=1 / 2 volume ratio) to filter the corresponding crude product to obtain 1.7g of light yellow solid. Confirm that the solid obtained is 545m / z by FAB-MS measurement, thus confirm the intermediate M14 as the target.
[0474] (2) Synthesis of Compound 25 and Compound 41
[0475] The polycyclic compound 25 and the polycyclic compound 41 according to one or more embodiments may be synthesized, for example, through the steps of Reaction Formula 1.
[0476] Reaction 1
[0477]
[0478] 3.3g of carbazole and 220mL of NMP are put into a 500mL three-necked flask, and then 1.1g of NaH is added thereto while being immersed in ice, and then 3.6g of intermediate M8 is added thereto. Next, after the mixture is stirred at room temperature for 2 hours, the temperature is raised to 180°C, and the mixture is stirred for 4 hours. The reaction solution obtained is cooled to room temperature, water is added, and then stirred for 10 minutes, and a saline solution and dichloromethane are added thereto. Thereafter, the organic layer is extracted with dichloromethane, washed with water, and then dried with anhydrous magnesium sulfate to filter out solids, and the organic layer is concentrated with an evaporator. Next, the crude product is recrystallized with toluene and ethanol to obtain 8g of a yellow solid. The solid obtained is measured by FAB-MS and confirmed to be 968m / z, so as to obtain a mixture of compound 25 and compound 41. Thereafter, compound 25 and compound 41 are separated using preparative HPLC, and 1.3g of compound 25 and 3.9g of compound 41 are obtained. Thereafter, each compound was purified by sublimation and used for the evaluation of its properties.
[0479] (3) Synthesis of Compound 26
[0480] The polycyclic compound 26 according to one or more embodiments may be synthesized, for example, through the steps of Reaction Scheme 2.
[0481] Reaction 2
[0482]
[0483] 3.3g of carbazole and 220mL of NMP are put into a 500mL three-necked flask, and then 1.1g of NaH is added thereto while being immersed in ice, and then 3.6g of intermediate M6 is added thereto. Afterwards, the mixture is stirred at room temperature for 2 hours, and then stirred for 4 hours while heating and refluxing. The reaction solution obtained is cooled to room temperature, and then water is added, and stirred for 10 minutes. Next, saline solution and dichloromethane are added thereto, and then the organic layer is extracted with dichloromethane, washed with water, and then dried with anhydrous magnesium sulfate. Afterwards, the solid is filtered and then concentrated with an evaporator. Next, the crude product is recrystallized with toluene and ethanol to obtain 4.5g of yellow solid. The solid obtained is measured by FAB-MS and confirmed to be 968m / z, thereby confirming the compound 26 as the target. Afterwards, the compound is purified by sublimation, and is used for the evaluation of its properties.
[0484] (4) Synthesis of Compound 29
[0485] The polycyclic compound 29 according to one or more embodiments can be synthesized, for example, through the steps of Reaction Scheme 3.
[0486] Reaction 3
[0487]
[0488] 5.4g of carbazole and 360mL of THF are added to a 500mL three-necked flask, and then 1.7g of NaH is added thereto while being immersed in ice, and then 3.6g of intermediate M3 is added thereto. Next, the mixture is stirred at room temperature for 2 hours, and then stirred for 4 hours while heating and refluxing. The reaction solution obtained is cooled to room temperature, water is added, and then stirred for 10 minutes, and a saline solution and dichloromethane are added thereto. Thereafter, the organic layer is extracted with dichloromethane, washed with water, and then dried over anhydrous magnesium sulfate. Next, the solid is filtered and then concentrated using an evaporator. The crude product obtained is recrystallized using toluene and ethanol to obtain 8g of a yellow solid. The solid obtained is measured by FAB-MS and confirmed to be 762m / z, thereby confirming the compound 29 as the target. Thereafter, the compound is purified by sublimation and is used for the evaluation of its properties.
[0489] (5) Synthesis of Compound 30
[0490] The polycyclic compound 30 according to one or more embodiments may be synthesized, for example, through the steps of Reaction Formula 4.
[0491] Reaction 4
[0492]
[0493] 10g of 3,6-diphenylcarbazole and 360mL of THF were added to a 500mL three-necked flask, and then 1.7g of NaH was added thereto while being immersed in ice, and then 3.6g of intermediate M3 was added thereto. Next, the mixture was stirred at room temperature for 2 hours, and then stirred for 4 hours while heating and refluxing. The reaction solution obtained was cooled to room temperature, water was added, and then stirred for 10 minutes, and a saline solution and dichloromethane were added thereto. Thereafter, the organic layer was extracted with dichloromethane, washed with water, and then dried over anhydrous magnesium sulfate. The solid was filtered and then concentrated using an evaporator. Next, the crude product was recrystallized using toluene and ethanol to obtain 7.4g of a yellow solid. The solid obtained was measured by FAB-MS and confirmed to be 762m / z, thereby confirming the target compound 30. Thereafter, the compound was purified by sublimation and used for the evaluation of its properties.
[0494] (6) Synthesis of Compound 44
[0495] The polycyclic compound 44 according to one or more embodiments may be synthesized, for example, through the steps of Reaction Scheme 5.
[0496] Reaction 5
[0497]
[0498] 6.7g of 3,6-di-tert-butylcarbazole and 270mL of THF were added to a 500mL three-necked flask, and then 1.3g of NaH was added thereto while being immersed in ice, and then 3.6g of intermediate M5 was added thereto. Next, the mixture was stirred at room temperature for 2 hours, and then stirred for 4 hours while heating and refluxing. The reaction solution obtained was cooled to room temperature, water was added, and then stirred for 10 minutes, and a saline solution and dichloromethane were added thereto. Thereafter, the organic layer was extracted with dichloromethane, washed with water, and then dried with anhydrous magnesium sulfate to filter out the solid, and the organic layer was concentrated with an evaporator. Next, the crude product was recrystallized with toluene and ethanol to obtain 6.2g of a yellow solid. The solid obtained was measured by FAB-MS and confirmed to be 1211m / z, thereby confirming the target compound 44. Thereafter, the compound was purified by sublimation and used for the evaluation of its properties.
[0499] (7) Synthesis of Compound 57
[0500] The polycyclic compound 57 according to one or more embodiments may be synthesized, for example, through the steps of Reaction Scheme 6.
[0501] Reaction 6
[0502]
[0503] 2.8 g of carbazole and 140 mL of dimethylformamide (DMF) were placed in a 300 mL three-necked flask, and 3.5 g of K 3 PO 4 And 1.4g of intermediate M12. After that, the mixture was stirred for 4 hours while heating. The reaction solution obtained was cooled to room temperature, water was added, and then stirred for 10 minutes, and a saline solution and dichloromethane were added thereto. After that, the organic layer was extracted with dichloromethane, washed with water, and then dried over anhydrous magnesium sulfate, and the obtained solid was filtered, and then the organic layer was concentrated using an evaporator. The crude product obtained was recrystallized using toluene and ethanol to obtain 2.0g of a yellow solid. The solid obtained was confirmed to be 927m / z by FAB-MS measurement, thereby confirming the target compound 57. After that, the compound was purified by sublimation and used for the evaluation of its properties.
[0504] (8) Synthesis of Compound 61
[0505] The polycyclic compound 61 according to one or more embodiments may be synthesized, for example, through the steps of Reaction Scheme 7.
[0506] Reaction 7
[0507]
[0508] 2.1 g of carbazole and 110 mL of DMF were added to a 300 mL three-necked flask, and then 2.7 g of K 3 PO 4 Afterwards, 1.7g of intermediate M14 was added thereto. Afterwards, the mixture was stirred for 4 hours while being heated at 160°C. The reaction solution obtained was cooled to room temperature, water was added, and then stirred for 10 minutes, and a saline solution and dichloromethane were added thereto, and the organic layer was extracted with dichloromethane. Afterwards, the extracted organic layer was washed with water, and then dried over anhydrous magnesium sulfate, and the solid was filtered, and then the organic layer was concentrated using an evaporator. Afterwards, the crude product was recrystallized using toluene and ethanol to obtain 1.4g of a yellow solid. The solid obtained was confirmed to be 1133m / z by FAB-MS measurement, thereby confirming the target compound 61. Afterwards, the compound was purified by sublimation and used for the evaluation of its properties.
[0509] 2. Evaluation of polycyclic compounds
[0510] The polycyclic compounds used in the examples and comparative examples are shown in Table 1.
[0511] Table 1
[0512]
[0513]
[0514]
[0515] The results of evaluating the luminescent properties of the polycyclic compounds used in the examples and comparative examples are shown in Table 2. The maximum luminescent wavelength (PLλ) of the luminescent spectrum of each compound max), fluorescence quantum yield (PLQY), Z stimulus value, blue fluorescence efficiency index and half-maximum full width (FWHM) are evaluated and shown in Table 2. The maximum emission wavelength and half-maximum full width of the luminescent properties of the examples and comparative examples were measured under an inert gas atmosphere using an F-7000 fluorescence spectrophotometer manufactured by Hitachi High-Tech. The fluorescence quantum yield was measured using Quantaurus QY manufactured by Hamamatsu Photonics. In addition, the Z stimulus value of the CIE equation function (color matching function) at the maximum emission wavelength, a value based on the CIE1931 color space was used. The blue fluorescence efficiency index corresponds to a value defined as the product of the fluorescence quantum yield and the Z stimulus value at each maximum emission wavelength. The spectral luminescence of each material is relatively compared by the value of the blue fluorescence efficiency index. The evaluation of the luminescent properties of the compounds shown in Table 2 was performed in the toluene solution state of the example compound and the comparative example compound.
[0516] Table 2
[0517]
[0518] Referring to Table 2, the exemplified polycyclic compounds are confirmed to emit blue light having a maximum emission wavelength of about 470 nm or less. When compared with the comparative exemplified compounds, the exemplified compounds exhibit high fluorescence quantum yield properties and high blue luminescence efficiency index properties. In addition, when compared with the comparative exemplified compounds, the exemplified compounds exhibit narrow half-maximum full width properties.
[0519] For example, when considering the evaluation results of the luminescent properties of the compounds, it can be seen that, compared with the comparative example compounds, the example compounds including an indolecarbazole core, a cyano group or a triazine group and multiple carbazole groups (wherein the multiple carbazole groups are all bonded to one aromatic (benzene) ring) exhibit high luminescent efficiency, excellent or suitable color properties and high color purity properties.
[0520] 3. Manufacturing and evaluation of light-emitting components
[0521] (1) Manufacturing of light-emitting elements
[0522] Light-emitting elements including one or more polycyclic compounds of the embodiments or including comparative example compounds in the light-emitting layer were manufactured in the following manner. The polycyclic compounds of one or more embodiments were used as dopant materials for the light-emitting layer to manufacture light-emitting elements of Examples 1 to 8, respectively. Comparative Example Compounds X1 to X7 were used as dopant materials for the light-emitting layer to manufacture light-emitting elements of Comparative Examples 1 to 7, respectively.
[0523] As the first electrode, the glass substrate patterned with ITO was ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes each. After ultrasonic cleaning, UV irradiation was performed for 30 minutes, and ozone treatment was performed. Thereafter, a hole transport region was formed by sequentially depositing HAT-CN to a thickness of about 10 nm, Tris-PCz to a thickness of about 30 nm, and mCBP to a thickness of about 5 nm.
[0524] Next, the example compound or comparative example compound and mCBP were co-deposited to form a light-emitting layer with a thickness of about 30 nm. The example compound or comparative example compound and mCBP were co-deposited at a weight ratio of 10:90. In the manufacture of the light-emitting element, the example compound or comparative example compound was used as a dopant material.
[0525] Thereafter, an electron transport region was formed by sequentially depositing SF3-TRZ to a thickness of about 10 nm, SF3-TRZ:Liq at a weight ratio of 50:50 to a thickness of about 20 nm, and Liq to a thickness of about 2 nm.
[0526] Next, Al was deposited to a thickness of about 100 nm to form a second electrode.
[0527] In the examples and comparative examples, the hole transport region, the light emitting layer, the electron transport region, and the second electrode were provided using a vacuum deposition apparatus.
[0528] The compounds used for production of the light-emitting element are as follows.
[0529] Materials used in the manufacture of light-emitting devices
[0530]
[0531] (2) Evaluation of light-emitting elements
[0532] Table 3 shows the evaluation of the light-emitting elements of the examples and the comparative examples. In Table 3, the maximum emission wavelength (λ max ), maximum external quantum yield (EQE max ), blue element efficiency index and relative element life. The blue element efficiency index is defined as the product of the maximum external quantum yield and the Z stimulus value at each maximum emission wavelength, and the Z stimulus value is the value of the CIE equation function (color matching function) at each maximum emission wavelength, and uses a value based on the CIE 1931 color space. The life is expressed as a relative element life, which is obtained by averaging each element at about 1000 cd / m 2 The time taken for the initial luminance to deteriorate by 50% during continuous driving of is obtained by comparing the time taken for the initial luminance to deteriorate by 50% of Comparative Example 1, the time taken for the initial luminance to deteriorate by 50% of Comparative Example 1 being set to 100%.
[0533] Table 3
[0534]
[0535]
[0536] Referring to the results of Table 3, the light-emitting element of the example is confirmed to emit blue light having a maximum emission wavelength of about 470 nm or less. In addition, when the evaluation properties of the blue element efficiency index are evaluated in consideration of the color properties, it can be seen that the light-emitting element of the example exhibits excellent or suitable efficiency properties compared to the light-emitting element of the comparative example. In addition, with respect to the relative element life, each of the examples exhibits excellent or suitable results compared to all the comparative examples.
[0537] For example, the example polycyclic compound used in the example light-emitting element of the present disclosure has a specific binding structure of indolecarbazole-triazine (or cyano)-carbazole (which is different from the structure of the comparative example), and therefore, compared with the compound of the comparative example, it can have excellent or suitable maximum external quantum yield, half-maximum full width and / or material stability and other properties, and the light-emitting element including the example polycyclic compound can also exhibit excellent or suitable luminous efficiency and element life properties.
[0538] The comparative example compound X1 utilized in comparative example 1 has a substituent binding property similar to that of the polycyclic compound of the example of the present disclosure, but differs in that the core portion as the central skeleton includes carbazole instead of indolecarbazole. Compared with the example compounds of the present disclosure, the comparative example compound X1 exhibits degraded properties in terms of fluorescence quantum yield and half-maximum full width. In addition, the comparative example compound X1 includes carbazole having a smaller number of condensed rings than indolecarbazole in the core portion, and therefore has greater central skeleton mobility, and is therefore more susceptible to material degradation, so that the light-emitting element of comparative example 1 including the comparative example compound X1 is considered to have exhibited degraded element life properties compared to the example light-emitting element.
[0539] Comparative Example Compound X2 and Comparative Example Compound X3 do not include a cyano group or a triazine group, which is an electron withdrawing group included (e.g., substantially included) in the exemplary compounds of the present disclosure. Therefore, Comparative Example Compound X2 and Comparative Example Compound X3 do not exhibit thermally activated delayed fluorescence (TADF) or have weaker TADF properties, and therefore, because triplet excitons are not effectively utilized for luminescence, lower maximum external quantum yield properties are exhibited. In addition, degradation occurs starting from triplet excitons, so that it is observed that the light-emitting elements of Comparative Examples 2 and Comparative Examples 3 exhibit degraded element life properties compared to the illustrated light-emitting elements.
[0540] The light-emitting element of comparative example 4 using comparative example compound X4 has a maximum light-emitting wavelength of about 505 nm, and thus exhibits light-emitting properties of light with a wavelength longer than blue light, and exhibits low element life properties compared to the examples. In the case of comparative example compound X4, it is believed that green light emission is shown because a strong charge separation state is formed in the carbazolyl group as an electron-donating group and the triazine group as an electron-withdrawing group. In addition, in the case of comparative example compound X4, the carbazolyl group is not directly substituted to the indole and carbazole core, and therefore, compared to the example compound, the effect of suppressing or reducing the rotational movement of the carbazolyl group is low, resulting in reduced material stability, so that it is observed that the life properties of the light-emitting element of comparative example 4 are also deteriorated.
[0541] Comparative Example Compound X5, Comparative Example Compound X6 and Comparative Example Compound X7 have a structure in which an electron withdrawing group and indole and carbazole are directly bonded, and due to such structural features, the charge separation state becomes suitable for blue light emission. However, compared with the example compounds, Comparative Example Compound X5, Comparative Example Compound X6 and Comparative Example Compound X7 exhibit low fluorescence quantum yield and wide half-maximum full width. Compared with the example compounds in which multiple carbazole groups are all bound to one ring to suppress or reduce the rotation of the carbazole group, in the case of Comparative Example Compound X5, Comparative Example Compound X6 and Comparative Example Compound X7, the movement of the carbazole group is not suppressed or reduced, so that it is observed that the light-emitting elements of Comparative Examples 5 to Comparative Examples 7 exhibit degraded external quantum efficiency and element life properties.
[0542] The polycyclic compound of one or more embodiments has a structure including a condensed ring core of indole and carbazole, at least one electron withdrawing group directly bonded to the condensed ring core, and a plurality of carbazole groups in one ring (a benzene ring) of the ring of the condensed ring core. The polycyclic compound of one or more embodiments can exhibit excellent or desired (high) luminous efficiency and excellent or desired (high) material stability properties. In addition, the polycyclic compound of one or more embodiments can be used as a thermally activated delayed fluorescent material. In addition, the light-emitting element of one or more embodiments including the polycyclic compound of one or more embodiments in the light-emitting layer exhibits excellent or desired luminous efficiency properties in the blue light emission region, and can exhibit long life properties.
[0543] The light-emitting element of one or more embodiments includes the polycyclic compound of one or more embodiments in a light-emitting layer, and thus can exhibit high light-emitting efficiency and long life properties.
[0544] The polycyclic compound of one or more embodiments may contribute to improvement in luminous efficiency and long lifetime of a light emitting element.
[0545] The display device of one or more embodiments may exhibit excellent or desired (high) display quality.
[0546] When describing embodiments of the present disclosure, the use of “may” refers to “one or more embodiments of the present disclosure”. As used herein, the term “and / or” includes any and all combinations of one or more of the relevant listed items. Throughout the disclosure, expressions such as “at least one selected from a, b, and c”, “at least one selected from the group consisting of a, b, and c”, “at least one among a, b, and c”, etc., mean only a, only b, only c, (e.g., simultaneously) both a and b, (e.g., simultaneously) both a and c, (e.g., simultaneously) both b and c, all of a, b, and c, or variations thereof.
[0547] As used herein, the terms "substantially," "about," and similar terms are used as terms of approximation rather than terms of degree, and are intended to take into account the inherent deviations of measured or calculated values that one of ordinary skill in the art will recognize. Taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., the limitations of the measurement system), "about" or "approximately" as used herein include the stated value and mean within an acceptable range of deviation of the specific value as determined by one of ordinary skill in the art. For example, "about" can mean within one or more standard deviations, or within ±30%, ±20%, ±10%, ±5% of the stated value.
[0548] Any numerical range described herein is intended to include all sub-ranges of the same numerical precision contained within the range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the minimum value 1.0 (and including the minimum value 1.0) and the maximum value 10.0 (and including the maximum value 10.0), that is, a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any sub-ranges contained within the range explicitly described herein.
[0549] Any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware, and hardware may be utilized to implement the electronic device, display device, and / or any other related device or component according to the embodiments of the present invention described herein. For example, the various components of the device may be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device may be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact with other system components for performing the various functions described herein. The computer program instructions are stored in a memory, which may be implemented in a computing device using a standard memory device (such as a random access memory (RAM) as an example). The computer program instructions may also be stored in other non-temporary computer-readable media (such as a CD-ROM, a flash drive, etc. as an example). In addition, it should be appreciated by those skilled in the art that, without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a specific computing device may be distributed to one or more other computing devices.
[0550] Although the present disclosure has been described with reference to example embodiments thereof, it will be understood by those skilled in the art that one or more suitable modifications and changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as set forth in the claims and their equivalents.
[0551] Therefore, 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.
[0552] Description of reference numerals or symbols
[0553] DD, DD-TD, DD-a, DD-b, DD-c: Display device
[0554] ED: Light-emitting element EL1: First electrode
[0555] EL2: second electrode EML: light emitting layer.
Claims
1. A light-emitting element, comprising: a first electrode; a second electrode, opposite to the first electrode; as well as A light emitting layer is between the first electrode and the second electrode and includes a first compound represented by Formula 1: Formula 1 Among them, in formula 1, R1 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, Selected from R1 to R 11 At least one of them is a first substituent, wherein the first substituent is selected from a cyano group or a substituted or unsubstituted triazine group, and Selected from R1 to R 11 Two or more of the remaining parts in are independently a second substituent, and the second substituent is a substituted or unsubstituted carbazolyl group.
2. The light-emitting element according to claim 1, wherein Formula 1 is represented by any one selected from Formula 1-1 to Formula 1-3: Formula 1-1 Formula 1-2 Formula 1-3 In Formula 1-1 to Formula 1-3, Sb1 is a cyano group or is represented by Formula 2, and Sb2 is represented by Formula 3, Ra to Rc are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n1 is 1, n2 is an integer selected from 1 to 3, and n3 is an integer selected from 1 to 4, m1 is 2 or 3, and m2 is an integer selected from 2 to 4, p1 is 0 or 1, p2 is an integer selected from 0 to 2, q is an integer selected from 0 to 2, and r is an integer selected from 0 to 3, and R5 to R 11 are independently the same as defined in Formula 1: Formula 2 Formula 3 In equation 2 and equation 3, W1, W2 and R 21 To R 28 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and and Each represents the position of bonding to the corresponding ring among Ar1 to Ar3.
3. The light-emitting element according to claim 2, wherein Formula 1-1 is represented by Formula 1-1a: Formula 1-1a Wherein, in Formula 1-1a, Sb1 and Sb2 are independently the same as defined in Formula 1-1, and R5 to R 11 are independently the same as defined in Formula 1.
4. The light-emitting element according to claim 2, wherein Formula 1-2 is represented by Formula 1-2a: Formula 1-2a Wherein, in Formula 1-2a, Sb1, Sb2 and Rb are independently the same as defined in Formula 1-2, and R8 to R 11 are independently the same as defined in Formula 1.
5. The light emitting element according to claim 1, wherein At least one hydrogen atom of the first compound is substituted with a deuterium atom.
6. The light-emitting element according to claim 1, wherein The light-emitting layer further includes at least one selected from a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1: Formula HT-1 In formula HT-1, A1 to A8 are independently N or CR 51 , L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a It is a direct key, CR 52 R 53 or SiR 54 R 55 , Ar1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 51 To R 55 are each 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and are optionally bonded to an adjacent group to form a ring; Formula ET-1 In formula ET-1, At least one selected from X1 to X3 is N, and the rest of X1 to X3 are CR 56 , R 56 is 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, b1 to b3 are each independently an integer selected from 0 to 10, Ar2 to Ar4 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, and L2 to L4 are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
7. The light-emitting element according to claim 6, wherein The light-emitting layer further comprises a fourth compound represented by formula D-1: Formula D-1 Wherein, in formula D-1, Q1 to Q4 are independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms, L 11 To L 13 Each is independently a direct key, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, b11 to b13 are independently 0 or 1, R 61 To R 66 are each 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, and d1 to d4 are each independently an integer selected from 0 to 4.
8. The light-emitting element according to claim 7, wherein The light emitting layer includes the first compound, the second compound, the third compound, and the fourth compound.
9. The light-emitting element according to claim 1, wherein The light-emitting layer emits delayed fluorescence.
10. The light emitting element according to claim 1, wherein The light-emitting layer emits blue light.
11. The light emitting element according to claim 1, wherein The first compound is represented by any one of the compounds selected from compound group 1: Compound Group 1 In compound group 1, d represents a deuterium atom.
12. The light emitting element according to claim 6, wherein The second compound is represented by any one of the compounds selected from Compound Group 2: Compound Group 2 However, in compound group 2, "D" represents a deuterium atom, and "Ph" represents a substituted or unsubstituted phenyl group.
13. The light emitting element according to claim 6, wherein The third compound is represented by any one of the compounds selected from compound group 3: Compound Group 3 However, in compound group 3, "D" represents a deuterium atom, and "Ph" represents an unsubstituted phenyl group.
14. The light emitting element according to claim 7, wherein The fourth compound is represented by any one of the compounds selected from compound group 4: Compound Group 4 However, in compound group 4, "D" represents a deuterium atom.
15. A polycyclic compound, the polycyclic compound being represented by Formula 1: Formula 1 in, In formula 1, R1 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, Selected from R1 to R 11 At least one of them is a first substituent, wherein the first substituent is selected from a cyano group or a substituted or unsubstituted triazine group, and Selected from R1 to R 11 Two or more of the remaining parts in are independently a second substituent, and the second substituent is a substituted or unsubstituted carbazolyl group.
16. The polycyclic compound according to claim 15, wherein Formula 1 is represented by any one selected from Formula 1-1 to Formula 1-3: Formula 1-1 Formula 1-2 Formula 1-3 In Formula 1-1 to Formula 1-3, Sb1 is a cyano group or is represented by Formula 2, and Sb2 is represented by Formula 3, Ra to Rc are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n1 is 1, n2 is an integer selected from 1 to 3, and n3 is an integer selected from 1 to 4, m1 is 2 or 3, and m2 is an integer selected from 2 to 4, p1 is 0 or 1, p2 is an integer selected from 0 to 2, q is an integer selected from 0 to 2, and r is an integer selected from 0 to 3, and R5 to R 11 are independently the same as defined in Formula 1: Formula 2 Formula 3 In equation 2 and equation 3, W1, W2 and R 21 To R 28 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and and Each represents the position of bonding to the corresponding ring among Ar1 to Ar3.
17. The polycyclic compound according to claim 16, wherein Formula 1-1 is represented by Formula 1-1a: Formula 1-1a Wherein, in Formula 1-1a, Sb1 and Sb2 are independently the same as defined in Formula 1-1, and R5 to R 11 are independently the same as defined in Formula 1.
18. The polycyclic compound according to claim 16, wherein Formula 1-2 is represented by Formula 1-2a: Formula 1-2a Wherein, in Formula 1-2a, Sb1, Sb2 and Rb are independently the same as defined in Formula 1-2, and R8 to R 11 are independently the same as defined in Formula 1.
19. The polycyclic compound according to claim 15, wherein R1 to R selected from Formula 1 11 At least one of them is deuterium or R1 to R 11 At least one hydrogen atom in the ions is replaced by a deuterium atom.
20. The polycyclic compound according to claim 15, wherein The polycyclic compound represented by Formula 1 is a blue light emitting dopant.
21. The polycyclic compound according to claim 15, wherein The polycyclic compound represented by Formula 1 is a thermally activated delayed fluorescent material.
22. The polycyclic compound according to claim 15, wherein The polycyclic compound is represented by any one of the compounds selected from Compound Group 1: Compound Group 1 In compound group 1, d represents a deuterium atom.
23. A display device, comprising: Base layer; A circuit layer, on the substrate layer; as well as A display element layer is on the circuit layer and includes a light-emitting element, wherein the light-emitting element includes a first electrode, a second electrode opposite to the first electrode, and a light-emitting layer between the first electrode and the second electrode, and the light-emitting layer includes a polycyclic compound represented by Formula 1: Formula 1 Among them, in formula 1, R1 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, Selected from R1 to R 11 At least one of them is a first substituent, wherein the first substituent is selected from a cyano group or a substituted or unsubstituted triazine group, and Selected from R1 to R 11 Two or more of the remaining parts in are independently a second substituent, and the second substituent is a substituted or unsubstituted carbazolyl group.
24. The display device according to claim 23, wherein: The light emitting element emits blue light.
25. The display device of claim 23, further comprising a light control layer comprising quantum dots.
Citation Information
Patent Citations
Controlled Reactivity Biocarbon Pellets
KR1020230131495A