Light-emitting element, amine compound for light-emitting element, and display device including light-emitting element
By using amine compounds with specific structures as hole transport zone materials in the light emitting element, the problem of insufficient luminescence efficiency and lifetime is solved, and more efficient and longer lifetime display performance is achieved.
Patent Information
- Application Number
- CN202510027128.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-01-10
- Filing Date
- 2025-01-08
- Publication Date
- 2025-07-11
AI Technical Summary
In the prior art, when the light emitting element is applied to a display device, there is a problem of insufficient luminous efficiency and lifetime, and it is difficult to achieve efficient display stably.
The amine compounds of a specific structure are used as the hole transport region material, including amine compounds with arylene, heteroarylene, aryl and heteroaryl groups with a specific structure, to improve the hole transport performance of the light emitting element, thereby improving the luminous efficiency and extending life.
By using improved amine compound materials, the luminous efficiency and lifetime of the luminous emitting element are improved, and more stable display performance is achieved.
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Figure CN120289399A_ABST
Abstract
Description
[0001] Cross - reference to related applications
[0002] This application claims priority and the benefit of Korean Patent Application No. 10 - 2024 - 0004046, filed with the Korean Intellectual Property Office on January 10, 2024, the entire content of which is incorporated herein by reference. Technical field
[0003] The present disclosure relates to a light - emitting element, an amine compound for a light - emitting element, and a display device including the light - emitting element. Background art
[0004] Continuous development of an organic electroluminescent display device or the like as an image display device is underway. The organic electroluminescent display device or the like is a display device including a light - emitting element with so - called self - emission, in which holes and electrons injected from a first electrode and a second electrode respectively recombine in an emission layer, such that a light - emitting material in the emission layer emits light to achieve display.
[0005] When applying the light - emitting element to a display device, there is a continuous need to improve light - emitting efficiency and lifespan, etc. Continuous development of materials for the light - emitting element capable of stably achieving these characteristics is required.
[0006] It should be understood that this background art section is partly intended to provide useful background for understanding the technology. However, this background art section may also include ideas, concepts, or cognitions that were not known or understood by those skilled in the relevant art before the effective filing date of the corresponding application for the subject matter disclosed herein. Summary of the invention
[0007] The present disclosure provides a light - emitting element having improved light - emitting efficiency and lifespan, and a display device including the light - emitting element.
[0008] The present disclosure also provides an amine compound that improves light - emitting efficiency and lifespan as a material for a light - emitting element.
[0009] According to an embodiment, the light - emitting element may include a first electrode, a hole - transport region disposed on the first electrode, an emission layer disposed on the hole - transport region, an electron - transport region disposed on the emission layer, and a second electrode disposed on the electron - transport region, wherein the hole - transport region may include an amine compound represented by Formula 1:
[0010] [Formula 1]
[0011]
[0012] In Formula 1, X1 can be O or S; L1 and L2 can each independently be a direct bond, a substituted or unsubstituted arylene having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 15 ring carbon atoms; Ar1 can be a substituted or unsubstituted aryl having 6 to 15 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 15 ring carbon atoms; Ar2 can be a group represented by Formula 2; Ar3 can be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms; and R1 to R6 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 15 ring carbon atoms.
[0013] [Formula 2]
[0014]
[0015] In Formula 2, n1 can be an integer selected from 0 to 3; R a1 to R a7 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 15 ring carbon atoms; and -* represents a bond connecting to an adjacent atom.
[0016] In an embodiment, the amine compound represented by Formula 1 can be represented by one of Formula 1-B1 to Formula 1-B4:
[0017] [Formula 1-B1]
[0018]
[0019] [Formula 1-B2]
[0020]
[0021] [Formula 1-B3]
[0022]
[0023] [Formula 1-B4]
[0024]
[0025] In Formula 1-B1 to Formula 1-B4, X1, L1, L2, Ar1, Ar3, R1 to R6, R a1 to R a7and n1 is the same as that defined in Formula 1 and Formula 2.
[0026] In an embodiment, in Formulae 1-B1 to 1-B4, R a1 to R a7 may each independently be a hydrogen atom or a deuterium atom.
[0027] In an embodiment, in Formula 1, Ar1 may be a group represented by one of Formulae AR-1 to AR-4:
[0028]
[0029] In Formula AR-2, D is a deuterium atom. In Formulae AR-1 to AR-4, -* represents a bond connected to an adjacent atom.
[0030] In an embodiment, in Formula 1, L1 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent dibenzofuranyl group, or a substituted or unsubstituted divalent dibenzothiophenyl group.
[0031] In an embodiment, in Formula 1, L1 may be a direct bond or a group represented by one of Formulae L1-1 to L1-5.
[0032]
[0033] In Formula L1-2, D is a deuterium atom. In Formulae L1-1 to L1-5, -* represents a bond connected to an adjacent atom.
[0034] In an embodiment, in Formula 1, L2 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent carbazolyl group, a substituted or unsubstituted divalent dibenzofuranyl group, or a substituted or unsubstituted divalent dibenzothiophenyl group.
[0035] In an embodiment, in Formula 1, Ar3 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
[0036] In an embodiment, in Formula 1, *-L2-Ar3 may be a moiety represented by one of Formulae LA-1 to LA-79:
[0037]
[0038]
[0039]
[0040]
[0041] In Formulas LA-69 to LA-79, D is a deuterium atom. In Formulas LA-1 to LA-79, -* represents a bond connecting to an adjacent atom.
[0042] In an embodiment, the amine compound represented by Formula 1 may include at least one compound selected from Compound Group 1, which is explained below.
[0043] According to an embodiment, the amine compound may be represented by Formula 1, which is explained herein.
[0044] In an embodiment, the amine compound represented by Formula 1 may be represented by one of Formulas 1-B1 to 1-B4, which is explained herein.
[0045] In an embodiment, in Formulas 1-B1 to 1-B4, R a1 to R a7 may each independently be a hydrogen atom or a deuterium atom.
[0046] In an embodiment, in Formula 1, Ar1 may be a group represented by one of Formulas AR-1 to AR-4, which is explained herein.
[0047] In an embodiment, in Formula 1, L1 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent dibenzofuranyl group, or a substituted or unsubstituted divalent dibenzothiophenyl group.
[0048] In an embodiment, in Formula 1, L1 may be a direct bond or a group represented by one of Formulas L1-1 to L1-5, which is explained herein.
[0049] In an embodiment, in Formula 1, L2 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent carbazolyl group, a substituted or unsubstituted divalent dibenzofuranyl group, or a substituted or unsubstituted divalent dibenzothiophenyl group; and Ar3 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
[0050] In an embodiment, in Formula 1, *-L2-Ar3 may be a moiety represented by one of Formulas LA-1 to LA-79, which is explained herein.
[0051] In an embodiment, the amine compound represented by Formula 1 may be selected from Compound Group 1, which is explained below.
[0052] According to an embodiment, a display device may include: a circuit layer disposed on a base layer; and a display element layer disposed on the circuit layer and including a light-emitting element, wherein:
[0053] The light-emitting element may include a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region; and the hole transport region may include the amine compound represented by Formula 1, which is explained herein.
[0054] It should be understood that the above embodiments are described only in a general and explanatory sense and not for the purpose of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0055] The accompanying drawings are included to provide a further understanding of the embodiments, and the accompanying drawings are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and their principles. The above and other aspects and features of the present disclosure will become more apparent by describing in detail its embodiments with reference to the accompanying drawings, in which:
[0056] Figure 1 is a schematic plan view of a display device according to an embodiment;
[0057] Figure 2 is a schematic cross-sectional view of a display device according to an embodiment;
[0058] Figure 3 is a schematic cross-sectional view of a light-emitting element according to an embodiment;
[0059] Figure 4 is a schematic cross-sectional view of a light-emitting element according to an embodiment;
[0060] Figure 5 is a schematic cross-sectional view of a light-emitting element according to an embodiment;
[0061] Figure 6 is a schematic cross-sectional view of a light-emitting element according to an embodiment;
[0062] Figure 7 is a schematic cross-sectional view of a display device according to an embodiment;
[0063] Figure 8 is a schematic cross-sectional view of a display device according to an embodiment;
[0064] Figure 9Schematic cross-sectional view of a display device according to an embodiment;
[0065] Figure 10 Schematic cross-sectional view of a display device according to an embodiment; and
[0066] Figure 11 Schematic diagram of the interior of a vehicle including a display device according to an embodiment. Detailed embodiments
[0067] The present disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. However, the present disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
[0068] In the drawings, for ease of description and clarity, the sizes, ratios, and dimensions (e.g., thickness) of elements may be enlarged. Throughout the text, the same reference numerals and the same reference characters refer to the same elements.
[0069] In the specification, it will be understood that when an element (or region, layer, portion, etc.) is referred to as being "on", "connected to", or "coupled to" another element (or region, layer, portion, etc.), it may be directly on, directly connected to, or directly coupled to the other element (or region, layer, portion, etc.), or there may be one or more intervening elements therebetween. In a similar sense, when an element (or region, layer, portion, etc.) is described as "covering" another element (or region, layer, portion, etc.), it may directly cover the other element (or region, layer, portion, etc.), or there may be one or more intervening elements therebetween.
[0070] In the specification, when an element is "directly on", "directly connected to", or "directly coupled to" another element, there is no intervening element. For example, "directly on..." may mean that two layers or two elements are disposed without another element (such as an adhesive element) therebetween.
[0071] As used herein, expressions used in the singular form, such as "a", "an", and "the", are also intended to include the plural form unless the context clearly indicates otherwise.
[0072] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" can be understood to mean "A, B, or A and B". The terms "and" and "or" can be used in a conjunctive sense or a disjunctive sense and can be understood to be equivalent to "and / or".
[0073] In the specification and claims, the term "at least one of... " is intended to include the meaning of "at least one selected from the group consisting of... " for purposes of its meaning and interpretation. For example, "at least one of A, B, and C" can be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When following a list of elements, the term "at least one of... " modifies the entire list of elements and not a single element of the list.
[0074] It will be understood that although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, without departing from the teachings of the present disclosure, a first element may be referred to as a second element. Similarly, without departing from the scope of the present disclosure, a second element may be referred to as a first element.
[0075] For ease of description, spatial relative terms such as "below", "beneath", "under", "above", or "on" etc. may be used herein to describe the relationship between one element or component and another element or component as illustrated in the figures. It will be understood that the spatial relative terms are intended to include different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, in the case of flipping the device illustrated in the figures, a device located "below" or "beneath" another device may be positioned "above" the other device. Accordingly, the illustrative term "below" can include both a lower position and an upper position. The device may also be oriented in other directions and thus the spatial relative terms may be interpreted differently depending on the orientation.
[0076] As used herein, the term "about" or "approximately" includes the recited value and means within an acceptable deviation range of the recited value determined by a person of ordinary skill in the art considering the measurement in question and the errors associated with the measurement of the recited quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the recited value, or within ±20%, ±10%, or ±5% of the recited value.
[0077] It should be understood that the terms "comprises", "comprising", "includes", "including", "have", "having", "contains", and "containing" etc. are intended to indicate the presence of the recited features, integers, steps, operations, elements, components, or combinations thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
[0078] Unless otherwise defined or implied herein, all terms used (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and should not be interpreted in an idealized or overly formal sense unless clearly defined in the specification.
[0079] In the specification, the term "substituted or unsubstituted" may describe a group that is unsubstituted or substituted with at least one substituent selected from the group consisting of: deuterium atom, halogen atom, cyano group, nitro group, amino group, amido group, silyl group, oxy group, thio group, sulfinyl group, sulfonyl group, carbonyl group, boron group, phosphinyl group, phosphinothioyl group, alkyl group, alkenyl group, alkynyl group, hydrocarbon ring group, aryl group, and heterocyclic group. Each of the substituents listed above may itself be substituted or unsubstituted. For example, biphenyl may be interpreted as an aryl group or may be interpreted as a phenyl group substituted with a phenyl group.
[0080] In the specification, the phrase "bonded to an adjacent group to form a ring" may refer to a group that is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring may be aliphatic or aromatic. The heterocyclic ring may be aliphatic or aromatic. The hydrocarbon ring and the heterocyclic ring may each independently be monocyclic or polycyclic. The ring formed by bonding adjacent groups to each other may itself be connected to another ring to form a spiro structure.
[0081] In the specification, the term "adjacent group" may be interpreted as a substituent that substitutes an atom directly connected to an atom substituted with a corresponding substituent, as another substituent that substitutes an atom substituted with a corresponding substituent, or as a substituent that is spatially located closest to a corresponding substituent. For example, the two methyl groups in 1,2-xylene 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. For example, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.
[0082] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0083] In the specification, the alkyl group may be straight-chain or branched-chain. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., but the embodiments are not limited thereto.
[0084] In the specification, the cycloalkyl group may be a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of the cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, bicycloheptyl, etc., but the embodiments are not limited thereto.
[0085] In the specification, the alkenyl group may be a hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be straight-chain or branched-chain. The number of carbon atoms in the alkenyl group is not particularly limited and may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkenyl group may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylethylene, etc., but the embodiments are not limited thereto.
[0086] In the specification, an alkynyl group may be a hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having two or more carbon atoms. The alkynyl group may be straight-chain or branched-chain. The number of carbon atoms in the alkynyl group is not particularly limited and may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkynyl group may include ethynyl, propynyl, etc., but the embodiments are not limited thereto.
[0087] In the specification, a hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring. For example, the hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.
[0088] In the specification, an aryl group may be any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be monocyclic or polycyclic. The number of ring-forming carbon atoms in the aryl group may be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, triphenylene, pyrenyl, benzofluoranthenyl, 1,2-benzophenanthryl, etc., but the embodiments are not limited thereto.
[0089] 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 may include the groups shown below. However, the embodiments are not limited thereto.
[0090]
[0091] In the specification, a heterocyclic group may be any functional group or substituent derived from a ring including at least one of B, O, N, P, Si, and S as a heteroatom. The heterocyclic group may be aliphatic or aromatic. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocyclic group and the aromatic heterocyclic group may each independently be monocyclic or polycyclic
[0092] If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.
[0093] Examples of the aliphatic heterocyclic group may include oxiranyl, thiiranyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydrothienyl, thianyl, tetrahydropyranyl, 1,4-dioxanyl, etc., but the embodiments are not limited thereto.
[0094] Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzosilolyl, dibenzofuranyl, etc., but embodiments are not limited thereto.
[0095] In the specification, the above description of aryl groups may be applicable to arylene groups, except that arylene groups are divalent groups. In the specification, the above description of heteroaryl groups may be applicable to heteroarylene groups, except that heteroarylene groups are divalent groups.
[0096] In the specification, silyl groups may be alkylsilyl groups or arylsilyl groups. The alkyl group in the alkylsilyl group may be linear, branched or cyclic. The number of carbon atoms in the alkylsilyl group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylsilyl group is not particularly limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of silyl groups may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but embodiments are not limited thereto.
[0097] In the specification, the number of carbon atoms in the carbonyl group (or acyl group) is not particularly limited and may be 1 to 40, 1 to 30 or 1 to 20. For example, the carbonyl group may have one of the following structures, but embodiments are not limited thereto.
[0098]
[0099] In the specification, the number of carbon atoms in the sulfinyl group or sulfonyl group is not particularly limited and may be 1 to 30. The sulfinyl group may be an alkylsulfinyl group or an arylsulfinyl group. The sulfonyl group may be an alkylsulfonyl group or an arylsulfonyl group.
[0100] In the specification, the thio group may be an alkylthio group or an arylthio group. The thio group may be a sulfur atom bonded to an alkyl group or an aryl group as defined above. The alkyl group in the alkylthio group may be straight-chain, branched-chain, or cyclic. The number of carbon atoms in the alkylthio group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylthio group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the thio group may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, naphthylthio, etc., but the embodiments are not limited thereto.
[0101] In the specification, the oxy group may be an oxygen atom bonded to an alkyl group or an aryl group as defined above. The oxy group may be an alkoxy group or an aryloxy group. The alkoxy group may be straight-chain, branched-chain, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited and may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryloxy group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the oxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but the embodiments are not limited thereto.
[0102] In the specification, the boron group may be a boron atom bonded to an alkyl group or an aryl group as defined above. The alkyl group in the alkylboron group may be straight-chain, branched-chain, or cyclic. The number of carbon atoms in the alkylboron group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylboron group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. The boron group may be an alkylboron group or an arylboron group. Examples of the boron group may include dimethylboron, tert-butylmethylboron, diphenylboron, phenylboron, etc., but the embodiments are not limited thereto.
[0103] In the specification, the amino group may be an alkylamino group or an arylamino group. The alkyl group in the alkylamino group may be straight-chain, branched-chain, or cyclic. The number of carbon atoms in the alkylamino group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylamino group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the amino group may include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthrylamino, etc., but the embodiments are not limited thereto.
[0104] In the specification, the phosphine oxide group may mean an alkyl group or an aryl group as defined above bonded to -P(=O)-. The number of carbon atoms in 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 alkylphosphine oxide group and an arylphosphine 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 the above-defined alkyl or aryl group bonded to -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 structures, but is not limited thereto.
[0107]
[0108] In the specification, the alkyl group in an alkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, an alkylaryl group, an alkylamino group, an alkylboron group, an alkylsilyl group, an alkylamido group, an alkylphosphinyl group, or an alkylphosphinosulfide group may be the same as the examples of the alkyl group described above.
[0109] In the specification, the aryl group in an aryloxy group, an arylthio group, an arylsulfinyl group, an arylsulfonyl group, an alkylaryl group, an arylamino group, an arylboron group, an arylsilyl group, an arylamido group, an arylphosphinyl group, or an arylphosphinosulfide group may be the same as the examples of the aryl group described above.
[0110] In the specification, the direct bond may be a single bond.
[0111] In the specification, the symbol each represents a bond connecting to an adjacent atom in the corresponding formula or moiety.
[0112] Hereinafter, embodiments will be described with reference to the accompanying drawings.
[0113] Figure 1 is a schematic plan view of a display device DD according to an embodiment. Figure 2 is a schematic cross-sectional view of a display device DD according to an embodiment. Figure 2 is for explaining Figure 1 a schematic cross-sectional view of a part taken along the dashed line I-I' in
[0114] The display device DD may include a display panel DP and an optical layer PP provided on the display panel DP. The display panel DP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include a plurality of light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be provided on the display panel DP to control the light reflected at the display panel DP from external light. The optical layer PP may include, for example, a polarization layer or a color filter layer. Although not shown in the drawings, in an embodiment, the optical layer PP may be omitted from the display device DD.
[0115] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may provide a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.
[0116] The display device DD according to an embodiment may further include a filling layer (not shown). The filling layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The filling layer (not shown) may be an organic material layer. The filling layer (not shown) may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.
[0117] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include a pixel defining film PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between respective portions of the pixel defining film PDL, and a encapsulation layer TFE disposed on the light emitting elements ED-1, ED-2, and ED-3.
[0118] The base layer BS may provide a base surface on which the display element layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base layer BS may include an inorganic layer, an organic layer, or a composite material layer.
[0119] In an embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors (not shown). The plurality of transistors (not shown) may each include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include switching transistors and driving transistors for driving the light emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.
[0120] The light emitting elements ED-1, ED-2, and ED-3 may each have the structure of the light emitting element ED according to any of the embodiments Figures 3 to 6 which will be described later. The light emitting elements ED-1, ED-2, and ED-3 may each 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.
[0121] Figure 2An embodiment is illustrated in which the emission layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 are disposed in the opening OH defined by the pixel-defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are each provided as a common layer for the light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto. Although not shown in Figure 2 In the embodiment, the hole transport region HTR and the electron transport region ETR may each be provided by being patterned in the opening OH defined by the pixel-defining film PDL. For example, in the embodiment, the hole transport regions HTR of the light-emitting elements ED-1, ED-2, and ED-3, the emission layers EML-R, EML-G, and EML-B, and the electron transport region ETR may each be provided by being patterned by an inkjet printing method.
[0122] 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 element layer DP-ED. The encapsulation layer TFE may be a thin-film encapsulation layer. The encapsulation layer TFE may be formed of a single layer or multiple layers. The encapsulation layer TFE may include at least one insulating layer. The encapsulation layer TFE according to the embodiment may include at least one inorganic film (hereinafter, the encapsulation inorganic film). In the embodiment, the encapsulation layer TFE may include at least one organic film (hereinafter, the encapsulation organic film) and at least one encapsulation inorganic film.
[0123] The encapsulation inorganic film protects the display element layer DP-ED from moisture and / or oxygen, and the encapsulation organic film protects the display element layer DP-ED from foreign substances (such as dust particles). The encapsulation inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, etc., but the embodiment is not limited thereto. The encapsulation organic film may include an acrylic compound or an epoxy compound, etc. The encapsulation organic film may include a photo-polymerizable organic material, but the embodiment is not limited thereto.
[0124] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.
[0125] Reference Figure 1 and Figure 2 , the display device DD may include a non-light-emitting region NPXA and light-emitting regions PXA-R, PXA-G, and PXA-B. The light-emitting regions PXA-R, PXA-G, and PXA-B may each be a region that emits light generated by the light-emitting elements ED-1, ED-2, and ED-3, respectively. The light-emitting regions PXA-R, PXA-G, and PXA-B may be spaced apart from each other in a plan view.
[0126] The light-emitting regions PXA-R, PXA-G, and PXA-B may be regions separated from each other by a pixel-defining film PDL. The non-light-emitting region NPXA may be a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and it may correspond to the pixel-defining film PDL. In an embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B may each correspond to a pixel. The pixel-defining film PDL may separate the light-emitting elements ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be disposed in openings OH defined by the pixel-defining film PDL and separated from each other.
[0127] The light-emitting regions PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the color of light generated from the light-emitting elements ED-1, ED-2, and ED-3. In Figure 1 and Figure 2 the display device DD of the embodiment illustrated, three light-emitting regions PXA-R, PXA-G, and PXA-B that respectively emit red light, green light, and blue light are illustrated as an example. For example, the display device DD may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are different from each other.
[0128] In the display device DD according to an embodiment, the light-emitting elements ED-1, ED-2, and ED-3 may emit light having different wavelength ranges from each other. For example, in an embodiment, the display device DD may include a first light-emitting element ED-1 that emits red light, a second light-emitting element ED-2 that emits green light, and a third light-emitting element ED-3 that emits blue light. For example, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may respectively correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3.
[0129] However, the embodiment is not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light within the same wavelength range, or at least one light-emitting element may emit light within a wavelength range different from that of the remaining light-emitting elements. For example, the first to third light-emitting elements ED-1, ED-2, and ED-3 may each emit blue light.
[0130] The light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to an embodiment may be arranged in a stripe configuration. Refer to Figure 1, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B may be arranged along the second direction axis DR2, respectively. In another embodiment, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B may be arranged in this repeating order along the first direction axis DR1.
[0131] Figure 1 and Figure 2 illustrates that the light-emitting regions PXA-R, PXA-G, and PXA-B all have the same area, but the embodiments are not limited thereto. In an embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other in size or shape according to the wavelength range of the emitted light. The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be the areas in the plan view 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.
[0132] The arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to Figure 1 the configuration illustrated in, and the arrangement order of the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B may be provided in various combinations according to the display quality characteristics required by the display device DD. For example, the light-emitting regions PXA-R, PXA-G, and PXA-B may be arranged in a honeycomb configuration (such as ) or a rhombus configuration (such as Diamond ).
[0133] The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other in size. For example, in an embodiment, the area of the green light-emitting region PXA-G may be smaller than the area of the blue light-emitting region PXA-B, but the embodiments are not limited thereto.
[0134] Hereinafter, Figures 3 to 6 are respectively schematic cross-sectional views of a light-emitting element ED according to an embodiment. In the Figure 3 illustrated embodiment, the light-emitting element ED 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.
[0135] Compared with Figure 3 , Figure 4 is a schematic cross-sectional view of a light-emitting element ED according to an embodiment, in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Compared with Figure 3 , Figure 5Schematic cross-sectional view of a light-emitting element ED according to an embodiment, where 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. Compared with Figure 4 compared, Figure 6 Schematic cross-sectional view of a light-emitting element ED according to an embodiment further including a capping layer CPL provided on the second electrode EL2.
[0136] The first electrode EL1 has conductivity. The first electrode EL1 can be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 can be an anode or a cathode. However, the embodiments are not limited thereto. In an embodiment, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. The first electrode EL1 can include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, its oxides, its compounds, or a mixture thereof.
[0137] If the first electrode EL1 is a transmissive electrode, the first electrode EL1 can include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). If the first electrode EL1 is a transmissive-reflective electrode or a reflective electrode, the first electrode EL1 can include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, and W, its compounds, or a mixture thereof (e.g., a mixture of Ag and Mg), or a multilayer structure material such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In another embodiment, the first electrode EL1 can have a multilayer structure that includes a reflective film or a transmissive-reflective film formed of the above materials, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 can have a three-layer structure of ITO / Ag / ITO, but the embodiments are not limited thereto. In an embodiment, the first electrode EL1 can include the above metal materials, a combination of at least two of the above metal materials, or oxides of the above metal materials, etc. The thickness of the first electrode EL1 can be in the range of about to about For example, the thickness of the first electrode EL1 can be in the range of about to about in the range.
[0138] The light-emitting element ED according to an embodiment may include an amine compound according to an embodiment. In the light-emitting element ED, the hole transport region HTR may include an amine compound according to an embodiment. For example, at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL may include an amine compound according to an embodiment.
[0139] The amine compound according to an embodiment may be a monoamine compound. In the specification, the term "amino group" does not include a carbazolyl group, and the term "heterocyclic group" includes a carbazolyl group.
[0140] The amine compound according to an embodiment may include a first substituent, a second substituent, and a third substituent bonded to the amino group. The first substituent may include a substituted dibenzofuranyl group or a substituted dibenzothiophenyl group. The second substituent may include a substituted or unsubstituted phenanthryl group. The third substituent may include 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. The amino group including the first substituent and the second substituent may exhibit excellent material stability and hole transport characteristics. Therefore, the light-emitting element ED including the amine compound according to an embodiment may exhibit characteristics of low driving voltage, high luminous efficiency, and long lifespan.
[0141] The light-emitting element ED according to an embodiment may include an amine compound according to an embodiment. The amine compound according to an embodiment may be represented by Formula 1:
[0142] [Formula 1]
[0143]
[0144] In Formula 1, X1 may be O or S. The fused tricyclic ring including X1 may correspond to the first substituent described above. If X1 is O, the first substituent may include a substituted dibenzofuranyl group. If X1 is S, the first substituent may include a substituted dibenzothiophenyl group.
[0145] In Formula 1, L1 and L2 may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 15 ring carbon atoms. In an embodiment, L2 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent carbazolyl group, a substituted or unsubstituted divalent dibenzofuranyl group, or a substituted or unsubstituted divalent dibenzothiophenyl group. In an embodiment, L1 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent dibenzofuranyl group, or a substituted or unsubstituted divalent dibenzothiophenyl group.
[0146] In an embodiment, L1 may be a direct bond or a group represented by one of Formula L1-1 to Formula L1-5. In Formula L1-2, D is a deuterium atom. In Formula L1-1 to Formula L1-5, -* represents a bond connecting to an adjacent atom.
[0147]
[0148] In Formula 1, Ar1 may be a substituted or unsubstituted aryl group having 6 to 15 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 15 ring-forming carbon atoms. For example, Ar1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
[0149] In an embodiment, Ar1 may be a group represented by one of Formula AR-1 to Formula AR-4. In Formula AR-2, D is a deuterium atom. In Formula AR-1 to Formula AR-4, -* represents a bond connecting to an adjacent atom.
[0150]
[0151] In Formula 1, Ar3 may be 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. Ar3 may correspond to the above-mentioned third substituent. In an embodiment, Ar3 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
[0152] In an embodiment, in Formula 1, *-L2-Ar3 may be a moiety represented by one of Formula LA-1 to Formula LA-79. In Formula LA-69 to Formula LA-79, D is a deuterium atom. In Formula LA-1 to Formula LA-79, -* represents a bond connecting to an adjacent atom.
[0153]
[0154]
[0155]
[0156]
[0157] In Formula 1, R1 to R6 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms. For example, R1 to R6 may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted phenyl group. However, this is merely an example, and the embodiments are not limited thereto.
[0158] In Formula 1, Ar2 may be a group represented by Formula 2. Formula 2 may represent a substituted or unsubstituted phenanthryl group. Ar2 may correspond to the second substituent described above.
[0159] [Formula 2]
[0160]
[0161] In Formula 2, n1 may be an integer selected from 0 to 3. In Formula 2, R a1 to R a7 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms. In an embodiment, R a1 to R a7 may each independently be a hydrogen atom or a deuterium atom. In Formula 2, -* represents a bond connected to an adjacent atom. For example, -* may represent a bond connected to N in Formula 1.
[0162] If n1 is 2 or greater, multiple R a7 groups may be the same as each other or at least one of them may be different from the rest. The case where n1 is 0 may be the same as the case where n1 is 3 and all three R a7 groups are hydrogen atoms.
[0163] In an embodiment, the amine compound represented by Formula 1 may be represented by Formula 1-A1 or Formula 1-A2. Formula 1-A1 may represent the case where X1 in Formula 1 is O. Formula 1-A2 may represent the case where X1 in Formula 1 is S.
[0164] [Formula 1-A1]
[0165]
[0166] [Formula 1-A2]
[0167]
[0168] In Formula 1-A1 and Formula 1-A2, L1, L2, Ar1, Ar2, Ar3, and R1 to R6 are the same as those defined in Formula 1.
[0169] In an embodiment, the amine compound represented by Formula 1 may be represented by one of Formula 1-B1 to Formula 1-B4. Each of Formula 1-B1 to Formula 1-B4 represents a case where the bonding position of the group represented by Formula 2 to Formula 1 is further defined.
[0170] [Formula 1-B1]
[0171]
[0172] [Formula 1-B2]
[0173]
[0174] [Formula 1-B3]
[0175]
[0176] [Formula 1-B4]
[0177]
[0178] In Formula 1-B1 to Formula 1-B4, X1, L1, L2, Ar1, Ar3, R1 to R6, R a1 to R a7 and n1 are the same as those defined in Formula 1 and Formula 2.
[0179] In an embodiment, in Formula 1-B1 to Formula 1-B4, R a1 to R a7 may each independently be a hydrogen atom or a deuterium atom.
[0180] In an embodiment, the amine compound represented by Formula 1 may be any compound selected from Compound Group 1. In an embodiment, in the light-emitting element ED, the amine compound represented by Formula 1 may include at least one compound selected from Compound Group 1:
[0181] [Compound Group 1]
[0182]
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[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]
[0270]
[0271]
[0272]
[0273]
[0274]
[0275]
[0276]
[0277]
[0278]
[0279]
[0280]
[0281]
[0282]
[0283]
[0284]
[0285]
[0286]
[0287]
[0288]
[0289]
[0290]
[0291]
[0292]
[0293]
[0294]
[0295]
[0296]
[0297]
[0298] In the compound group 1, D is a deuterium atom.
[0299] The amine compound represented by Formula 1 according to the embodiment may include a first substituent, a second substituent, and a third substituent bonded to the amine group. The first substituent may include a substituted dibenzofuranyl group or a substituted dibenzothiophenyl group. In Formula 1, the fused tricyclic ring containing X1 may correspond to the first substituent. The second substituent may include a substituted or unsubstituted phenanthryl group. In Formula 1, Ar2 may be a group represented by Formula 2 and may correspond to the second substituent. The third substituent may include a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In Formula 1, Ar3 may correspond to the third substituent.
[0300] In the specification, the carbon atoms of the dibenzofuranyl group and the carbon atoms of the dibenzothiophenyl group are numbered as follows:
[0301]
[0302] In the first substituent (substituted dibenzofuranyl group (or substituted dibenzothiophenyl group)), the 1st carbon atom (C 1 ) in the ring-forming atoms may be directly bonded to the amine group. A substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms (corresponding to Ar1 in Formula 1) may be bonded to the 4th carbon atom (C 4 ). Therefore, in the amine compound according to the embodiment, the conjugated system extends to the aryl group (or heteroaryl group) bonded to the 4th carbon atom (C 4 ) and the 3rd carbon atom (C 3 ), and thus the resonance energy can be stabilized and excellent material stability can be exhibited.
[0303] The phenanthryl group as the second substituent may include a tricyclic group constituting the phenanthryl group, and the inwardly disposed ring group in the tricyclic group (including R in Formula 2 a7The ring group) can be directly bonded to the amine group. In Formula 2, the ring group disposed in the center of the tricyclic group (including R in Formula 2 a1 and R a2 The ring group) may not be bonded to the amine group. Compared with the compound in which the ring group disposed in the center is directly bonded to the amine group, the amine compound in which the inwardly disposed ring group is directly bonded to the amine group according to the embodiment can prevent steric distortion and thus can exhibit excellent thermal stability. Therefore, the amine compound according to the embodiment can contribute to the reduction of the driving voltage and the improvement of the luminous efficiency and lifetime of the light-emitting element ED.
[0304] The hole transport region HTR can be provided on the first electrode EL1. The hole transport region HTR can include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer (not shown), an emission assist layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR can be, for example, in the range of about to about The range of.
[0305] The hole transport region HTR can have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multi-layer structure including multiple layers containing different materials.
[0306] In an embodiment, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or can have a structure of a single layer made of a hole injection material and a hole transport material. In an embodiment, the hole transport region HTR can have a structure of a single layer made of different materials, or can have a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), a hole injection layer HIL / buffer layer (not shown), a hole transport layer HTL / buffer layer (not shown), or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, where the layers in each structure are stacked in the order described from the first electrode EL1, but the embodiment is not limited thereto.
[0307] The hole transport region HTR can be formed by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI) method.
[0308] In addition to the amine compound according to the embodiment, the hole transport region HTR can further include other hole transport compounds described below.
[0309] In the light-emitting element ED according to the embodiment, the hole transport region HTR can include a compound represented by Formula H-1:
[0310] [Formula H-1]
[0311]
[0312] In Formula H-1, L1 and L2 can each independently be a direct bond, a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms. In Formula H-1, a and b can each independently be an integer selected from 0 to 10. When a or b is 2 or greater, multiple L1 groups or multiple L2 groups can each independently be a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms.
[0313] In Formula H-1, Ar1 and Ar2 can each independently be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. In Formula H-1, Ar3 can be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms.
[0314] In an embodiment, the compound represented by Formula H-1 can be a monoamine compound. In another embodiment, the compound represented by Formula H-1 can be a diamine compound in which at least one of Ar1 to Ar3 includes an amino group as a substituent. In an embodiment, the compound represented by Formula H-1 can be a carbazole compound in which at least one of Ar1 and Ar2 includes a substituted or unsubstituted carbazolyl group, or can be a fluorene compound in which at least one of Ar1 and Ar2 includes a substituted or unsubstituted fluorenyl group.
[0315] The compound represented by Formula H-1 can be any compound selected from Compound Group H. However, the compounds listed in Compound Group H are only examples, and the compound represented by Formula H-1 is not limited to Compound Group H:
[0316] [Compound Group H]
[0317]
[0318]
[0319] The hole transport region HTR can include a phthalocyanine compound (such as copper phthalocyanine), N 1 ,N 1 '-([1,1'-Biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-Di(m-tolyl)phenyl-1,4-diamine (DNTPD), 4,4',4"-[Tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-Tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-Tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), Poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), Polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), Polyaniline / camphorsulfonic acid (PANI / CSA), Polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-Di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), Triphenylamine-containing polyether ketone (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], Dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.
[0320] The hole transport region HTR may include carbazole derivatives (such as N-phenylcarbazole or polyvinylcarbazole), fluorene derivatives, triphenylamine derivatives (such as N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4”-Tris(carbazol-9-yl)triphenylamine (TCTA), N,N'-Di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-Cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-Bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD) or 1,3-Bis(carbazol-9-yl)benzene (mCP)), etc.
[0321] In an embodiment, 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), 1,3-Bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mDCP), etc.
[0322] The hole transport region HTR may include the above compounds of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0323] The thickness of the hole transport region HTR may be in the range of about to about For example, the thickness of the hole transport region HTR may be in the range of about to about within the range. When the hole transport region HTR includes a hole injection layer HIL, the hole injection layer HIL may have, for example, about to about a thickness within the range. When the hole transport region HTR includes a hole transport layer HTL, the hole transport layer HTL may have about to about a thickness within the range. When the hole transport region HTR includes an electron blocking layer EBL, the electron blocking layer EBL may have about to about a thickness within the range. If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above ranges, satisfactory hole transport properties can be achieved without significantly increasing the driving voltage.
[0324] In addition to the above materials, the hole transport region HTR may further include a charge generation material to increase conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may include at least one of metal halides, quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments are not limited thereto. For example, the p-dopant may include metal halides (such as CuI or RbI), quinone derivatives (such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ)), metal oxides (such as tungsten oxide or molybdenum oxide), cyano-containing compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiments are not limited thereto.
[0325] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer (not shown) and an electron blocking layer EBL. The buffer layer (not shown) may compensate for the resonance distance according to the wavelength of the light emitted from the emission layer EML, and may thus increase the light emission efficiency. The materials that can be included in the hole transport region HTR can be used as the materials in the buffer layer (not shown). The electron blocking layer EBL can prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.
[0326] The emission layer EML may be provided on the hole transport region HTR. The emission layer EML may have about to about a thickness within a range of. For example, the emission layer EML may have about to about a thickness within a range of. The emission layer EML may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multi-layer structure including multiple layers containing different materials.
[0327] In the light-emitting element ED, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a 1,2-benzophenanthrene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. For example, the emission layer EML may include an anthracene derivative or a pyrene derivative.
[0328] In the light-emitting element ED according to an embodiment shown in each of Figures 3 to 6 the emission layer EML may further include a host and a dopant in the relevant art.
[0329] In an embodiment, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 can be used as a fluorescent host material:
[0330] [Formula E-1]
[0331]
[0332] In Formula E-1, R 31 to R 40 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio 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 bonded to an adjacent group to form a ring. For example, R 31 to R 40 may be bonded to an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.
[0333] In Formula E-1, c and d may each independently be an integer selected from 0 to 5.
[0334] In an embodiment, the compound represented by Formula E-1 may be any compound selected from Compound E1 to Compound E19:
[0335]
[0336]
[0337] In an embodiment, 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 can be used as a host material for a phosphorescent element.
[0338] [Formula E-2a]
[0339]
[0340] In Formula E-2a, a may be an integer selected from 0 to 10; and L a may be a direct bond, a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms. When a is 2 or greater, multiple L a groups may each independently be a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms.
[0341] In Formula E-2a, A1 to A5 may each independently be N or C(R i ). In Formula E-2a, R a to R i may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio 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 bonded to an adjacent group to form a ring. For example, R a to R i may be bonded to an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O, S, etc. as ring atoms.
[0342] In Formula E-2a, two or three of A1 to A5 may each be N, and the rest of A1 to A5 may each independently be C(R i ).
[0343] [Formula E-2b]
[0344]
[0345] 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. In Formula E-2b, L bIt can be a direct - connecting, substituted or unsubstituted arylene having 6 to 30 ring - forming carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring - forming carbon atoms. In formula E - 2b, b can be an integer selected from 0 to 10. When b is 2 or greater, multiple L b groups can each independently be a substituted or unsubstituted arylene having 6 to 30 ring - forming carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring - forming carbon atoms.
[0346] In an embodiment, the compound represented by formula E - 2a or formula E - 2b can be any compound selected from compound group E - 2. However, the compounds listed in compound group E - 2 are only examples, and the compounds represented by formula E - 2a or formula E - 2b are not limited to compound group E - 2:
[0347] [Compound group E - 2]
[0348]
[0349]
[0350]
[0351] The emission layer EML can further include materials in the relevant field as host materials. For example, the emission layer EML can 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 - carbazolyl)-1,1'-biphenyl (CBP), 1,3 - bis(carbazol - 9 - yl)benzene (mCP), 2,8 - bis(diphenylphosphoryl)dibenz[b,d]furan (PPF), 4,4',4”-tris(carbazol - 9 - yl)triphenylamine (TCTA), and 1,3,5 - tris(1 - phenyl - 1H - benzimidazol - 2 - yl)benzene (TPBi) as host materials. However, the embodiment is not limited thereto. For example, tris(8 - hydroxyquinoline)aluminum (Alq3), 9,10 - bis(naphthalen - 2 - yl)anthracene (ADN), 2 - tert - butyl - 9,10 - bis(naphthalen - 2 - yl)anthracene (TBADN), stilbenylarene (DSA), 4,4'-bis(9 - carbazolyl)-2,2'-dimethyl - biphenyl (CDBP), 2 - methyl - 9,10 - bis(naphthalen - 2 - yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4 - bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), etc. can be used as host materials.
[0352] In an embodiment, the emission layer EML may include a compound represented by Formula M-a or Formula M-b. The compound represented by Formula M-a or Formula M-b can be used as a phosphorescent dopant material:
[0353] [Formula M-a]
[0354]
[0355] In Formula M-a, Y1 to Y4 and Z1 to Z4 may each independently be C(R1) or N; and R1 to R4 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted sulfide 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 bonded to an adjacent group to form a ring. In Formula M-a, m may be 0 or 1, and n may be 2 or 3. In Formula M-a, when m is 0, n may be 3, and when m is 1, n may be 2.
[0356] In an embodiment, the compound represented by Formula M-a may be any compound selected from Compound M-a1 to Compound M-a25. However, Compound M-a1 to Compound M-a25 are only examples, and the compound represented by Formula M-a is not limited to Compound M-a1 to Compound M-a25:
[0357]
[0358]
[0359] In an embodiment, Compound M-a1 and Compound M-a2 may each be used as a red dopant material, and Compound M-a3 to Compound M-a5 may each be used as a green dopant material.
[0360] [Formula M-b]
[0361]
[0362] In Formula M-b, Q1 to Q4 may each independently be C or N. In Formula M-b, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.
[0363] In Formula M-b, L 21 to L 24Each may independently be a direct bond, *-o-*, *-o-*, 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. In formula M-b, e1 to e4 may each independently be 0 or 1.
[0364] In formula M-b, R 31 to R 39 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino 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 bonded to an adjacent group to form a ring. In formula M-b, d1 to d4 may each independently be an integer selected from 0 to 4. If d1 is 2 or greater, multiple R 31 groups may be the same as each other, or at least one of them may be different from the rest. If d2 is 2 or greater, multiple R 32 groups may be the same as each other, or at least one of them may be different from the rest. If d3 is 2 or greater, multiple R 33 groups may be the same as each other, or at least one of them may be different from the rest. If d4 is 2 or greater, multiple R 34 groups may be the same as each other, or at least one of them may be different from the rest.
[0365] The compound represented by formula M-b can be used as a blue phosphorescent dopant or as a green phosphorescent dopant. In an embodiment, the compound represented by formula M-b can be any compound selected from Compound AD-01 to Compound AD-40. However, Compound AD-01 to Compound AD-40 are only examples, and the compound represented by formula M-b is not limited to Compound AD-01 to Compound AD-40. In Compound AD-01 to Compound AD-40, D represents a deuterium atom.
[0366]
[0367]
[0368]
[0369]
[0370] In an embodiment, the emission layer EML may include a compound represented by one of formula F-a to formula F-c. The compound represented by one of formula F-a to formula F-c can be used as a fluorescent dopant material.
[0371] [Formula F-a]
[0372]
[0373] In Formula F-a, R a to R j Two of them may each independently be substituted with a group represented by *-NAr1Ar2. R a to R j The remaining parts that are not substituted with a group represented by *-NAr1Ar2 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino 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.
[0374] In the group represented by *-NAr1Ar2, Ar1 and Ar2 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. For example, at least one of Ar1 and Ar2 may each independently be a heteroaryl group containing O or S as a ring atom.
[0375] [Formula F-b]
[0376]
[0377] In Formula F-b, R a and R b may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 bonded to an adjacent group to form a ring. In Formula F-b, Ar1 to Ar4 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. For example, at least one of Ar1 to Ar4 may each independently be a heteroaryl group containing O or S as a ring atom.
[0378] In Formula F-b, U and V may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.
[0379] In formula F-b, the number of rings represented by U and V can each independently be 0 or 1. In formula F-b, when the number of U or V is 1, a fused ring can be present in the portion indicated by U or V, and when the number of U or V is 0, a fused ring may not be present in the portion indicated by U or V. When the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring having a fluorene nucleus in formula F-b can be a cyclic compound having four rings. When the numbers of U and V are each 0, the fused ring having a fluorene nucleus in formula F-b can be a cyclic compound having three rings. When the numbers of U and V are each 1, the fused ring having a fluorene nucleus in formula F-b can be a cyclic compound having five rings.
[0380] [Formula F-c]
[0381]
[0382] In formula F-c, A1 and A2 can each independently be O, S, Se or N(R m ); and R m can 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In formula F-c, R1 to R 11 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio 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 bond to an adjacent group to form a ring.
[0383] In formula F-c, A1 and A2 can each independently bond to a substituent of an adjacent ring to form a fused ring. For example, when A1 and A2 are each independently N(R m ), A1 can bond to R4 or R5 to form a fused ring. For example, A2 can bond to R7 or R8 to form a fused ring.
[0384] In an embodiment, the emission layer EML may further include styryl derivatives (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)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi), and 4,4'-bis[2-(4-(N,N'-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, and 1,4-bis(N,N'-diphenylamino)pyrene), etc. as dopant materials in the relevant art.
[0385] The emission layer EML may further include phosphorescent dopant materials in the relevant art. For example, metal complexes containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) can be used as phosphorescent dopants. For example, bis(4,6-difluorophenylpyridinato-N,C2')iridium(III) picolinate (FIrpic), bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)boratoiridium(III) (FIr6), or platinum octaethylporphyrin (PtOEP) can be used as phosphorescent dopants. However, the embodiment is not limited thereto.
[0386] In an embodiment, the emission layer EML may include quantum dot materials. The quantum dots can be group II-VI compounds, group I-II-VI compounds, group II-IV-VI compounds, group I-II-IV-VI compounds, group II-IV-V compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, or any combination thereof.
[0387] Examples of Group II-VI compounds can include: binary compounds such as CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and mixtures thereof; and quaternary compounds such as HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and mixtures thereof.
[0388] In an embodiment, the Group II-VI compound may further include a Group I metal and / or a Group IV element. Examples of Group I-II-VI compounds can include CuSnS and CuZnS. Examples of Group II-IV-VI compounds can include ZnSnS, etc. Examples of Group I-II-IV-VI compounds can include quaternary compounds such as Cu2ZnSnS2, Cu2ZnSnS4, Cu2ZnSnSe4, Ag2ZnSnS2, and mixtures thereof.
[0389] Examples of Group II-IV-V compounds can include ternary compounds such as ZnSnP, ZnSnP2, ZnSnAs2, ZnGeP2, ZnGeAs2, CdSnP2, CdGeP2, and mixtures thereof.
[0390] Examples of Group III-VI compounds can include: binary compounds such as GaS, Ga2S3, GaSe, Ga2Se3, GaTe, InTe, InS, InSe, In2S3, and In2Se3; ternary compounds such as InGaS3 and InGaSe3; and any combination thereof.
[0391] Examples of Group I-III-VI compounds can include: ternary compounds such as AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, and mixtures thereof; and quaternary compounds such as AgInGaS2 and CuInGaS2.
[0392] Examples of group III-V compounds may include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. In an embodiment, the group III-V compound may further include a group II metal. Examples of group III-II-V compounds may include InZnP and the like.
[0393] Examples of group IV-VI compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Examples of group IV elements may include Si, Ge, and mixtures thereof. Examples of group IV compounds may include binary compounds such as SiC, SiGe, and mixtures thereof.
[0394] Each element included in a compound (such as a binary compound, a ternary compound, or a quaternary compound) may be present in the particles in a uniform concentration distribution or a non-uniform concentration distribution. For example, the formula may indicate the elements included in the compound, and the elemental ratio of the compound may vary. For example, AgInGaS2 may indicate AgIn x Ga 1-x S2 (where 0 < x < 1).
[0395] In an embodiment, the quantum dots may have a single structure, or the quantum dots may have a core-shell structure. For example, the material included in the core may be different from the material included in the shell.
[0396] The shell of the quantum dots can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or can be used as a charging layer to impart electrophoretic properties to the quantum dots. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the elements present in the shell decreases towards the center of the core.
[0397] In an embodiment, the quantum dots can have a core-shell structure including a core and a shell surrounding the core. Examples of the shell of the quantum dots can include metal oxides, non-metal oxides, semiconductor compounds, and combinations thereof.
[0398] Examples of the metal oxide or non-metal oxide can include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO; and ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the embodiments are not limited thereto.
[0399] Examples of the semiconductor compound can include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and AlSb, etc., but the embodiments are not limited thereto.
[0400] The quantum dots can have a full width at half maximum (FWHM) of the emission spectrum equal to or less than about 45 nm. For example, the quantum dots can have an FWHM of the emission spectrum equal to or less than about 40 nm. For example, the quantum dots can have an FWHM of the emission spectrum equal to or less than about 30 nm. Within any of the above ranges, the color purity or color reproducibility can be improved. The light emitted by the quantum dots can be emitted in all directions, so that the wide viewing angle can be improved.
[0401] The form of the quantum dots is not particularly limited and can be any form used in the relevant field. For example, the quantum dots can have a spherical shape, a conical shape, a multi-arm shape, or a cubic shape, or the quantum dots can be in the form of nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc.
[0402] Since the size of the quantum dots is adjusted or the elemental ratio of the quantum dot compound is adjusted, the band gap can be adjusted accordingly so that light in various wavelength ranges can be obtained from the quantum dot emission layer. Therefore, by using the quantum dots as described above (e.g., by using quantum dots of different sizes or quantum dot compounds of different elemental ratios), a light-emitting element that emits light in various wavelength ranges can be implemented. For example, the size of the quantum dots or the elemental ratio of the quantum dot compound can be adjusted to emit red, green, and / or blue light. In an embodiment, the quantum dots can be configured to emit white light by combining various colors of light.
[0403] In the light-emitting element ED according to an embodiment shown in each of Figures 3 to 6 the electron transport region ETR can be provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiment is not limited thereto.
[0404] The electron transport region ETR can have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multi-layer structure including multiple layers containing different materials.
[0405] For example, the electron transport region ETR can have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL, or can have a single-layer structure formed of an electron injection material and an electron transport material. In an embodiment, the electron transport region ETR can have a single-layer structure formed of different materials, or can have a structure in which the electron transport layer ETL / electron injection layer EIL or the hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL is stacked in their respective recited order starting from the emission layer EML, but the embodiment is not limited thereto. The electron transport region ETR can have, for example, a thickness in the range of about to about .
[0406] The electron transport region ETR can be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser-induced thermal imaging (LITI) method.
[0407] In the light-emitting element ED according to an embodiment, the electron transport region ETR can include a compound represented by Formula ET-2:
[0408] [Formula ET-2]
[0409]
[0410] In formula ET-2, at least one of X1 to X3 may each be N, and the rest of X1 to X3 may each independently be C(R a ). In formula ET-2, R a 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. In formula ET-2, Ar1 to Ar3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0411] In formula ET-2, a to c may each independently be an integer selected from 0 to 10. In formula ET-2, L1 to L3 may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. When a to c are each 2 or greater, the multiple groups of each of L1 to L3 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0412] The electron transport region ETR may include an anthracene compound. However, the embodiments are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridinyl)-3-phenyl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole( tBis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-ol) aluminum (BAlq), bis(benzoquinolin-10-ol) beryllium (Bebq2), 9,10-bis(naphthalen-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or a mixture thereof.
[0413] In an embodiment, the electron transport region ETR may include at least one compound selected from Compounds ET1 to ET36:
[0414]
[0415]
[0416]
[0417]
[0418] In an embodiment, the electron transport region ETR may include: metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI; lanthanide metals such as Yb; or co-deposited materials of metal halides and lanthanide metals. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as co-deposited materials. The electron transport region ETR may include metal oxides (such as Li2O or BaO) or lithium 8-hydroxyquinolate (Liq), etc., but the embodiments are not limited thereto. The electron transport region ETR may also be formed of a mixture material of an electron transport material and an insulating organometallic salt. The insulating organometallic salt may be a material having a band gap equal to or greater than about 4 eV. For example, the insulating organometallic salt may include metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, or metal stearates.
[0419] In addition to the above materials, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiments are not limited thereto.
[0420] The electron transport region ETR may include the above compounds of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.
[0421] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have about to about a thickness within a range of. For example, the electron transport layer ETL may have a thickness within a range of about to about If the thickness of the electron transport layer ETL satisfies any of the foregoing ranges, 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 within a range of about to about For example, the electron injection layer EIL may have a thickness within a range of about to about If the thickness of the electron injection layer EIL satisfies any of the above ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0422] The second electrode EL2 may be provided over the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiments are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.
[0423] The second electrode EL2 may be a transmissive electrode, a transmissive-reflective 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), indium tin zinc oxide (ITZO), etc.).
[0424] When the second electrode EL2 is a transmissive-reflective electrode or a reflective electrode, the second electrode EL2 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, and W, a compound thereof, or a mixture thereof (e.g., AgMg, AgYb, or MgYb), or a multilayer structure material such as LiF / Ca or LiF / Al. In an embodiment, the second electrode EL2 may have a multilayer structure including a reflective layer or a transmissive-reflective layer formed of the above materials and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include the above metal materials, a combination of at least two of the above metal materials, or an oxide of the above metal materials, etc.
[0425] Although not shown in the drawings, the second electrode EL2 may be electrically connected to an auxiliary electrode. If the second electrode EL2 is electrically connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
[0426] In an embodiment, the light-emitting element ED may further include a capping layer CPL provided on the second electrode EL2. The capping layer CPL may have a multilayer structure or a single-layer structure.
[0427] In an embodiment, the capping layer CPL may include an organic layer or an inorganic layer. For example, when the capping layer CPL contains an inorganic material, the inorganic material may include an alkali metal compound (e.g., LiF), an alkaline earth metal compound (e.g., MgF2), SiON, SiN x , SiO y , etc.
[0428] For example, when the capping layer CPL includes an organic material, the organic material may include 2,2′-dimethyl-N,N′-bis[(1-naphthyl)-N,N′-diphenyl]-1,1′-biphenyl-4,4′-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4″-tris(carbazol-9-yl)triphenylamine (TCTA), etc., or the organic material may include an epoxy resin or an acrylate (such as a methacrylate). However, the embodiments are not limited thereto. In an embodiment, the capping layer CPL may include at least one of Compound P1 to Compound P5:
[0429]
[0430] The refractive index of the capping layer CPL may be equal to or greater than about 1.6. For example, with respect to light in the wavelength range of about 550 nm to about 660 nm, the refractive index of the capping layer CPL may be equal to or greater than about 1.6.
[0431] Figures 7 to 10 Each is a schematic cross-sectional view of a display device according to an embodiment. Hereinafter, when describing the display device according to an embodiment as shown in Figures 7 to 10 , the features described above will not be described again, but different features will be described. Figures 1 to 6 has been described, but different features will be described.
[0432] Referring to Figure 7 , a display device DD-a according to an embodiment may include: a display panel DP including a display element layer DP-ED, a light control layer CCL provided on the display panel DP, and a color filter layer CFL.
[0433] In Figure 7 the embodiment shown, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED, and the display element layer DP-ED may include a light-emitting element ED.
[0434] 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. In an embodiment, Figure 7 the structure of the light-emitting element ED shown in may be the same as that of the light-emitting element ED described according to Figures 3 to 6 one of the. Figure 7 The light-emitting element ED illustrated in may include an amine compound according to an embodiment. The light-emitting element ED including the amine compound according to the embodiment may exhibit characteristics of low driving voltage, high luminous efficiency, and long lifespan.
[0435] Referring to Figure 7 , the emission layer EML may be disposed in an opening OH defined by a pixel defining film PDL. For example, the emission layer EML separated by the pixel defining film PDL and provided corresponding to each of the light-emitting regions PXA-R, PXA-G, and PXA-B may emit light within the same wavelength range. In the display device DD-a, the emission layer EML may emit blue light. Although not shown in the drawings, in an embodiment, the emission layer EML may be provided as a common layer for each of the light-emitting regions PXA-R, PXA-G, and PXA-B.
[0436] A light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot or a phosphor, etc. The light converter may convert the wavelength of the provided light and emit the resulting light. For example, the light control layer CCL may be a layer including quantum dots or a layer including phosphors.
[0437] The light control layer CCL may include light control portions CCP1, CCP2, and CCP3. The light control portions CCP1, CCP2, and CCP3 may be spaced apart from each other.
[0438] Referring to Figure 7 , a dividing pattern BMP may be disposed between the light control portions CCP1, CCP2, and CCP3 spaced apart from each other, but the embodiment is not limited thereto. Figure 7 shows that the dividing pattern BMP does not overlap with the light control portions CCP1, CCP2, and CCP3, but the edges of the light control portions CCP1, CCP2, and CCP3 may overlap at least a part of the dividing pattern BMP.
[0439] The light control layer CCL may include: a first light control portion CCP1 including a first quantum dot QD1 that converts first color light provided from a light emitting element ED into second color light; a second light control portion CCP2 including a second quantum dot QD2 that converts the first color light into third color light; and a third light control portion CCP3 that transmits the first color light.
[0440] In an embodiment, the first light control portion CCP1 may provide red light as the second color light, and the second light control portion CCP2 may provide green light as the third color light. The third light control portion CCP3 may provide blue light by transmitting blue light as the first color light provided from the light emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The quantum dots QD1 and QD2 may each be a quantum dot as described above.
[0441] The light control layer CCL may further include a scatterer SP. The first light control portion CCP1 may include the first quantum dot QD1 and the scatterer SP, the second light control portion CCP2 may include the second quantum dot QD2 and the scatterer SP, and the third light control portion CCP3 may not include a quantum dot but may include the scatterer SP.
[0442] The scatterer SP may be inorganic particles. For example, the scatterer SP may include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica. The scatterer SP may include any one of TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica, or may be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica.
[0443] The first light control portion CCP1, the second light control portion CCP2, and the third light control portion CCP3 may include base resins BR1, BR2, and BR3 in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed. In an embodiment, the first light control portion CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in the first base resin BR1, the second light control portion CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in the second base resin BR2, and the third light control portion CCP3 may include the scatterer SP dispersed in the third base resin BR3.
[0444] The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1 and QD2 and the scatterers SP are dispersed, and can be formed from various resin compositions that can be referred to as binders. For example, the base resins BR1, BR2, and BR3 can be acrylic resins, urethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 can each be transparent resins. In an embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 can be the same as or different from each other.
[0445] The light control layer CCL can include the barrier layer BFL1. The barrier layer BFL1 can prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 can block the light control portions CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. The barrier layer BFL1 can cover the light control portions CCP1, CCP2, and CCP3. In an embodiment, the barrier layer BFL2 can be provided between the light control portions CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3.
[0446] The barrier layers BFL1 and BFL2 can each independently include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 can each independently include inorganic materials. For example, the barrier layers BFL1 and BFL2 can each independently 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, a metal thin film that ensures light transmittance, etc. The barrier layers BFL1 and BFL2 can each independently further include an organic film. The barrier layers BFL1 and BFL2 can be formed of a single layer or multiple layers.
[0447] In the display device DD-a, the color filter layer CFL can be provided on the light control layer CCL. In an embodiment, the color filter layer CFL can be directly provided on the light control layer CCL. For example, the barrier layer BFL2 can be omitted.
[0448] The color filter layer CFL can include the filters CF1, CF2, and CF3. The color filter layer CFL can include a first filter CF1 that transmits second color light, a second filter CF2 that transmits third color light, and a third filter CF3 that transmits first color light. For example, the first filter CF1 can be a red filter, the second filter CF2 can be a green filter, and the third filter CF3 can be a blue filter. The filters CF1, CF2, and CF3 can each include a polymer photosensitive resin and / or a pigment or dye. The first filter CF1 can include a red pigment or dye, the second filter CF2 can include a green pigment or dye, and the third filter CF3 can include a blue pigment or dye.
[0449] However, the embodiments are not limited thereto, and the third color filter CF3 may not include pigments or dyes. The third color filter CF3 may include a polymerizable photosensitive resin and may not include pigments or dyes. The third color filter CF3 may be transparent. The third color filter CF3 may be formed of a transparent photosensitive resin.
[0450] In an embodiment, the first color filter CF1 and the second color filter CF2 may each be a yellow color filter. The first color filter CF1 and the second color filter CF2 may not be provided as different color filters, but may be provided as an integral color filter.
[0451] Although not shown in the drawings, the color filter layer CFL may further include a light-shielding portion (not shown). The light-shielding portion (not shown) may be a black matrix. The light-shielding portion (not shown) may include an organic light-shielding material or an inorganic light-shielding material each including a black pigment or dye. The light-shielding portion (not shown) may prevent light leakage and may separate adjacent color filters CF1, CF2, and CF3. In an embodiment, the light-shielding member (not shown) may be formed of a blue color filter.
[0452] The first color filter CF1, the second color filter CF2, and the third color filter CF3 may be arranged to respectively correspond to a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B.
[0453] The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may provide a base surface on which the color filter layer CFL, the light control layer CCL, etc. are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.
[0454] Figure 8 A schematic cross-sectional view of a part of a display device according to an embodiment. In a display device DD-TD according to an embodiment, the light-emitting element ED-BT may include emission 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 emission structures OL-B1, OL-B2, and OL-B3 stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. The emission structures OL-B1, OL-B2, and OL-B3 may each include a hole transport region HTR, an emission layer EML ( Figure 7 ) and an electron transport region ETR disposed in this order between the first electrode EL1 and the second electrode EL2. For example, the light-emitting element ED-BT included in the display device DD-TD according to an embodiment may be a light-emitting element having a tandem structure including a plurality of emission layers EML.
[0455] Figure 8 The light-emitting element ED-BT described in may include an amine compound according to an embodiment. The light-emitting element ED-BT including the amine compound according to the embodiment may exhibit characteristics of low driving voltage, high luminous efficiency, and long lifespan.
[0456] In Figure 8 the embodiment shown in Figure 8 , the light emitted from the emission structures OL-B1, OL-B2, and OL-B3 may each be blue light. However, the embodiment is not limited thereto, and the light emitted from each of the emission structures OL-B1, OL-B2, and OL-B3 may have different wavelength ranges from each other. For example, the light-emitting element ED-BT including the emission structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelength ranges may emit white light.
[0457] The charge generation layers CGL1 and CGL2 may each be disposed between two adjacent ones of the emission structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.
[0458] Figure 9 is a schematic cross-sectional view of a display device DD-b according to an embodiment. Figure 10 is a schematic cross-sectional view of a display device DD-c according to an embodiment.
[0459] Referring to Figure 9 , the display device DD-b according to an embodiment may include light-emitting elements ED-1, ED-2, and ED-3 in which two emission layers are stacked. Compared with the display device DD shown in Figure 2 Figure 2 , the display device DD-b of the embodiment shown in Figure 9 Figure 9 is different at least in 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 the same wavelength range. At least one of the first to third light-emitting elements ED-1, ED-2, and ED-3 may include an amine compound according to an embodiment. At least one light-emitting element (at least one of the light-emitting elements ED-1, ED-2, and ED-3) including the amine compound according to the embodiment may exhibit characteristics of low driving voltage, high luminous efficiency, and long lifespan.
[0460] 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. The third light-emitting element ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. An emission assist part OG may be disposed between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.
[0461] The emission assist part OG may have a single-layer structure or a multi-layer structure. The emission assist part OG may include a charge generation layer. For example, the emission assist part OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown) stacked in this order. The emission assist part OG may be provided as a common layer for each of the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments are not limited thereto, and the emission assist part OG may be provided by patterning in an opening OH defined by a pixel defining film PDL.
[0462] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may each be disposed between the emission assist part OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may each be disposed between the hole transport region HTR and the emission assist part OG.
[0463] 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 assist part OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in this order. 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 assist part OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in this order. 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 assist part OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in this order.
[0464] The optical auxiliary layer PL can be disposed on the display element layer DP-ED. The optical auxiliary layer PL can include a polarization layer. The optical auxiliary layer PL can be disposed on the display panel DP and can control the light reflected at the display panel DP from the outside. Although not shown in the drawings, in an embodiment, the optical auxiliary layer PL can be omitted from the display device DD-b.
[0465] Compared with Figure 8 and Figure 9 , Figure 10 FIG. shows a display device DD-c, which is different at least in that it includes four emission structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting element ED-CT can include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth emission structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked in the thickness direction between the first electrode EL1 and the second electrode EL2.
[0466] 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. Figure 10 The light-emitting element ED-CT illustrated in can include an amine compound according to an embodiment. The light-emitting element ED-CT including the amine compound according to the embodiment can exhibit characteristics of low driving voltage, high luminous efficiency, and long lifespan.
[0467] Among the four emission structures, the first to third emission structures OL-B1, OL-B2, and OL-B3 can each emit blue light, and the fourth emission structure OL-C1 can emit green light. However, the embodiment is not limited thereto, and the first to fourth emission structures OL-B1, OL-B2, OL-B3, and OL-C1 can each emit light having different wavelength ranges from each other.
[0468] The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent emission structures among the first to fourth emission structures OL-B1, OL-B2, OL-B3, and OL-C1 can each independently include a p-type charge generation layer and / or an n-type charge generation layer.
[0469] In an embodiment, an electronic device may include: a display device including a light-emitting element, and a control portion controlling the display device. The electronic device may be a device activated by an electrical signal. The electronic device may include a display device according to various embodiments. Examples of the electronic device may include large electronic devices (such as televisions, monitors, and outdoor billboards), and may also include small and medium-sized electronic devices (such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, and cameras).
[0470] Figure 11 FIG. is a schematic perspective view of a vehicle AM including first to fourth display devices DD-1, DD-2, DD-3, and DD-4. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may each have a structure according to one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c as described in reference Figure 1 , Figure 2 and Figures 7 to 10 described.
[0471] In Figure 11 , the vehicle AM is shown as an automobile, but this is only an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be provided in various transportation means (such as bicycles, motorcycles, trains, ships, and airplanes). In an embodiment, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 each having a structure according to one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c may be included in a personal computer, laptop computer, personal digital terminal, game console, portable electronic device, television, monitor, or billboard, etc. However, these are only listed as examples, and thus may be included in other electronic devices.
[0472] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may each independently include a light-emitting element ED according to an embodiment as described in any one of references Figures 3 to 6 . At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may each independently include an amine compound according to an embodiment. A display device (at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4) including an amine compound according to an embodiment may exhibit excellent display efficiency and display life.
[0473] Referring to Figure 11 , the vehicle AM may include a steering wheel HA and a shift lever GR for operating the vehicle AM. The vehicle AM may include a front window GL provided to face the driver.
[0474] The first display device DD-1 can be arranged in a first area overlapping with the steering wheel HA. For example, the first display device DD-1 can be a digital instrument panel that displays first information of the vehicle AM. The first information can include a first scale indicating the driving speed of the vehicle AM, a second scale indicating the engine speed (e.g., in revolutions per minute (RPM)), an image representing the fuel state, etc. The first scale and the second scale can each be represented by a digital image.
[0475] The second display device DD-2 can be arranged in a second area facing the driver's seat and overlapping with the front window GL. The driver's seat can be the seat provided with the steering wheel HA. For example, the second display device DD-2 can be a head-up display (HUD) that displays second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a digital value indicating the driving speed of the vehicle AM, and can further include information such as the current time. Although not shown in the drawings, in an embodiment, the second information of the second display device DD-2 can be displayed by projecting it onto the front window GL.
[0476] The third display device DD-3 can be arranged in a third area adjacent to the shift lever GR. For example, the third display device DD-3 can be arranged between the driver's seat and the passenger seat, and can be a center information display (CID) of the vehicle for displaying third information. The passenger seat can be a seat spaced apart from the driver's seat, and the shift lever GR can be arranged between the driver's seat and the passenger seat. The third information can include information about traffic or road conditions (e.g., navigation information), information about the music or radio being played, the video (or image) being displayed, information about the temperature inside the vehicle AM, etc.
[0477] The fourth display device DD-4 can be arranged in a fourth area spaced apart from the steering wheel HA and the shift lever GR and adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 can be a digital side mirror that displays fourth information. The fourth display device DD-4 can display an image of the outside of the vehicle AM that can be captured by a camera module CM arranged outside the vehicle AM. The fourth information can include an external image of the vehicle AM.
[0478] The first to fourth information described above is only provided as an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 can further display information about the inside and outside of the vehicle AM. The first to fourth information can include different information from each other. However, the embodiment is not limited thereto, and a part of the first to fourth information can include the same information from each other.
[0479] Hereinafter, an amine compound according to an embodiment and a light-emitting element according to an embodiment will be described with reference to examples and comparative examples. The examples described below are provided only to facilitate understanding of the present disclosure, and the scope thereof is not limited thereto.
[0480] [Examples]
[0481] 1. Synthesis of amine compound according to an embodiment
[0482] The synthesis method of the amine compound according to the embodiment will be explained by describing the synthesis methods for Compound A70, Compound A71, Compound A508, Compound A1005, Compound A862, Compound A866, Compound A128, and Compound A178. The synthesis methods of the amine compounds described below are provided only as examples, and the synthesis method of the amine compound according to the embodiment is not limited to the following examples.
[0483] In the synthesis methods of the amine compounds to be described below, the molecular weight of each compound was measured by FAB-MS using JMS-700V (JEOL Ltd.). The 1 H-NMR of each compound was measured as the NMR of the compound using an AVAVCE300M spectrometer (Bruker Biospin K.K.Co.).
[0484] (1) Synthesis of Compound A70
[0485] Compound A70 according to the embodiment can be synthesized, for example, by Reaction Scheme 1.
[0486] [Reaction Scheme 1]
[0487]
[0488] ><Synthesis of Compound A-70>
[0489] Under an Ar atmosphere, compound S1 (10.18 g, 46.41 mmol), 1.33 g of Pd(dba)2 (0.05 equivalent, 2.32 mmol), 4.46 g of NaO(tBu) (1 equivalent, 46.41 mmol), 464 mL of toluene, 13.61 g of compound S2 (1.0 equivalent, 46.41 mmol), and 2.69 g of PBuHBF4 (0.2 equivalent, 9.28 mmol) were sequentially added to a 1,000 mL three-necked flask, and the mixture was heated, refluxed, and stirred for about 6 hours. After cooling the reactants to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further separate the organic layer, and the organic layer was collected, washed with a brine solution, and dried over MgSO4. Filtration of MgSO4 and concentration of the organic layer were carried out, and the obtained crude product was purified by silica gel column chromatography to obtain white solid compound A-70 (17.6 g, yield 87%). By FAB-MS, the mass number m / z = 435 was measured from the molecular ion peak, confirming that the obtained compound was compound A-70.
[0490] <Synthesis of Compound A70>
[0491] Under an Ar atmosphere, compound A-70 (9.5 g, 21.67 mmol), 0.62 g of Pd(dba)2 (0.05 equivalent, 1.08 mmol), 2.08 g of NaO(tBu) (1 equivalent, 21.67 mmol), 216 mL of toluene, 5.05 g of compound S3 (1.0 equivalent, 21.67 mmol), and 1.261 g of PBuHBF4 (0.2 equivalent, 4.33 mmol) were sequentially added to a 500 mL three-necked flask, and the mixture was heated, refluxed, and stirred for about 6 hours. After cooling the reactants to room temperature, water was added to the reaction solvent, and the organic layer was separated. Toluene was added to the aqueous layer to further separate the organic layer, and the organic layer was collected, washed with a brine solution, and dried over MgSO4. Filtration of MgSO4 and concentration of the organic layer were carried out, and the obtained crude product was purified by silica gel column chromatography to obtain white solid compound A70 (8.9 g, yield 70%). By FAB-MS, the mass number m / z = 587 was measured from the molecular ion peak, confirming that the obtained compound was compound A70.
[0492] (2) Synthesis of Compound A71
[0493] Compound A71 according to the embodiment can be synthesized, for example, by Reaction Scheme 2.
[0494] [Reaction Scheme 2]
[0495]
[0496] <Synthesis of Compound A71>
[0497] Compound A71 was synthesized in substantially the same manner as the synthesis of Compound A70, except that Compound S4 was used instead of Compound S3. The obtained compound was confirmed to be Compound A71 by measuring the mass number m / z = 587 from the molecular ion peak by FAB-MS.
[0498] (3) Synthesis of Compound A508
[0499] Compound A508 according to the embodiment can be synthesized, for example, by Reaction Scheme 3.
[0500] [Reaction Scheme 3]
[0501]
[0502] <Synthesis of Compound A-508>
[0503] Compound A-508 was synthesized in substantially the same manner as the synthesis of Compound A-70, except that Compound S5 was used instead of Compound S2.
[0504] <Synthesis of Compound A508>
[0505] Compound A508 was synthesized in substantially the same manner as the synthesis of Compound A70, except that Compound A-508 was used instead of Compound A-70 and Compound S6 was used instead of Compound S3. The obtained compound was confirmed to be Compound A508 by measuring the mass number m / z = 663 from the molecular ion peak by FAB-MS.
[0506] (4) Synthesis of Compound A1005
[0507] Compound A1005 according to the embodiment can be synthesized, for example, by Reaction Scheme 4.
[0508] [Reaction Scheme 4]
[0509]
[0510] <Synthesis of Compound A1005>
[0511] Compound A1005 was synthesized in substantially the same manner as the synthesis of Compound A70, except that Compound A-508 was used instead of Compound A-70 and Compound S7 was used instead of Compound S3. The obtained compound was confirmed to be Compound A1005 by measuring the mass number m / z = 611 from the molecular ion peak by FAB-MS.
[0512] (5) Synthesis of Compound A862
[0513] Compound A862 according to the embodiment can be synthesized, for example, by Reaction Scheme 5.
[0514] [Reaction Scheme 5]
[0515]
[0516] <Synthesis of Compound A-862>
[0517] Compound A-862 is synthesized in substantially the same manner as the synthesis of Compound A-70, except that Compound S8 is used instead of Compound S1 and Compound S5 is used instead of Compound S2.
[0518] <Synthesis of Compound A862>
[0519] Compound A862 is synthesized in substantially the same manner as the synthesis of Compound A70, except that Compound A-862 is used instead of Compound A-70 and Compound S4 is used instead of Compound S3. By FAB-MS, the mass number m / z = 603 is measured from the molecular ion peak, and the obtained compound is confirmed to be Compound A862.
[0520] (6) Synthesis of Compound A866
[0521] Compound A866 according to the embodiment can be synthesized, for example, by Reaction Scheme 6.
[0522] [Reaction Scheme 6]
[0523]
[0524] <Synthesis of Compound A866>
[0525] Compound A866 is synthesized in substantially the same manner as the synthesis of Compound A70, except that Compound A-862 is used instead of Compound A-70 and Compound S9 is used instead of Compound S3. By FAB-MS, the mass number m / z = 653 is measured from the molecular ion peak, and the obtained compound is confirmed to be Compound A866.
[0526] (7) Synthesis of Compound A128
[0527] Compound A128 according to the embodiment can be synthesized, for example, by Reaction Scheme 7.
[0528] [Reaction Scheme 7]
[0529]
[0530] <Synthesis of Compound A-128>
[0531] Compound A-128 was synthesized in substantially the same manner as the synthesis of compound A-70, except that compound S10 was used instead of compound S2.
[0532] <Synthesis of Compound A128>
[0533] Compound A128 was synthesized in substantially the same manner as the synthesis of compound A70, except that compound A-128 was used instead of compound A-70 and compound S6 was used instead of compound S3. By FAB-MS, the mass number m / z = 663 was measured from the molecular ion peak, and the obtained compound was confirmed to be compound A128.
[0534] (8) Synthesis of Compound A178
[0535] Compound A178 according to the embodiment can be synthesized, for example, by Reaction Scheme 8.
[0536] [Reaction Scheme 8]
[0537]
[0538] <Synthesis of Compound A178>
[0539] Compound A178 was synthesized in substantially the same manner as the synthesis of compound A70, except that compound A-128 was used instead of compound A-70 and compound S11 was used instead of compound S3. By FAB-MS, the mass number m / z = 676 was measured from the molecular ion peak, and the obtained compound was confirmed to be compound A178.
[0540] 2. Fabrication and Evaluation of Light-Emitting Elements
[0541] (1) Fabrication of Light-Emitting Elements
[0542] Light-emitting elements including the amine compound or comparative compound according to the embodiment in the hole transport layer were fabricated in the following manner. The light-emitting elements of Examples 1 to 8 were fabricated using compound A70, compound A71, compound A508, compound A1005, compound A862, compound A866, compound A128, and compound A178 as the materials for the hole transport layer, which are the amine compounds according to the embodiment. The light-emitting elements of Comparative Examples 1 to 11 were fabricated using comparative compounds CX1 to comparative compound CX11 as the materials for the hole transport layer.
[0543] A glass substrate with a 150-nm-thick ITO layer patterned thereon as the first electrode was ultrasonically cleaned with isopropyl alcohol and pure water for about five minutes each. After ultrasonic cleaning, the glass substrate was irradiated with ultraviolet light for about 30 minutes and exposed to ozone. 1-TNATA was deposited with a thickness of about 60 nm to form a hole injection layer. An example compound or a comparative compound was deposited on the hole injection layer with a thickness of about 30 nm to form a hole transport layer.
[0544] TBP and ADN were co-deposited on the hole transport layer with a thickness of about 25 nm to form an emission layer. TBP and ADN were co-deposited at a weight ratio of about 3:97. Alq3 with a thickness of about 25 nm and LiF with a thickness of about 1 nm were sequentially deposited to form an electron transport region. Al was deposited with a thickness of 100 nm to form a second electrode. The hole injection layer, the hole transport layer, the emission layer, the electron transport region, and the second electrode were each formed by using a vacuum deposition apparatus.
[0545] <Materials used in the manufacture of light-emitting elements>
[0546]
[0547] [Example compound]
[0548]
[0549] [Comparative compound]
[0550]
[0551] (2) Evaluation of light-emitting elements
[0552] The light-emitting elements according to the examples and comparative examples were evaluated, and the results are listed in Table 1. By using a 2400 series source meter manufactured by Keithley Instruments LLC., a color luminance meter manufactured by Konica Minolta Inc., and LabVIEW 8.2, which is PC software for measurement manufactured by National Instruments Japan, the drive voltage, luminous efficiency, and lifetime were measured in a dark room at a current density of about 10 mA / cm 2 The time taken for the initial luminance to decrease from 100% to 50% was measured as the lifetime (LT50).
[0553] [Table 1]
[0554]
[0555] Referring to Table 1, it can be seen that, compared with the light-emitting elements according to Comparative Examples 1 to 11, the light-emitting elements according to Examples 1 to 8 each have high luminous efficiency and long lifespan. It can be seen that the light-emitting elements according to Examples 1 to 8 each have a driving voltage lower than that of the light-emitting elements according to Comparative Examples 1 to 11. The light-emitting elements according to Examples 1 to 8 respectively include Compound A70, Compound A71, Compound A508, Compound A1005, Compound A862, Compound A866, Compound A128, and Compound A178, where Compound A70, Compound A71, Compound A508, Compound A1005, Compound A862, Compound A866, Compound A128, and Compound A178 are amine compounds according to the embodiment.
[0556] Compound A70, Compound A71, Compound A508, Compound A1005, Compound A862, Compound A866, Compound A128, and Compound A178 each include a dibenzofuranyl (or dibenzothiophenyl) and a phenanthryl group that are each directly bonded to an amino group.
[0557] The dibenzofuranyl (or dibenzothiophenyl) corresponds to the above-mentioned first substituent, and the phenanthryl group corresponds to the above-mentioned second substituent. Due to the substitution of substituents (such as a phenyl group at the 4th carbon atom of the first substituent), Compound A70, Compound A71, Compound A508, Compound A1005, Compound A862, Compound A866, Compound A128, and Compound A178 each have an extended conjugated system. Therefore, it can be seen that Compound A70, Compound A71, Compound A508, Compound A1005, Compound A862, Compound A866, Compound A128, and Compound A178 exhibit excellent material stability and hole transport characteristics, and the light-emitting elements according to Examples 1 to 8 exhibit characteristics of low driving voltage, high luminous efficiency, and long lifespan.
[0558] The light-emitting element according to Comparative Example 1 includes Comparative Example Compound CX1, and the light-emitting element according to Comparative Example 6 includes Comparative Example Compound CX6. Comparative Example Compound CX1 includes a dibenzofuranyl group and a phenanthryl group, and Comparative Example Compound CX6 includes a dibenzothiophenyl group and a phenanthryl group. However, in Comparative Example Compound CX1 and Comparative Example Compound CX6, the phenanthryl group is not directly bonded to the amino group, but is bonded to the amino group via a phenylene group (corresponding to a linking group), which is different from the amine compounds according to the embodiment. Therefore, for Comparative Example Compound CX1 and Comparative Example Compound CX6, the deposition temperature of the compound increases, and thermal decomposition becomes more likely to occur during deposition. Therefore, the light-emitting elements according to Comparative Example 1 and Comparative Example 6 show high driving voltage, low luminous efficiency, and short lifespan.
[0559] The light-emitting element according to Comparative Example 2 includes a comparative example compound CX2, and the light-emitting element according to Comparative Example 3 includes a comparative example compound CX3. Each of the comparative example compound CX2 and the comparative example compound CX3 includes a dibenzofuranyl group but does not include a phenanthryl group, which is different from the amine compound according to the embodiment. Therefore, the light-emitting elements according to Comparative Example 2 and Comparative Example 3 exhibit a high driving voltage, low luminous efficiency, and short lifespan.
[0560] The light-emitting element according to Comparative Example 4 includes a comparative example compound CX4, wherein the comparative example compound CX4 includes a dibenzofuranyl group and a phenanthryl group. However, in the comparative example compound CX4, the central ring group (the ring group including R a1 and R a2 in Formula 2) of the phenanthryl group is directly bonded to the amine group, which is different from the amine compound according to the embodiment. The comparative example compound CX4 in which the central ring group of the phenanthryl group is directly bonded to the amine group has a large steric distortion around the amine group. Therefore, the light-emitting element according to Comparative Example 4 exhibits a high driving voltage, low luminous efficiency, and short lifespan.
[0561] The light-emitting element according to Comparative Example 5 includes a comparative example compound CX5, wherein the comparative example compound CX5 includes a dibenzothiophenyl group and a phenanthryl group. However, in the comparative example compound CX5, the phenyl group as a substituent of the dibenzothiophenyl group is bonded at the 3rd carbon atom, which is different from the amine compound according to the embodiment. The comparative example compound CX5 in which the phenyl group is bonded to the 3rd carbon atom of the dibenzothiophenyl group lacks resonance stability. Therefore, the light-emitting element according to Comparative Example 5 exhibits a high driving voltage, low luminous efficiency, and short lifespan.
[0562] The light-emitting element according to Comparative Example 7 includes a comparative example compound CX7, wherein the comparative example compound CX7 includes a phenanthryl group but does not include a dibenzofuranyl group, which is different from the amine compound according to the embodiment. Therefore, the light-emitting element according to Comparative Example 7 exhibits a high driving voltage, low luminous efficiency, and short lifespan.
[0563] The light-emitting elements according to Comparative Example 8, Comparative Example 9, and Comparative Example 10 include a comparative example compound CX8, a comparative example compound CX9, and a comparative example compound CX10, respectively. Each of the comparative example compound CX8, the comparative example compound CX9, and the comparative example compound CX10 includes a dibenzofuranyl group and a phenanthryl group. However, in the comparative example compound CX8, the comparative example compound CX9, and the comparative example compound CX10, the dibenzofuranyl group is unsubstituted, which is different from the amine compound according to the embodiment. Therefore, the light-emitting elements according to Comparative Example 8, Comparative Example 9, and Comparative Example 10 exhibit a high driving voltage, low luminous efficiency, and short lifespan.
[0564] The light-emitting element according to Comparative Example 11 includes a comparative example compound CX11, and the comparative example compound CX11 includes a dibenzofuranyl group and a phenanthryl group. However, in the comparative example compound CX11, the dibenzofuranyl group is bonded to the amine group at the 2nd carbon atom, which is different from the amine compound according to the embodiment. Therefore, the light-emitting element according to Comparative Example 11 exhibits a high driving voltage, low luminous efficiency, and short lifetime.
[0565] The light-emitting element according to the embodiment and the display device according to the embodiment each include the amine compound according to the embodiment, and thus can exhibit characteristics of high luminous efficiency and long lifetime.
[0566] The amine compound according to the embodiment can contribute to improving high luminous efficiency and long lifetime.
[0567] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted only in a general and descriptive sense and not for purposes of limitation. In some instances, as will be apparent to those of ordinary skill in the art, features, characteristics, and / or elements described in connection with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless specifically indicated otherwise. Accordingly, those of ordinary skill in the art will understand that various forms and details may be changed without departing from the spirit and scope of the present disclosure as set forth in the claims.
Claims
1. An amine compound represented by Formula 1: Formula 1 Wherein in Formula 1, X1 is O or S, L1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 15 ring carbon atoms, Ar1 is a substituted or unsubstituted aryl having 6 to 15 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 15 ring carbon atoms, Ar2 is a group represented by Formula 2, Ar3 is a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, R1 to R6 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 15 ring carbon atoms; Formula 2 Wherein in Formula 2, n1 is an integer selected from 0 to 3, R a1 to R a7 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms, and -* represents a bond connecting to an adjacent atom.
2. The amine compound according to claim 1, wherein the amine compound represented by Formula 1 is represented by one of Formula 1-B1 to Formula 1-B4: Formula 1-B1 Formula 1-B2 Formula 1-B3 Formula 1-B4 Wherein in Formula 1-B1 to Formula 1-B4, X1, L1, L2, Ar1, Ar3, R1 to R6, R a1 to R a7 and n1 are the same as those defined in Formula 1 and Formula 2.
3. The amine compound according to claim 2, wherein in Formula 1-B1 to Formula 1-B4, R a1 to R a7 are each independently a hydrogen atom or a deuterium atom.
4. The amine compound according to claim 1, wherein in Formula 1, Ar1 is a group represented by one of Formula AR-1 to Formula AR-4: Wherein in Formula AR-2, D is a deuterium atom, and in Formula AR-1 to Formula AR-4, -* represents a bond connecting to an adjacent atom.
5. The amine compound according to claim 1, wherein in Formula 1, L1 is a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted divalent dibenzofuranyl, or a substituted or unsubstituted divalent dibenzothiophenyl.
6. The amine compound according to claim 1, wherein in Formula 1, L1 is a direct bond or a group represented by one of Formula L1-1 to Formula L1-5: Wherein in Formula L1-2, D is a deuterium atom, and in Formula L1-1 to Formula L1-5, -* represents a bond connecting to an adjacent atom.
7. The amine compound according to claim 1, wherein in Formula 1, L2 is a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted divalent carbazolyl, a substituted or unsubstituted divalent dibenzofuranyl, or a substituted or unsubstituted divalent dibenzothiophenyl.
8. The amine compound according to claim 1, wherein in Formula 1, Ar3 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.
9. The amine compound according to claim 1, wherein in Formula 1, *-L2-Ar3 is a moiety represented by one of Formulae LA-1 to LA-79: Wherein in Formulae LA-69 to LA-79, D is a deuterium atom, and in Formulae LA-1 to LA-79, -* represents a bond connecting to an adjacent atom.
10. The amine compound according to claim 1, wherein the amine compound represented by Formula 1 is selected from Compound Group 1: Compound Group 1 Wherein in Compound Group 1, D is a deuterium atom.
11. A light-emitting element, comprising: a first electrode; a hole transport region provided on the first electrode; a light-emitting layer provided on the hole transport region; an electron transport region provided on the light-emitting layer; and a second electrode provided on the electron transport region, wherein: the hole transport region includes the amine compound represented by Formula 1 according to any one of claims 1 to 10.
12. A display device, comprising: a circuit layer provided on a base layer; and a display element layer provided on the circuit layer and including a light-emitting element, wherein: the light-emitting element includes: a first electrode; a hole transport region provided on the first electrode; a light-emitting layer provided on the hole transport region; an electron transport region provided on the light-emitting layer; and a second electrode provided on the electron transport region, and the hole transport region includes the amine compound represented by Formula 1 according to any one of claims 1 to 10.
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