Light-emitting element, polycyclic compound for light-emitting element, and display device including light-emitting element
The introduction of a polycyclic compound in the emission layer of light-emitting elements addresses efficiency and longevity issues in organic electroluminescent display devices, enhancing performance.
Patent Information
- Application Number
- CN202410793992.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-06-20
- Filing Date
- 2024-06-19
- Publication Date
- 2024-12-20
AI Technical Summary
Existing organic electroluminescent display devices face challenges in achieving improved light-emitting efficiency and service life of light-emitting elements.
Incorporation of a polycyclic compound represented by specific formulas in the emission layer of light-emitting elements, enhancing light-emitting efficiency and lifetime through optimized chemical structures.
The use of the polycyclic compound improves the light-emitting efficiency and extends the service life of the light-emitting elements in display devices.
Smart Images

Figure CN119161369A_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0079243 filed in the Korean Intellectual Property Office on June 20, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[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. Background Art
[0003] Recently, the development of organic electroluminescent display devices as image display devices is actively underway. Organic electroluminescent display devices and the like include so-called "self-luminescent" light-emitting elements, in which holes and electrons injected from a first electrode and a second electrode, respectively, are recombined in an emission layer of the display device. Subsequently, the light-emitting material of the emission layer (e.g., light-emitting layer) emits light to realize display (e.g., of an image).
[0004] The application of light-emitting elements to display devices requires, or desires or requires, light-emitting elements having improved light-emitting efficiency and / or improved service life, etc. Therefore, research and development of materials for light-emitting elements capable of stably obtaining such characteristics or desired properties are required, and such development is being continuously performed.
[0005] In recent years, in order to realize high-efficiency light-emitting elements, two research fields underway include technologies related to phosphorescent emission utilizing triplet energy or delayed fluorescence utilizing triplet-triplet annihilation (TTA) (for example, in which singlet excitons are generated by collision of triplet excitons). Another research field under development is thermally activated delayed fluorescence (TADF) materials utilizing the delayed fluorescence phenomenon. Summary of the invention
[0006] One or more aspects of the embodiments of the present disclosure relate to a light emitting element in which light emitting efficiency and lifetime are improved.
[0007] One or more aspects of an embodiment of the present disclosure relate to a polycyclic compound as a material for a light emitting element, the material improving light emitting efficiency and lifetime.
[0008] In some embodiments, the present disclosure also provides a display device including a light emitting element in which light emitting efficiency and service life are improved.
[0009] One or more embodiments of the present disclosure provide a light-emitting element, the light-emitting element comprising a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer comprises a first compound represented by Formula 1:
[0010] Formula 1
[0011]
[0012] In formula 1, X 1 It can be NR 8 , O or S. In Formula 1, R 1 To R 5 R may be independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms. 6 It may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms. 7 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and R 8 It may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. n1, n4 and n5 may each independently be an integer from 0 to 3, and n2 and n3 may each independently be an integer from 0 to 4.
[0013] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 2:
[0014] Formula 2
[0015]
[0016] In formula 2, R 11 , R 21 and R 31 R may be independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms. 12 , R 22 and R 32Each of n11 and n21 may be independently an integer from 0 to 3. In Formula 2, X 1 , R 4 To R 7 , n4 and n5 may all independently be the same as defined in Formula 1.
[0017] In one or more embodiments, R in Formula 2 12 , R 22 and R 32 At least one of them can be in a para-position relationship with the boron atom in Formula 2.
[0018] In one or more embodiments, the first compound represented by Formula 2 may be represented by any one selected from Formula 2-1 to Formula 2-3:
[0019] Formula 2-1
[0020]
[0021] Formula 2-2
[0022]
[0023] Formula 2-3
[0024]
[0025] In Formula 2-1 to Formula 2-3, X 1 , R 4 To R 7 , R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , n4, n5, n11, n21 and n31 may all independently be the same as defined in Formula 1 and Formula 2.
[0026] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 3 or Formula 4:
[0027] Formula 3
[0028]
[0029] Formula 4
[0030]
[0031] In equations 3 and 4, X 2 It can be NR i5 , O or S, and R i1 It may be a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. i2 and R i3 R may be independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms. i4 It may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, R i5 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and i1 may be an integer from 0 to 5. i2 and i3 may each independently be an integer from 0 to 3. In Formula 3 and Formula 4, X 1 , R 1 To R 6 and n1 to n5 may each independently be as defined in Formula 1.
[0032] In one or more embodiments, the first compound represented by Formula 3 may be represented by Formula 3-1 or Formula 3-2:
[0033] Formula 3-1
[0034]
[0035] Formula 3-2
[0036]
[0037] In formula 3-1 and formula 3-2, Y 1 Can be CR j4 R j5 NR j6 , O or S, and R j1 , R j2 and R j3 R may be each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. j4 , R j5 and R j6 may each independently be a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, and R j4 and R j5may be bonded to form a ring or may not be bonded. j1 may be an integer from 0 to 5, j2 may be an integer from 0 to 3, and j3 may be an integer from 0 to 4. X 1 , R 1 To R 5 , R i1 , n1 to n5 and i1 may each independently be as defined in Formula 1 and Formula 3.
[0038] In one or more embodiments, the first compound represented by Formula 4 may be represented by Formula 4-1 or Formula 4-2:
[0039] Formula 4-1
[0040]
[0041] Formula 4-2
[0042]
[0043] In formula 4-1 and formula 4-2, Y 2 and Y 3 Can be independently CR k7 R k8 NR k9 , O or S, and R k1 To R k6 R may be each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. k7 , R k8 and R k9 may each independently be a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, and R k7 and R k8 k1 and k2 may each independently be an integer from 0 to 5, k3 and k5 may each independently be an integer from 0 to 3, and k4 and k6 may each independently be an integer from 0 to 4. In Formula 4-1 and Formula 4-2, X 1 , X 2 , R 1 To R 5 , R i2 , R i3 , n1 to n5, i2 and i3 may all be independently defined as in Formula 1 and Formula 4.
[0044] In one or more embodiments, as described in more detail elsewhere herein, in the first compound represented by Formula 1, R 6 It may be represented by any one of the substituents selected from Substituent Group 1.
[0045] In one or more embodiments, X is selected from Formula 1 1 and R 1 To R 7 At least one of them may be a deuterium atom or may include a substituent including a deuterium atom.
[0046] In one or more embodiments, R 1 , R 2 and R 3 Each of them independently may be a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.
[0047] In one or more embodiments, the emission layer may also include at least one of a second compound represented by formula HT-1 to be described later, a third compound represented by formula ET-1 to be described later, and a fourth compound represented by formula D-1 as described in more detail elsewhere herein.
[0048] In one or more embodiments, the emission layer may include a first compound, a second compound, and a third compound.
[0049] In one or more embodiments, the emission layer may include a first compound, a second compound, a third compound, and a fourth compound.
[0050] In one or more embodiments of the present disclosure, the polycyclic compound is represented by Formula 1 as described herein.
[0051] In one or more embodiments of the present disclosure, a display device includes: a base layer; a circuit layer disposed on the base layer; and a display device layer disposed on the circuit layer and including a light-emitting element, wherein the light-emitting element includes a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode, and the emission layer includes at least one of a first compound represented by Formula 1 as described herein and a second compound represented by Formula HT-1 as described in more detail elsewhere herein, a third compound represented by Formula ET-1 as described in more detail elsewhere herein, and a fourth compound represented by Formula D-1 as described in more detail elsewhere herein. BRIEF DESCRIPTION OF THE DRAWINGS
[0052] 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 example embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure. In the drawings:
[0053] Figure 1 is a plan view showing a display device according to one or more embodiments of the present disclosure;
[0054] Figure 2 It shows that along Figure 1 A cross-sectional view of a portion taken along line II';
[0055] Figure 3 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0056] Figure 4 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0057] Figure 5 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0058] Figure 6 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0059] Figure 7 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0060] Figure 8 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure;
[0061] Fig. 9 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure;
[0062] Fig.10 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure;
[0063] Fig.11 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure; and
[0064] Fig.12 is a view showing the interior of a vehicle in which a display device according to one or more embodiments of the present disclosure is provided. DETAILED DESCRIPTION
[0065] The present disclosure can be modified in one or more suitable ways and has many forms, so specific embodiments will be illustrated in the drawings and described in more detail in the detailed description of the present disclosure. However, it should be understood that it is not intended to limit the present disclosure to the specific forms disclosed, but is intended to cover all modifications, equivalents and substitutes falling within the spirit and scope of the present disclosure.
[0066] When explaining each of the drawings, the same reference numerals are used to refer to the same elements, and repeated description thereof may not be provided. In the drawings, the size of each structure is exaggeratedly shown for clarity of the present disclosure.
[0067] It will be understood that, although the terms "first" and / or "second" etc. may be used herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only used to distinguish one component from another component. For example, without departing from the scope of the exemplary embodiments of the present disclosure, the first component may be named as the second component, and similarly, the second component may be named 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.
[0068] In the present application, it will be understood that the terms "comprises", "includes", "has" and / or their variations indicate the existence of the features, quantities, steps, operations, components, parts or combinations thereof disclosed in the specification, but do not exclude the possibility of the existence or addition of one or more other features, quantities, steps, operations, components, parts or combinations thereof.
[0069] As utilized herein, the term "use" and variations thereof may be considered synonymous with the term "utilize" and variations thereof, respectively.
[0070] As utilized herein, expressions such as “at least one of,” “one of,” “selected from,” and “selected from” when preceding (preceding) a list of elements modify the entire list of elements and do not modify the individual elements of the list. For example, the expressions “at least one of a through c” and “at least one of a, b, and c” may mean only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all of a, b, and c, or variations thereof.
[0071] The term "and / or" includes all combinations of one or more of the associated listed elements.
[0072] For ease of description, terms such as "below (lower part)", "above..." and / or "on (upper part)" are used herein to describe the relationship between one element and another (other) element as shown in the drawings. The terms are relative concepts and are described based on the directions shown in the drawings. It will be understood that the terms have relative concepts and are described based on the orientations depicted in the drawings. It will be understood that the spatially relative terms are intended to cover different orientations of the device in use or operation other than the orientation depicted in the drawings. For example, if the device in the drawings is turned over, the element described as "below" other elements or features will then be positioned as "above" or "on" the other elements or features. Therefore, the term "below..." can cover both the above and below orientations. The device can be positioned otherwise (rotated 90 degrees or in other orientations), and the spatially relative descriptive terms used herein should be interpreted accordingly.
[0073] As used herein, the term "may" will be understood to refer to "one or more embodiments of the present disclosure," some of which include the described elements, and some of which exclude the elements and / or include alternative elements. Similarly, alternative language such as "or" refers to "one or more embodiments of the present disclosure" that all include the corresponding listed items.
[0074] Unless otherwise defined, all terms (including chemical terms, technical terms, and scientific terms) utilized herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present disclosure belongs. It will also be understood that terms (such as those defined in general dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and will not be interpreted in an idealized or overly formal sense, unless explicitly so defined herein.
[0075] As utilized herein, the phrase "consisting essentially of" means that any additional components will not substantially affect the chemical, physical, optical, or electrical properties of the semiconductor film.
[0076] As utilized herein, the phrase “on a plane” or “plan view” refers to viewing a target portion from the top, and the phrase “on a cross-section” means viewing a cross-section formed by vertically cutting the target portion from the side.
[0077] In the present disclosure, "not including one or any 'component'", "excluding one or any 'component'" and / or "no 'component'" etc. means that the 'component' is not added, selected or used as a component in the composition, but due to other impurities and / or external factors, less than the appropriate amount of the 'component' may still be included.
[0078] definition
[0079] In the present application, when a layer, film, region or plate is referred to as being "on" another layer, film, region or plate or "in the upper portion of" another layer, film, region or plate, the layer, film, region or plate may not only be "directly on" the other layer, film, region or plate, but also there may be intervening layers, films, regions or plates. In contrast, when a layer, film, region or plate is referred to as being "below" another layer, film, region or plate 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 also there may be intervening layers, films, regions or plates. In some embodiments, it will be understood that when a part is referred to as being "on" another part, the part may be disposed above the other part, or may also be disposed below the other part.
[0080] In the specification, the term "substituted or unsubstituted" may refer to being unsubstituted or being substituted by at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino (amino group), a silyl group, an oxy group, a sulfenyl group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In certain embodiments, each of the substituents exemplified herein may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.
[0081] 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 some embodiments, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.
[0082] 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 positioned closest to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. In some embodiments, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.
[0083] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
[0084] In the specification, the alkyl group may be a straight chain or a branched chain. The number of carbon atoms in the alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl , n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heonicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl and / or n-triacontyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0085] In the specification, cycloalkyl may refer to a cyclic alkyl. The carbon number in the cycloalkyl is 3 to 50, 3 to 30, 3 to 20 or 3 to 10. Examples of cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl and / or bicycloheptyl, but embodiments of the present disclosure are not limited thereto.
[0086] In the specification, alkenyl refers to a hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be straight chain or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but is 2 to 30, 2 to 20 or 2 to 10. Examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl and / or styryl vinyl, etc., but embodiments of the present disclosure are not limited thereto.
[0087] In the specification, alkynyl refers to a hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 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 is 2 to 30, 2 to 20, or 2 to 10. Specific examples of the alkynyl group may include ethynyl and / or propynyl, etc., but are not limited thereto.
[0088] 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.
[0089] 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 embodiments of the present disclosure are not limited thereto.
[0090] 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 substituted fluorenyl groups are as follows. However, embodiments of the present disclosure are not limited thereto.
[0091]
[0092] Heterocyclic groups herein refer to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si and Se as a heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups can be monocyclic or polycyclic.
[0093] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si and S as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and includes a heteroaryl group. The number of ring carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.
[0094] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si and S as a heteroatom. The number of ring carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, an oxirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thianyl group, a tetrahydropyranyl group and / or a 1,4-dioxane group, etc., but the embodiments of the present disclosure are not limited thereto.
[0095] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si and S as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothirolyl and / or dibenzofuranyl, but embodiments of the present disclosure are not limited thereto.
[0096] In the specification, the previous description of the aryl group may be applied to the arylene group except that the arylene group is a divalent group. The previous description of the heteroaryl group may be applied to the heteroarylene group except that the heteroarylene group is a divalent group.
[0097] 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.
[0098] In the specification, the number of ring-forming carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but embodiments of the present disclosure are not limited thereto.
[0099]
[0100] 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.
[0101] In the specification, thio groups may include alkylthio groups and arylthio groups. A thio group may refer to a sulfur atom bonded to an alkyl group or an aryl group as defined herein. Examples of thio groups may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, naphthylthio, but embodiments of the present disclosure are not limited thereto.
[0102] In the specification, an oxy group may refer to an oxygen atom bonded to an alkyl group or an aryl group as defined herein. The oxy group may include an alkoxy group and an aryloxy group. The alkoxy group may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms in the alkoxy group is not 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.
[0103] Boryl herein may refer to a boron atom bonded to an alkyl or aryl group as defined herein. Boryl includes alkyl boryl and aryl boryl. Examples of boryl may include dimethyl boryl, tert-butyl methyl boryl, diphenyl boryl and / or phenyl boryl, etc., but embodiments of the present disclosure are not limited thereto.
[0104] In the specification, the number of carbon atoms in the amine group is not particularly limited, but can 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 embodiments of the present disclosure are not limited thereto.
[0105] In the specification, the alkyl group among the alkylthio group, the alkylsulfinyl group, the alkylsulfonyl group, the alkylaryl group, the alkoxy group, the alkylamino group, the alkylboryl group, the alkylsilyl group and the alkylamine group is the same as the examples of the alkyl group described herein.
[0106] In the specification, the aryl group among the aryloxy group, the arylthio group, the arylsulfinyl group, the arylsulfonyl group, the arylamino group, the arylboryl group, the arylsilyl group and the arylamine group is the same as the examples of the aryl group described herein.
[0107] In the specification, a direct key may refer to a single key.
[0108] In some embodiments, in the specification, and "-*" refers to the location to be linked.
[0109] Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.
[0110] Display device
[0111] Figure 1 is a plan view showing one or more embodiments of a display device DD. Figure 2 is a cross-sectional view of a display device DD according to the embodiment. Figure 2 It shows that along Figure 1 A cross-sectional view of a portion taken along line II'.
[0112] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP on a third direction axis DR3. 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 disposed on the display panel DP to control reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. In some embodiments, unlike the configuration shown in the drawings, the optical layer PP may not be disposed in the display device DD of one or more embodiments.
[0113] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member that provides a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the illustrated configuration, in one or more embodiments, the base substrate BL may not be disposed.
[0114] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be disposed between the display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic resin, a siloxane resin, and an epoxy resin (e.g., at least one selected from acrylic resins, siloxane resins, and epoxy resins).
[0115] The display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between portions of the pixel defining film PDL, and an encapsulation layer TFE disposed on the light emitting elements ED-1, ED-2, and ED-3.
[0116] The base layer BS may be a member providing a base surface on which the display device layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
[0117] In one or more embodiments, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.
[0118] Each of the light emitting elements ED-1, ED-2, and ED-3 may have a configuration according to 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, a layer selected from emission layers EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.
[0119] Figure 2 One or more embodiments are shown, in which the emission layers EML-R, EML-G and EML-B of the light-emitting elements ED-1, ED-2 and ED-3 are disposed in the opening OH defined in the pixel definition film PDL, and the hole transport region HTR, the electron transport region ETR and the second electrode EL2 are disposed as a common layer in the entire light-emitting elements ED-1, ED-2 and ED-3. However, the embodiments of the present disclosure are not limited thereto, and Figure 2 In one or more embodiments, the hole transport region HTR and the electron transport region ETR may be provided by patterning in an opening OH defined in a pixel defining film PDL. For example, in one or more embodiments, the hole transport region HTR, the emission layers EML-R, EML-G and EML-B, and the electron transport region ETR of the light-emitting elements ED-1, ED-2, and ED-3 may be provided by patterning in an inkjet printing method.
[0120] 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 formed by stacking one or more layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to one or more embodiments may include at least one inorganic film (hereinafter, encapsulation-inorganic film). The encapsulation layer TFE according to one or more embodiments may also include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.
[0121] The encapsulation-inorganic film protects the light-emitting elements ED-1, ED-2, and ED-3 from moisture and / or oxygen, and the encapsulation-organic film protects the light-emitting elements ED-1, ED-2, and ED-3 from foreign matter such as dust particles. The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, and / or aluminum oxide, etc., but the embodiments of the present disclosure are not particularly limited thereto. The encapsulation-organic film may include acrylic compounds and / or epoxy compounds, etc. The encapsulation-organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.
[0122] The encapsulation layer TFE may be disposed on the second electrode EL2 , and may be disposed to fill the opening OH.
[0123] Reference Figure 1 and Figure 2 , the display device DD may include one or more non-light emitting regions NPXA and also include light emitting regions PXA-R, PXA-G, and PXA-B. The light emitting regions PXA-R, PXA-G, and PXA-B may be regions in which light generated by the corresponding light emitting elements ED-1, ED-2, and ED-3 is emitted. The light emitting regions PXA-R, PXA-G, and PXA-B may be spaced apart and / or separated from each other on a plane (e.g., in a plan view).
[0124] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a region divided (i.e., defined) by a pixel defining film PDL. The non-light-emitting region NPXA may be a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B corresponding to the pixel defining film PDL. In some embodiments, in the specification, the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel defining film PDL may divide the light-emitting elements ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be disposed in an opening OH defined in the pixel defining film PDL and separated from each other.
[0125] 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.
[0126] In the display device DD according to one or more embodiments, a plurality of light emitting elements ED-1, ED-2, and ED-3 may emit light beams having different wavelengths from each other. For example, in one or more embodiments, the display device DD may include a first light emitting element ED-1 emitting red light, a second light emitting element ED-2 emitting green light, and a third light emitting element ED-3 emitting blue light. For example, a red light emitting region PXA-R, a green light emitting region PXA-G, and a blue light emitting region PXA-B of the display device DD may correspond to the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element ED-3, respectively.
[0127] However, the embodiments of the present disclosure are not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light beams in substantially the same wavelength range, or at least one light-emitting element may emit a light beam in a wavelength range different from the others. For example, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.
[0128] 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 arranged alternately with each other in this order along the first direction axis DR1.
[0129] Figure 1 and Figure 2It is shown that all the light emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but the embodiments of the present disclosure are not limited thereto. Therefore, the light emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other according to the wavelength range of the emitted light. In this case, the areas of the light emitting regions PXA-R, PXA-G, and PXA-B may refer to the areas when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2.
[0130] In some embodiments, the arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B is not limited to Figure 1 In the configuration shown in FIG. 1 , 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 suitable combinations according to the display quality characteristics required by 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( and Diamond is a registered trademark owned by Samsung Display Co., Ltd.).
[0131] In some embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one or more embodiments, the area of the green light-emitting region PXA-G may be smaller than the area of the blue light-emitting region PXA-B, but the embodiments of the present disclosure are not limited thereto.
[0132] In the following, Figures 3 to 7 is a cross-sectional view schematically illustrating a light emitting element ED according to one or more embodiments. The light emitting element ED of one or more embodiments may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 stacked in sequence.
[0133] and Figure 3 compared to, Figure 4 1 shows a cross-sectional view of a light emitting element ED of one or more embodiments, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5A cross-sectional view of a light emitting element ED according to one or more embodiments is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 3 compared to, Figure 6 A cross-sectional view of a light emitting element ED according to one or more embodiments is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an emission auxiliary layer EAL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 4 compared to, Figure 7 A cross-sectional view of a light emitting element ED including one or more embodiments of a cover layer CPL disposed on the second electrode EL2 is shown.
[0134] 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 embodiments of the present disclosure are not limited thereto. In some embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound selected from two or more of these, a mixture selected from two or more of these, and / or an oxide thereof.
[0135] When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, a compound or mixture thereof (e.g., a mixture of Ag and Mg), or a material having a multilayer structure such as LiF / Ca (a stacking structure of LiF and Ca) or LiF / Al (a stacking structure of LiF and Al). In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the described materials and a transparent conductive film formed of ITO, IZO, ZnO, and / or ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto. In some embodiments, the embodiments of the present disclosure are not limited thereto, and the first electrode EL1 may include the described metal material, a combination of at least two of the described metal materials, and / or an oxide of the described metal material, etc. The thickness of the first electrode EL1 may be about 700 angstroms. to about For example, the thickness of the first electrode EL1 may be about to about
[0136] 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, an emission 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 The emission assistance layer EAL may also be referred to as a buffer layer.
[0137] 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.
[0138] 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 / emission auxiliary layer EAL, a hole injection layer HIL / emission auxiliary layer EAL, a hole transport layer HTL / emission auxiliary layer EAL, or a hole injection layer HIL / hole transport layer HTL / emission auxiliary layer EBL are stacked in order from the first electrode EL1, but the embodiments of the present disclosure are not limited thereto.
[0139] The hole transport region HTR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).
[0140] The hole transport region HTR may include a compound represented by Formula H-1:
[0141] Formula H-1
[0142]
[0143] In formula H-1, L 1 and L 2 L and L may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b may each independently be an integer from 0 to 10. In some embodiments, when a or b is an integer of 2 or more, multiple L 1 and multiple L 2 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0144] In formula H-1, 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. 3 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0145] The compound represented by formula H-1 may be a monoamine compound. In some embodiments, the compound represented by formula H-1 may be wherein Ar 1 To Ar 3 In some embodiments, the compound represented by formula H-1 may be a diamine compound in which at least one of the diamine compounds includes an amine group as a substituent. 1 and Ar 2 At least one of the carbazole compounds includes a substituted or unsubstituted carbazole group or in Ar 1 and Ar 2 A fluorene compound in which at least one of the compounds includes a substituted or unsubstituted fluorenyl group.
[0146] 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 examples, and the compound represented by Formula H-1 is not limited to the compounds represented by Compound Group H:
[0147] Compound Group H
[0148]
[0149] The hole transport region HTR may include a phthalocyanine compound (such as copper phthalocyanine), N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / At least one of poly(4-styrene sulfonate) (PANI / PSS), poly(DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate] and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN).
[0150] The hole transport region HTR may include at least one selected from carbazole derivatives (such as N-phenylcarbazole or polyvinylcarbazole), fluorene derivatives, triphenylamine derivatives (such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl[1,1'-biphenyl]-4,4'-diamine (TPD) or 4,4',4"-tri(N-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 1,3-bis(N-carbazolyl)benzene (mCP).
[0151] In some embodiments, the hole transport region HTR may include 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP) and / or 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), etc.
[0152] The hole transport region HTR may include the described compound of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0153] The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the described ranges, satisfactory hole transport properties may be achieved without significantly increasing the driving voltage.
[0154] In addition to the described materials, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be 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 embodiments of the present disclosure are not limited thereto. For example, the p-dopant may include a halogenated metal compound (such as CuI or RbI), a quinone derivative (such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 -TCNQ)), metal oxides (such as tungsten oxide or molybdenum oxide) and / or cyano-containing compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiments of the present disclosure are not limited thereto.
[0155] As described herein, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of an emission auxiliary layer EAL and an electron blocking layer EBL. The emission auxiliary layer EAL may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, and may improve the luminous efficiency by controlling the hole charge balance. In some embodiments, the emission auxiliary layer EAL may play a role in preventing or reducing the injection of electrons into the hole transport region HTR. In the emission auxiliary layer EAL, a material that may be included in the hole transport region HTR may be included. 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.
[0156] The emission layer EML in the light-emitting element ED of one or more embodiments may include a polycyclic compound according to one or more embodiments. In the light-emitting element ED of one or more embodiments, the emission layer EML may include a first compound as a polycyclic compound of one or more embodiments and at least one of a second compound and a third compound. In addition, in the light-emitting element ED of one or more embodiments, the emission layer EML may further include a fourth compound. The second compound may include a tricyclic fused ring including a nitrogen atom as a ring-forming atom. The third compound may include a hexagonal ring group including at least one nitrogen atom as a ring-forming atom. The fourth compound may include an organic metal complex. The second compound to the fourth compound are described in more detail elsewhere herein.
[0157] Polycyclic compounds
[0158] In this specification, the first compound may be referred to as the polycyclic compound of one or more embodiments. The polycyclic compound of one or more embodiments includes a five-ring fused ring containing two nitrogen (N) atoms and one boron (B) atom as ring atoms as a central structure. The two nitrogen atoms may be referred to as (e.g., divided into) a first nitrogen atom and a second nitrogen atom. In this specification, the five-ring fused ring central structure may be referred to as a "core portion (e.g., region)".
[0159] The polycyclic compound of one or more embodiments may include a structure in which the first aromatic ring to the third aromatic ring are fused via the first nitrogen atom, the second nitrogen atom and the boron atom. The first aromatic ring may be connected to the second aromatic ring via a boron atom and the first nitrogen atom. The second aromatic ring may be connected to the third aromatic ring via a boron atom and the second nitrogen atom. The second aromatic ring may be connected to each (e.g., all) of the first nitrogen atom, the second nitrogen atom and the boron atom. In certain embodiments, the first aromatic ring to the third aromatic ring may be all connected to the boron atom.
[0160] The polycyclic compound of one or more embodiments may have a substituent introduced into at least one selected from the first to third aromatic rings in the five-ring fused ring center structure. For example, the introduction of a substituent into each of the first to third aromatic rings may protect the boron atom of the core portion (e.g., region). Therefore, the polycyclic compound of one or more embodiments may exhibit characteristics having improved or suitable material stability.
[0161] In the polycyclic compound of one or more embodiments, the first nitrogen atom and the part (e.g., region) of the second nitrogen atom in the core part may have a high electron density. In the polycyclic compound of one or more embodiments, the substituent capable of suppressing Dexter energy transfer may be connected to at least one of the first nitrogen atom and the second nitrogen atom in the core part (e.g., region). For example, the substituent connected to at least one of the first nitrogen atom and the second nitrogen atom in the core part (e.g., region) may be a heteroaryl containing nitrogen (N) atom, oxygen (O) atom or sulfur (S) atom as a ring-forming atom. The polycyclic compound of one or more embodiments includes a first substituent connected to the core part (e.g., region) to more effectively protect the boron atom of the core part (e.g., region), and thus may have a chemical stabilization effect of the compound, and may contribute to improving the service life of the light-emitting element ED by suppressing Dexter energy transfer. In some embodiments, the polycyclic compound of one or more embodiments includes a first substituent connected to the nitrogen atom of the core part (e.g., region), and thus has an improved absorbance, thereby promoting energy transfer from the main body in the light-emitting element ED. Therefore, the light emitting element ED including the polycyclic compound of one or more embodiments as a light emitting material may have improved light emitting efficiency and lifetime. In the present specification, the heteroaryl group connected to at least one of the first nitrogen atom and the second nitrogen atom may be referred to as a first substituent.
[0162] The first substituent may be represented by Formula A. In Formula A, X may be NR a , O or S, and R a It can be a substituted or unsubstituted aryl. The first substituent represented by formula A can exhibit electron suction (e.g., electron-withdrawing) properties at positions 1 and 4. The first substituent can be connected to the nitrogen atom of the core part at a position with electron suction (e.g., electron-withdrawing) properties. When the first substituent is connected to the nitrogen atom of the core part (e.g., region) of the polycyclic compound at position 1, the planar properties of the core part (e.g., region) may be destroyed, so the first substituent included in the polycyclic compound of one or more embodiments can be connected to at least one of the first nitrogen atom and the second nitrogen atom of the core part (e.g., region) at position 4. As a result, the polycyclic compound of one or more embodiments can have an enhanced multi-resonance effect due to the sequential separation of the highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) between the atoms in the core part (e.g., region) including nitrogen atoms and boron atoms.
[0163] Formula A
[0164]
[0165] The polycyclic compound of one or more embodiments may also include a substituent (or second substituent) with high (e.g., a large amount) steric hindrance further substituted at the first substituent connected to the core part (e.g., region), so that the protective effect of the core part (e.g., region) can be enhanced, thereby further improving the material stability. For example, in the polycyclic compound of one or more embodiments, the introduction of a second substituent at position 6 of the first substituent of the nitrogen atom connected to the core part (e.g., region) can maximize or increase the inhibition of Dexter energy transfer, and can maintain the intermolecular distance between the polycyclic compound included in the light-emitting element ED and the main body, etc. Therefore, the polycyclic compound of one or more embodiments can have maximized or increased material stability in the light-emitting element ED, thereby improving the service life.
[0166] 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. In the polycyclic compound represented by Formula 1, R 3 The benzene ring connected thereto may correspond to the first aromatic ring described above, R 1 The benzene ring connected thereto may correspond to the second aromatic ring described above, and R 2 The benzene ring connected thereto may correspond to the third aromatic ring described above.
[0167] Formula 1
[0168]
[0169] In formula 1, X 1 It can be NR 8 , O or S. In the polycyclic compound represented by Formula 1, X 1 The heteroaryl group as a ring atom and connected to the nitrogen atom of the core part (eg, region) may correspond to the first substituent described above. The first substituent may be connected to the nitrogen atom of the core part at position 4, and thus may inhibit or reduce intermolecular interactions.
[0170] In formula 1, R 1 To R 5 They may each independently be a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms.
[0171] For example, R 1 To R 3and R are independently hydrogen atoms, deuterium atoms, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 30 ring carbon atoms. 1 To R 3 and R are independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. 1 To R 3 When each of R is substituted with another substituent, it may be substituted with a deuterium atom, a cyano group, or a substituted or unsubstituted alkyl group. For example, it may be substituted with a deuterium atom, a cyano group, and / or an unsubstituted tert-butyl group, etc., but the embodiments of the present disclosure are not limited thereto. For example, R 4 and R 5 Each may independently be a hydrogen atom or a deuterium atom, but the embodiments of the present disclosure are not limited thereto.
[0172] In formula 1, R 6 It may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms. 6 It may be a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group or a substituted or unsubstituted carbazolyl group. 6 When substituted with another substituent, R 6 It may be substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. 6 It may be substituted with an unsubstituted tert-butyl group and / or an unsubstituted phenyl group, etc., but the embodiments of the present disclosure are not limited thereto.
[0173] In one or more embodiments, R 6 It may be represented by any one of the substituents in Substituent Group 1 (for example, selected from the substituents in Substituent Group 1).
[0174] Substituent Group 1
[0175]
[0176] The polycyclic compound of one or more embodiments may exhibit a steric hindrance effect, which may prevent or reduce other materials (e.g., compounds) from approaching the core portion (e.g., region) (e.g., it is difficult for other materials to enter the core portion (e.g., region)). For example, when a substituent R is additionally introduced at position 6 of the first substituent of the nitrogen atom connected to the core portion (e.g., region), 6 Therefore, in the polycyclic compound of one or more embodiments, the suppression of Dexter energy transfer is maximized or increased, and the material stability in the light-emitting element ED can be further improved.
[0177] In formula 1, R 7 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms. 7 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group. 7 When substituted with another substituent, R 7 It may be substituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 7 It may be substituted with a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group and / or a substituted or unsubstituted dibenzothiophenyl group, etc., but the embodiments of the present disclosure are not limited thereto.
[0178] In formula 1, R 8 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 8 The phenyl group may be substituted or unsubstituted.
[0179] In Formula 1, n1, n4, and n5 may each independently be an integer from 0 to 3. n2 and n3 may each independently be an integer from 0 to 4. When each of n1 to n5 is 0, the polycyclic compound according to one or more embodiments may not be R 1 , R 2 , R 3 , R 4 and R 5 The case where each of n1, n4 and n5 is 0 can be replaced by each of n1, n4 and n5 is 3 and 3 R 1 , 3 Rs 4 and 3 Rs 5In some embodiments, the case where each of n2 and n3 is 0 can be the same as the case where each of n2 and n3 is 4 and 4 R 2 and 4 R's 3 The same is true when all R are hydrogen atoms. When each of n1 to n5 is an integer of 2 or greater, the plurality of R 1 , multiple R 2 , multiple R 3 , multiple R 4 and multiple R 5 They may all be the same or at least one may be different from the others.
[0180] For example, when n1 is 3, the boron atom in the core is in a para-position relationship with the R of the second aromatic ring. 1 It may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and the remaining two R bonded to the second aromatic ring are 1 All of them may be hydrogen atoms or deuterium atoms. However, the embodiments of the present disclosure are not limited thereto, and the substituted R 1 The number and type or kind of may vary with one or more embodiments of the polycyclic compound.
[0181] For example, when each of n2 and n3 is 4, R is bonded to the first aromatic ring in a para-position relationship with the boron atom of the core portion. 3 and R bound to the third aromatic ring 2 It may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and is bonded to the remaining three R 3 and the remaining three R bound to the third aromatic ring 2 All of them may be hydrogen atoms or deuterium atoms. However, the embodiments of the present disclosure are not limited thereto, and the substituted R 2 and R 3 The number and type (species) of may vary with one or more embodiments of the polycyclic compound.
[0182] In one or more embodiments, n1+n2+n3≠0, and R 1 To R 3 At least one of them may not be a hydrogen atom. For example, the polycyclic compound represented by Formula 1 in one or more embodiments may have a substituted atom selected from R 1 To R 3 At least one substituent other than hydrogen atom is present in 1 To R3 Each of can be set to multiple and selected from multiple R 1 To multiple R 3 At least one of them may not be a hydrogen atom.
[0183] In one or more embodiments of the polycyclic compound represented by Formula 1, at least one hydrogen atom may be substituted by a deuterium atom. 1 and R 1 To R 7 At least one hydrogen atom in may be replaced by a deuterium atom. For example, 1 and R 1 To R 7 At least one of them may be a deuterium atom or a substituent including a deuterium atom.
[0184] The polycyclic compound represented by Formula 1 of one or more embodiments can be represented by Formula 2. For example, Formula 2 represents a structure in which a substituent can be substituted at each of the first aromatic ring to the third aromatic ring. Therefore, because the first substituent is connected to the nitrogen atom of the core part (e.g., region), and the substituent is connected to the first aromatic ring to the third aromatic ring, the polycyclic compound of one or more embodiments can show a steric hindrance effect, which can prevent other materials (e.g., compounds) from approaching the core part (e.g., region) (e.g., it is difficult for other materials to approach the core part (e.g., region)). Therefore, the polycyclic compound of one or more embodiments can maximize the effect of protecting the core part or increase the effect of protecting the core part.
[0185] For example, the boron atom contained in the core portion has an electron-deficient characteristic due to an empty p orbital, and therefore (for example, in the light-emitting element ED) can be easily bonded to other nucleophiles or degradation products (deterioration products) (for example, free radicals, etc.). When the boron atom is bonded to other nucleophiles or degradation products, the boron atom having a triangular face bonding structure in the core portion (for example, region) of the polycyclic compound can be transformed into a tetrahedral bonding structure, which may be the cause of the degradation of the light-emitting element ED. Because the first substituent is connected to the nitrogen atom of the core portion (for example, region) and the substituent that can have a steric hindrance effect on each of the first aromatic ring to the third aromatic ring, the polycyclic compound of one or more embodiments can effectively protect the empty p orbital of the boron atom, thereby preventing or reducing the degradation caused by the structural deformation of the material.
[0186] Formula 2
[0187]
[0188] In Formula 2, the definition described in Formula 1 can be applied to X1 , R 4 To R 7 , n4 and n5.
[0189] In formula 2, R 11 , R 21 and R 31 and R and R are independently hydrogen atoms, deuterium atoms, cyano groups, halogen atoms, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 30 ring carbon atoms. 11 , R 21 and R 31 Each may independently be a hydrogen atom or a deuterium atom.
[0190] In Formula 2, n11 may be an integer from 0 to 2, and n21 and n31 may each independently be an integer from 0 to 3. In Formula 2, when each of n11, n21, and n31 is 0, the polycyclic compound of one or more embodiments may not be R 11 , R 21 and R 31 When each of n11, n21 and n31 is 2 or greater, multiple R 11 , multiple R 21 and multiple R 31 They may all be the same or at least one may be different from the others.
[0191] In formula 2, R 12 , R 22 and R 32 and R and R are independently substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 30 ring carbon atoms. 12 , R 22 and R 32 and R are independently substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl or substituted or unsubstituted carbazolyl. 12 , R 22 and R 32 When each of is substituted, each may be substituted with a deuterium atom and / or a tert-butyl group, etc., but the embodiments of the present disclosure are not limited thereto.
[0192] In one or more embodiments, R 12 , R 22 and R 32 At least one of the R can be in a para-positional relationship with a boron atom of the core portion (e.g., region). 12can be attached to the second aromatic ring in a para-position relationship with the boron atom of the core portion (eg, region). 22 may be attached to the third aromatic ring in a para-positional relationship with the boron atom of the core portion (eg, region), and R 32 The boron atom of the core portion (eg, region) may be attached to the first aromatic ring in a para-position relationship. However, the embodiments of the present disclosure are not limited thereto, and R 22 and R 32 The boron atom may be bonded to the third aromatic ring and the first aromatic ring, respectively, in a meta relationship with the boron atom of the core portion (eg, region).
[0193] For example, the polycyclic compound represented by Formula 2 of one or more embodiments may be represented by any one selected from Formula 2-1 to Formula 2-3:
[0194] Formula 2-1
[0195]
[0196] Formula 2-2
[0197]
[0198] Formula 2-3
[0199]
[0200] In Formula 2-1 to Formula 2-3, the definitions described in Formula 1 and Formula 2 can be applied to X 1 , R 4 To R 7 , R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , n4, n5, n11, n21 and n31.
[0201] In one or more embodiments, the polycyclic compound represented by Formula 1 may be represented by Formula 3 or Formula 4.
[0202] Formula 3
[0203]
[0204] Formula 4
[0205]
[0206] In Formula 3, i1 may be an integer from 0 to 5. When i1 is an integer of 2 or more, a plurality of R i1 All may be the same or at least one may be different from the others.i1 It may be a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. i1 It may be a substituted or unsubstituted tert-butyl group or a substituted or unsubstituted phenyl group.
[0207] For example, in the polycyclic compound represented by Formula 3, the first substituent may be connected to the first nitrogen atom of the core part, and the substituted or unsubstituted terphenyl group may be connected to the second nitrogen atom of the core part (e.g., region). The polycyclic compound represented by Formula 3 has an increased diameter in the horizontal direction of the molecule, and effectively protects the boron atom of the core part (e.g., region), so that chemical stability can be improved.
[0208] In formula 4, X 2 It can be NR i5 , O or S. R i5 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. i5 It may be a substituted or unsubstituted phenyl group. 1 The first substituent as a ring-forming atom is attached to the first nitrogen atom of the core part (eg, region) and comprises X 2 The first substituent as a ring-forming atom is connected to the second nitrogen atom of the core part (eg, region), and thus the polycyclic compound of one or more embodiments can suppress or reduce intermolecular interactions.
[0209] In Formula 4, i2 and i3 may each independently be an integer from 0 to 3. i2 and R i3 and R and R are independently hydrogen atoms, deuterium atoms, cyano groups, halogen atoms, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 30 ring carbon atoms. i2 and R i3 Each may independently be a hydrogen atom or a deuterium atom.
[0210] When each of i2 and i3 is 0, the polycyclic compound of one or more embodiments may not be R i2 and R i3 The case where each of i2 and i3 is 0 can be replaced by each of i2 and i3 being 3 and 3 R i2 and 3 Rs i3 The same is true for the case where all R atoms are hydrogen atoms. When each of i2 and i3 is an integer of 2 or greater, the multiple R i2 and multiple R i3 They may all be the same or at least one may be different from the others.
[0211] In formula 4, R i4 It may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms. i4 It may be a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group or a substituted or unsubstituted carbazolyl group. i4 When substituted with another substituent, R i4 It may be substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. i4 It may be substituted with an unsubstituted tert-butyl group and / or an unsubstituted phenyl group, etc., but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, R i4 may be represented by any one selected from the substituents listed in Substituent Group 1 as described herein.
[0212] In Equation 3 and Equation 4, the definition described in Equation 1 can be applied to X 1 , R 1 To R 6 and n1 to n5.
[0213] In one or more embodiments, the polycyclic compound represented by Formula 3 may be represented by Formula 3-1 or Formula 3-2:
[0214] Formula 3-1
[0215]
[0216] Formula 3-2
[0217]
[0218] In Formula 3-1, j1 may be an integer from 0 to 5. When j1 is 0, the polycyclic compound represented by Formula 3-1 may not be j1 When j1 is an integer of 2 or more, multiple R j1 They may all be the same or at least one may be different from the rest.
[0219] R j1 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. j1It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group. j1 When substituted with another substituent, R j1 A deuterium atom, an unsubstituted tert-butyl group, and / or an unsubstituted phenyl group, etc. may be substituted, but the embodiments of the present disclosure are not limited thereto.
[0220] In formula 3-2, R j2 and R j3 and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. j2 and R j3 Each may independently be a hydrogen atom or a deuterium atom.
[0221] In Formula 3-2, j2 may be an integer from 0 to 3, and j3 may be an integer from 0 to 4. When each of j2 and j3 is 0, the polycyclic compound represented by Formula 3-2 may not be R j2 and R j3 When each of j2 and j3 is an integer of 2 or more, multiple R j2 and multiple R j3 They may all be the same or at least one may be different from the others.
[0222] In formula 3-2, Y 1 Can be CR j4 R j5 NR j6 , O or S. R j4 , R j5 and R j6 Each of R and R is independently a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. j4 , R j5 and R j6 can be independently substituted or unsubstituted phenyl. In some embodiments, R j4 and R j5 They may optionally be combined with each other to form a ring. j4 and R j5 The ring formed by the combination can form a spiral structure.
[0223] In Formula 3-1 and Formula 3-2, the definitions described in Formula 1 and Formula 3 can be applied to X 1 , R 1 To R 5 , R i1 , n1 to n5 and i1.
[0224] In one or more embodiments, the polycyclic compound represented by Formula 4 may be represented by Formula 4-1 or Formula 4-2:
[0225] Formula 4-1
[0226]
[0227] Formula 4-2
[0228]
[0229] In formula 4-1, R k1 and R k2 and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. k1 and R k2 Each of them may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
[0230] In Formula 4-1, k1 and k2 may each independently be an integer of 0 to 5. When each of k1 and k2 is 0, the polycyclic compound of one or more embodiments may not be R k1 and R k2 When each of k1 and k2 is an integer of 2 or more, multiple R k1 and multiple R k2 They may all be the same or at least one may be different from the others.
[0231] In formula 4-2, R k3 To R k6 and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. k3 To R k6 Each may independently be a hydrogen atom or a deuterium atom.
[0232] k3 and k5 may each independently be an integer from 0 to 3, and k4 and k6 may each independently be an integer from 0 to 4. When each of k3 to k6 is 0, the polycyclic compound of one or more embodiments may not be R k3 To R k6 When each of k3 to k6 is an integer of 2 or more, a plurality of R k3 To multiple R k6 They may all be the same or at least one may be different from the others.
[0233] In formula 4-2, Y 2 and Y 3Can be independently CR k7 R k8 NR k9 , O or S. R k7 , R k8 and R k9 Each of R and R is independently a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms. k7 , R k8 and R k9 can be independently substituted or unsubstituted phenyl. In some embodiments, R k7 and R k8 They may optionally be combined with each other to form a ring. k7 and R k8 The ring formed by the combination can form a spiral structure.
[0234] In Formula 4-1 and Formula 4-2, the definitions described in Formula 1 and Formula 4 can be applied to X 1 , X 2 , R 1 To R 5 , R i2 , R i3 , n1 to n5, i2 and i3.
[0235] The polycyclic compound of one or more embodiments may be represented by any one of the compounds in compound group 1. The light emitting element ED according to one or more embodiments may include at least one of the compounds in compound group 1. In compound group 1, D is a deuterium atom.
[0236] Compound Group 1
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248] In the polycyclic compound of one or more embodiments, the emission spectrum may have a full width at half maximum (FWHM) of about 10 nanometers (nm) to about 50 nm and about 20 nm to about 40 nm. Since the emission spectrum has a FWHM within the range, the polycyclic compound according to one or more embodiments of the present disclosure may exhibit excellent or suitable optical properties. For example, the polycyclic compound of one or more embodiments may be used as a dopant material for a light-emitting element ED, thereby improving the luminous efficiency and service life of the light-emitting element ED.
[0249] The polycyclic compound of one or more embodiments 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 be used as a thermally activated delayed fluorescence material having an energy level difference (ΔE ) between the lowest singlet exciton energy level (S1 energy level) and the lowest triplet exciton energy level (T1 energy level) of about 0.2 electron volts (eV) or less. ST ).
[0250] In the light emitting element ED according to one or more embodiments, the emission layer EML may be a delayed fluorescence emission layer including a host and a dopant. More specifically, the emission 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.
[0251] In some embodiments, the emission layer EML of the light emitting element ED may emit blue light. For example, the emission layer EML of the light emitting element ED of one or more embodiments may emit blue light within a wavelength range of about 490 nm or less. However, the embodiments of the present disclosure are not limited thereto, and the emission layer EML may emit green light or red light.
[0252] In one or more embodiments, the emission layer EML may include the polycyclic compound of one or more embodiments and at least one selected from the second compound to the fourth compound. In one or more embodiments, the emission 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 emission layer EML.
[0253] Formula HT-1
[0254]
[0255] In formula HT-1, A 1 To A 8 can be independently N or CR51 For example, A 1 To A 8 Each (eg, all) of may be CR 51 In some embodiments, selected from A 1 To A 8 Any one of them can be N, and the rest (e.g., any remaining A 1 To A 8 ) can be CR 51 .
[0256] 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 biphenylene group, and / or a substituted or unsubstituted carbazolylene group, etc., but the embodiments of the present disclosure are not limited thereto.
[0257] In formula HT-1, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 For example, Y a It may refer to the two benzene rings connected to the nitrogen atom in formula HT-1 via a direct bond, In formula HT-1, when Y a When it is a direct bond, the second compound represented by Formula HT-1 may include a carbazole moiety.
[0258] 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 embodiments of the present disclosure are not limited thereto.
[0259] In formula HT-1, R 51 To R 55and R 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 some embodiments, R 51 To R 55 Each of R may optionally be bonded to an adjacent group to form a ring. 51 To R 55 R may each independently be a hydrogen atom or a deuterium atom. 51 To R 55 Each may independently be an unsubstituted methyl group or an unsubstituted phenyl group.
[0260] In one or more embodiments, the second compound represented by Formula HT-1 may be represented by any one selected from the compounds represented by Compound Group 2. The emission layer EML may include at least one selected from the compounds represented by Compound Group 2 as a hole transport host material.
[0261] Compound Group 2
[0262]
[0263]
[0264]
[0265] In the example compounds given in compound group 2, "D" may refer to a deuterium atom, and "Ph" may refer to a substituted or unsubstituted phenyl group. For example, in the example compounds given in compound group 2, "Ph" may refer to an unsubstituted phenyl group.
[0266] In one or more embodiments, the emission layer EML may include a third compound represented by Formula ET-1. For example, the third compound may be used as an electron transport host material for the emission layer EML.
[0267] Formula ET-1
[0268]
[0269] In formula ET-1, X 1a To X 3a At least one of them may be N, and the rest (e.g., any remaining X 1a To X 3a ) can be CR 56For example, selected from X 1a To X 3a Any one of them can be N, and the rest (e.g., any remaining X 1a To X 3a ) can all independently be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyridine moiety. In some embodiments, the compound selected from X 1a To X 3a Two of them can be N, and the rest (e.g., any remaining X 1a To X 3a ) can be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In some embodiments, X 1a To X 3a All (eg, all) may be N. In this case, the third compound represented by Formula ET-1 may include a triazine moiety.
[0270] 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.
[0271] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.
[0272] 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 may independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.
[0273] In formula ET-1, L 2 To L 4 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 some embodiments, when b1 to b3 are integers of 2 or greater, 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.
[0274] 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 any one of the compounds selected from the compound group 3.
[0275] Compound Group 3
[0276]
[0277]
[0278]
[0279]
[0280]
[0281]
[0282] In the example compounds given in Compound Group 3, "D" refers to a deuterium atom, and "Ph" refers to an unsubstituted phenyl group.
[0283] The emission layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, an exciplex may be formed by a hole transport host and an electron transport host. In this case, 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.
[0284] For example, the absolute value of the triplet energy (T1) of the exciplex formed by the hole transport host and the electron transport host can be about 2.4 eV to about 3.0 eV. In some embodiments, the triplet energy of the exciplex can be a value less than the energy gap of each host material. The exciplex can have a triplet energy of about 3.0 eV or less, that is, less than the energy gap between the hole transport host and the electron transport host.
[0285] In one or more embodiments, the emission layer EML may further include a fourth compound in addition to the first to third compounds described herein. The fourth compound may be used as a phosphorescence sensitizer of the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.
[0286] For example, the emission layer EML may include an organic metal complex including platinum (Pt) as a central metal atom and a ligand connected to the central metal atom as the fourth compound. The emission layer EML in the light emitting element ED of one or more embodiments may include a compound represented by Formula D-1 as the fourth compound:
[0287] Formula D-1
[0288]
[0289] In formula D-1, Q 1 To Q 4 can all independently be C or N.
[0290] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.
[0291] In formula D-1, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 11 To L 13 In the figure, “-*” refers to the part connected to C1 to C4.
[0292] In Formula D-1, b11 to b13 may each independently be 0 or 1. When b11 is 0, C1 and C2 may not be connected to each other. When b12 is 0, C2 and C3 may not be connected to each other. When b13 is 0, C3 and C4 may not be connected to each other.
[0293] In formula D-1, R 61 To R 66 and R 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 some embodiments, R 61 To R 66 Each of R may optionally bind to an adjacent group to form a ring. 61 To R66 Each may independently be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.
[0294] In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. In Formula D-1, when each of d1 to d4 is 0, the fourth compound may not be R 61 To R 64 Each of d1 to d4 is 4 and R 61 To R 64 The case where all R are hydrogen atoms may be the same as the case where each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or more, the plurality of R 61 To multiple R 64 Can be the same, or multiple R 61 To multiple R 64 At least one of them may be different from the others.
[0295] In formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle represented by any one selected from C-1 to C-4:
[0296]
[0297] 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 , P 4 Can be C-* or CR 88 . R 71 To R 88 Each may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and may be optionally bonded to an adjacent group to form a ring.
[0298] In some embodiments, in C-1 to C-4, The "-*" corresponds to a portion connected to Pt as the central metal atom, and the "-*" corresponds to a portion connected to an adjacent ring group (C1 to C4) or a linker (L 11 To L 13 ) part.
[0299] The emission layer EML of one or more embodiments may include a first compound as a fused polycyclic compound and at least one of the second compound to the fourth compound. For example, the emission layer EML may include a first compound, a second compound, and a third compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the first compound, thereby emitting light.
[0300] In some embodiments, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In one or more embodiments, the fourth compound may be a sensitizer. The fourth compound in the emission layer EML included in the light-emitting element ED of one or more embodiments may be used as a sensitizer to transfer energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound used as an auxiliary dopant accelerates the energy transfer to the first compound as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emission layer EML of one or more embodiments may improve the luminous efficiency. In some embodiments, when the energy transfer to the first compound increases, the excitons formed in the emission layer EML are not accumulated inside the emission layer EML and emit light quickly, so the degradation of the light-emitting element ED may be reduced. Therefore, the service life of the light-emitting element ED of one or more embodiments may be improved.
[0301] The light-emitting element ED of one or more embodiments may include all of the first compound, the second compound, the third compound, and the fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light-emitting element ED of one or more embodiments, the emission layer EML may simultaneously (e.g., concurrently) include the second compound and the third compound as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound including an organic metal complex, thereby exhibiting excellent or suitable luminous efficiency characteristics.
[0302] In one or more embodiments, the fourth compound represented by Formula D-1 may be represented by at least one of the compounds represented by Compound Group 4. The emission layer EML may include at least one selected from among the compounds represented by Compound Group 4 as a sensitizer material.
[0303] Compound Group 4
[0304]
[0305]
[0306] In the example compounds given in Compound Group 4, "D" refers to a deuterium atom.
[0307] When the emission layer EML in the light-emitting element ED of one or more embodiments includes each (e.g., all) of the first compound, the second compound, and the third compound, the content (e.g., amount) of the first compound relative to the total weight of the first compound, the second compound, and the third compound may be about 0.1 wt% to about 5 wt%. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the first compound satisfies the ratio, the energy transfer from the second compound and the third compound to the first compound may be increased, so that the luminous efficiency and the element service life may be increased.
[0308] The content of the second compound and the third compound in the emission layer EML may be the remaining amount (e.g., the remaining amount of the total weight of the emission layer EML) except the weight (e.g., amount) of the first compound. For example, the content of the second compound and the third compound in the emission layer EML 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.
[0309] A weight ratio of the second compound to the third compound may be about 3:7 to about 7:3.
[0310] When the content (e.g., amount) of the second compound and the third compound satisfies the described ratio, the charge balance characteristics in the emission layer EML are improved, so the luminous efficiency and the element life can be increased. When the content (e.g., amount) of the second compound and the third compound is outside the described ratio range, the charge balance in the emission layer EML is destroyed, so the luminous efficiency may be reduced and the light-emitting element ED may be easily degraded.
[0311] When the emission layer EML includes a fourth compound, the content (e.g., amount) of the fourth compound in the emission layer EML may be about 4 wt% to about 30 wt% relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. The content of the second compound and the third compound in the emission layer EML may be about 65 wt% to about 95 wt% relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the fourth compound satisfies the described content (e.g., amount), the energy transfer from the host to the first compound as a light-emitting dopant can be increased, so that the luminous ratio can be improved, and thus the luminous efficiency of the emission layer EML can be improved. When the first compound, the second compound, the third compound, and the fourth compound included in the emission layer EML meet the described content (e.g., amount) ratio range, excellent or suitable luminous efficiency and long service life can be achieved.
[0312] The emission layer EML may have a thickness of, for example, about to about or about to about The emission layer EML may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure having a plurality of layers formed of a plurality of different materials.
[0313] exist Figures 3 to 7 In the light emitting element ED of the embodiment shown in FIG. 1 , the emission layer EML may include the polycyclic compound described in one or more embodiments as a dopant material. Figures 3 to 7 In each of the light emitting elements ED of the embodiments shown in , the emission layer EML may include a first compound that is a polycyclic compound of one or more embodiments and at least one of a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1. In some embodiments, Figures 3 to 7 In each of the light-emitting elements ED of the embodiments shown in , the emission 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.
[0314] In the light emitting element ED of one or more embodiments, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, Derivatives, dihydrobenzanthracene derivatives or benzo[9,10]phenanthrene derivatives. For example, the emission layer EML may include anthracene derivatives or pyrene derivatives.
[0315] exist Figures 3 to 7 In each light emitting element ED of the embodiment shown in , in addition to the described host and dopant, the emission layer EML may further include a suitable host and dopant, for example, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.
[0316] Formula E-1
[0317]
[0318] In formula E-1, R 31 To R 40may each independently be 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 be bonded to an adjacent group to form a ring. In some embodiments, R 31 To R 40 It may be optionally bonded to an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.
[0319] In Formula E-1, c and d may each independently be an integer of 0 to 5.
[0320] Formula E-1 can be represented by any one selected from Compound E1 to Compound E19:
[0321]
[0322]
[0323] In one or more embodiments, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.
[0324] Formula E-2a
[0325]
[0326] In Formula E-2a, a may be an integer from 0 to 10, and L a It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when a is an integer of 2 or greater, multiple L a Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0327] In some embodiments, in Formula E-2a, A 1 To A 5 can be independently N or CR i . R a To R iEach of R and R 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 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 bind to an adjacent group to form a ring. a To R i It may be optionally 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.
[0328] In some embodiments, in Formula E-2a, selected from A 1 To A 5 Two or three of them may be N, and the rest (i.e., any remaining A 1 To A 5 ) can be CR i .
[0329] Formula E-2b
[0330]
[0331] 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. b 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. In some embodiments, b is an integer from 0 to 10, and when b is an integer of 2 or more, multiple L b Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0332] 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 examples, and the compounds represented by formula E-2a or formula E-2b are not limited to the compounds represented in compound group E-2.
[0333] Compound Group E-2
[0334]
[0335]
[0336] The emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.
[0337] Formula Ma
[0338]
[0339] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 Can be CR independently 1 or N, R 1 To R 4 Each of the above-mentioned groups may be 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 may be optionally bonded to an adjacent group to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, and when m is 1, n is 2.
[0340] The compound represented by the formula Ma may be used as a phosphorescent dopant.
[0341] The compound represented by the formula Ma may be represented by any one of the compounds M-a1 to M-a25. However, the compounds M-a1 to M-a25 are examples, and the compound represented by the formula Ma is not limited to the compounds represented by the compounds M-a1 to M-a25.
[0342]
[0343]
[0344] The emission layer EML may include a compound represented by any one selected from Formula Fa to Formula Fc. The compound represented by Formula Fa to Formula Fc may be used as a fluorescent dopant material.
[0345] Formula
[0346]
[0347] In the formula Fa, R a To R j Two of them can be independently substituted with *-NAr 1 Ar 2 . Ra To R j Among the unrecognized 1 Ar 2 The other substituted 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0348] In *-NAr 1 Ar 2 in Ar 1 and Ar 2 and Ar may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of may be a heteroaryl group containing O or S as a ring-forming atom.
[0349] Formula Fb
[0350]
[0351] In 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and may be optionally bonded to an adjacent group to form 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.
[0352] In formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of them may be a heteroaryl group containing O or S as a ring-constituting atom.
[0353] In formula Fb, the number of rings represented by U and V can be 0 or 1 independently. For example, in formula Fb, it means that when the number of U or V is 1, one ring constitutes a fused ring at the part represented by U or V, and when the number of U or V is 0, there is no ring represented by U or V. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with a fluorene core in formula Fb can be a cyclic compound with four rings. In some embodiments, when each number of U and V is 0, the fused ring with a fluorene core in formula Fb can be a cyclic compound with three rings. In some embodiments, when each number of U and V is 1, the fused ring with a fluorene core in formula Fb can be a cyclic compound with five rings.
[0354] Formula Fc
[0355]
[0356] In Formula Fc, A 1 and A 2 can be independently O, S, Se or NR m , and R m 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 R 11 Each 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 bind to an adjacent group to form a ring.
[0357] In Formula Fc, A 1 and A 2 can each independently bind to a substituent of an adjacent ring to form a fused ring. 1 and A 2 can all independently be NR m When A 1 Can optionally be combined with R 4 or R 5 To form a ring. In some embodiments, A 2 Can optionally be combined with R 7 or R 8 to form a ring.
[0358] In one or more embodiments, the emission layer EML may further include a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)- At least one of N-phenylaniline (N-BDAVBi) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) and / or pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and 1,4-bis(N,N-diphenylamino)pyrene) is used as a suitable dopant material.
[0359] The emission layer EML may further include a suitable phosphorescent dopant material. For example, a metal complex containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm) may be used as a phosphorescent dopant. For example, bis(4,6-difluorophenylpyridine-N,C2) picolinyl iridium (III) (FIrpic), bis(2,4-difluorophenylpyridine)-tetrakis(1-pyrazolyl) borate iridium (III) (FIrpic), 6 ) or platinum octaethylporphyrin (PtOEP) may be used as a phosphorescent dopant. However, the embodiments of the present disclosure are not limited thereto.
[0360] The emission 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, or a combination thereof.
[0361] The II-VI compounds may be selected from the group consisting of: binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof.
[0362] III-VI compounds may include: binary compounds such as In 2 S 3 or In 2 Se 3 ; Ternary compounds such as InGaS 3 or InGaSe 3 ; or any combination thereof.
[0363] The I-III-VI group compound can be selected from: a ternary compound selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof; or quaternary compounds such as AgInGaS 2 or CuInGaS 2 .
[0364] The III-V compound may be selected from the group consisting of: a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; a ternary compound selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and a quaternary compound selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. In some embodiments, the III-V compound may also include a Group II metal. For example, InZnP or the like may be selected as the III-II-V group compound.
[0365] The IV-VI compound may be selected from the group consisting of: a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof. The IV group element may be selected from the group consisting of Si, Ge and mixtures thereof. The IV group compound may be a binary compound selected from the group consisting of SiC, SiGe and mixtures thereof.
[0366] Each element included in a multi-element (i.e., multi-element) compound (such as a binary compound, a ternary compound, or a quaternary compound) may be present in the particle in a substantially uniform or substantially non-uniform concentration distribution. For example, the chemical formula refers to the kind (type) of elements included in the compound, and the ratio of 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).
[0367] In some embodiments, the quantum dot may have a single structure or a core-shell dual structure in which the concentration of each element included in the quantum dot is substantially uniform. For example, the material included in the core may be different from the material included in the shell.
[0368] 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 charge layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell becomes lower toward the center.
[0369] Examples of the shell of a quantum dot may include metal or non-metal oxides, semiconductor compounds, or 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 or NiO; or ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 or CoMn 2 O 4 , but the embodiments of the present disclosure are not limited thereto.
[0370] 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 embodiments of the present disclosure are not limited thereto.
[0371] 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 substantially non-uniform concentration distribution. For example, a chemical formula refers to the kind (type) of elements included in the compound, and the ratio of elements in the compound may be different.
[0372] The quantum dots can have a full width at half maximum (FWHM) of the 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 described range. In some embodiments, the light emitted by such quantum dots is emitted in all directions, so that a wide viewing angle can be improved.
[0373] In some embodiments, the form of quantum dots is not specifically limited as long as it is a form commonly used in the art. More specifically, quantum dots in the form of spherical, pyramidal, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers and / or nanoplates can be utilized.
[0374] When the size of the quantum dots is adjusted or the ratio of elements in the quantum dot compound is adjusted, the energy band gap can be controlled, so that light within one or more suitable wavelength ranges can be obtained in the quantum dot emission layer. Therefore, quantum dots as described can be utilized (utilizing quantum dots of different sizes or different ratios of elements in quantum dot compounds), and thus a light-emitting element ED emitting light of one or more suitable wavelengths can be realized. For example, the size of the quantum dots or the ratio of elements in the quantum dot compound can be selected to emit red light, green light, and / or blue light. In some embodiments, quantum dots can be configured to emit white light by combining one or more suitable colors of light.
[0375] 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 emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiments of the present disclosure are not limited thereto.
[0376] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure including a plurality of layers formed of a plurality of different materials.
[0377] 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, and 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 order from the emission layer EML, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, about to about Thickness.
[0378] The electron transport region ETR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and / or laser induced thermal imaging (LITI) method.
[0379] The electron transport region ETR may include a compound represented by Formula ET-2:
[0380] Formula ET-2
[0381]
[0382] In formula ET-2, selected from X 1 To X 3 At least one of them may be N, and the rest (e.g., the remaining X 1 To X 3 Any or each of the remaining ) may be 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.
[0383] 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 some embodiments, when a to c are independently an integer of 2 or more, L 1 To L 3 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0384] The electron transport region ETR may include an anthracene compound. However, the embodiments of the present disclosure are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl 1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) or a mixture thereof.
[0385] The electron transport region ETR may include at least one selected from compounds ET1 to ET36:
[0386]
[0387]
[0388]
[0389]
[0390] In some embodiments, the electron transport region ETR may include metal halides (such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI), lanthanide metals (such as Yb), and co-deposited materials of metal halides and lanthanide metals. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, and / or LiF:Yb as co-deposited materials. In some embodiments, the electron transport region ETR may utilize metal oxides (such as Li 2O or BaO) or 8-hydroxy-quinoline lithium (Liq), etc., but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR can also be formed by a mixed material of an electron transport material and an insulating organic metal salt. The organic metal salt can be a material with an energy band gap of about 4eV or greater. For example, the organic metal salt can include, for example, metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate or metal stearate.
[0391] In addition to the described 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 embodiments of the present disclosure are not limited thereto.
[0392] The electron transport region ETR may include the described compound of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.
[0393] 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 ). When 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 When the thickness of the electron injection layer EIL satisfies the described range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0394] 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 embodiments of the present disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.
[0395] 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.).
[0396] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, a compound or mixture thereof (e.g., AgMg, AgYb or MgYb) or a material having a multilayer structure such as LiF / Ca or LiF / Al. In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the described materials and a transparent conductive film formed of ITO, IZO, ZnO and / or ITZO, etc. For example, the second electrode EL2 may include the described metal material, a combination of at least two of the described metal materials, and / or an oxide of the described metal material, etc.
[0397] In some embodiments, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
[0398] In some embodiments, the cover layer CPL may be further disposed on the second electrode EL2 of the light emitting element ED of one or more embodiments. The cover layer CPL may include a plurality of layers or a single layer.
[0399] In one or more embodiments, the cover layer CPL may be an organic layer or an inorganic layer. For example, when the cover 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 wait.
[0400] For example, when the cover layer CPL includes an organic material, the organic material may include α-NPD (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine), NPB, TPD, m-MTDATA, Alq 3 , CuPc (copper phthalocyanine (II)), N4,N4,N4',N4'-tetrakis (biphenyl-4-yl) biphenyl-4,4'-diamine (TPD15) and / or 4,4',4"-tris (carbazole-9-yl) triphenylamine (TCTA), etc., or epoxy resin or acrylate (such as methacrylate). However, the embodiments of the present disclosure are not limited thereto, and the cover layer CPL may include at least one selected from the group consisting of compounds P1 to P5:
[0401]
[0402] In some embodiments, the refractive index of the cover layer CPL may be about 1.6 or more. For example, with respect to light in a wavelength range of about 550 nm to about 660 nm, the refractive index of the cover layer CPL may be about 1.6 or more.
[0403] Figures 8 to 11 Each of them is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. 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 Rather than describing repeated features described in , their differences will be described primarily (e.g., in more detail).
[0404] Reference Figure 8 The display device DD-a according to one or more embodiments may include a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. 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 device layer DP-ED disposed on the base layer BS, and the display device layer DP-ED may include a light emitting element ED.
[0405] The light emitting element ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. 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 8 The light emitting element ED shown in FIG. 1 may include the polycyclic compound of one or more embodiments and at least one of the second to fourth compounds. Therefore, the light emitting element ED may exhibit high light emission efficiency and long lifespan characteristics.
[0406] Reference Figure 8 , the emission layer EML can be arranged in the opening OH defined in the pixel defining film PDL. For example, the emission layer EML divided by the pixel defining film PDL and arranged corresponding to each light emitting area PXA-R, PXA-G and PXA-B can emit light in substantially the same wavelength range. In the display device DD-a of one or more embodiments, the emission layer EML can emit blue light. In some embodiments, unlike the illustrated construction, in one or more embodiments, the emission layer EML can be set as a common layer in the entire light emitting area PXA-R, PXA-G and PXA-B.
[0407] The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot and / or a phosphor, etc. The light converter may emit the provided light by converting the wavelength of the provided light. For example, the light control layer CCL may be a layer including quantum dots or a layer including phosphors.
[0408] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced apart and / or separated from each other.
[0409] Reference Figure 8 , the separation pattern BMP may be disposed between the light-control parts CCP1 , CCP2 , and CCP3 that are spaced apart and / or separated from each other, but the embodiments of the present disclosure are not limited thereto. Figure 8 It is shown that the separation pattern BMP does not overlap the light-control parts CCP1 , CCP2 , and CCP3 , but at least a portion of the edges of the light-control parts CCP1 , CCP2 , and CCP3 may overlap the separation pattern BMP.
[0410] The light control layer CCL may include a first light control part CCP1 including first quantum dots QD1 that convert the first color light provided from the light emitting element ED into second color light, a second light control part CCP2 including second quantum dots QD2 that convert the first color light into third color light, and a third light control part CCP3 that transmits the first color light.
[0411] In one or more embodiments, the first light control unit CCP1 may provide red light as the second color light, and the second light control unit CCP2 may provide green light as the third color light. The third light control unit CCP3 may provide blue light by transmitting blue light as the first color light provided from the light emitting 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. For quantum dots QD1 and QD2, the same as described may be applied.
[0412] In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control part CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control part CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control part CCP3 may not include (e.g., may exclude) any quantum dot but include a scatterer SP.
[0413] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2and 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.
[0414] The first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 may each include base resins BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed, respectively. In one or more embodiments, the first light control unit CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control unit CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control unit CCP3 may include scatterers SP dispersed in the third base resin BR3.
[0415] The matrix resins BR1, BR2 and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may be formed of one or more suitable resin compositions that may generally be referred to as binders. For example, the matrix resins BR1, BR2 and BR3 may be acrylic resins, urethane resins, siloxane resins and / or epoxy resins, etc. The matrix resins BR1, BR2 and BR3 may be transparent resins. In one or more embodiments, the first matrix resin BR1, the second matrix resin BR2 and the third matrix resin BR3 may be the same or different from each other.
[0416] 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 some 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.
[0417] 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 some 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.
[0418] 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 disposed.
[0419] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit a second color light, a second filter CF2 configured to transmit a third color light, and a third filter CF3 configured to transmit the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The filters CF1, CF2, and CF3 may each include a polymerized photosensitive resin and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye.
[0420] In some embodiments, the embodiments of the present disclosure are not limited thereto, and the third filter CF3 may not include (e.g., may exclude) a pigment or a dye. The third filter CF3 may include a polymerized photosensitive resin and may not include (e.g., may exclude) a pigment or a dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.
[0421] 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 separate but may be provided as one filter.
[0422] In one or more embodiments, the color filter layer CFL may further include a light shielding portion. The light shielding portion may be a black matrix. The light shielding portion may include an organic light shielding material or an inorganic light shielding material containing a black pigment or dye. The light shielding portion may prevent or reduce light leakage and may separate the boundaries between adjacent filters CF1, CF2, and CF3.
[0423] The first to third filters CF1 , CF2 , and CF3 may be disposed to correspond to the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B, respectively.
[0424] 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 embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the illustrated configuration, in one or more embodiments, the base substrate BL may not be disposed.
[0425] 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 of one or more embodiments, the light emitting element ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. At least one selected from the plurality of light emitting structures OL-B1, OL-B2, and OL-B3 may include the polycyclic compound of one or more embodiments and at least one of the second compound to the fourth compound. Therefore, the light emitting element ED-BT may exhibit high light emitting efficiency and long service life characteristics.
[0426] 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 an emission layer EML ( Figure 8 ) and a hole transport region HTR ( Figure 8 ) and the electron transport region ETR ( Figure 8 ). For example, the light emitting elements ED-BT included in the display devices DD-TD of one or more embodiments may be light emitting elements having a tandem structure and including a plurality of emission layers.
[0427] exist Fig. 9 In one or more embodiments shown in , all light beams emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may be blue light. However, the embodiments of the present disclosure are not limited thereto, and the light beams emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may have wavelength ranges different from each other. For example, the light emitting element ED-BT including a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 emitting light beams having wavelength ranges different from each other may emit white light.
[0428] The charge generation layers CGL1 and CGL2 may be disposed between two of the adjacent light emitting structures OL-B1, OL-B2, and OL-B3, respectively. The charge generation layers CGL1 and CGL2 may include a p-type or p-like charge generation (e.g., p-charge generation) layer and / or an n-type or n-like charge generation (e.g., n-charge generation) layer.
[0429] 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 emission 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 and at least one of the second to fourth compounds. Therefore, the light-emitting elements ED-1, ED-2, and ED-3 may exhibit high luminous efficiency and long service life characteristics.
[0430] and Figure 2 Compared with the display device DD of one or more embodiments shown in FIG. Fig.10 The difference of one or more embodiments shown in is that the first to third light-emitting elements ED-1, ED-2 and ED-3 each include two emission layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2 and ED-3, the two emission layers can emit light in substantially the same wavelength region.
[0431] The first light-emitting element ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting element ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. In some embodiments, the third light-emitting element ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary part OG may be disposed between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.
[0432] The emission auxiliary part OG may include a single layer or multiple layers. The emission auxiliary part OG may include a charge generation layer. More specifically, the emission auxiliary part OG may include an electron transport region, a charge generation layer, and a hole transport region stacked sequentially. The emission auxiliary part OG may be provided as a common layer throughout the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and the emission auxiliary part OG may be provided by being patterned within an opening OH defined in the pixel defining film PDL.
[0433] The first red emission layer EML-R1, the first green emission layer EML-G1 and the first blue emission layer EML-B1 may be disposed between the emission auxiliary part OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2 and the second blue emission layer EML-B2 may be disposed between the hole transport region HTR and the emission auxiliary part OG.
[0434] For example, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary portion OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked sequentially. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary portion OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked sequentially. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary portion OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked sequentially.
[0435] In some embodiments, an optical auxiliary layer PL may be provided on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be provided on the display panel DP and control light reflected in the display panel DP due to external light. Unlike the illustrated configuration, the optical auxiliary layer PL in the display device DD-b according to one or more embodiments may not be provided.
[0436] 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 facing each other and first to fourth light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3 sequentially stacked between the first electrode EL1 and the second electrode EL2 in the thickness direction. The charge generation layers CGL1, CGL2 and CGL3 may be disposed between the first to fourth light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3. Among the four light emitting structures, the second to fourth light emitting structures OL-B1, OL-B2 and OL-B3 may emit blue light, and the first light emitting structure OL-C1 may emit green light. However, the embodiments of the present disclosure are not limited thereto, and the first to fourth light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3 may emit light beams in different wavelength regions.
[0437] 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 a p-type or p-like charge generation layer and / or an n-type or n-like charge generation layer.
[0438] In one or more embodiments, the electronic device may include a display device including a plurality of light emitting elements and a control unit for controlling the display device. The electronic device of one or more embodiments may be a device activated according to an electrical signal. The electronic device may include a display device of one or more suitable embodiments. For example, the electronic device may include not only large electronic devices such as televisions, monitors, or outdoor billboards, but also small and medium-sized electronic devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, or cameras.
[0439] Fig.12 is a view showing a vehicle AM in which first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are provided. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a Figure 1 , Figure 2 and Figures 8 to 11 The described display devices DD, DD-a, DD-TD, DD-b and DD-c have the same construction.
[0440] Fig.12The vehicle AM is shown, but this is an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be provided 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 to fourth display devices DD-1, DD-2, DD-3, and DD-4 including the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one or more embodiments may be used for 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 adopted in other electronic devices unless departing from the present disclosure.
[0441] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include Figures 3 to 7 The light emitting element ED of one or more embodiments described. At least one of (e.g., selected from) the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the polycyclic compound of one or more embodiments and at least one of the second to fourth compounds. Therefore, the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may exhibit high luminous efficiency and long service life characteristics.
[0442] 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 disposed to face the driver.
[0443] The first display device DD-1 may be disposed in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital cluster displaying first information of the vehicle AM. The first information may include a first scale indicating the driving speed of the vehicle AM, a second scale indicating the engine speed (i.e., revolutions per minute (RPM)), and / or an image indicating the fuel status, etc. The first scale and the second scale may be indicated as digital images.
[0444] The second display device DD-2 can be arranged in a second area facing the driver's seat and overlapping with the front window GL. The driver's seat can be a seat in which the steering wheel HA 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. Different from the illustrated construction, the second information of the second display device DD-2 can be projected onto the front window GL for display.
[0445] The third display device DD-3 may be arranged in a third area adjacent to the 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 separated and / or spaced apart from the driver's seat and the GR is arranged between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), playing music or radio or video (or images) and / or the temperature inside the vehicle AM, etc.
[0446] The fourth display device DD-4 may be separated and / or spaced apart from the steering wheel HA and the gear GR, and may be disposed 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 captured by a camera module CM disposed outside the vehicle AM. The fourth information may include an image of the outside of the vehicle AM.
[0447] The first to fourth information described may be examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may also display information about the interior and exterior of the vehicle AM. The first to fourth information may include different information. However, the embodiments of the present disclosure are not limited thereto, and a portion of the first to fourth information may include the same information as each other.
[0448] Terms such as "substantially", "about", and "approximately" are used as relative terms rather than terms of degree, and are intended to take into account the inherent deviations in measured or calculated values that one of ordinary skill in the art will recognize. They may include the stated value and an acceptable range of deviation determined by one of ordinary skill in the art taking into account the limitations and errors associated with the measurement of that amount. For example, "about" may refer to one or more standard deviations, or ±30%, ±20%, ±10%, ±5% of the stated value.
[0449] The numerical ranges disclosed herein include and are intended to disclose all subranges of the same numerical precision. For example, a range of "1.0 to 10.0" includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Therefore, the applicant reserves the right to amend this specification (including the claims) to explicitly recite any subranges contained within the ranges explicitly recited herein.
[0450] Any suitable hardware, firmware (e.g., an application specific integrated circuit), software, or a combination of software, firmware, and hardware may be used to implement the light emitting device, light emitting element, and / or any other related device or component according to the embodiments of the present disclosure described herein. For example, the various components of the light emitting device and / or light emitting element may be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the light emitting device and / or light emitting element 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 and / or element may be processes or threads that execute computer program instructions and interact with other system components to perform various functions described herein, running on one or more processors in one or more computing devices. The computer program instructions are stored in a memory, which may be implemented in a computing device using a standard memory device (such as a random access memory (RAM) as an example). The computer program instructions may also be stored in other non-temporary computer-readable media (such as a CD-ROM, a flash drive, etc. as an example). In addition, those skilled in the art should recognize that the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a particular computing device may be distributed to one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
[0451] In the present disclosure, when the particles are spherical, "diameter" means the average particle diameter, and when the particles are non-spherical, "diameter" means the length of the major axis. The diameter (or size) of the particles can be measured by particle size analysis, dynamic light scattering, scanning electron microscopy and / or transmission electron microscopy photography. When the size of the particles is measured using a particle size analyzer, the average particle diameter (or size) can be referred to as D50. The term "D50" as used herein refers to the average diameter (or size) of the particles corresponding to 50% by volume of the cumulative volume and particle size distribution (e.g., cumulative distribution), and refers to the particle size value corresponding to 50% of the smallest particles accumulated in the distribution curve in the order of the smallest particle size to the largest particle size when the total number of particles is 100%. Particle size analysis can be performed with a HORIBA LA-950 laser particle size analyzer.
[0452] Hereinafter, referring to Examples and Comparative Examples, a polycyclic compound according to one or more embodiments of the present disclosure and a light-emitting element according to one or more embodiments will be specifically explained. In some embodiments, the examples are illustrative to help understand the present disclosure, but the scope of the present disclosure is not limited thereto.
[0453] Example
[0454] 1. Synthesis of Exemplary Polycyclic Compounds
[0455] The synthesis method of the polycyclic compound according to the current embodiment will be described by showing the synthesis methods of Compound 24, Compound 47, Compound 112, and Compound 135. In some embodiments, in the following description, the synthesis method of the polycyclic compound is provided as an example, but the synthesis method of the compound according to one or more embodiments of the present disclosure is not limited to the examples described herein.
[0456] (1) Synthesis of Compound 24
[0457] Compound 24 according to the example can be synthesized by, for example, the steps shown in Reaction Scheme 1:
[0458] Reaction Scheme 1
[0459]
[0460] Synthesis of Intermediate 24-1
[0461] 1,3-Dibromo-5-(tert-butyl)benzene (1 equivalent), N-([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5 )-[2,4'-dibenzo[b,d]furan]-6'-amine (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3 , 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in o-xylene, and the resulting mixture was stirred at about 130° C. for about 20 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 24-1 (yield: 68%).
[0462] Synthesis of intermediate 24-2
[0463] Intermediate 24-1 (1 equivalent), 5'-(tert-butyl)-N-(3-chlorophenyl)-[1,1':3',1"-terphenyl]-2'-amine (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalents), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in o-xylene, and the resulting mixture was stirred at about 150° C. for about 20 hours in a high-pressure reactor under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 24-2 (yield: 63%).
[0464] Synthesis of intermediate 24-3
[0465] Intermediate 24-2 (1 equivalent) was dissolved in o-dichlorobenzene (oDCB), the flask was cooled to about 0 °C under nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was slowly injected into it. 3 (5 equivalents). After the addition is complete, the temperature is raised to about 190°C, and the resulting mixture is stirred for about 24 hours. After the resulting mixture is cooled to about 0°C, triethylamine is slowly added dropwise to the flask until heating is stopped to terminate the reaction, and then n-hexane and methanol are added to the flask to precipitate a solid. The precipitated solid is obtained by filtration. The obtained solid is purified by silica filtration, and then purified again by recrystallization in dichloromethane / hexane (MC / Hex) to obtain intermediate 24-3 (yield: 9%).
[0466] Synthesis of compound 24
[0467] Intermediate 24-3 (1 equivalent), 9H-carbazole-1,2,3,4,5,6,7,8-d 8 (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3, 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 150° C. for about 24 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 24 (yield: 61%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was determined to be compound 24 by ESI-LCMS. ESI-LCMS: [M] +: 1195.8
[0468] (2) Synthesis of Compound 47
[0469] Compound 47 according to the example can be synthesized by, for example, the steps shown in Reaction Scheme 2:
[0470] Reaction Scheme 2
[0471]
[0472] Synthesis of Intermediate 47-1
[0473] 1,3-Dibromo-5-(tert-butyl)benzene (1 equivalent), N-(3-fluorophenyl)-6-(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]furan-4-amine (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3 , 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 2 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 100° C. for about 20 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 47-1 (yield: 73%).
[0474] Synthesis of Intermediate 47-2
[0475] Intermediate 47-1 (1 equivalent), N-(3-chlorophenyl)-[1,1':3',1"-terphenyl]-4'-amine (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2(dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3 , 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 2 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 150° C. for about 20 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 47-2 (yield: 75%).
[0476] Synthesis of Intermediate 47-3
[0477] Intermediate 47-2 (1 equivalent) was dissolved in o-dichlorobenzene (oDCB), the flask was cooled to about 0°C under a nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was slowly injected into it. 3 (5 equivalents). After the addition is complete, the temperature is raised to about 190°C, and the resulting mixture is stirred for about 24 hours. After the resulting mixture is cooled to about 0°C, triethylamine is slowly added dropwise to the flask until heating is stopped to terminate the reaction, and then n-hexane and methanol are added to the flask to precipitate a solid. The precipitated solid is obtained by filtration. The obtained solid is purified by silica filtration, and then purified again by recrystallization in dichloromethane / hexane (MC / Hex) to obtain intermediate 47-3 (yield: 11%).
[0478] Synthesis of Intermediate 47-4
[0479] Intermediate 47-3 (1 equivalent) and tripotassium phosphate (K 3 PO 4 , 3 equivalents) was dissolved in N,N-dimethylformamide (DMF), and then the resulting mixture was stirred for 24 hours by raising the temperature to about 150°C. After cooling, the resulting mixture was dried under reduced pressure, and DMF was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 47-4 (yield: 64%).
[0480] Synthesis of compound 47
[0481] Intermediate 47-4 (1 equivalent), 3,6-di-tert-butyl-9H-carbazole (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2(dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3 , 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 150° C. for about 24 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 47 (yield: 60%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 47 by ESI-LCMS. ESI-LCMS: [M] +: 1411.1
[0482] (3) Synthesis of Compound 112
[0483] Compound 112 according to the example can be synthesized by, for example, the steps shown in Reaction Scheme 3:
[0484] Reaction Scheme 3
[0485]
[0486] Synthesis of Intermediate 112-1
[0487] 1,3-Dibromo-5-chlorobenzene (1 equivalent), (16-(9,9'-spirobi[fluorene]-4-yl)-N-([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d 5 ) dibenzo[b,d]thiophene-4-amine (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3 , 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 1.5 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 90° C. for about 20 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 112-1 (yield: 69%).
[0488] Synthesis of Intermediate 112-2
[0489] Intermediate 112-1 (1 equivalent), 5'-(tert-butyl)-N-(3',5'-di-tert-butyl-[1,1'-biphenyl]-3-yl)-[1,1':3',1"-terphenyl]-2'-amine (1.2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalents), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in o-xylene, and the resulting mixture was stirred at about 150° C. for about 20 hours in a high-pressure reactor under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 112-2 (yield: 64%).
[0490] Synthesis of intermediate 112-3
[0491] Intermediate 112-2 (1 equivalent) was dissolved in o-dichlorobenzene (oDCB), the flask was cooled to about 0 °C under nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was slowly injected into it. 3 (5 equivalents). After the addition is complete, the temperature is raised to about 190°C, and the resulting mixture is stirred for about 24 hours. After the resulting mixture is cooled to about 0°C, triethylamine is slowly added dropwise to the flask until heating is stopped to terminate the reaction, and then n-hexane and methanol are added to the flask to precipitate a solid. The precipitated solid is obtained by filtration. The obtained solid is purified by silica filtration, and then purified again by recrystallization in dichloromethane / hexane (MC / Hex) to obtain intermediate 112-3 (yield: 12%).
[0492] Synthesis of compound 112
[0493] Intermediate 112-3 (1 equivalent), 3,6-di-tert-butyl-9H-carbazole (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3, 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 150° C. for about 24 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 112 (yield: 67%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 112 by ESI-LCMS. ESI-LCMS: [M] +: 1596.4
[0494] (4) Synthesis of Compound 135
[0495] Compound 135 according to the example can be synthesized by, for example, the steps shown in Reaction Scheme 4:
[0496] Reaction Scheme 4
[0497]
[0498] Synthesis of Intermediate 135-1
[0499] 3,5-dibromo-3',5'-di-tert-butyl-1,1'-biphenyl (1 equivalent), N-(3-chlorophenyl)-6-(3,5-di-tert-butylphenyl)dibenzo[b,d]furan-4-amine (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3 , 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 1.5 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 90° C. for about 20 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 Drying and then drying under reduced pressure The obtained product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain Intermediate 135-1 (yield: 74%).
[0500] Synthesis of Intermediate 135-2
[0501] Intermediate 135-2 (1 equivalent) was dissolved in o-dichlorobenzene (oDCB), the flask was cooled to about 0 °C under nitrogen atmosphere, and then BBr dissolved in o-dichlorobenzene was slowly injected into it.3 (5 equivalents). After the addition is complete, the temperature is raised to about 190°C, and the resulting mixture is stirred for about 24 hours. After the resulting mixture is cooled to about 0°C, triethylamine is slowly added dropwise to the flask until heating is stopped to terminate the reaction, and then n-hexane and methanol are added to the flask to precipitate a solid. The precipitated solid is obtained by filtration. The obtained solid is purified by silica filtration, and then purified again by recrystallization in dichloromethane / hexane (MC / Hex) to obtain intermediate 135-2 (yield: 13%).
[0502] Synthesis of compound 135
[0503] Intermediate 135-2 (1 equivalent), 9H-carbazole-1,2,3,4,5,6,7,8-d 8 (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 0.05 equivalent), tri-tert-butylphosphine (PtBu 3 , 0.10 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in o-xylene, and the resulting mixture was then stirred at about 150° C. for about 24 hours under a nitrogen atmosphere. After cooling, the resulting mixture was dried under reduced pressure, and the o-xylene was removed. Then, the resulting product was washed with water and extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was washed with anhydrous MgSO 4 The product was purified by column chromatography (dichloromethane: n-hexane) and recrystallized to obtain compound 135 (yield: 70%). The product was then further purified by sublimation purification to obtain the final purity. The obtained compound was identified as compound 135 by ESI-LCMS. ESI-LCMS: [M] +: 1512.3
[0504] 2. Evaluation of polycyclic compounds
[0505] The polycyclic compounds used in the Examples and Comparative Examples are listed in Table 1.
[0506] Table 1
[0507]
[0508]
[0509] 2. Manufacturing and evaluation of light-emitting components
[0510] (1) Manufacturing of light-emitting elements
[0511] A light-emitting element including the exemplified polycyclic compound or the comparative example compound in the emission layer was manufactured as follows. The exemplified polycyclic compounds were respectively used as dopant materials for the emission layer to manufacture the light-emitting elements of Examples 1 to 4. Comparative example compounds C1 to C3 were respectively used as dopant materials for the emission layer to manufacture the light-emitting elements of Comparative Examples 1 to 3.
[0512] A first electrode having a resistance of about 15 ohms per square centimeter (Ω / cm 2 )(About 1200 Angstroms ) of an ITO electrode (manufactured by Corning Co.) was cut into a size of about 50 millimeters (mm) × 50 mm × 0.7 mm, cleaned by ultrasonic wave using isopropyl alcohol and pure water for about 5 minutes each, then irradiated with ultraviolet light for about 30 minutes, exposed to ozone and cleaned. The glass substrate was mounted on a vacuum deposition device.
[0513] On the first electrode, NPD (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was vacuum deposited to form A thick hole injection layer is formed by vacuum depositing compound H-1-1 on the hole injection layer. Next, CzSi was vacuum deposited on the hole transport layer to form Thick emission assist layer.
[0514] On the emission auxiliary layer, a host mixture, a phosphorescent sensitizer, and a dopant are co-deposited in a weight ratio of about 85:14:1 to form As the host mixture, the compound HT1 as the hole transport host and the compound ETH66 as the electron transport host are provided in a weight ratio of about 5:5. As the phosphorescent sensitizer material, the compound AD-37 is used. As the dopant material, the exemplified polycyclic compound or the comparative exemplified compound is used.
[0515] On the emission layer, TSPO1 is vacuum deposited to form Then, TPBi is vacuum deposited on the hole blocking layer to form Then, on the upper portion of the electron transport layer, LiF is vacuum deposited to form Next, Al is vacuum deposited on the upper portion of the electron injection layer to form A thick second electrode is formed to manufacture a light-emitting element.
[0516] The compounds used to make the light emitting element are as follows:
[0517] Materials used to make light-emitting components
[0518]
[0519] (2) Evaluation of light-emitting elements
[0520] The light-emitting elements of the examples and comparative examples were evaluated, and the results are shown in Table 2. In the light-emitting elements of the examples and comparative examples, the luminance at 1000 (mA / cm2) was measured by using Keithley MU 236 and a luminance meter PR650. 2 )) at a current density of 1.5 20 ℃ and a driving voltage (V) and a luminous efficiency (candela per ampere per year (cd / A / y)) of each, and the results are shown in Table 2. The service life is expressed as a relative element service life by measuring the time taken to reach 95% brightness relative to the initial brightness and comparing the measurement with the measurement of Comparative Example 3. The service life of Comparative Example 3 is set to 100%, and in Table 2, the service life of the example and the comparative example is expressed as a relative ratio.
[0521] Table 2
[0522]
[0523] Referring to the results of Table 2, the light-emitting elements of the examples and comparative examples all emit blue light. In some embodiments, the light-emitting elements of Examples 1 to 3 use the polycyclic compounds according to the examples as light-emitting materials, and therefore exhibit low driving voltage characteristics compared to the light-emitting elements of Comparative Examples 1 to 3.
[0524] It can be seen that, compared with the light-emitting elements of Comparative Examples 1 to 3, the light-emitting elements of Examples 1 to 3 exhibit high luminous efficiency and long service life characteristics. Specifically, it can be seen that, compared with Comparative Examples 1 to 3, the light-emitting elements of Examples 1 to 3 exhibit high luminous efficiency and significantly improved service life characteristics. For example, the polycyclic compound utilized in the example may have a structure (which includes a five-ring fused ring containing two nitrogen atoms and one boron atom as ring atoms as a central structure, and wherein a substituent capable of inhibiting Dexter energy transfer is connected to at least one of the two nitrogen atoms), thereby exhibiting excellent or suitable material stability. Therefore, compared with the light-emitting element of the comparative example including the comparative example compound in the emission layer, the light-emitting element of the example of the polycyclic compound included in the emission layer can concurrently (e.g., simultaneously) exhibit excellent or suitable luminous efficiency and service life characteristics.
[0525] The light emitting element of one or more embodiments may include the polycyclic compound of one or more embodiments, thereby exhibiting high light emitting efficiency and long lifespan characteristics.
[0526] The polycyclic compound of one or more embodiments may contribute to improved luminous efficiency and long lifespan of a light emitting element.
[0527] In some embodiments, the display device of one or more embodiments may include a light emitting element that exhibits the described effects, thereby exhibiting characteristics of improving image quality and display efficiency.
[0528] Although the present disclosure has been described with reference to preferred embodiments thereof, it will be understood that the present disclosure should not be limited to these preferred embodiments, but one or more suitable changes and modifications may be made by one skilled in the art without departing from the spirit and scope of the present disclosure.
[0529] Therefore, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the specific embodiments of the specification, but is intended to be defined by the appended claims and their equivalents.
Claims
1. A polycyclic compound, the polycyclic compound is represented by Formula 1: Formula 1 in, In formula 1, X 1 YesNR 8 , O or S, R 1 To R 5 are each independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, R 6 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, R 7 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, R 8 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, n1, n4 and n5 are each independently an integer from 0 to 3, and n2 and n3 are each independently an integer from 0 to 4.
2. The polycyclic compound according to claim 1, in, Formula 1 is expressed by Formula 2: Formula 2 Among them, in formula 2, R 11 , R 21 and R 31 are each independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, R 12 , R 22 and R 32 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, n11 is an integer from 0 to 2, n21 and n31 are each independently an integer from 0 to 3, and X 1 , R 4 To R 7 , n4 and n5 are as defined in Formula 1.
3. The polycyclic compound according to claim 2, in, In Formula 2, R 12 , R 22 and R 32 At least one of them is in a para position relationship with the boron atom.
4. The polycyclic compound according to claim 3, in, Formula 2 is represented by any one selected from Formula 2-1 to Formula 2-3: Formula 2-1 Formula 2-2 Formula 2-3 Among them, in Formula 2-1 to Formula 2-3, X 1 , R 4 To R 7 , R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , n4, n5, n11, n21 and n31 are defined as in Formula 1 and Formula 2.
5. The polycyclic compound according to claim 1, in, Formula 1 is represented by Formula 3 or Formula 4: Formula 3 Formula 4 Among them, in formula 3 and formula 4, X 2 YesNR i5 , O or S, R i1 is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, R i2 and R i3 are each independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, R i4 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, R i5 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, i1 is an integer from 0 to 5, i2 and i3 are each independently an integer from 0 to 3, and X 1 , R 1 To R 6 and n1 to n5 are as defined in Formula 1.
6. The polycyclic compound according to claim 5, in, Formula 3 is represented by Formula 3-1 or Formula 3-2, and Formula 4 is represented by Formula 4-1 or Formula 4-2: Formula 3-1 Formula 3-2 Formula 4-1 Formula 4-2 Among them, in formula 3-1 and formula 3-2, Y 1 Yes CR j4 R j5 NR j6 , O or S, R j1 , R j2 and R j3 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, R j4 , R j5 and R j6 are independently substituted or unsubstituted aryl groups having 6 to 15 ring carbon atoms, and R j4 and R j5 optionally combined to form a ring, j1 is an integer from 0 to 5, j2 is an integer from 0 to 3, j3 is an integer from 0 to 4, and Among them, in formula 4-1 and formula 4-2, Y 2 and Y 3 CR k7 R k8 NR k9 , O or S, R k1 To R k6 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, R k7 , R k8 and R k9 are independently substituted or unsubstituted aryl groups having 6 to 15 ring carbon atoms, R k7 and R k8 Not combined or combined to form a ring, k1 and k2 are each independently an integer from 0 to 5, k3 and k5 are each independently an integer from 0 to 3, k4 and k6 are each independently an integer from 0 to 4, and X 1 , X 2 , R 1 To R 5 , R i1 , R i2 , R i3 , n1 to n5, i1, i2 and i3 are as defined in Equation 1, Equation 3 and Equation 4.
7. The polycyclic compound according to claim 1, in, R 6 It is represented by any one of the substituents selected from Substituent Group 1: Substituent Group 1 8. The polycyclic compound according to claim 1, in, R 1 , R 2 and R 3 Each is independently a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.
9. The polycyclic compound according to claim 1, in, Formula 1 is represented by any one of the compounds selected from compound group 1: Compound Group 1 10. A light-emitting element, wherein the light-emitting element include: a first electrode; a second electrode, on the first electrode; as well as an emission layer, between the first electrode and the second electrode, Wherein, the emission layer comprises the polycyclic compound according to any one of claims 1 to 9 as the first compound.
11. The light-emitting element according to claim 10, in, The emission layer includes at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1: Formula HT-1 Among them, in formula HT-1, A 1 To A 8 are independently N or CR 51 , L 1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a It is a direct key, CR 52 R 53 or SiR 54 R 55 , Ar 1 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 Among them, in formula ET-1, Selected from X 1a To X 3a At least one of them is N, and any remaining X 1a To X 3a Yes 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 from 0 to 10, Ar 2 To Ar 4 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 L 2 To L 4 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, Formula D-1 Wherein, in formula D-1, Q 1 To Q 4 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 are independently direct bonds, *-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, 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 from 0 to 4.
12. The light-emitting element according to claim 11, wherein the second compound represented by the formula HT-1 is represented by any one of the compounds of compound group 2: Compound Group 2 in, "D" refers to a deuterium atom, and "Ph" refers to a substituted or unsubstituted phenyl group.
13. The light-emitting element according to claim 11, wherein the third compound represented by Formula ET-1 is represented by any one of the compounds of Compound Group 3: Compound Group 3 in, "D" refers to a deuterium atom, and "Ph" refers to an unsubstituted phenyl group.
14. The light-emitting element according to claim 11, wherein the fourth compound represented by Formula D-1 is represented by any one of the compounds of Compound Group 4: Compound Group 4 in, "D" refers to a deuterium atom.
15. A display device, the display device include: Base layer; A circuit layer, on the substrate layer; as well as a display device layer on the circuit layer and including a light emitting element, The light emitting element includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode. Wherein, the emission layer includes: The polycyclic compound according to any one of claims 1 to 9 as the first compound; and At least one of the second compound represented by formula HT-1, the third compound represented by formula ET-1, or the fourth compound represented by formula D-1: Formula HT-1 Among them, in formula HT-1, A 1 To A 8 are independently N or CR 51 , L 1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a It is a direct key, CR 52 R 53 or SiR 54 R 55 , Ar 1 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 Among them, in formula ET-1, Selected from X 1a To X 3a At least one of them is N, and any remaining X 1a To X 3a Yes 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 from 0 to 10, Ar 2 To Ar 4 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 L 2 To L 4 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, Formula D-1 Wherein, in formula D-1, Q 1 To Q 4 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 are independently direct bonds, *-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, 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 from 0 to 4.
16. The display device according to claim 15, wherein the display device further comprises: include: a light control layer including quantum dots; and The color filter layer is on the light control layer and includes a first filter configured to transmit red light, a second filter configured to transmit green light, and a third filter configured to transmit blue light.
17. The light-emitting element according to claim 15, wherein the second compound represented by Formula HT-1 is represented by any one of the compounds of Compound Group 2: Compound Group 2 in, "D" refers to a deuterium atom, and "Ph" refers to a substituted or unsubstituted phenyl group.
18. The light-emitting element according to claim 15, wherein the third compound represented by Formula ET-1 is represented by any one of the compounds of Compound Group 3: Compound Group 3 in, "D" refers to a deuterium atom, and "Ph" refers to an unsubstituted phenyl group.
19. The light-emitting element according to claim 15, wherein the fourth compound represented by Formula D-1 is represented by any one of the compounds of Compound Group 4: Compound Group 4 in, "D" refers to a deuterium atom.
