Light-emitting element, amine compound for light-emitting element, and display device including the light-emitting element
By using a specific amine compound, such as an amine compound represented by Formula 1, as a functional layer, the problem of insufficient emission efficiency and lifetime of the light emitting element in the prior art is solved, and the effects of efficient emission and long lifetime are achieved.
Patent Information
- Application Number
- CN202411392616.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-06
- Filing Date
- 2024-10-08
- Publication Date
- 2025-04-08
AI Technical Summary
When used in display devices, it is difficult to achieve high emission efficiency and long component life.
A functional layer containing a specific amine compound, such as an amine compound represented by Formula 1, is used as a hole transport region or an emitting layer in a light emitting element to improve emission efficiency and extend the lifetime of the element.
By using these amine compounds, the emission efficiency and component life of the light emitting element are significantly improved, and the display quality is improved.
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Figure CN119775265A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0133643 filed in the Korean Intellectual Property Office on October 6, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] The present disclosure relates to a light-emitting element, an amine compound used for the light-emitting element, and a display device including the light-emitting element. Background Art
[0004] Recently, the development of organic electroluminescent display devices (e.g., as image display devices) is being actively pursued or sought. The organic electroluminescent display device may be a so-called "self-luminous" type or kind of light-emitting element, 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 (e.g., an organic compound) in the emission layer (e.g., a light-emitting layer) emits light to achieve display (e.g., display of an image).
[0005] The application of light-emitting elements to display devices requires or expects to increase emission efficiency and element life. For example, it is expected or required to develop materials for light-emitting elements that can stably achieve the above-mentioned goals and / or requirements, and these goals and / or requirements are being continuously pursued. Summary of the invention
[0006] One or more aspects of the embodiments of the present disclosure are directed to a light emitting element having improved emission efficiency and element life characteristics.
[0007] One or more aspects of embodiments of the present disclosure relate to an amine compound that can improve emission efficiency and lifetime of a light-emitting element.
[0008] One or more aspects of embodiments of the present disclosure are directed to a display device including a light emitting element and having excellent or appropriate display quality.
[0009] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments of the disclosure.
[0010] The light emitting element according to one or more embodiments includes a first electrode, a second electrode disposed on the first electrode, and at least one functional layer disposed between the first electrode and the second electrode and including the amine compound of one or more embodiments. The amine compound of one or more embodiments may be represented by Formula 1.
[0011] Formula 1
[0012]
[0013] In Formula 1, X can be O or S, 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. 2 and Ar 3 may be each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted aromatic group of 6 to 30 ring carbon atoms, wherein the aromatic group selected from Ar 2 and Ar 3 At least one of R is a substituted or unsubstituted aromatic group having 10 to 30 ring carbon atoms. 1 To R 5 Each of "a", "c" and "e" may be independently an integer selected from 0 to 3, and "b" and "d" may be independently an integer selected from 0 to 4. In the case where the nitrogen atom of the amine compound is connected to the 2-position or 7-position of the carbazole part, and is not connected to Ar 1 The 3-position or 6-position of the dibenzothiophene part or dibenzofuran part of the amine compound is connected (for example, when the nitrogen atom of the amine compound is connected to the 2-position or 7-position of the carbazole part, and is not connected to the Ar 1 In the case of formula 1 wherein the nitrogen atom of the amine compound is connected to the 4-position or 5-position of the carbazole portion and is not connected to the 3-position or 6-position of the dibenzothiophene portion or the dibenzofuran portion, and / or wherein the nitrogen atom of the amine compound is connected to the 4-position or 5-position of the carbazole portion and is not connected to the 4-position or 5-position of the carbazole portion 1 The 3-position or 6-position of the dibenzothiophene part or dibenzofuran part of the amine compound is connected (for example, when the nitrogen atom of the amine compound is connected to the 4-position or 5-position of the carbazole part, and is not connected to the Ar 1 In the case of formula 1), a+b≥1 may be satisfied, and R 1 and R 2 In the case of Formula 1 where the nitrogen atom of the amine compound is connected to the 3-position of the carbazole moiety (for example, when the nitrogen atom of the amine compound is connected to the 3-position of the carbazole moiety), R 3 It can be a hydrogen atom or a deuterium atom. Ar 1 Including those directly bonded to the nitrogen atom of the amine compound The case of formula 1 where Y is O or S.
[0014] In one or more embodiments, at least one functional layer may include an emission layer, a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode, and the hole transport region may include an amine compound represented by Formula 1.
[0015] In one or more embodiments, the hole transport region may include at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and at least one selected from the hole injection layer, the hole transport layer, and the electron blocking layer may include an amine compound represented by Formula 1.
[0016] In one or more embodiments, the hole transport region may include a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer, and the hole transport layer may include the amine compound represented by Formula 1.
[0017] In one or more embodiments, the amine compound represented by Formula 1 may be a monoamine compound.
[0018] In one or more embodiments, the amine compound represented by Formula 1 may be represented by Formula 2-1 or Formula 2-2.
[0019] Formula 2-1
[0020]
[0021] Formula 2-2
[0022]
[0023] In formula 2-1, R 6 It may be a hydrogen atom, a deuterium atom, 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 "f" is an integer selected from 0 to 5.
[0024] In formula 2-2, Z can be O or S, R 7 and R 8 "g" may be an integer selected from 0 to 3, and "h" may be an integer selected from 0 to 4.
[0025] In Formula 2-1 and Formula 2-2, X, Ar 2 ,Ar 3 , R 1 To R 5 and "a" to "e" may each independently be as defined in Formula 1.
[0026] In one or more embodiments, selected from Ar 2 and Ar 3At least one of the groups may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted pyrenyl group.
[0027] In one or more embodiments, the amine compound represented by Formula 1 may be represented by Formula 3-1 or Formula 3-2.
[0028] Formula 3-1
[0029]
[0030] Formula 3-2
[0031]
[0032] In formula 3-1 and formula 3-2, R 9 , R 10 ,Ar 21 and Ar 31 may each independently be a hydrogen atom, a deuterium atom or a substituted or unsubstituted aromatic group of 6 to 30 ring carbon atoms, "i" and "k" may each independently be an integer selected from 0 to 7, and X, Ar 1 , R 1 To R 5 and "a" to "e" may each independently be the same as defined in Formula 1.
[0033] In one or more embodiments, R 1 To R 5 They may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.
[0034] In one or more embodiments, the amine compound represented by Formula 1 may be represented by any one selected from Formula 4-1 to Formula 4-4.
[0035] Formula 4-1
[0036]
[0037] Formula 4-2
[0038]
[0039] Formula 4-3
[0040]
[0041] Formula 4-4
[0042]
[0043] In Formula 4-1 to Formula 4-4, R 11 To R13 , R 21 To R 23 , R 31 To R 33 , R 41 and R 42 R may be each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms. 14 , R 24 , R 34 and R 44 may be each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, R 15 , R 25 , R 35 , R 43 and R 45 a1 to a4, c1 to c4 and e1 to e4 may each independently be an integer selected from 0 to 3, and b1 to b4 and d1 to d4 may each independently be an integer selected from 0 to 4. X and Ar 1 To Ar 3 may each independently be as defined in Formula 1.
[0044] In which the nitrogen atom of the amine compound is not Ar 1 In the case of the formula 4-2 connected to the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part, a2+b2≥1 may be satisfied, and R 21 and R 22 At least one of the may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
[0045] In some embodiments, the nitrogen atom of the amine compound is not Ar 1 In the case of formula 4-4 connected to the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part, a4+b4≥1 may be satisfied, and R 41 and R 42 At least one of the may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.
[0046] In one or more embodiments, selected from Ar 2 and Ar 3 At least one of may be represented by one of the substituents selected from Substituent Group 1.
[0047] In one or more embodiments, the amine compound may be selected from at least one of the compounds in Compound Group 1.
[0048] The display device of one or more embodiments includes a substrate layer, a circuit layer arranged on the substrate layer, and a display element layer arranged on the circuit layer and including a light-emitting element. Here, the light-emitting element includes a first electrode, a second electrode on the first electrode, and at least one functional layer between the first electrode and the second electrode, and at least one functional layer includes an amine compound represented by Formula 1. In one or more embodiments, the light-emitting element includes a first electrode, a hole transport region arranged on the first electrode, an emission layer arranged on the hole transport region, an electron transport region arranged on the emission layer, and a second electrode arranged on the electron transport region, and the hole transport region includes an amine compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS
[0049] 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:
[0050] Figure 1 A plan view showing a display device according to one or more embodiments of the present disclosure;
[0051] Figure 2 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0052] Figure 3 A cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0053] Figure 4 A cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0054] Figure 5 A cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0055] Figure 6 A cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0056] Figure 7 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0057] Figure 8 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0058] Fig. 9 A cross-sectional view showing a display device according to one or more embodiments of the present disclosure;
[0059] Fig.10 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure; and
[0060] Fig.11 A view showing a vehicle in which a display device is arranged according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0061] The present disclosure can be modified in one or more suitable ways, and the present disclosure has many forms, and therefore specific embodiments will be exemplified in the drawings and described in more detail in the detailed description of the present disclosure. However, it should be understood that the present disclosure is not intended to be limited to the specific form disclosed, but is intended to cover all modifications, equivalents and alternatives that fall within the spirit and scope of the present disclosure.
[0062] When explaining each drawing, the same reference numerals are used to refer to the same elements. In the attached drawings, for the clarity of the present disclosure, the size of each structure is enlarged and explained. It will be understood that although the terms "first" and / or "second" etc. can be used to describe one or more appropriate components in this article, these components should not be limited by these terms. These terms are only used to distinguish one component from another component. For example, without departing from the scope of the example embodiments of the present disclosure, the first component may be referred to as the second component, and similarly, the second component may be referred to as the first component. As used herein, unless the context clearly indicates otherwise, the singular forms "a", "an" and "said" are intended to also include plural forms.
[0063] In the present application, it will be understood that the terms “include,” “includes,” “including,” “comprise,” “comprises,” “comprising,” and / or “has,” “have,” “having,” etc. indicate the presence of features, quantities, steps, operations, components, parts, and / or combinations thereof disclosed in the specification, but do not exclude the possibility of the presence or addition of one or more other features, quantities, steps, operations, components, parts, or combinations thereof.
[0064] In the present application, when a layer, film, region or plate is referred to as being "on" another layer, film, region or plate or "on the upper part of" another layer, film, region or plate, it may not only be "directly on" the layer, film, region or plate, but also there may be intervening layers, films, regions or plates. In contrast, when a layer, film, region or plate is referred to as being "below" another layer, film, region or plate, "on the lower part of" another layer, film, region or plate, it 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 component is referred to as being "on" another component, it may be arranged above the other component, or it may also be arranged below the other component.
[0065] For example, for ease of description, terms such as "below", "above" and / or "on" are used herein to describe the relationship between one element and another element as illustrated in the accompanying drawings. These terms are relative concepts and are described based on the directions indicated in the accompanying drawings. It will be understood that the terms have relative concepts and are described based on the orientations depicted in the accompanying drawings. It will be understood that in addition to the orientations depicted in the accompanying drawings, spatially relative terms are also intended to encompass different orientations of devices in use or operation. For example, if the device in the accompanying drawings is turned over, the elements described as "below" other elements or features will then be oriented "above" or "on" other elements or features. Therefore, the term "below" can encompass both above and below orientations. The device can be oriented in other ways (rotated 90 degrees or in other orientations), and the spatially relative descriptors used in this article should be interpreted accordingly.
[0066] As utilized herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.
[0067] As utilized herein, expressions such as “at least one of,” “one of,” “selected from,” and “selected from,” when preceding / following a list of elements, modify the entire list of elements and do not modify the individual elements of the list. For example, the expressions “at least one of a through c,” “at least one of a, b, and c,” and “at least one of a, b, and / or c” may indicate only a, only b, only c, both a and b (e.g., a and b simultaneously), both a and c (e.g., a and c simultaneously), both b and c (e.g., b and c simultaneously), all of a, b, and c, or variations thereof.
[0068] The term "and / or" includes all combinations of one or more of the associated listed elements.
[0069] 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 do not include the elements and / or include alternative elements. Similarly, optional language such as "or" refers to "one or more embodiments of the present disclosure" that each include the corresponding enumerated items.
[0070] Unless otherwise defined, all terms (including chemical terms, technical terms and scientific terms) used in this article have the same meaning as those commonly understood by ordinary technicians in the field to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and will not be interpreted in an idealized or overly formal sense unless explicitly defined in this article.
[0071] 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.
[0072] As utilized herein, the phrase “on a plane” or “plan view” refers to observing a target portion from the top, and the phrase “in cross section” refers to observing a cross section formed by vertically cutting the target portion from the side.
[0073] In the present disclosure, "not including a component or any component", "excluding a component or any component" and / or "not containing a component" and the like mean that the "component" is not added, selected or utilized as a component in the composition, but due to other impurities and / or external factors, the "component" may still be included in an amount less than an appropriate amount.
[0074] definition
[0075] 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 including (e.g., consisting of) deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, amido groups, silyl groups, oxy groups, sulfenyl groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. In some embodiments, each of the substituents exemplified herein may be substituted or unsubstituted. For example, biphenyl groups may be interpreted as aryl groups or phenyl groups substituted by phenyl groups.
[0076] In the specification, the phrase "bonded to an adjacent group to form a ring" may refer to a group bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. In some embodiments, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.
[0077] In the specification, the term "adjacent group" may refer to a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or a substituent that is spatially located 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.
[0078] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
[0079] In the specification, the alkyl group may be linear or branched. 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-dodecanyl, and n-dodecyl. alkyl, 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 one or more embodiments of the present disclosure are not limited thereto.
[0080] In the specification, cycloalkyl may refer to a cyclic alkyl. The number of carbon atoms 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 one or more embodiments of the present disclosure are not limited thereto.
[0081] 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 linear or branched. The number of carbon atoms in the alkenyl group is not specifically limited, but may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl and / or styrylvinyl, etc., but one or more embodiments of the present disclosure are not limited thereto.
[0082] 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. Although the number of carbon atoms in the alkynyl group is not specifically limited, it may be 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.
[0083] 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.
[0084] In the specification, aryl refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl may be a monocyclic aryl or a polycyclic aryl. The number of ring carbon atoms in the aryl may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrenyl, benzofluoranthenyl and / or 1,2-triphenylenyl, etc., but one or more embodiments of the present disclosure are not limited thereto.
[0085] In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the substituted fluorenyl group are as follows. However, one or more embodiments of the present disclosure are not limited thereto.
[0086]
[0087] Heterocyclic groups herein refer to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, Se and S as a heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups may be monocyclic or polycyclic.
[0088] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si, Se and S as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. 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.
[0089] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, Se, and S as a heteroatom. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, a thiirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, a thianyl group, a tetrahydropyranyl group, and / or a 1,4-dioxanyl group, but one or more embodiments of the present disclosure are not limited thereto.
[0090] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si, Se and S as a heteroatom. If the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl The invention may be any of a plurality of different embodiments, including, but not limited to, a benzothiophene group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a phenothiazinyl group, a dibenzothiorol group and / or a dibenzofuranyl group, etc., but one or more embodiments of the present disclosure are not limited thereto.
[0091] In the specification, the above description of the aryl group can be applied to the arylene group, except that the arylene group is a divalent group. The above description of the heteroaryl group can be applied to the heteroarylene group, except that the heteroarylene group is a divalent group.
[0092] In the specification, silyl includes alkylsilyl and arylsilyl. The alkyl in the alkylsilyl may be linear, branched or cyclic. The number of carbon atoms in the alkylsilyl is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylsilyl is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of silyl may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and / or phenylsilyl, etc., but one or more embodiments of the present disclosure are not limited thereto.
[0093] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but one or more embodiments of the present disclosure are not limited thereto.
[0094]
[0095] 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.
[0096] In the specification, the thio group may include an alkylthio group and an arylthio group. The alkyl group in the alkylthio group may be linear, branched or cyclic. The number of carbon atoms in the alkylthio group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylthio group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. The thio group may refer to a sulfur atom bonded to an alkyl or aryl group as defined herein. Examples of thio groups may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, naphthylthio, but one or more embodiments of the present disclosure are not limited thereto.
[0097] In the specification, oxy may refer to an oxygen atom bonded to an alkyl or aryl group as defined herein. Oxy may include alkoxy and aryloxy. The number of carbon atoms in the aryloxy is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Alkoxy may be linear, branched or cyclic. The number of carbon atoms in the alkoxy is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy and / or benzyloxy, etc., but one or more embodiments of the present disclosure are not limited thereto.
[0098] Boryl in this article may refer to a boron atom bonded to an alkyl or aryl group as defined in this article. Boryl includes alkylboryl and arylboryl. The alkyl in the alkylboryl may be a linear group, a branched group or a cyclic group. The number of carbon atoms in the alkylboryl is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylboryl is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of boryl may include dimethylboryl, tert-butylmethylboryl, diphenylboryl and / or phenylboryl, etc., but one or more embodiments of the present disclosure are not limited thereto.
[0099] In the specification, the number of carbon atoms in the amine group is not specifically limited, but may be 1 to 30. The amine group may include an alkylamine group and an arylamine group. The alkyl group in the alkylamine group may be a linear group, a branched group, or a cyclic group. The number of carbon atoms in the alkylamine group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylamine group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the amine group may include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, and / or a 9-methyl-anthrylamine group, etc., but one or more embodiments of the present disclosure are not limited thereto.
[0100] In the specification, the sulfinyl group may mean an alkyl group or an aryl group defined above combined with -S(=O)-. The number of carbon atoms of the sulfinyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. For example, the sulfinyl group may have the following structure, but is not limited thereto.
[0101]
[0102] In the specification, sulfonyl may refer to -S(=O) 2 - combined with the above-defined alkyl or aryl groups. The number of carbon atoms of the sulfonyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group. For example, the sulfonyl group may have the following structure, but is not limited thereto.
[0103]
[0104] In the specification, the phosphine oxide group may mean an alkyl group or an aryl group defined above combined with -P(=O)-. The number of carbon atoms of the phosphine oxide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine oxide group may include an alkyl phosphine oxide group and an aryl phosphine oxide group. For example, the phosphine oxide group may have the following structure, but is not limited thereto.
[0105]
[0106] In the specification, the phosphinosulfide group may mean an alkyl or aryl group defined above in combination with -P(=S)-. The number of carbon atoms of the phosphinosulfide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphinosulfide group may include an alkylphosphinosulfide group and an arylphosphinosulfide group. For example, the phosphinosulfide group may have the following structure, but is not limited thereto.
[0107]
[0108] In the specification, the alkyl group in the alkoxy group, alkylthio group, alkylsulfonyl group, alkylsulfinyl group, alkylaryl group, alkylamino group, alkylboryl group, alkylsilyl group, alkylphosphine oxide group, alkylphosphine sulfide group and alkylamine group is the same as the examples of the alkyl group described herein.
[0109] In the specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylsulfinyl group, arylamino group, arylboryl group, arylsilyl group, arylphosphine oxide group, arylphosphine sulfide group and arylamine group is the same as the examples of the aryl group described herein.
[0110] In the specification, a direct connection may refer to a single bond.
[0111] In one or more embodiments, in the specification, "-*"and Indicates the location to be connected.
[0112] Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.
[0113] Display device
[0114] Figure 1 A plan view of a display device DD for explaining one or more embodiments. Figure 2 is a cross-sectional view of a display device DD according to an embodiment. Figure 2 To explain along Figure 1 A cross-sectional view of the portion taken along line II'.
[0115] The display device DD may include a display panel DP and an optical layer PP arranged on the display panel DP. The display panel DP includes light emitting elements ED-1, ED-2, and ED-3. The display device DD may include a plurality of light emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be arranged on the display panel DP to control light reflected 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 one or more embodiments, unlike the configuration illustrated in the drawings, the optical layer PP may not be provided in the display device DD of one or more embodiments.
[0116] The base substrate BL may be arranged on the optical layer PP. The base substrate BL may be a member providing a base surface, and the optical layer PP is arranged on the base surface. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, one or more 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 provided.
[0117] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be arranged between the display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.
[0118] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light emitting elements ED-1, ED-2, and ED-3 arranged between a plurality of portions of the pixel defining film PDL, and an encapsulation layer TFE arranged on the light emitting elements ED-1, ED-2, and ED-3.
[0119] The base layer BS may be a member providing a base surface on which the display device layer DP-ED is arranged. The base layer BS may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, one or more embodiments are not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
[0120] In one or more embodiments, the circuit layer DP-CL is arranged on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the plurality of 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.
[0121] Each of the light emitting elements ED-1, ED-2 and ED-3 may have a configuration as described in more detail elsewhere herein according to Figures 3 to 6 Each of the light emitting elements ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, emission layers EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.
[0122] Figure 2One or more embodiments are explained in which the emission layers EML-R, EML-G and EML-B of the light-emitting elements ED-1, ED-2 and ED-3 are arranged 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 provided as a common layer in the entire light-emitting elements ED-1, ED-2 and ED-3. However, one or more embodiments of the present disclosure are not limited thereto, and are not limited to Figure 2 Different from the configuration explained in the above, the hole transport region HTR and the electron transport region ETR in one or more embodiments may be provided by patterning in the opening OH defined in the pixel defining film PDL. For example, the hole transport region HTR, the emission layers EML-R, EML-G and EML-B, and the electron transport region ETR of the light-emitting elements ED-1, ED-2 and ED-3 in one or more embodiments may be provided by patterning using an inkjet printing method.
[0123] The encapsulation layer TFE may cover the light-emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the light-emitting elements ED-1, ED-2 and ED-3 in the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one or more layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to one or more embodiments may include at least one inorganic film (hereinafter, encapsulation-inorganic film). The encapsulation layer TFE according to one or more embodiments may also include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.
[0124] The encapsulation-inorganic film protects the display device layer DP-ED from moisture and / or oxygen, and the encapsulation-organic film protects the display device layer DP-ED from foreign substances (e.g., dust particles). The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide and / or aluminum oxide, etc., but one or more embodiments of the present disclosure are not specifically 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 one or more embodiments of the present disclosure are not specifically limited thereto.
[0125] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the open holes OH.
[0126] refer to Figure 1 and Figure 2, the display device DD may include one or more non-light-emitting areas NPXA, and also include light-emitting areas PXA-R, PXA-G, and PXA-B. The light-emitting areas PXA-R, PXA-G, and PXA-B may be areas in which light generated by the respective light-emitting elements ED-1, ED-2, and ED-3 is emitted. In a plane (e.g., in a plan view), the light-emitting areas PXA-R, PXA-G, and PXA-B may be spaced and / or separated (e.g., spaced or separated) from each other.
[0127] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B may be an area divided (i.e., defined) by a pixel-defining film PDL. The non-light-emitting area NPXA may be an area corresponding to the pixel-defining film PDL between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B. In one or more embodiments, in the specification, the light-emitting areas PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel-defining film PDL may divide the light-emitting elements ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be arranged in the openings OH defined in the pixel-defining film PDL and separated from each other.
[0128] The light emitting areas 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 illustrated in , three light emitting areas PXA-R, PXA-G, and PXA-B that emit red light, green light, and blue light, respectively, are schematically illustrated. For example, the display device DD of one or more embodiments may include a red light emitting area PXA-R, a green light emitting area PXA-G, and a blue light emitting area PXA-B that are separated from each other.
[0129] 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 wavelength ranges different 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.
[0130] However, one or more embodiments of the present disclosure are not limited thereto, and the first to third light emitting elements ED-1, ED-2, and ED-3 may emit light beams in substantially the same wavelength range or at least one light emitting element may emit light beams in a wavelength range different from other wavelength ranges. For example, the first to third light emitting elements ED-1, ED-2, and ED-3 may all emit blue light.
[0131] The light emitting areas PXA-R, PXA-G, and PXA-B in the display device DD according to one or more embodiments may be arranged in a stripe form. Figure 1 , a plurality of red light emitting areas PXA-R may be arranged along the second direction axis DR2, a plurality of green light emitting areas PXA-G may be arranged along the second direction axis DR2, and a plurality of blue light emitting areas PXA-B may each be arranged along the second direction axis DR2. In some embodiments, the red light emitting areas PXA-R, the green light emitting areas PXA-G, and the blue light emitting areas PXA-B may be alternately arranged in this order along the first direction axis DR1.
[0132] Figure 1 and Figure 2 It is explained that all the light emitting regions PXA-R, PXA-G, and PXA-B have the same area, but one or more 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. The third direction axis DR3 may be perpendicular to the plane defined by the first direction axis DR1 and the second direction axis DR2.
[0133] In one or more embodiments, the arrangement of the light-emitting areas PXA-R, PXA-G, and PXA-B is not limited to Figure 1 The configuration explained in the above description and the order of arranging the red light emitting areas PXA-R, the green light emitting areas PXA-G and the blue light emitting areas PXA-B can be provided in one or more appropriate combinations according to the characteristics of the display quality desired or required in the display device DD. For example, the arrangement form of the light emitting areas PXA-R, PXA-G and PXA-B can be a honeycomb shape. Layout or diamond )Layout( and Diamond is a registered trademark owned by Samsung Display Co., Ltd.).
[0134] 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 one or more embodiments of the present disclosure are not limited thereto.
[0135] Below, Figures 3 to 6 Schematically shows a cross-sectional view of a light emitting element according to one or more embodiments. The light emitting element ED according to one or more embodiments may include a first electrode EL1, a second electrode EL2 arranged opposite to the first electrode EL1, and at least one functional layer arranged between the first electrode EL1 and the second electrode EL2. The light emitting element ED of one or more embodiments may include an amine compound of one or more embodiments to be explained later in at least one functional layer.
[0136] The light emitting element ED may include a hole transport region HTR, an emission layer EML, and / or an electron transport region ETR, etc., which are stacked in sequence as at least one functional layer. Figure 3 , 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 this order.
[0137] and Figure 3 compared to, Figure 4 A cross-sectional view of a light emitting element ED of one or more embodiments is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5 A cross-sectional view of a light emitting element ED according to one or more embodiments is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 compared to, Figure 6 A cross-sectional view of a light emitting element ED of one or more embodiments is illustrated, which includes a capping layer CPL disposed on the second electrode EL2 .
[0138] The light-emitting element ED of one or more embodiments may include an amine compound of one or more embodiments to be explained later in the hole transport region HTR. The light-emitting element ED of one or more embodiments may include an amine compound of one or more embodiments in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL of the hole transport region HTR. For example, in the light-emitting element ED of one or more embodiments, the hole transport layer HTL may include an amine compound of one or more embodiments.
[0139] 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, one or more embodiments of the present disclosure are not limited thereto. In some embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound selected from two or more of these, a mixture selected from two or more of these, or an oxide thereof.
[0140] If the first electrode EL1 is a transmissive electrode (for example, when the first electrode EL1 is a transmissive electrode), the first electrode EL1 may include a transparent metal oxide (for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO)). If the first electrode EL1 is a transflective electrode or a reflective electrode (for example, 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 thereof, or a mixture thereof (for example, a mixture of Ag and Mg), or a material having a multilayer structure, such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In one or more embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the materials described herein, 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 one or more embodiments of the present disclosure are not limited thereto. One or more embodiments of the present disclosure are not limited thereto, and the first electrode EL1 may include the metal material described herein, a combination of at least two metal materials described herein, and / or an oxide of the metal material described herein, etc. The thickness of the first electrode EL1 may be about 700 angstroms. to about For example, the thickness of the first electrode EL1 may be about to about
[0141] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL. In some embodiments, although not shown, the hole transport region HTR may include a plurality of stacked hole transport layers.
[0142] 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 hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer, hole injection layer HIL / buffer layer, hole transport layer HTL / buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in sequence from the first electrode EL1, but one or more embodiments of the present disclosure are not limited thereto.
[0143] The thickness of the hole transport region HTR may be, for example, about to about The hole transport region HTR may be formed using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brokett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI).
[0144] The light-emitting element ED of one or more embodiments may include the amine compound of one or more embodiments in the hole transport region HTR. In the light-emitting element ED of one or more embodiments, the hole transport region HTR includes at least one selected from the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL, and the amine compound of one or more embodiments may be included in at least one selected from the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL. For example, the hole transport layer HTL may include the amine compound of one or more embodiments.
[0145] Amine compounds
[0146] The amine compound of one or more embodiments includes an amine group, and may include a first substituent, a second substituent and a third substituent connected to the amine group (e.g., connected to the amine group). For example, the amine compound of one or more embodiments may include a structure in which the first substituent to the third substituent are connected to the nitrogen atom of the amine group (e.g., connected to the nitrogen atom of the amine group).
[0147] The first substituent may include a carbazole moiety. The carbazole moiety may be connected to the nitrogen atom of the amine group at position 1, position 2, position 3, or position 4 of the carbazole moiety (e.g., connected to the nitrogen atom of the amine group). In one or more embodiments, the carbazole moiety may be connected to the nitrogen atom of the amine group at position 8 relative to position 1, position 7 relative to position 2, position 6 relative to position 3, or position 5 relative to position 4 (e.g., connected to the nitrogen atom of the amine group). The first substituent may be directly bonded to the nitrogen atom of the amine group. The carbazole moiety in the first substituent may be connected to the substituted phenyl at position 9 of the carbazole moiety (e.g., connected to the phenyl substituted at position 9 of the carbazole moiety). For example, the carbazole moiety may be combined with the substituted phenyl at the nitrogen atom of the carbazole moiety. The substituted phenyl group connected to the nitrogen atom of the carbazole moiety (e.g., connected to the nitrogen atom of the carbazole moiety) may refer to a phenylene linker substituted with 10 to 30 ring-forming carbon atoms that is substituted or unsubstituted at least one of the meta and para positions relative to the carbon atom connected to the nitrogen atom of the carbazole moiety. In the present disclosure, the atom number (e.g., carbon number) (e.g., carbon atom position number) of the carbazole moiety is provided as represented in Formula ST1.
[0148] Formula ST1
[0149]
[0150] The second substituent may include a dibenzofuran moiety or a dibenzothiophene moiety. The second substituent may be directly bonded to the nitrogen atom of an amine group. In the present disclosure, the carbon numbering (e.g., carbon atom position numbering) of the second substituent may be provided as represented in formula ST2. In formula ST2, X may be an oxygen atom (O) or a sulfur atom (S). In formula ST2, if X is O, the second substituent may include a dibenzofuran moiety. In some embodiments, in formula ST2, if X is S, the second substituent may include a dibenzothiophene moiety. For ease of explanation, the substituent substituted at a dibenzofuran moiety or a dibenzothiophene moiety is omitted in formula ST2.
[0151] Formula ST2
[0152]
[0153] The third substituent may be an aryl group or a heteroaryl group. The third substituent may be directly bonded to the nitrogen atom of the amine group without a separate linker.
[0154] The amine compound of one or more embodiments may be a monoamine compound including a single amine group.The amine compound of one or more embodiments may be a monoamine compound in which only one amine group exists in a molecular structure without forming a ring.
[0155] In one or more embodiments, the amine compound may be represented by Formula 1. In Formula 1, the carbazole moiety may correspond to the first substituent, wherein Ar 2 and Ar 3 The phenylene linker is connected to the nitrogen atom of the carbazole moiety. In some embodiments, the dibenzofuran moiety or dibenzothiophene moiety including an oxygen atom (O) or a sulfur atom (S) as a ring-forming atom X may correspond to the second substituent, and Ar 1 May correspond to the third substituent.
[0156] Formula 1
[0157]
[0158] In Formula 1, X may be O or S. If X is O, the amine compound represented by Formula 1 may include a dibenzofuran moiety. If X is S, the amine compound represented by Formula 1 may include a dibenzothiophene moiety.
[0159] In formula 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 phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group. However, in Formula 1, Ar 1 Including those directly bonded to the nitrogen atom of the amine compound ) (Y is O or S). Because the amine compound of one or more embodiments represented by Formula 1 does not include a part (Y is O or S) as Ar 1 , so the hole transport characteristics can be improved, and improved emission efficiency and element life can be shown.
[0160] In formula 1, Ar 2 and Ar 3 may be each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms. In this case, the group selected from Ar 2 and Ar 3At least one of the substituted or unsubstituted aryl groups of 10 to 30 ring-forming carbon atoms may be a substituted or unsubstituted aryl group of 10 to 30 ring-forming carbon atoms. In Formula 1, the aryl group of 10 to 30 ring-forming carbon atoms may refer to the entire aryl group connected to the phenylene linking group at at least one selected from the para position and the meta position relative to the carbon atom connected to the nitrogen atom of the carbazole moiety. For example, in Formula 1, the substituted or unsubstituted aryl group of 10 to 30 ring-forming carbon atoms connected to the phenylene linking group of the carbazole moiety may include naphthyl, phenanthrenyl, triphenylene and / or pyrenyl, etc., and one or more embodiments of the present disclosure are not limited thereto.
[0161] In one or more embodiments, selected from Ar 2 and Ar 3 One of the may be a substituted or unsubstituted aryl group of 10 to 30 ring-forming carbon atoms, and the remainder may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms. 2 and Ar 3 Both (eg, at the same time) may be substituted or unsubstituted aromatic groups of 10 to 30 ring-forming carbon atoms.
[0162] For example, selected from Ar 2 and Ar 3 At least one of the groups may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted pyrenyl group. 2 and Ar 3 At least one of may be represented by one of the substituents selected from Substituent Group 1. However, one or more embodiments of the present disclosure are not limited thereto. In Substituent Group 1, "D" may be a deuterium atom, and * represents a position bonded to Formula 1.
[0163] Substituent Group 1
[0164]
[0165] In formula 1, R 1 To R 5 Each of R and R is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 5 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group, but one or more embodiments of the present disclosure are not limited thereto.
[0166] In one or more embodiments, R1 , R 2 , R 3 and R 5 R may be each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms. 4 It may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
[0167] In Formula 1, "a", "c" and "e" may each independently be an integer selected from 0 to 3, and "b" and "d" may each independently be an integer selected from 0 to 4. In Formula 1, if "a" is 0, the amine compound of one or more embodiments may not be R 1 In Formula 1, where "a" is 3 and three R 1 Each (for example, three R 1 The case where any or all of R is a hydrogen atom may be the same as the case where "a" is 0. If "a" is an integer of 2 or more, then the plurality of R 1 Can be the same, or selected from multiple R 1 At least one of may be different.
[0168] In Formula 1, if "b" is 0, the amine compound of one or more embodiments may not be R 2 In Formula 1, where "b" is 4 and the four R 2 Each (for example, four R 2 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "b" is 0. If "b" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 2 Can be the same, or selected from multiple R 2 At least one of may be different.
[0169] In Formula 1, if "c" is 0, the amine compound of one or more embodiments may not be R 3 In Formula 1, where "c" is 3 and three R 3 Each (for example, three R 3 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "c" is 0. If "c" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 3 Can be the same, or selected from multiple R 3 At least one of may be different.
[0170] In Formula 1, if "d" is 0, the amine compound of one or more embodiments may not be R 4 In Formula 1, where "d" is 4 and the four R 4 Each (for example, four R4 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "d" is 0. If "d" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 4 Can be the same, or selected from multiple R 4 At least one of may be different.
[0171] In Formula 1, if "e" is 0, the amine compound of one or more embodiments may not be R 5 In Formula 1, where "e" is 3 and three R 5 Each (for example, three R 5 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "e" is 0. If "e" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 5 Can be the same, or selected from multiple R 5 At least one of may be different.
[0172] In the amine compound of one or more embodiments represented by Formula 1, for the amine compound wherein the nitrogen atom of the amine compound is connected to the 2-position or 7-position of the carbazole moiety and is not connected to an Ar 1 In the case where the nitrogen atom of the amine compound is connected to the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part, and / or in the case where the nitrogen atom of the amine compound is connected to the 4-position or 5-position of the carbazole part and is not Ar 1 In the case of the 3-position or 6-position connection of the dibenzothiophene part or the dibenzofuran part, a+b≥1 may be satisfied and the compound is selected from R 1 and R 2 At least one of may not be a hydrogen atom.
[0173] For example, the nitrogen atom of the amine compound is connected to the 2-position or 7-position of the carbazole moiety and is not connected to an Ar 1 The case where the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part is connected can be represented by Formula 1-A.
[0174] Formula 1-A
[0175]
[0176] For example, the nitrogen atom of the amine compound is connected to the 4-position or 5-position of the carbazole moiety and is not connected to an Ar 1 The case where the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part is connected can be represented by Formula 1-B.
[0177] Formula 1-B
[0178]
[0179] In Formula 1-A and Formula 1-B, the same definitions (eg, contents) explained in Formula 1 can be applied to X, Ar1 To Ar 3 , R 1 To R 5 and "a" to "e". However, if the amine compound of one or more embodiments is represented by Formula 1-A or Formula 1-B, a+b≥1 may be satisfied, and in Formula 1-A and Formula 1-B, R 1 and R 2 At least one of may not be a hydrogen atom. For example, in Formula 1-A and Formula 1-B, R 1 and R 2 At least one of may be a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, but one or more embodiments of the present disclosure are not limited thereto.
[0180] In the amine compound of one or more embodiments represented by Formula 1, in the case where the nitrogen atom of the amine compound is connected to the 3-position of the carbazole moiety, R 3 It may be a hydrogen atom or a deuterium atom. For example, the case where the nitrogen atom of the amine compound of Formula 1 is connected to the 3-position of the carbazole moiety may be represented by Formula 1-C.
[0181] Formula 1-C
[0182]
[0183] In Formula 1-C, the same definitions (eg, contents) explained in Formula 1 can be applied to X, Ar 1 To Ar 3 , R 1 , R 2 , R 4 , R 5 and "a" to "e". However, if the amine compound of one or more embodiments is represented by Formula 1-C, then R 3 It can be a hydrogen atom or a deuterium atom. For example, in Formula 1-C, R 3 It may be a hydrogen atom.
[0184] The amine compound of one or more embodiments may include a deuterium atom as a substituent. For example, in the amine compound represented by Formula 1, the amine compound selected from Ar 1 To Ar 3 and R 1 To R 5 At least one of may include a deuterium atom or a substituent including a deuterium atom. However, this is merely an illustrative example, and one or more embodiments of the present disclosure are not limited thereto.
[0185] In one or more embodiments, the amine compound represented by Formula 1 may be represented by Formula 2-1 or Formula 2-2. Formula 2-1 and Formula 2-2 correspond to the following: 1In Formula 2-1 and Formula 2-2, the same definitions (eg, contents) explained in Formula 1 can be applied to X, Ar 2 ,Ar 3 , R 1 To R 5 and "a" through "e".
[0186] Formula 2-1
[0187]
[0188] Formula 2-2
[0189]
[0190] In formula 2-1, R 6 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 6 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
[0191] In Formula 2-1, "f" may be an integer selected from 0 to 5. In Formula 2-1, if "f" is 0, the amine compound of one or more embodiments may not be R 6 In Formula 2-1, where "f" is 5 and the five R 6 Each (e.g., five R 6 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "f" is 0. If "f" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 6 Can be the same, or selected from multiple R 6 At least one of may be different.
[0192] In Formula 2-2, Z may be O or S. If Z is O, the amine compound represented by Formula 2-2 may include a dibenzofuran moiety as a third substituent. If Z is S, the amine compound represented by Formula 2-2 may include a dibenzothiophene moiety as a third substituent.
[0193] In formula 2-2, R 7 and R 8 "g" may be an integer selected from 0 to 3, and "h" may be an integer selected from 0 to 4. In Formula 2-2, if "g" is 0, the amine compound of one or more embodiments may include an amine compound not covered by R 7 A substituted dibenzofuran moiety or a substituted dibenzothiophene moiety is used as the third substituent. In Formula 2-2, where "g" is 3 and three R7 Each (for example, three R 7 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "g" is 0. If "g" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 7 Each (for example, multiple R 7 any or all of) are the same, or are selected from multiple R 7 At least one of may be different.
[0194] In Formula 2-2, if "h" is 0, the amine compound of one or more embodiments may include 8 A substituted dibenzofuran moiety or a substituted dibenzothiophene moiety is used as the third substituent. In Formula 2-2, where "h" is 4 and the four R 8 Each (for example, four R 8 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "h" is 0. If "h" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 8 Each (for example, multiple R 8 any or all of) are the same, or are selected from multiple R 8 At least one of may be different.
[0195] In one or more embodiments, the amine compound represented by Formula 1 may be represented by Formula 3-1 or Formula 3-2. Formula 3-1 and Formula 3-2 represent wherein Ar 2 and Ar 3 In the case of Formula 1, one of the groups is a substituted or unsubstituted naphthyl group. Formula 3-1 may correspond to the case in which Ar 2 In the case of Formula 1 where Ar is a substituted or unsubstituted naphthyl group, Formula 3-2 may correspond to 3 The case of Formula 1 which is a substituted or unsubstituted naphthyl group.
[0196] Formula 3-1
[0197]
[0198] Formula 3-2
[0199]
[0200] In Formula 3-1 and Formula 3-2, the same definitions (eg, contents) explained in Formula 1 can be applied to X, Ar 1 , R 1 To R 5 and "a" through "e".
[0201] In formula 3-1 and formula 3-2, R 9 , R 10 ,Ar 21 and Ar31 may be each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aromatic group of 6 to 30 ring carbon atoms. 9 , R 10 ,Ar 21 and Ar 31 They may each independently be a hydrogen atom, a deuterium atom or a substituted or unsubstituted phenyl group.
[0202] In Formula 3-1 and Formula 3-2, "i" and "k" may each independently be an integer selected from 0 to 7. If "i" is 0, in the amine compound of one or more embodiments, the amine compound not covered by R 9 The substituted naphthyl group can be attached to the phenylene linker in a para-position relative to the carbon atom attached to the nitrogen atom of the carbazole moiety (e.g., to the phenylene linker). 9 Each (e.g., seven R 9 The case where any or all of R is a hydrogen atom may be the same as the case where "i" is 0. If "i" is an integer of 2 or more, then the plurality of R 9 Each (for example, multiple R 9 any or all of) are the same, or are selected from multiple R 9 At least one of may be different. For example, "i" may be 7, selected from seven R 9 One of the R may be an unsubstituted phenyl group, and the remaining six R 9 If "k" is 0, then in the amine compound of one or more embodiments, R 10 The substituted naphthyl group may be attached to the phenylene linker in an ortho relationship relative to the carbon atom attached to the nitrogen atom of the carbazole moiety (e.g., to the phenylene linker). 10 Each (e.g., seven R 10 The case where any or all of the R atoms are hydrogen atoms may be the same as the case where "k" is 0. If "k" is an integer of 2 or more, then the plurality of R atoms may be hydrogen atoms. 10 Each (for example, multiple R 10 any or all of) are the same, or are selected from multiple R 10 At least one of may be different. For example, "k" may be 7, selected from seven R 10 One of the R may be an unsubstituted phenyl group, and the remaining six R 10 It may be a hydrogen atom.
[0203] In one or more embodiments, the amine compound represented by Formula 1 may be represented by any one selected from Formula 4-1 to Formula 4-4. In Formula 4-1 to Formula 4-4, the same definitions (eg, contents) explained in Formula 1 may be applied to X and Ar. 1To Ar 3 .
[0204] Formula 4-1
[0205]
[0206] Formula 4-2
[0207]
[0208] Formula 4-3
[0209]
[0210] Formula 4-4
[0211]
[0212] In Formula 4-1 to Formula 4-4, R 11 To R 13 , R 21 To R 23 , R 31 To R 33 , R 41 and R 42 may be each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aromatic group of 6 to 30 ring carbon atoms. 11 To R 13 , R 21 To R 23 , R 31 To R 33 , R 41 and R 42 They may each independently be a hydrogen atom, a deuterium atom or a substituted or unsubstituted phenyl group.
[0213] In Formula 4-1 to Formula 4-4, R 14 , R 24 , R 34 and R 44 Each of R and R is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms. 14 , R 24 , R 34 and R 44 They may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.
[0214] In Formula 4-1 to Formula 4-4, R 15 , R 25 , R 35 , R 43 and R45 Each may independently be a hydrogen atom or a deuterium atom, but one or more embodiments of the present disclosure are not limited thereto.
[0215] In Formula 4-1 to Formula 4-4, a1 to a4, c1 to c4, and e1 to e4 may each independently be an integer selected from 0 to 3. b1 to b4 and d1 to d4 may each independently be an integer selected from 0 to 4.
[0216] In Formula 4-1 to Formula 4-4, if a1, a2, a3, and a4 are 0, the amine compound of one or more embodiments may be respectively not R 11 , R 21 , R 31 and R 41 In formula 4-1, a1 is 3 and three R 11 The case where all R are hydrogen atoms may be the same as the case where a1 is 0. If a1 is an integer of 2 or more, then the plurality of R 11 Each (for example, multiple R 11 any or all of) are the same, or are selected from multiple R 11 At least one of may be different. The definition of a1 (eg, the interpretation of a1) may be applied to a2, a3, and a4 in substantially the same manner.
[0217] In Formula 4-1 to Formula 4-4, if b1, b2, b3, and b4 are 0, the amine compound of one or more embodiments may be respectively not R 12 , R 22 , R 32 and R 42 In formula 4-1, b1 is 4 and four R 12 Each (for example, four R 12 The case where any or all of R is a hydrogen atom may be the same as the case where b1 is 0. If b1 is an integer of 2 or more, then the plurality of R 12 Each (for example, multiple R 12 any or all of) are the same, or are selected from multiple R 12 The definition of b1 (eg, the interpretation of b1) may be applied to b2, b3, and b4 in substantially the same manner.
[0218] In Formula 4-1 to Formula 4-4, if c1, c2, c3, and c4 are 0, the amine compound of one or more embodiments may be respectively not R 13 , R 23 , R 33 and R 43 In formula 4-1, where c1 is 3 and three R 13The case where all R are hydrogen atoms may be the same as the case where c1 is 0. If c1 is an integer of 2 or more, then the plurality of R 13 Each (for example, multiple R 13 any or all of) are the same, or are selected from multiple R 13 At least one of may be different. The definition of c1 (eg, the interpretation of c1) may be applied to c2, c3, and c4 in substantially the same manner.
[0219] In Formula 4-1 to Formula 4-4, if d1, d2, d3, and d4 are 0, the amine compound of one or more embodiments may be respectively not R 14 , R 24 , R 34 and R 44 In formula 4-1, d1 is 4 and four R 14 Each (for example, four R 14 The case where any or all of R is a hydrogen atom may be the same as the case where d1 is 0. If d1 is an integer of 2 or more, then the plurality of R 14 Each (for example, multiple R 14 any or all of) are the same, or are selected from multiple R 14 At least one of may be different. The definition of d1 (eg, the interpretation of d1) may be applied to d2, d3, and d4 in substantially the same manner.
[0220] In Formula 4-1 to Formula 4-4, if e1, e2, e3, and e4 are 0, the amine compound of one or more embodiments may be respectively not R 15 , R 25 , R 35 and R 45 In formula 4-1, where e1 is 3 and three R 15 The case where all R are hydrogen atoms may be the same as the case where e1 is 0. If e1 is an integer of 2 or more, then the plurality of R 15 Each (for example, multiple R 15 any or all of) are the same, or are selected from multiple R 15 At least one of may be different. The definition of e1 (eg, the interpretation of e1) may be applied to e2, e3, and e4 in substantially the same manner.
[0221] In one or more embodiments, in Formula 4-2, if the nitrogen atom of the amine compound is not Ar 1 The 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part of the present invention is connected, then a2+b2≥1 can be satisfied, and the compound is selected from R 21 and R 22At least one of the amine compounds may be a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms. 1 The 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part of the present invention is connected, then a2+b2≥1 can be satisfied, and the compound is selected from R 21 and R 22 At least one of the may be a substituted or unsubstituted phenyl group.
[0222] In Formula 4-4, if the nitrogen atom of the amine compound is not Ar 1 The 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part of the present invention is connected, then a4+b4≥1 can be satisfied, and the compound is selected from R 41 and R 42 At least one of the amine compounds may be a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms. 1 The 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part of the present invention is connected, then a4+b4≥1 can be satisfied, and the compound is selected from R 41 and R 42 At least one of the may be a substituted or unsubstituted phenyl group.
[0223] The amine compound of one or more embodiments represented by Formula 1 may be selected from one (e.g., any one) of the compounds in Compound Group 1. The hole transport region HTR of the light-emitting element ED of one or more embodiments may include at least one selected from the amine compounds shown in Compound Group 1. For example, at least one selected from the amine compounds shown in Compound Group 1 may be included in the electron blocking layer EBL of the light-emitting element ED. In Compound Group 1, "D" is a deuterium atom.
[0224] Compound Group 1
[0225]
[0226]
[0227]
[0228]
[0229]
[0230]
[0231]
[0232]
[0233]
[0234]
[0235]
[0236]
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264]
[0265]
[0266]
[0267]
[0268]
[0269] In compound group 1, "D" is a deuterium atom.
[0270] The light-emitting element ED of one or more embodiments may include at least one selected from the amine compounds explained in compound group 1 in the hole transport region HTR. The amine compound according to one or more embodiments may include a first substituent, a second substituent, and a third substituent connected to a nitrogen atom of the amine compound, and may achieve high emission efficiency and long element life of the light-emitting element ED.
[0271] For example, the amine compound of one or more embodiments may include a first substituent including a carbazole moiety directly connected to the nitrogen atom of the amine compound, and a second substituent directly connected to the nitrogen atom of the amine compound and including a dibenzofuran moiety or a dibenzothiophene moiety. In some embodiments, an aryl or heteroaryl group may be included as a third substituent. For example, in the amine compound of one or more embodiments, a substituted or unsubstituted aryl group (e.g., naphthyl) of 10 to 30 ring-forming carbon atoms may be connected to the 9th position of the carbazole moiety of the first substituent via a phenylene linker, and excellent or appropriate hole transport characteristics and improved electronic tolerance may be shown, thereby showing a characteristic that is not easily decomposed by heat. Accordingly, if the amine compound of one or more embodiments is used or applied to a light-emitting element ED, the element life and emission efficiency may be improved.
[0272] The hole transport region HTR may further include a compound represented by Formula H-1:
[0273] Formula H-1
[0274]
[0275] In formula H-1, L 1 and L 2 Each of a and b may be independently a directly connected, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b may be independently an integer selected from 0 to 10. In one or more embodiments, when a or b is an integer of 2 or more, a plurality of 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.
[0276] In formula H-1, Ar a and Ar b and Ar may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. c 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.
[0277] The compound represented by formula H-1 may be a monoamine compound. In one or more embodiments, the compound represented by formula H-1 may be a compound selected from Ar a To Ar c In some embodiments, the compound represented by formula H-1 may be a diamine compound in which at least one of Ar a and Ar b At least one of the carbazole compounds includes a substituted or unsubstituted carbazole group, or in Ar a and Ar b A fluorene compound in which at least one of the compounds includes a substituted or unsubstituted fluorenyl group.
[0278] The compound represented by Formula H-1 may be selected from any one of 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 those listed in Compound Group H:
[0279] Compound Group H
[0280]
[0281]
[0282] In some embodiments, the hole transport region HTR may further include an appropriate hole transport material. For example, the hole transport region HTR may include at least one selected from the following: a phthalocyanine compound (eg, copper phthalocyanine), N 1 ,N 1’ -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PAN I / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate] and / or dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.
[0283] The hole transport region HTR may include carbazole derivatives (e.g., at least one selected from N-phenylcarbazole and polyvinylcarbazole), fluorene derivatives and / or triphenylamine derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 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), 1,3-bis(N-carbazolyl)benzene (mCP)), etc.
[0284] 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.
[0285] The hole transport region HTR may include a compound of the hole transport region HTR described herein in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0286] The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about 100 nm. to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about For example, if the hole transport region HTR includes the electron blocking layer EBL (eg, when the hole transport region HTR includes the electron blocking layer EBL), the electron blocking layer EBL may have a thickness of about to about If the thickness of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the ranges described herein, satisfactory hole transport characteristics may be achieved without significantly increasing the driving voltage.
[0287] In addition to the materials described herein, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be uniformly (e.g., substantially uniformly) or non-uniformly (e.g., substantially non-uniformly) dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide, a quinone derivative, a metal oxide, and a cyano-containing compound, but one or more embodiments of the present disclosure are not limited thereto. For example, the p-dopant may include a metal halide (e.g., CuI or RbI), a quinone derivative (e.g., tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), a metal oxide (e.g., tungsten oxide or molybdenum oxide) and / or a cyano-containing compound (e.g., dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but one or more embodiments of the present disclosure are not limited thereto.
[0288] As described herein, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer and an electron blocking layer EBL. The buffer layer may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, and thus may increase the emission efficiency. The material that may be included in the hole transport region HTR may be used as the material included in the buffer layer. The electron blocking layer EBL is a layer for preventing or reducing the injection of electrons from the electron transport region ETR to the hole transport region HTR.
[0289] In the light-emitting element ED of one or more embodiments, the emission layer EML may emit blue light. The light-emitting element ED of one or more embodiments may include the amine compound of one or more embodiments in the hole transport region HTR, and may show high emission efficiency and long element life characteristics in the blue emission region. However, one or more embodiments of the present disclosure are not limited thereto.
[0290] 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, a 1,2-triphenylene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. For example, the emission layer EML may include an anthracene derivative or a pyrene derivative.
[0291] exist Figures 3 to 6 In each light emitting element ED of the embodiment illustrated in , in addition to the host and dopant described herein, the emission layer EML may further include a suitable host and dopant, and for example, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.
[0292] Formula E-1
[0293]
[0294] In formula E-1, R 31 To R 40 Each of R and R may be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. In one or more embodiments, R 31 To R 40 It may bond with an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.
[0295] In Formula E-1, c and d may be an integer selected from 0 to 5, each independently.
[0296] The compound represented by formula E-1 may be selected from any one of compound E1 to compound E19:
[0297]
[0298]
[0299] 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.
[0300] Formula E-2a
[0301]
[0302] In Formula E-2a, a may be an integer selected from 0 to 10, and L a It may be a directly connected, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, if a is an integer of 2 or more (for example, when a is an integer of 2 or more), multiple L a Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0303] In some embodiments, in Formula E-2a, A 1 To A 5 Can be N or CR independently i . R a To R i Each 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. a To R i It may bond with an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O and / or S as ring atoms.
[0304] In one or more embodiments, in formula E-2a, selected from A 1 To A 5Two or three of them may be N, and the rest may be CR i .
[0305] Formula E-2b
[0306]
[0307] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aryl group having 6 to 30 ring carbon atoms. b is a directly connected, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, b is an integer selected from 0 to 10, and if b is an integer of 2 or more (for example, 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.
[0308] The compound represented by formula E-2a or formula E-2b can be selected from any one of the compounds of compound group E-2. However, the compounds listed in compound group E-2 are only examples, and the compounds represented by formula E-2a or formula E-2b are not limited to those compounds listed in compound group E-2.
[0309] Compound Group E-2
[0310]
[0311]
[0312] The emission layer EML may further include an appropriate general material in the art as a host material. For example, the emission layer EML may include at least one of bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazyl)-1,1'-biphenyl (CBP), 1,3-bis(N-carbazyl)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4"-tri(N-carbazyl)triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, one or more embodiments of the present disclosure are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq 3), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO 3 ) and / or octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.
[0313] The emission layer EML may include a compound represented by Formula Ma or Formula Mb. The compound represented by Formula Ma or Formula Mb may be used as a phosphorescent dopant material.
[0314] Formula Ma
[0315]
[0316] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 Can be independently CR 1 or N, R 1 To R 4 Each independently may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, if m is 0 (for example, when m is 0), n is 3, and if m is 1 (for example, when m is 1), n is 2.
[0317] The compound represented by the formula Ma may be used as a phosphorescent dopant.
[0318] The compound represented by the formula Ma may be selected from 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 M-a1 to M-a25.
[0319]
[0320]
[0321] Compound M-a1 and Compound M-a2 may be used as red dopant materials, and Compound M-a3 to Compound M-a7 may be used as green dopant materials.
[0322] Formula Mb
[0323]
[0324] In formula Mb, Q 1 To Q 4 may each independently be C or N, and C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms. 21 To L 24 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, and e1 to e4 may each independently be 0 or 1. -* indicates a site of bonding to C1 to C4. R 31 To R 39 Each of d1 to d4 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 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, or may form a ring by combining with an adjacent group, and d1 to d4 may independently be an integer selected from 0 to 4.
[0325] The compound represented by Formula Mb may be used as a blue phosphorescent dopant or a green phosphorescent dopant. In some embodiments, the compound represented by Formula Mb may be further included in the emission layer EML as an auxiliary dopant.
[0326] The compound represented by Formula Mb may be selected from any one of Compound Mb-1 to Compound Mb-11. However, these compounds are merely examples, and the compound represented by Formula Mb is not limited to Compound Mb-1 to Compound Mb-11.
[0327]
[0328] In the compounds described herein, R, R 38 and R 39Each 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 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.
[0329] The emission layer EML may include a compound represented by any one selected from Formula Fa to Formula Fc. The compound represented by any one selected from Formula Fa to Formula Fc may be used as a fluorescent dopant material.
[0330] Formula
[0331]
[0332] In the formula Fa, R a To R j At least two of them can be independently replaced by *-NAr 1 Ar 2 Substituted. Selected from R a To R j Not *-NAr 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0333] In *-NAr 1 Ar 2 in Ar 1 and Ar 2 and Ar may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of the may be a heteroaryl group containing O or S as a ring-forming atom.
[0334] [Formula Fb]
[0335]
[0336] In formula Fb, R a and R bEach 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 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, or may be 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.
[0337] 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 the may be a heteroaryl group containing O or S as a ring-forming atom.
[0338] In formula Fb, the number of rings represented by U and V may be 0 or 1 independently. For example, in formula Fb, it means that if the number of U or V is 1 (for example, when the number of U or V is 1), one ring constitutes a condensed ring in the portion indicated by U or V, and if the number of U or V is 0 (for example, when the number of U or V is 0), there is no ring indicated by U or V. For example, if the number of U is 0 and the number of V is 1 (for example, when the number of U is 0 and the number of V is 1), or if the number of U is 1 and the number of V is 0 (for example, when the number of U is 1 and the number of V is 0), the condensed ring having a fluorene core in formula Fb may be a cyclic compound having four rings. In some embodiments, if the number of U and V is each 0 (for example, when the number of U and V is each 0), the condensed ring having a fluorene core in formula Fb may be a cyclic compound having three rings. In some embodiments, if the number of U and V is each 1 (for example, when the number of U and V is each 1), the condensed ring having a fluorene core in Formula Fb may be a cyclic compound having five rings.
[0339] Formula Fc
[0340]
[0341] In Formula Fc, A 1 and A 2 can be independently O, S, Se or NR m , and R mR 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, or may be bonded to an adjacent group to form a ring.
[0342] In Formula Fc, A 1 and A 2 Each of A and B may independently bond to a substituent of an adjacent ring to form a fused ring. 1 and A 2 Each independently is NR m (For example, when A 1 and A 2 Each independently is NR m ), A 1 Can be used with R 4 or R 5 In some embodiments, A 2 Can be used with R 7 or R 8 bonded to form a ring.
[0343] In one or more embodiments, the emission layer EML may further include a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)benzene As suitable dopant materials, perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) and / or pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene) can be used.
[0344] 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-difluorophenylpyridyl-N, C2) picolinyl iridium (III) (FIrpic), bis (2,4-difluorophenylpyridyl)-tetrakis (1-pyrazolyl) borate iridium (III) (FIr6) or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, one or more embodiments of the present disclosure are not limited thereto.
[0345] In one or more embodiments, the emission layer EML may include a hole transport host and an electron transport host. In some embodiments, the emission layer EML may include an auxiliary dopant and a luminescent dopant. In one or more embodiments, a phosphorescent dopant material or a thermally activated delayed fluorescent dopant material may be included as an auxiliary dopant. For example, in one or more embodiments, the emission layer EML may include a hole transport host, an electron transport host, an auxiliary dopant, and a luminescent dopant.
[0346] In some embodiments, 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 level (T1) of the exciplex formed by the hole transport host and the electron transport host may correspond to the energy gap between the LUMO energy level of the electron transport host and the HOMO energy level of the hole transport host.
[0347] In one or more embodiments, the triplet energy level (T1) of the excited complex formed by the hole transport host and the electron transport host may be about 2.4 electron volts (eV) to about 3.0 eV. In some embodiments, the triplet energy level of the excited complex may be a value smaller than the energy gap of each host material. Accordingly, the excited complex may have a triplet energy level of about 3.0 eV or less as the energy gap between the hole transport host and the electron transport host.
[0348] In one or more embodiments, at least one emission layer EML may include a quantum dot material.
[0349] In the description, quantum dots refer to crystals of semiconductor compounds. Depending on the size of the crystal, quantum dots can emit light within one or more appropriate emission wavelength ranges. By controlling the ratio of elements in the quantum dot compound, quantum dots can emit light within one or more appropriate emission wavelength ranges. The diameter of a quantum dot can be, for example, from about 1 nanometer (nm) to about 10 nm. Unless otherwise defined, in the present disclosure, if a particle or dot is spherical (e.g., when the particle or dot is spherical), the term "particle size" or "dot diameter" refers to the average diameter, and if a particle or dot is non-spherical (e.g., when the particle or dot is non-spherical), the term "particle size" or "dot diameter" refers to the average major axis length.
[0350] In one or more embodiments, quantum dots may be synthesized by chemical bath deposition, metal organic chemical vapor deposition (MOCVD), molecular beam epitaxy (MBE), or a process similar thereto. For example, chemical bath deposition is a method of mixing an organic solvent and a precursor material, and then growing quantum dot particle crystals. During the growth of the quantum dot particle crystals, the organic solvent may naturally act as a dispersant coordinated on the surface of the quantum dot particle crystals and may control the growth of the quantum dot particle crystals. Accordingly, if compared with a vapor deposition method including metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE) (for example, when compared with a vapor deposition method including metal organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE)), chemical bath deposition is more advantageous, and the growth of quantum dot particle crystals may be controlled or selected by a low-cost process.
[0351] The core of the quantum dot can be selected from Group II-VI compounds, Group III-VI compounds, Group I-III-VI compounds, Group III-V compounds, Group III-II-V compounds, Group IV-VI compounds, Group IV elements, Group IV compounds, Group II-IV-V compounds and / or combinations thereof (e.g., any suitable combination).
[0352] The Group II-VI compound may be selected from the group comprising (e.g., consisting of) CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and / or mixtures thereof (e.g., any suitable mixture) a binary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of CdSeS, Cd tternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and / or mixtures thereof (e.g., any suitable mixture); and ternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and / or mixtures thereof (e.g., any suitable mixture); e, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or mixtures thereof (e.g., any suitable mixture)). In one or more embodiments, the Group II-VI compound may further include a Group I metal and / or a Group IV element. The Group I-II-VI compound may be selected from CuZnS, and the Group II-IV-VI compound may be selected from ZnSnS, etc. The Group I-II-IV-VI compound may be selected from: selected from a group including Cu 2 ZnSnS 2 , Cu 2 ZnSnS 4 , Cu 2 ZnSnSe 4 、Ag 2 ZnSnS 2 and mixtures thereof (e.g., Cu2 ZnSnS 2 , Cu 2 ZnSnS 4 , Cu 2 ZnSnSe 4 、Ag 2 ZnSnS 2 and mixtures thereof).
[0353] Group III-VI compounds may include binary compounds, such as GaS, Ga 2 S 3 ,GaSe,Ga 2 Se 3 、GaTe、InS、InSe、In 2 Se 3 、InTe、In 2 S 3 ; Ternary compounds, such as InGaS 3 or InGaSe 3 ; or any combination thereof.
[0354] The I-III-VI group compound may be selected from: selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 、AgInSe 2 、AgGaS、AgGaSe 2 、CuInSe 2 、CuGaSe 2 and / or mixtures thereof (e.g., any suitable mixture) (e.g., AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 、AgInSe 2 、AgGaS、AgGaSe 2 、CuInSe 2 、CuGaSe 2 and / or mixtures thereof (eg, any suitable mixture)); or ternary compounds in the group consisting of quaternary compounds (eg, AgInGaS 2、AgInGaSe 2 、CuInGaS 2 ).
[0355] The III-V compound may be selected from the group comprising (e.g., consisting of): a binary compound selected from the group comprising GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and / or mixtures thereof (e.g., any suitable mixture)); a binary compound selected from the group comprising GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlP a ternary compound selected from the group consisting of GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb and / or mixtures thereof (e.g., any suitable mixture); a ternary compound selected from the group consisting of GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb and / or mixtures thereof (e.g., any suitable mixture). In one or more embodiments, the Group III-V compound may further include a Group II metal. For example, InZnP, InGaZnP, and / or InAlZnP, etc. may be selected as the Group III-II-V compound.
[0356] The Group IV-VI compound may be selected from the group comprising (e.g., consisting of): a binary compound selected from the group comprising SnS, SnSe, SnTe, PbS, PbSe, PbTe and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and / or mixtures thereof (e.g., any suitable mixture)); a binary compound selected from the group comprising SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and / or mixtures thereof (e.g., any suitable mixture) For example, a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of SnPbSSe, SnPbSeTe, SnPbSTe and / or mixtures thereof (e.g., any suitable mixture)); a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of SnPbSSe, SnPbSeTe, SnPbSTe and / or mixtures thereof (e.g., any suitable mixture)). Group IV elements may be selected from the group consisting of Si, Ge and / or mixtures thereof (e.g., any suitable mixture) (e.g., consisting of Si, Ge and / or mixtures thereof (e.g., any suitable mixture)). The Group IV compound may be a binary compound selected from the group consisting of (eg, consisting of) SiC, SiGe, and / or mixtures thereof (eg, any suitable mixture).
[0357] The II-IV-V group compound can be selected from ternary compounds, and the ternary compound is selected from ZnSnP, ZnSnP 2 、ZnSnAs 2 、ZnGeP 2 、ZnGeAs 2 、CdSnP 2 or CdGeP 2 and / or mixtures thereof (eg, any suitable mixture) (eg, consisting of ZnSnP, ZnSnP 2 、ZnSnAs 2 、ZnGeP 2 、ZnGeAs 2 、CdSnP 2 or CdGeP 2 and / or mixtures thereof (e.g., any suitable mixture)).
[0358] Each element included in the multi-component compound (e.g., binary compound, ternary compound, or quaternary compound) may be present in the particle in a substantially uniform or substantially non-uniform concentration distribution. For example, the general formula refers to the type (species) 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 0 <x<1)。
[0359] In addition, the quantum dots of one or more embodiments may have a core / shell structure in which one quantum dot surrounds another quantum dot. In the core / shell structure, the interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.
[0360] In one or more embodiments, the quantum dot may have a core / shell structure as described herein, including a core containing nanocrystals and a shell around the core (e.g., surrounding the core). The shell of the quantum dot may be used as a protective layer to prevent or reduce chemical denaturation of the core to maintain semiconductor properties, and / or as a charging layer to give the quantum dot electrophoretic properties. The shell may be a single layer or multiple layers. Examples of the shell of the quantum dot may include metal oxides or non-metal oxides, semiconductor compounds, and / or combinations thereof (e.g., any suitable combination).
[0361] For example, the metal oxide 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 one or more embodiments of the present disclosure are not limited thereto.
[0362] Furthermore, 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 one or more embodiments of the present disclosure are not limited thereto.
[0363] The quantum dots may 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 may improve color purity and / or color reproducibility within the ranges described herein. In some embodiments, light emitted by such quantum dots is emitted in all directions, thereby improving wide viewing angles.
[0364] In some embodiments, although the form of quantum dots is not specifically limited as long as it is a form commonly used in the art, more specifically, quantum dots in the form of spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles or cubic nanoparticles, nanotubes, nanowires, nanofibers and / or nanoplates, etc. can be used.
[0365] Depending on the size of the particles, quantum dots can control the color of the emitted light, and accordingly, quantum dots can emit light of one or more appropriate colors (eg, blue, red, and green).
[0366] With the adjustment of the size of the quantum dots or the adjustment of the ratio of elements in the quantum dot compound, it is possible to control the band gap, and thus light in one or more appropriate wavelength ranges can be obtained in the quantum dot emission layer. Therefore, the quantum dots described in this article are used (using quantum dots of different sizes or different ratios of elements in quantum dot compounds), and thus a light-emitting element that emits light in one or more appropriate wavelength ranges can be implemented. For example, the size of the quantum dots or the ratio of elements in the quantum dot compound can be selected to emit red light, green light, and / or blue light. In some embodiments, the quantum dots can be configured to emit white light by combining one or more appropriate colors of light.
[0367] exist Figures 3 to 6 In each of the light emitting elements ED of the embodiments illustrated in , an electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but one or more embodiments of the present disclosure are not limited thereto.
[0368] The electron transport region ETR may have a single-layer structure of a single layer formed of a single material, a single-layer structure of a single layer formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.
[0369] For example, the electron transport region ETR may have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single-layer structure formed of an electron injection material and an electron transport material. In some embodiments, the electron transport region ETR may have a single-layer structure formed of a plurality of different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL, a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked in order from the emission layer EML, but one or more embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, a thickness of about 1,000 angstroms. to about Thickness.
[0370] The electron transport region ETR may be formed using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brokett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI).
[0371] The electron transport region ETR may include at least one compound represented by Formula ET-1:
[0372] Formula ET-1
[0373]
[0374] In formula ET-1, selected from X 1 To X 3 At least one of them is N, and the rest are CR a . R a Ar may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 3 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0375] In Formula ET-1, a to c may each independently be an integer selected from 0 to 10. In Formula ET-1, L 1 To L 3Each L may be independently a directly connected, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, if a to c may each be independently an integer of 2 or more (for example, when a to c may each be independently an integer of 2 or more), a plurality of L 1 To multiple 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.
[0376] The electron transport region ETR may include an anthracene compound. However, one or more embodiments of the present disclosure are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3 ), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthothracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl 1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or mixtures thereof (eg, any suitable mixture).
[0377] The electron transport region ETR may include at least one selected from the group consisting of compounds ET1 to ET36:
[0378]
[0379]
[0380]
[0381] In some embodiments, the electron transport region ETR may include metal halides (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and KI), lanthanide metals (e.g., 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 one or more embodiments, metal oxides (e.g., Li 2 O or BaO) and / or 8-hydroxyquinoline lithium (Liq) etc. form an electron transport region ETR, but one or more embodiments of the present disclosure are not limited thereto. The electron transport region ETR may also be formed by a mixture material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt may be a material having an energy band gap of about 4 eV or greater. For example, the insulating organic metal salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates and / or metal stearates, etc.
[0382] In addition to the materials described herein, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but one or more embodiments of the present disclosure are not limited thereto.
[0383] The electron transport region ETR may include the compound of the electron transport region ETR described herein in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.
[0384] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about to about For example, about to about If the thickness of the electron transport layer ETL satisfies the aforementioned range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about to about For example, about to about If the thickness of the electron injection layer EIL satisfies the range described herein, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0385] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but one or more embodiments of the present disclosure are not limited thereto. For example, if the first electrode EL1 is an anode (for example, when the first electrode EL1 is an anode), the second electrode EL2 may be a cathode, and if the first electrode EL1 is a cathode (for example, when the first electrode EL1 is a cathode), the second electrode EL2 may be an anode.
[0386] 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.).
[0387] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W or a compound thereof or a mixture thereof (e.g., AgMg, AgYb or MgYb), or a material having a multilayer structure, such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In one or more embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the material described herein and a transparent conductive film formed of ITO, IZO, ZnO and / or ITZO, etc. For example, the second electrode EL2 may include a metal material described herein, a combination of at least two of the metal materials described herein, and / or an oxide of the metal material described herein, etc.
[0388] In one or more embodiments, the second electrode EL2 may be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
[0389] In one or more embodiments, a capping layer CPL may be further disposed on the second electrode EL2 of the light emitting element ED of one or more embodiments. The capping layer CPL may include a plurality of layers or a single layer.
[0390] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, if the capping layer CPL contains an inorganic material (for example, when the capping layer CPL contains an inorganic material), the inorganic material may include an alkali metal compound (for example, LiF), an alkaline earth metal compound (for example, MgF 2 )、SiON、SiN x and / or SiO ywait.
[0391] For example, if the capping layer CPL includes an organic material (eg, when the capping layer CPL includes an organic material), the organic material may include N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine (α-NPD), NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), epoxy resins and / or acrylates (e.g., methacrylates), etc. However, one or more embodiments of the present disclosure are not limited thereto, and the capping layer CPL may include at least one selected from compounds P1 to P5:
[0392]
[0393] In one or more embodiments, the capping layer CPL may have a refractive index of about 1.6 or more. For example, with respect to light in a wavelength range of about 550 nm to about 660 nm, the capping layer CPL may have a refractive index of about 1.6 or more.
[0394] Figures 7 to 10 Each of them is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. Figures 7 to 10 When describing the display device of the embodiment, the description of the display device already described is omitted. Figures 1 to 6 Rather than describing repeated features described in , their differences will be primarily described (e.g., described in more detail).
[0395] refer to Figure 7 According to one or more embodiments, a display device DD-a may include a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. Figure 7 In one or more embodiments explained in the accompanying drawings, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light emitting element ED.
[0396] 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 6 The structure of the light emitting element ED can also be applied to Figure 7The structure of the light-emitting element ED explained in FIG.
[0397] The hole transport region HTR of the light emitting element ED included in the display device DD-a according to one or more embodiments may include the amine compound of one or more embodiments.
[0398] refer to Figure 7 , the emission layer EML may 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 provided to correspond to each light emitting area PXA-R, PXA-G and PXA-B may emit light in substantially the same wavelength range. In the display device DD-a of one or more embodiments, the emission layer EML may emit blue light. In one or more embodiments, unlike the illustrated configuration, in one or more embodiments, the emission layer EML may be provided as a common layer in the entire light emitting areas PXA-R, PXA-G and PXA-B.
[0399] The light control layer CCL may be arranged on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot and / or a phosphor, etc. The light converter may emit the provided light by converting the wavelength of the provided light. For example, the light control layer CCL may be a layer containing quantum dots or a layer containing phosphors.
[0400] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced and / or separated (eg, spaced apart or separated) from each other.
[0401] refer to Figure 7 , the dividing pattern BMP may be disposed between the light control parts CCP1 , CCP2 , and CCP3 that are spaced apart and / or separated (eg, spaced apart or separated) from each other, but one or more embodiments of the present disclosure are not limited thereto. Figure 7 It is explained that the dividing pattern BMP does not overlap with 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 with the dividing pattern BMP.
[0402] The light control layer CCL may include: a first light control component CCP1, which contains first quantum dots QD1 that convert the first color light provided by the light emitting element ED into second color light; a second light control component CCP2, which contains second quantum dots QD2 that convert the first color light into third color light; and a third light control component CCP3 that transmits the first color light.
[0403] In one or more embodiments, the first light control component CCP1 may provide red light as the second color light, and the second light control component CCP2 may provide green light as the third color light. The third light control component CCP3 may provide blue light by transmitting blue light as the first color light provided from the light emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. With respect to the quantum dots QD1 and QD2, the same as described herein may apply.
[0404] In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control component CCP3 may not include (e.g., may exclude) any quantum dot, but include a scatterer SP.
[0405] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica. The scatterer SP may include a member selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica, or may be selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and a mixture of at least two of the materials selected from hollow spherical silica.
[0406] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may each include base resins BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In one or more embodiments, the first light control component CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control component CCP3 may include scatterers SP dispersed in the third base resin BR3.
[0407] The base resins BR1, BR2 and BR3 are media in which the quantum dots QD1 and QD2 and the scatterers SP are dispersed, and may be formed of one or more suitable resin compositions which may be generally referred to as binders. For example, the base resins BR1, BR2 and BR3 may be acrylic resins, urethane resins, silicone resins and / or epoxy resins, etc. The base resins BR1, BR2 and BR3 may be transparent resins. In one or more embodiments, the first base resin BR1, the second base resin BR2 and the third base resin BR3 may be the same or different from each other.
[0408] The light control layer CCL may include an isolation layer BFL1. The isolation layer BFL1 may be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The isolation layer BFL1 may block or reduce the exposure of the light control components CCP1, CCP2, and CCP3 to moisture / oxygen. In one or more embodiments, the isolation layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In some embodiments, the isolation layer BFL2 may be provided between the light control components CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3.
[0409] The isolation layers BFL1 and BFL2 may include at least one inorganic layer. For example, the isolation layers BFL1 and BFL2 may include an inorganic material. For example, the isolation layers BFL1 and BFL2 may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride and / or a metal film that ensures light transmittance, etc. In one or more embodiments, the isolation layers BFL1 and BFL2 may further include an organic film. The isolation layers BFL1 and BFL2 may be formed of a single layer or a plurality of layers.
[0410] 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 isolation layer BFL2 may not be provided.
[0411] 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 a red dye, the second filter CF2 may include a green pigment or a green dye, and the third filter CF3 may include a blue pigment or a blue dye.
[0412] In one or more embodiments, one or more 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.
[0413] In addition, in one or more embodiments, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may not be separated but provided as one filter.
[0414] In one or more embodiments, the color filter layer CFL may further include a light shielding member. The light shielding member may be a black matrix. The light shielding member may include an organic light shielding material or an inorganic light shielding material containing a black pigment or a black dye. The light shielding member may prevent or reduce light leakage and may separate adjacent filters CF1, CF2, and CF3.
[0415] The first to third filters CF1, CF2, and CF3 may be arranged to correspond to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.
[0416] The base substrate BL may be arranged on the color filter layer CFL. The base substrate BL may be a member providing a base surface, and the color filter layer CFL and / or the light control layer CCL, etc. are arranged on the base surface. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, one or more 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 provided.
[0417] Figure 8A cross-sectional view of a portion of a display device according to one or more embodiments is provided to explain the display device according to one or more embodiments. In the display device DD-TD of one or more embodiments, the light emitting element ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 sequentially stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. The light emitting structures OL-B1, OL-B2, and OL-B3 may each include an emission layer EML ( Figure 7 ) and the hole transport region HTR ( Figure 7 ) and the electron transport region ETR ( Figure 7 ), the emission layer EML is located between the hole transport region HTR and the electron transport region ETR.
[0418] 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 EML.
[0419] exist Figure 8 In one or more embodiments explained in , all light beams emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may be blue light. However, one or more 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.
[0420] 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 layer (e.g., a p-charge generation layer) and / or an n-type or n-like charge generation layer (e.g., an n-charge generation layer).
[0421] At least one of the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display devices DD-TD according to one or more embodiments may include the amine compound of one or more embodiments.
[0422] refer to Fig. 9 , the display device DD-b according to one or more embodiments may include light emitting elements ED-1, ED-2, and ED-3 in which two emission layers are stacked. Figure 2 Compared to the display device DD of one or more embodiments described in Fig. 9The difference from one or more embodiments explained in is that each of the first to third light-emitting elements ED-1, ED-2, and ED-3 includes two emission layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2, and ED-3, the two emission layers may emit light in substantially the same wavelength range.
[0423] The first light-emitting element ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting element ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. In some embodiments, the third light-emitting element ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary component OG may be arranged between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.
[0424] The emission auxiliary component OG may include a single layer or multiple layers. The emission auxiliary component OG may include a charge generation layer. For example, the emission auxiliary component OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown) stacked in sequence. The emission auxiliary component OG may be provided as a common layer throughout the first to third light-emitting elements ED-1, ED-2, and ED-3. However, one or more embodiments of the present disclosure are not limited thereto, and the emission auxiliary component OG may be provided by patterning in an opening OH defined in a pixel defining film PDL.
[0425] 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 electron transport region ETR and the emission auxiliary component OG. 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 emission auxiliary component OG and the hole transport region HTR.
[0426] For example, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary component OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in sequence. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary component OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in sequence. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary component OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in sequence.
[0427] In one or more embodiments, an optical auxiliary layer PL may be disposed on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed 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 may not be provided in the display device according to one or more embodiments.
[0428] and Figure 8 and Fig. 9 different, Fig.10 It is explained that the display device DD-c includes four light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1. The light emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. The light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3 are stacked in sequence, and a charge generation layer CGL1 is disposed between the light emitting structures OL-B1 and OL-C1, a charge generation layer CGL2 is disposed between the light emitting structures OL-B1 and OL-B2, and a charge generation layer CGL3 is disposed between the light emitting structures OL-B2 and OL-B3. Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2 and OL-B3 may emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, one or more embodiments of the present disclosure are not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light beams within different wavelength ranges.
[0429] The charge generation layers CGL1, CGL2 and CGL3 arranged between adjacent light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3 may include p-type or p-like charge generation layers (e.g., p-charge generation layers) and / or n-type or n-like charge generation layers (e.g., n-charge generation layers).
[0430] At least one of the light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-c selected from one or more embodiments may include the amine compound of one or more embodiments.
[0431] The light-emitting element ED according to one or more embodiments of the present disclosure may include an amine compound of one or more embodiments in at least one functional layer arranged between the first electrode EL1 and the second electrode EL2 to show improved emission efficiency and improved element life characteristics. The light-emitting element ED according to one or more embodiments may include an amine compound of one or more embodiments in at least one selected from the hole transport region HTR, the emission layer EML, and the electron transport region ETR arranged between the first electrode EL1 and the second electrode EL2, or in the capping layer CPL. For example, the amine compound according to one or more embodiments may be included in the hole transport region HTR of the light-emitting element ED of one or more embodiments, and the light-emitting element ED of one or more embodiments may show high emission efficiency and long element life characteristics.
[0432] The amine compound of one or more embodiments includes a first substituent, a second substituent, and a third substituent, and can improve the stability of the material and improve the hole transport characteristics. Accordingly, the emission efficiency and element life of the light-emitting element including the amine compound of one or more embodiments can be improved. For example, the light-emitting element of one or more embodiments may include the amine compound according to one or more embodiments in the electron blocking layer to show improved emission efficiency and element life characteristics.
[0433] Fig.11 For explaining a view of a vehicle AM in which first to fourth display devices DD-1, DD-2, DD-3 and DD-4 are arranged. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may include the same Figure 1 , Figure 2 as well as Figures 7 to 10 The described display devices DD, DD-TD, DD-a, DD-b and DD-c have the same configuration.
[0434] Fig.11The vehicle AM is explained, but this is an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be arranged in another transportation device (e.g., 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 selected from the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one or more embodiments including the same configuration may be used in a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, and / or an outdoor billboard, etc. In some embodiments, these are provided merely as embodiments, and therefore may be used in other electronic devices unless departing from the present disclosure.
[0435] At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may include as shown in reference Figures 3 to 6 The light emitting element ED according to one or more embodiments is described.
[0436] At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 includes a reference Figures 3 to 6 The light-emitting element ED of one or more embodiments described. The light-emitting element ED of one or more embodiments may include the amine compound of one or more embodiments. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 includes a light-emitting element ED (including the amine compound according to one or more embodiments), and the display life is improved.
[0437] refer to Fig.11 The vehicle AM may include a steering wheel HA and a gearshift GR for driving the vehicle AM. In some embodiments, the vehicle AM may include a front window GL arranged to face the driver.
[0438] The first display device DD-1 may be arranged in a first area overlapping with the steering wheel HA. For example, the first display device DD-1 may be a digital instrument panel 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.
[0439] The second display device DD-2 may be arranged in a second area facing the driver's seat and overlapping with the front window GL. The driver's seat may be a seat in which the steering wheel HA is arranged. For example, the second display device DD-2 may be a head-up display (HUD) that displays the second information of the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include a numerical value indicating the driving speed, and may further include information such as the current time. Different from the illustrated configuration, the second information of the second display device DD-2 may be projected onto the front window GL and displayed.
[0440] The third display device DD-3 may be arranged in a third zone adjacent to the gear 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) of the vehicle AM for displaying the third information. The passenger seat may be a seat that is separated and / or separated (e.g., spaced apart or separated) from the driver's seat, and the gear GR is arranged between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), information about playing music or radio or video (or images), and / or information about the temperature inside the vehicle AM, etc.
[0441] The fourth display device DD-4 may be separated and / or isolated (e.g., spaced or separated) from the steering wheel HA and the gearshift GR, and may be arranged in a fourth zone adjacent to one side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an image of the outside of the vehicle AM captured by a camera module CM arranged outside the vehicle AM. The fourth information may include an image of the outside of the vehicle AM.
[0442] The first to fourth information described herein may be examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the inside and outside of the vehicle AM. The first to fourth information may include different information. However, one or more 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.
[0443] Hereinafter, with reference to one or more embodiments and comparative embodiments, the amine compound according to one or more embodiments and the light-emitting element according to one or more embodiments of the present disclosure will be specifically explained. In some embodiments, one or more embodiments are explained to facilitate understanding of the present disclosure, but the scope of the present disclosure is not limited thereto.
[0444] Example
[0445] 1. Synthesis of amine compounds
[0446] First, the synthesis method of the amine compound according to one or more embodiments will be explained by specifically explaining the synthesis methods of Compound 209, Compound 295, Compound 296, Compound 300, Compound 327, Compound 480, Compound 495, Compound 504, Compound 566, Compound 584, Compound 784, Compound 923, and Compound 968. In some embodiments, the synthesis method of the amine compound explained below is merely an example embodiment, and the synthesis method of the amine compound according to one or more embodiments of the present disclosure is not limited to the one or more embodiments as described herein.
[0447] (1) Synthesis of intermediate compounds IM-1 to IM-15
[0448] 1) Synthesis of intermediate compound IM-1
[0449]
[0450] In an Ar atmosphere, 1-naphthalene boronic acid (20.0 g), 1,4-diiodobenzene (38.3 g), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 , 6.7 g) and potassium carbonate (K 2 CO 3 , 32.1 g) and dissolved in a mixed solvent of toluene, water and ethanol (10:2:1 by volume, 500 mL), followed by heating at about 80° C. and stirring for about 4 hours. Then, water was added and CH 2 Cl 2 Extraction was performed, and the organic layer was collected and purified by MgSO 4 Drying, and removing the solvent by distillation under reduced pressure. The crude product thus obtained was separated by silica gel column chromatography and recrystallized to obtain 22.7 g (yield 58%) of intermediate compound IM-1. The molecular weight of intermediate compound IM-1 measured by FAB-MS was 330.
[0451] 2) Synthesis of intermediate compound IM-2
[0452]
[0453] According to the same method as the synthesis of intermediate compound IM-1, 23.8 g (yield 62%) of intermediate compound IM-2 was obtained from naphthalene-2-ylboronic acid (20.0 g) and 1,4-diiodobenzene (38.3 g). The molecular weight of intermediate compound IM-2 measured by FAB-MS was 330.
[0454] 3) Synthesis of intermediate compound IM-3
[0455]
[0456] According to the same method as the synthesis of intermediate compound IM-1, 23.0 g (yield 60%) of intermediate compound IM-3 was obtained from naphthalene-1-ylboronic acid (20.0 g) and 1,3-diiodobenzene (38.3 g). The molecular weight of intermediate compound IM-3 measured by FAB-MS was 330.
[0457] 4) Synthesis of intermediate compound IM-4
[0458]
[0459] According to the same method as the synthesis of intermediate compound IM-1, 21.1 g (yield 55%) of intermediate compound IM-4 was obtained from naphthalene-2-ylboronic acid (20.0 g) and 1,3-diiodobenzene (38.3 g). The molecular weight of intermediate compound IM-4 measured by FAB-MS was 330.
[0460] 5) Synthesis of intermediate compound IM-5
[0461]
[0462] In an Ar atmosphere, 1-bromocarbazole (20.0 g), intermediate compound IM-1 (26.8 g), copper (I) iodide (CuI, 1.5 g), 1,10-phenanthroline (1,10-Phen, 2.9 g) and cesium carbonate (Cs 2 CO 3 , 52 g) and dissolved in 1,2-dichlorobenzene (400 mL), followed by heating at about 150° C. and stirring for about 12 hours. Then, water was added and CH 2 Cl 2 Extraction was performed, and the organic layer was collected and purified by MgSO 4 Dry, and remove the solvent by distillation under reduced pressure. The crude product thus obtained is separated by silica gel column chromatography and recrystallized to obtain 20.0 g (yield 55%) of intermediate compound IM-5. The molecular weight of intermediate compound IM-5 measured by FAB-MS is 448.
[0463] 6) Synthesis of intermediate compound IM-6
[0464]
[0465] According to the same method as the synthesis of intermediate compound IM-5, 21.1 g (yield 58%) of intermediate compound IM-6 was obtained from 2-bromocarbazole (20.0 g) and intermediate compound IM-1 (26.8 g). The molecular weight of intermediate compound IM-6 measured by FAB-MS was 448.
[0466] 7) Synthesis of intermediate compound IM-7
[0467]
[0468] According to the same method as the synthesis of intermediate compound IM-5, 18.9 g (yield 52%) of intermediate compound IM-7 was obtained from 2-bromocarbazole (20.0 g) and intermediate compound IM-3 (26.8 g). The molecular weight of intermediate compound IM-7 measured by FAB-MS was 448.
[0469] 8) Synthesis of intermediate compound IM-8
[0470]
[0471] According to the same method as the synthesis of intermediate compound IM-5, 19.6 g (yield 54%) of intermediate compound IM-8 was obtained from 2-bromocarbazole (20.0 g) and intermediate compound IM-4 (26.8 g). The molecular weight of intermediate compound IM-8 measured by FAB-MS was 448.
[0472] 9) Synthesis of intermediate compound IM-9 to intermediate compound IM-11
[0473]
[0474] In an Ar atmosphere, [1,1'-biphenyl]-3-ylboronic acid (10.0 g), 4-bromo-1-iodo-2-nitrobenzene (16.5 g), Pd(PPh 3 ) 4 (2.9 g) and K 2 CO 3 (13.9 g) and dissolved in a mixed solvent of toluene, water and ethanol (10:2:1 by volume, 300 mL), followed by heating at about 80° C. and stirring for about 4 hours. Then, water was added and CH 2 Cl 2 Extraction was performed, and the organic layer was collected and purified by MgSO 4Drying, and removing the solvent by distillation under reduced pressure. The crude product thus obtained was separated by silica gel column chromatography and recrystallized to obtain 13.6 g (yield 76%) of intermediate compound IM-9. The molecular weight of intermediate compound IM-9 measured by FAB-MS was 354.
[0475] Under Ar atmosphere, intermediate compound IM-9 (10.0 g) and triphenylphosphine (PPh 3 , 22.2 g) and dissolved in 1,2-dichlorobenzene (200 mL), followed by heating at about 180° C. and stirring for about 12 hours. Then, water was added and CH 2 Cl 2 Extraction was performed, and the organic layer was collected and purified by MgSO 4 Dry, and remove the solvent by distillation under reduced pressure. The crude product thus obtained was separated by silica gel column chromatography and recrystallized to obtain 7.7 g (yield 85%) of intermediate compound IM-10. The molecular weight of intermediate compound IM-10 measured by FAB-MS was 322.
[0476] According to the same method as the synthesis of intermediate compound IM-5, 4.5 g (yield 56%) of intermediate compound IM-11 was obtained from intermediate compound IM-10 (5.0 g) and intermediate compound IM-3 (5.1 g). The molecular weight of intermediate compound IM-11 measured by FAB-MS was 524.
[0477] 10) Synthesis of intermediate compound IM-12
[0478]
[0479] According to the same method as the synthesis of intermediate compound IM-5, 16.4 g (yield 45%) of intermediate compound IM-12 was obtained from 3-bromocarbazole (20.0 g) and intermediate compound IM-1 (26.8 g). The molecular weight of intermediate compound IM-12 measured by FAB-MS was 448.
[0480] 11) Synthesis of intermediate compound IM-13
[0481]
[0482] According to the same method as the synthesis of intermediate compound IM-5, 15.3 g (yield 42%) of intermediate compound IM-13 was obtained from 3-bromocarbazole (20.0 g) and intermediate compound IM-3 (26.8 g). The molecular weight of intermediate compound IM-13 measured by FAB-MS was 448.
[0483] 12) Synthesis of intermediate compound IM-14
[0484]
[0485] According to the same method as the synthesis of intermediate compound IM-5, 19.6 g (yield 54%) of intermediate compound IM-14 was obtained from 4-bromocarbazole (20.0 g) and intermediate compound IM-1 (26.8 g). The molecular weight of intermediate compound IM-14 measured by FAB-MS was 448.
[0486] 13) Synthesis of intermediate compound IM-15
[0487]
[0488] According to the same method as the synthesis of intermediate compound IM-5, 19.6 g (yield 54%) of intermediate compound IM-15 was obtained from 4-bromocarbazole (20.0 g) and intermediate compound IM-2 (26.8 g). The molecular weight of intermediate compound IM-15 measured by FAB-MS was 448.
[0489] (2) Synthesis of amine compound 209
[0490]
[0491] 1) Synthesis of intermediate compound A
[0492] In an Ar atmosphere, dibenzo[b,d]furan-3-amine (20.0 g), 4-bromo-1,1'-biphenyl (25.4 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)) were added to a 1 L three-necked flask. 2 , 3.1 g) and sodium tert-butoxide (NaOtBu, 15.7 g) were dissolved in toluene (400 mL), and tri-tert-butylphosphine (P(tBu) 3 , 2.0 M in toluene, 5.5 mL), followed by stirring at room temperature for about 4 hours. Then, water was added and CH 2 Cl 2 Extraction was performed, and the organic layer was collected and purified by MgSO 4 The crude product thus obtained was separated by silica gel column chromatography and recrystallized to obtain 30.7 g (yield 84%) of intermediate compound A. The molecular weight of intermediate compound A measured by FAB-MS was 335.
[0493] 2) Synthesis of amine compound 209
[0494] In an Ar atmosphere, intermediate compound A (5.0 g), intermediate compound IM-5 (6.6 g), Pd(dba) and 2 (0.4 g) and NaOtBu (2.1 g) were dissolved in toluene (100 mL), and P(tBu) was added thereto. 3 (2.0 M in toluene, 0.7 mL), followed by heating and reflux for about 24 hours. Then, water was added and CH 2 Cl 2 Extraction was performed, and the organic layer was collected and purified by MgSO 4 The crude product thus obtained was separated by silica gel column chromatography and recrystallized to obtain 3.7 g (yield 36%) of amine compound 209. The molecular weight of amine compound 209 measured by FAB-MS was 702.
[0495] (3) Synthesis of amine compound 295
[0496]
[0497] According to substantially the same method as the synthesis of intermediate compound A, 27.4 g (yield 75%) of intermediate compound B was obtained from dibenzo[b,d]furan-1-amine (20.0 g) and 4-bromo-1,1′-biphenyl (25.4 g). The molecular weight of intermediate compound B measured by FAB-MS was 335.
[0498] According to substantially the same method as the synthesis of amine compound 209, 7.8 g (yield 75%) of amine compound 295 was obtained from intermediate compound B (5.0 g) and intermediate compound IM-6 (6.6 g). The molecular weight of amine compound 295 measured by FAB-MS was 702.
[0499] (4) Synthesis of amine compound 296
[0500]
[0501] According to substantially the same method as the synthesis of intermediate compound A, 20.1 g (yield 55%) of intermediate compound C was obtained from dibenzo[b,d]furan-2-amine (20.0 g) and 4-bromo-1,1′-biphenyl (25.4 g). The molecular weight of intermediate compound C measured by FAB-MS was 335.
[0502] According to substantially the same method as the synthesis of amine compound 209, 7.3 g (yield 70%) of amine compound 296 was obtained from intermediate compound C (5.0 g) and intermediate compound IM-6 (6.6 g). The molecular weight of amine compound 296 measured by FAB-MS was 702.
[0503] (5) Synthesis of amine compound 300
[0504]
[0505] According to substantially the same method as the synthesis of intermediate compound A, 20.8 g (yield 59%) of intermediate compound D was obtained from dibenzo[b,d]thiophene-4-amine (20.0 g) and 4-bromo-1,1′-biphenyl (23.4 g). The molecular weight of intermediate compound D measured by FAB-MS was 351.
[0506] According to substantially the same method as the synthesis of amine compound 209, 7.1 g (yield 70%) of amine compound 300 was obtained from intermediate compound D (5.0 g) and intermediate compound IM-6 (6.6 g). The molecular weight of amine compound 300 measured by FAB-MS was 718.
[0507] (6) Synthesis of amine compound 327
[0508]
[0509] According to substantially the same method as the synthesis of Intermediate Compound A, 25.7 g (yield 65%) of Intermediate Compound E was obtained from [1,1′-biphenyl]-3-amine (20.0 g) and 4-bromodibenzo[b,d]furan (29.2 g). The molecular weight of Intermediate Compound E measured by FAB-MS was 335.
[0510] According to substantially the same method as the synthesis of amine compound 209, 7.9 g (yield 76%) of amine compound 327 was obtained from intermediate compound E (5.0 g) and intermediate compound IM-7 (6.7 g). The molecular weight of amine compound 327 measured by FAB-MS was 702.
[0511] (7) Synthesis of amine compound 480
[0512]
[0513] According to substantially the same method as the synthesis of intermediate compound A, 29.6 g (yield 81%) of intermediate compound F was obtained from 4-(naphthalen-2-yl)aniline (20.0 g) and 4-bromodibenzo[b,d]thiophene (29.2 g). The molecular weight of intermediate compound F measured by FAB-MS was 401.
[0514] According to substantially the same method as the synthesis of amine compound 209, 6.8 g (yield 71%) of amine compound 480 was obtained from intermediate compound F (5.0 g) and intermediate compound IM-8 (5.6 g). The molecular weight of amine compound 480 measured by FAB-MS was 768.
[0515] (8) Synthesis of amine compound 495
[0516]
[0517] According to substantially the same method as the synthesis of intermediate compound A, 21.4 g (yield 51%) of intermediate compound G was obtained from 4-(naphthalen-2-yl)aniline (20.0 g) and 3-chloro-6-phenyldibenzo[b,d]furan (25.4 g). The molecular weight of intermediate compound G measured by FAB-MS was 461.
[0518] According to substantially the same method as the synthesis of amine compound 209, 5.8 g (yield 65%) of amine compound 495 was obtained from intermediate compound G (5.0 g) and intermediate compound IM-7 (4.9 g). The molecular weight of amine compound 495 measured by FAB-MS was 829.
[0519] (9) Synthesis of amine compound 504
[0520]
[0521] According to substantially the same method as the synthesis of intermediate compound A, 34.5 g (yield 87%) of intermediate compound H was obtained from [1,1′:2′,1″-terphenyl]-4′-amine (20.0 g) and 4-bromo-6-phenyldibenzo[b,d]furan (26.3 g). The molecular weight of intermediate compound H measured by FAB-MS was 487.
[0522] According to substantially the same method as the synthesis of amine compound 209, 5.7 g (yield 65%) of amine compound 504 was obtained from intermediate compound H (5.0 g) and intermediate compound IM-7 (4.6 g). The molecular weight of amine compound 504 measured by FAB-MS was 855.
[0523] (10) Synthesis of amine compound 566
[0524]
[0525] According to essentially the same method as the synthesis of intermediate compound A, 28.1 g (yield 84%) of intermediate compound I was obtained from [1,1′:2′,1″-terphenyl]-4′-amine (20.0 g) and 4-bromodibenzo[b,d]furan (20.1 g). The molecular weight of intermediate compound I measured by FAB-MS was 411.
[0526] According to substantially the same method as the synthesis of amine compound 209, 6.3 g (yield 61%) of amine compound 566 was obtained from intermediate compound I (5.0 g) and intermediate compound IM-11 (5.4 g). The molecular weight of amine compound 566 measured by FAB-MS was 855.
[0527] (11) Synthesis of amine compound 584
[0528]
[0529] According to substantially the same method as the synthesis of intermediate compound A, 29.2 g (yield 80%) of intermediate compound J was obtained from dibenzo[b,d]furan-4-amine (20.0 g) and 4-bromo-1,1′-biphenyl (25.4 g). The molecular weight of intermediate compound J measured by FAB-MS was 335.
[0530] According to substantially the same method as the synthesis of amine compound 209, 7.9 g (yield 76%) of amine compound 584 was obtained from intermediate compound J (5.0 g) and intermediate compound IM-12 (6.7 g). The molecular weight of amine compound 584 measured by FAB-MS was 702.
[0531] (12) Synthesis of amine compound 784
[0532]
[0533] According to substantially the same method as the synthesis of amine compound 209, 7.0 g (yield 67%) of amine compound 784 was obtained from intermediate compound A (5.0 g) and intermediate compound IM-13 (6.7 g). The molecular weight of amine compound 784 measured by FAB-MS was 702.
[0534] (13) Synthesis of amine compound 923
[0535]
[0536] According to essentially the same method as the synthesis of intermediate compound A, 33.4 g (yield 78%) of intermediate compound K was obtained from dibenzo[b,d]thiophene-4-amine (20.0 g) and 4-bromo-1,1′:3′,1″-terphenyl (31.0 g). The molecular weight of intermediate compound K measured by FAB-MS was 427.
[0537] According to substantially the same method as the synthesis of amine compound 209, 6.3 g (yield 68%) of amine compound 923 was obtained from intermediate compound K (5.0 g) and intermediate compound IM-14 (5.3 g). The molecular weight of amine compound 923 measured by FAB-MS was 795.
[0538] (14) Synthesis of amine compound 968
[0539]
[0540] According to substantially the same method as the synthesis of amine compound 209, 6.1 g (yield 59%) of amine compound 968 was obtained from intermediate compound J (5.0 g) and intermediate compound IM-15 (6.7 g). The molecular weight of amine compound 968 measured by FAB-MS was 702.
[0541] 2. Manufacturing and evaluation of light-emitting components
[0542] The light-emitting element of one or more embodiments including the amine compound of one or more embodiments in the hole transport layer is manufactured by the method as described herein. The light-emitting elements of Examples 1 to 13 are manufactured using Example compounds of Compound 209, Compound 295, Compound 296, Compound 300, Compound 327, Compound 480, Compound 495, Compound 504, Compound 566, Compound 584, Compound 784, Compound 923, and Compound 968 as hole transport layer materials. Comparative Examples 1 to 9 correspond to light-emitting elements manufactured using Comparative Compounds X-1 to X-9 as hole transport layer materials.
[0543] Example compounds
[0544]
[0545]
[0546] Comparison Compounds
[0547]
[0548] Manufacturing of light-emitting components
[0549] As the first electrode, a Corning PCB with a resistance of about 15 ohms per square centimeter (Ω / cm 2 ) (about 150 nanometers (nm)) of indium tin oxide (ITO) glass substrate was cut into a size of 50 millimeters (mm) × 50 mm × 0.7 mm, rinsed with isopropyl alcohol and ultrapure water, cleaned using ultrasound for about 5 minutes, exposed to UV for about 30 minutes and treated with ozone. Then, 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA) was vacuum deposited to a thickness of about 60 nm to form a hole injection layer. Thereafter, the example compound or the comparative compound was vacuum deposited to a thickness of about 30 nm to form a hole transport layer.
[0550] On the hole transport layer, a blue fluorescent host 9,10-di(naphthalene-2-yl)anthracene (ADN) and a fluorescent dopant 2,5,8,11-tetra-tert-butylperylene (TBP) were co-deposited in a ratio (eg, amount) of about 97:3 by weight to form an emission layer having a thickness of about 25 nm.
[0551] On the emission layer, tris(8-hydroxyquinoline)aluminum (Alq 3 ) to form an electron transport layer with a thickness of about 25 nm, and then, an electron injection layer with a thickness of about 1 nm is formed by depositing LiF. On the electron injection layer, a second electrode with a thickness of about 100 nm is formed using aluminum (Al).
[0552] In some embodiments, the compound used to manufacture the functional layer of the light emitting element is as follows.
[0553]
[0554] Evaluation of light-emitting components
[0555] Table 1 shows evaluations of the light emitting elements of Example 1 to Example 13 and Comparative Examples 1 to Comparative Examples 9. In Table 1, evaluation results of emission efficiency and element lifetime of the manufactured light emitting elements are shown.
[0556] The evaluation results of the characteristics of the embodiments and comparative examples shown in Table 1 were measured using the Hamamatsu Optoelectronics C9920-11 light distribution measurement system. The emission efficiency represents the emission efficiency at about 10 mA / cm2. 2 ) current density, and the device life (LT50) will be about 1000 candela per square meter (cd / m 2) is reduced to half the initial brightness. In Table 1, the emission efficiency is shown as a relative value relative to Comparative Example 1, and the emission efficiency of Comparative Example 1 is regarded as 100%, and the element life (LT50) is shown as a relative value relative to Comparative Example 1, and the element life (LT50) of Comparative Example 1 is regarded as 100%.
[0557] Table 1
[0558]
[0559] With reference to the results of Table 1, it can be found that, when compared with the comparative examples, the (e.g., most) light-emitting elements of the embodiments using the amine compounds according to one or more embodiments of the present disclosure as hole transport layer materials show high emission efficiency. In some embodiments, it can be found that, when compared with the light-emitting elements of the comparative examples, the light-emitting elements of the embodiments show long element life characteristics.
[0560] For example, in the amine compound of one or more embodiments, it can be found that the carbazole part is directly connected to the nitrogen atom of the amine compound, and a substituted or unsubstituted aryl group of 10 to 30 ring carbon atoms (e.g., naphthyl) is connected to the 9-position of the carbazole part via a phenylene linker, and the electron tolerance is improved, and a long element life characteristic is shown. In some embodiments, in the amine compound of the embodiment, it can be confirmed that because dibenzoheterocyclopentadiene (e.g., dibenzofuran part or dibenzothiophene part) is directly bonded to the nitrogen atom of the amine compound, excellent or appropriate emission efficiency and long element life characteristics are shown.
[0561] In Comparative Compound X-1 and Comparative Compound X-7, since a dibenzofuran portion or a dibenzothiophene portion was not included, it was found that the emission efficiency was relatively low and the element life characteristics were deteriorated.
[0562] In comparative compound X-2, a naphthyl group is directly connected at the 9-position of the carbazole part connected to the nitrogen atom of the amine compound, and includes a structure in which a benzene ring is further condensed with a dibenzofuran part, and shows relatively low emission efficiency and element life characteristics compared with the examples.
[0563] In the comparative compound X-3, the naphthyl group is linked at the ortho position relative to the carbon atom linked to the nitrogen atom of the carbazole portion (for example, linked to the phenylene linking group at the ortho position relative to the carbon atom linked to the nitrogen atom of the carbazole portion), and does not include a dibenzofuran portion or a dibenzothiophene portion, and shows relatively low emission efficiency and element life characteristics compared to the embodiments.
[0564] In comparative compound X-4, a substituted or unsubstituted aromatic group of 10 to 30 ring-forming carbon atoms is not attached (e.g., introduced) to the phenyl group connected at the 9-position of the carbazole portion, and includes a structure in which a benzene ring is further condensed with a dibenzofuran portion, and shows significantly deteriorated element life compared to the examples.
[0565] Comparative compound X-5 corresponds to the case where the nitrogen atom of the amine compound is connected to the 2-position (or 7-position) of the carbazole part and is simultaneously connected to the 3-position (or 6-position) of the dibenzofuran part. However, comparative compound X-5 does not include a substituent connected to the dibenzofuran part, and compared with the examples, the results of degraded emission efficiency and element life are shown.
[0566] Comparative compound X-6 corresponds to the case where the nitrogen atom of the amine compound is bonded to the 3-position of the carbazole part. However, in comparative compound X-6, a naphthyl group rather than a hydrogen atom or a deuterium atom is bonded to the benzene ring of the carbazole part bonded to the nitrogen atom of the amine compound, and a significantly deteriorated element life result is shown compared to the example compounds.
[0567] Comparative compound X-8 substantially includes a heteroaryl group in which 9,9-dimethylfluorene is condensed with benzofuran to form a ring, and the element life is significantly deteriorated and the emission efficiency is low compared with the Examples.
[0568] In the comparative compound X-9, a phenyl group with 6 ring carbon atoms, rather than a substituted or unsubstituted aromatic group with 10 to 30 ring carbon atoms, is connected at the 9-position of the carbazole part via a phenylene linker, and the light-emitting element of comparative example 9 using comparative compound X-9 shows low emission efficiency and significantly deteriorated element life compared with the embodiment.
[0569] The light emitting element of one or more embodiments includes the amine compound of one or more embodiments, and may show high emission efficiency and long element life characteristics.
[0570] The amine compound of one or more embodiments has excellent or appropriate hole transport properties and electron tolerance, and if applied to a light-emitting element, the amine compound can contribute to increasing the emission efficiency and element life of the light-emitting element.
[0571] The display device of one or more embodiments includes a light emitting element and can show excellent or appropriate display quality.
[0572] Although one or more embodiments of the present disclosure have been described, it should be understood that the present disclosure should not be limited to these embodiments, but rather one or more appropriate changes and modifications may be made by one of ordinary skill in the art within the spirit and scope of the present disclosure as claimed in the claims and its equivalents.
[0573] Accordingly, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the detailed description of the specification, but is intended to be defined by the appended claims and their equivalents.
Claims
1. An amine compound, an amine compound represented by Formula 1: Formula 1 In formula 1, X is O or S, 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, Ar 2 and Ar 3 are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, wherein the group selected from Ar 2 and Ar 3 At least one of them is a substituted or unsubstituted aromatic group having 10 to 30 ring carbon atoms, R 1 To R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 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, "a", "c" and "e" are each independently an integer selected from 0 to 3, "b" and "d" are each independently an integer selected from 0 to 4, When the nitrogen atom of the amine compound is connected to the 2-position or 7-position of the carbazole moiety and is not Ar 1 When the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part is connected, or When the nitrogen atom of the amine compound is connected to the 4-position or 5-position of the carbazole moiety and to the 3-position or 6-position of the dibenzothiophene moiety or the dibenzofuran moiety, a+b≥1, and is selected from R 1 and R 2 At least one of is not a hydrogen atom, and When the nitrogen atom of the amine compound is linked to the 3-position of the carbazole moiety, R 3 is a hydrogen atom or a deuterium atom, and Excluding Ar 1 including directly bonded to the nitrogen atom of the amine compound part, and Y is O or S.
2. The amine compound according to claim 1, wherein the amine compound is represented by Formula 2-1 or Formula 2-2: Formula 2-1 Formula 2-2 In formula 2-1, R 6 is a hydrogen atom, a deuterium atom, 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 "f" is an integer selected from 0 to 5, In formula 2-2, Z is O or S, R 7 and R 8 are each independently a hydrogen atom or a deuterium atom, "g" is an integer selected from 0 to 3, and "h" is an integer selected from 0 to 4, and In formula 2-1 and formula 2-2, X、Ar 2 ,Ar 3 , R 1 To R 5 and "a" to "e" are each independently as defined in Formula 1.
3. The amine compound according to claim 2, wherein the amine compound is selected from Ar 2 and Ar 3 At least one of the groups is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted pyrenyl group.
4. The amine compound according to claim 1, wherein the amine compound is represented by Formula 3-1 or Formula 3-2: Formula 3-1 Formula 3-2 In formula 3-1 and formula 3-2, R 9 , R 10 ,Ar 21 and Ar 31 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, "i" and "k" are each independently an integer selected from 0 to 7, and X、Ar 1 , R 1 To R 5 and "a" to "e" are each independently as defined in Formula 1.
5. The amine compound according to claim 1, wherein R 1 To R 5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.
6. The amine compound according to claim 1, wherein the amine compound is represented by any one selected from Formula 4-1 to Formula 4-4: Formula 4-1 Formula 4-2 Formula 4-3 Formula 4-4 In Formula 4-1 to Formula 4-4, R 11 To R 13 , R 21 To R 23 , R 31 To R 33 , R 41 and R 42 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R 14 , R 24 , R 34 and R 44 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, R 15 , R 25 , R 35 , R 43 and R 45 are each independently a hydrogen atom or a deuterium atom, a1 to a4, c1 to c4 and e1 to e4 are each independently an integer selected from 0 to 3, b1 to b4 and d1 to d4 are each independently an integer selected from 0 to 4, X and Ar 1 To Ar 3 Each independently as defined in Formula 1, In Formula 4-2, when the nitrogen atom of the amine compound is not Ar 1 When the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part is connected, a2+b2≥1, and is selected from R 21 and R 22 At least one of the following is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and In Formula 4-4, when the nitrogen atom of the amine compound is not Ar 1 When the 3-position or 6-position of the dibenzothiophene part or the dibenzofuran part is connected, a4+b4≥1, and is selected from R 41 and R 42 At least one of the is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
7. The amine compound according to claim 1, wherein the amine compound is selected from Ar 2 and Ar 3 At least one of is represented by any one of the substituents selected from Substituent Group 1: Substituent Group 1 In Substituent Group 1, D is a deuterium atom, and * indicates a bonding position to Formula 1.
8. The amine compound according to claim 1, wherein the amine compound is selected from any one of the compounds in compound group 1: Compound Group 1 In compound group 1, D is a deuterium atom.
9. A light emitting element, comprising: a first electrode; a second electrode on the first electrode; as well as at least one functional layer between the first electrode and the second electrode, The at least one functional layer comprises the amine compound according to any one of claims 1 to 8.
10. A display device, comprising: basal layer; a circuit layer on the base layer; as well as A display element layer is on the circuit layer and includes the light emitting element according to claim 9.
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