Organic electroluminescence device and amine compound for organic electroluminescence device

Abstract

An organic electroluminescence device includes a first electrode, a hole transport zone disposed on the first electrode, an emission layer disposed on the hole transport zone, an electron transport zone disposed on the emission layer, and a second electrode disposed on the electron transport zone. The hole transport zone contains an amine compound represented by Formula 1, thereby exhibiting high light emission efficiency.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0063590, filed with the Korean Intellectual Property Office on May 27, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to organic electroluminescent devices and amine compounds used in said organic electroluminescent devices. Background Technology

[0004] Recently, there has been active development on organic electroluminescent displays (OLEDs) as image display devices. Compared with liquid crystal displays (LCDs), OLEDs are so-called self-emissive display devices, in which holes injected from a first electrode and electrons injected from a second electrode recombine in an emitting layer, and thus the luminescent material in the emitting layer, which includes organic compounds, emits light to achieve display.

[0005] In applications of organic electroluminescent devices to display devices, there is a continuous demand for the development of organic electroluminescent devices with low driving voltage, high light emission efficiency and long lifespan, as well as for materials for organic electroluminescent devices that can stably obtain such properties. Summary of the Invention

[0006] This disclosure provides an organic electroluminescent device with high efficiency and an amine compound contained in the hole transport region of the organic electroluminescent device.

[0007] The embodiments of the present invention provide amine compounds represented by Formula 1.

[0008] [Formula 1]

[0009]

[0010] In Formula 1, L can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, n can be an integer from 0 to 2, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and A can be represented by one of Formulas 2-1 to 2-5.

[0011] [Equation 2-1]

[0012]

[0013] [Equation 2-2]

[0014]

[0015] [Equation 2-3]

[0016]

[0017] [Equation 2-4]

[0018]

[0019] [Equation 2-5]

[0020]

[0021] In Formulas 2-1 to 2-5, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, m can be an integer from 0 to 4, Ar3 and Ar4 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and * indicates a binding site with an adjacent atom, provided that A in Formula 1 is represented by Formula 2-4 or Formula 2-5, n in Formula 1 can be 1 and Ar2 can be a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0022] In the implementation scheme, Equation 1 can be represented by one of Equations 3-1 to 3-3.

[0023] [Equation 3-1]

[0024]

[0025] [Equation 3-2]

[0026]

[0027] [Equation 3-3]

[0028]

[0029] In Formulas 3-1 to 3-3, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, m can be an integer from 0 to 4, and Ar3 and Ar4 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar1, Ar2, L and n can be the same as those defined in Formula 1.

[0030] In the implementation scheme, Equation 1 can be represented by Equation 4-1 or Equation 4-2.

[0031] [Equation 4-1]

[0032]

[0033] [Equation 4-2]

[0034]

[0035] In Formulas 4-1 and 4-2, Ar2 can be a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, m can be an integer from 0 to 4, and Ar3 and Ar4 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar1 and L can be the same as defined in Formula 1.

[0036] In the implementation scheme, Ar2 can be represented by Equation 5.

[0037] [Formula 5]

[0038]

[0039] In Formula 5, X can be O or S, R3 can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, b can be an integer from 0 to 7, and * indicates a binding site with an adjacent atom.

[0040] In the implementation scheme, Equation 3-1 can be represented by one of Equations 3-1-1 to 3-1-3.

[0041] [Equation 3-1-1]

[0042]

[0043] [Equation 3-1-2]

[0044]

[0045] [Equation 3-1-3]

[0046]

[0047] In Equations 3-1-1 to 3-1-3, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 3-1.

[0048] In the implementation scheme, Equation 3-2 can be represented by one of Equations 3-2-1 to 3-2-3.

[0049] [Equation 3-2-1]

[0050]

[0051] [Equation 3-2-2]

[0052]

[0053] [Equation 3-2-3]

[0054]

[0055] In Equations 3-2-1 to 3-2-3, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 3-2.

[0056] In the implementation scheme, Equation 3-3 can be represented by one of Equations 3-3-1 to 3-3-3.

[0057] [Equation 3-3-1]

[0058]

[0059] [Equation 3-3-2]

[0060]

[0061] [Equation 3-3-3]

[0062]

[0063] In Equations 3-3-1 to 3-3-3, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 3-3.

[0064] In the implementation scheme, Equation 4-1 can be represented by Equation 4-1-1 or Equation 4-1-2.

[0065] [Equation 4-1-1]

[0066]

[0067] [Equation 4-1-2]

[0068]

[0069] In Equations 4-1-1 and 4-1-2, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 4-1.

[0070] In the implementation scheme, Equation 4-2 can be represented by Equation 4-2-1 or Equation 4-2-2.

[0071] [Equation 4-2-1]

[0072]

[0073] [Equation 4-2-2]

[0074]

[0075] In Equations 4-2-1 and 4-2-2, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 4-2.

[0076] In the implementation scheme, L in Formula 1 can be a straight bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0077] In the implementation scheme, Equation 1 can be represented by one of Equations 6-1 to 6-4.

[0078] [Equation 6-1]

[0079]

[0080] [Equation 6-2]

[0081]

[0082] [Equation 6-3]

[0083]

[0084] [Equation 6-4]

[0085]

[0086] In Formulas 6-1 to 6-4, R2 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, a can be an integer from 0 to 4, and A, Ar1, and Ar2 can be the same as those defined in Formula 1.

[0087] An embodiment of the present invention provides an organic electroluminescent device comprising 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. The hole transport region may contain the amine compound represented by Formula 1.

[0088] In one embodiment, the hole transport region may include a hole injection layer disposed on the first electrode; and a hole transport layer disposed on the hole injection layer. The hole transport layer may contain the amine compound represented by Formula 1.

[0089] In an embodiment, the hole transport layer may further comprise a p-doper, and the p-doper may be at least one selected from quinone derivatives, metal oxides, and compounds containing cyano groups.

[0090] In an embodiment, the organic electroluminescent device may further include a capping layer disposed on the second electrode and having a refractive index equal to or greater than about 1.6.

[0091] In an implementation scheme, the covering layer may include at least one organic layer or at least one inorganic layer. Attached Figure Description

[0092] The accompanying drawings are included to provide a further understanding of the inventive concept, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the inventive concept and, together with the description, serve to explain the principles of the inventive concept. In the drawings:

[0093] Figure 1 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention;

[0094] Figure 2 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention;

[0095] Figure 3This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention; and

[0096] Figure 4 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. Detailed Implementation

[0097] The inventive concept can have various modifications and can be implemented in different forms, and the embodiments will be explained in detail with reference to the accompanying drawings. However, the inventive concept can be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. Rather, all modifications, equivalents, and substitutions included within the spirit and scope of the inventive concept should be included in the inventive concept.

[0098] In the description, it should be understood that when an element (area, layer, section, etc.) is referred to as being “on”, “connected to”, or “linked to” another element, it may be directly on, directly connected to, or directly linked to another element, or one or more intermediate elements may be disposed therebetween.

[0099] The same reference figures refer to the same components throughout the specification. The thickness, scale, and dimensions of components can be magnified in the accompanying drawings for effective description of the technical content.

[0100] The term “and / or” includes any combination and all combinations of one or more of the related listed items. For example, “A and / or B” can be understood as meaning “A, B, or A and B”. The terms “and” and “or” can be used in the sense of conjunctions or antonymous conjunctions and can be understood as equivalent to “and / or”.

[0101] The term "at least one of..." is intended to include the meaning of "selected from at least one of..." for the purpose of its meaning and explanation. When preceding a column of elements, the term "at least one of..." modifies the elements of the entire column but not any individual element in that column.

[0102] It should 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 used only to distinguish one element from another. For example, a first element may be referred to as a second element without departing from the scope of exemplary embodiments of the inventive concept, and similarly, a second element may be referred to as a first element. Singular terms may include plural forms unless the context clearly indicates otherwise.

[0103] The terms "below," "down," "above," "up," etc., are used to describe the relationships of the configurations shown in the accompanying drawings. These terms are used as relative concepts and are described with reference to the directions indicated in the accompanying drawings.

[0104] As used herein, the terms “about” or “approximately” include a specified value and mean within an acceptable range of deviation from the value, as determined by a person skilled in the art considering the relevant measurements and errors associated with the measurement of the quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the specified value.

[0105] It should be understood that terms such as “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” and / or “containing” are intended to indicate the presence of the features, integers, steps, operations, elements, components, or combinations thereof specified in this disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0106] 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 should be further understood that terms (e.g., those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and should not be interpreted in an idealized or overly formal sense unless expressly defined in the specification.

[0107] Hereinafter, an organic electroluminescent device according to an embodiment of the present invention and a compound of the embodiment contained in said organic electroluminescent device will be described with reference to the accompanying drawings.

[0108] Figures 1 to 4 This is a schematic cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. (Reference) Figures 1 to 4 In each of the organic electroluminescent devices 10 according to the embodiments, the first electrode EL1 and the second electrode EL2 are arranged to face each other, and the emission layer EML may be disposed between the first electrode EL1 and the second electrode EL2.

[0109] In addition to the emitter layer EML, each of the organic electroluminescent devices 10 in the embodiments may further include a functional layer between the first electrode EL1 and the second electrode EL2. The functional layer may include a hole transport region HTR and an electron transport region ETR. For example, each of the organic electroluminescent devices 10 according to the embodiments may include a first electrode EL1, a hole transport region HTR, an emitter layer EML, an electron transport region ETR, and a second electrode EL2 that can be stacked sequentially. The organic electroluminescent device 10 of the embodiments may include a capping layer CPL disposed on the second electrode EL2.

[0110] The organic electroluminescent device 10 of the embodiment may contain the amine compound of the embodiment described later in the hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2. However, the embodiments of the present invention are not limited thereto, and the organic electroluminescent device 10 of the embodiment may contain the amine compound of the embodiment described later not only in the hole transport region HTR, but also in the emitter layer EML or electron transport region ETR disposed between the first electrode EL1 and the second electrode EL2, or in the capping layer CPL disposed on the second electrode EL2.

[0111] and Figure 1 compared to, Figure 2 A schematic cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and wherein the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 1 compared to, Figure 3 A schematic cross-sectional view of an organic electroluminescent device 10 according to an embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and wherein the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 2 compared to, Figure 4 A schematic cross-sectional view of an organic electroluminescent device 10, including an embodiment of a capping layer CPL disposed on a second electrode EL2, is shown.

[0112] The first electrode EL1 is conductive. The first electrode EL1 can be formed of a metal alloy or a conductive compound. The first electrode EL1 can be a pixel electrode or a positive electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, it can contain a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO). When the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, it can contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg). For example, the first electrode EL1 can have a multilayer structure, which includes a reflective layer or a semi-transmissive reflective layer formed of the materials described above, and a transparent conductive layer 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 of the present invention are not limited thereto. The thickness of the first electrode EL1 can be approximately to approximately For example, the thickness of the first electrode EL1 can be approximately to approximately

[0113] The hole transport region HTR can be disposed on the first electrode EL1. The hole transport region HTR may include at least one of the following: hole injection layer HIL, hole transport layer HTL, hole buffer layer (not shown), and electron blocking layer EBL.

[0114] The hole transport region (HTR) can have a single layer formed of a single material, a single layer formed of different materials, or a multi-layer structure including layers formed of different materials.

[0115] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or a single-layer structure formed by a hole injection material and a hole transport material. The hole transport region HTR can have a single-layer structure formed by different materials, or it can have a structure of hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer sequentially laminated from the first electrode EL1, but the embodiments of the present invention are not limited thereto.

[0116] The hole transport region HTR in the organic electroluminescent device 10 may contain an amine compound according to an embodiment of the present invention.

[0117] In the description, the term "substituted or unsubstituted" can mean that it is substituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkoxy, cyclic, aryl, and heterocyclic groups, or unsubstituted. Each of the substituents listed above can be substituted or unsubstituted. For example, a biphenyl group can be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

[0118] In the description, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0119] In the description, alkyl groups can be straight-chain, branched, or cyclic. The number of carbons in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups may include, but are not limited to, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, isobutyl groups, 2-ethylbutyl groups, 3,3-dimethylbutyl groups, n-pentyl groups, isopentyl groups, neopentyl groups, tert-pentyl groups, cyclopentyl groups, 1-methylpentyl groups, 3-methylpentyl groups, 2-ethylpentyl groups, 4-methyl-2-pentyl groups, n-hexyl groups, 1-methylhexyl groups, 2 -Ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethylhexyl group The following groups are included: 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecanyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-octadecyl group, n-heptadecyl group, n-octadecyl group, n-hexadecyl group, n-octadecyl group, n-nonadecanyl group, n-eicosyl group, 2-ethyleicosyl group, 2-butyleicosyl group, 2-hexyleicosyl group, 2-octyleicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, etc.

[0120] In this description, an alkenyl group refers to a hydrocarbon group containing at least one carbon double bond at the middle or end of an alkyl group having two or more carbon atoms. The alkenyl group can be straight-chain or branched. While there is no specific limitation on the number of carbon atoms, it can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienylaryl groups, styryl groups, styrylvinyl groups, etc.

[0121] In this description, an alkynyl group means a hydrocarbon group containing at least one carbon triple bond at the middle or end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. While there is no specific limitation on the number of carbon atoms, it can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups include, but are not limited to, ethynyl groups, propynyl groups, etc.

[0122] In the description, the cyclic group can be any functional group or substituent derived from an aliphatic hydrocarbon ring, or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of cyclic carbon atoms in the cyclic group can be 5 to 60, 5 to 30, or 5 to 20.

[0123] In this description, aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl groups can be monocyclic or polycyclic. The number of cyclic carbon atoms in an aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[a]phenanthryl, pyrene, benzo[a]fluoranyl, and so on. Basic, etc., but not limited to this.

[0124] In the description, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spirostructure. Examples of substituted fluorenyl groups are given below. However, embodiments of the present invention are not limited thereto.

[0125]

[0126] In this description, a heterocyclic group refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, or S as a heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic and aromatic heterocycles can be monocyclic or polycyclic.

[0127] In the description, the heterocyclic group may contain at least one of B, O, N, P, Si, or S as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and includes a heteroaryl group. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0128] In the description, the aliphatic heterocyclic group may contain at least one of B, O, N, P, Si, or S as a heteroatom. The number of cyclic carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include, but are not limited to, oxetane propane groups, thiohepane propane groups, pyrrolidinyl groups, piperidinyl groups, tetrahydrofuran groups, tetrahydrothiophene groups, thiohepane pentane groups, tetrahydropyran groups, and 1,4-dioxane groups.

[0129] In the description, the heteroaryl group may contain at least one of B, O, N, P, Si, or S as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include thiophene, furanyl, pyrrole, imidazolyl, oxazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazine, acridine, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, and N-aryl. Carbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, thiophene-thiophene, benzofuranyl, phenanthrolinel, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, phenthiazolyl, phenthiazinyl, dibenzothiophenolyl, dibenzofuranyl, etc., but not limited to these.

[0130] In the description, the number of carbon atoms in the amine group is not particularly limited, but can be from 1 to 30. The amine group can include alkylamine groups, arylamine groups, or heteroarylamine groups. Examples of amine groups include, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthraylamine groups, etc.

[0131] In this description, the above description of aryl groups is applied to arylene groups, but arylene groups are divalent groups.

[0132] In the description, the above description of heteroaryl groups is applied to heteroaryl groups, but heteroaryl groups are divalent groups.

[0133] In the description, "-*" indicates a binding site with an adjacent atom.

[0134] The amine compounds according to embodiments of the present invention are represented by Formula 1.

[0135] [Formula 1]

[0136]

[0137] In Formula 1, L can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0138] In Equation 1, n can be an integer from 0 to 2, and when n is 2, the groups represented by L can be the same or different from each other.

[0139] In Formula 1, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0140] In Equation 1, A can be represented by one of Equations 2-1 to 2-5.

[0141] [Equation 2-1]

[0142]

[0143] [Equation 2-2]

[0144]

[0145] [Equation 2-3]

[0146]

[0147] [Equation 2-4]

[0148]

[0149] [Equation 2-5]

[0150]

[0151] In Formulas 2-1 to 2-5, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0152] In Equations 2-1 to 2-5, m can be an integer from 0 to 4, and when m is 2 or greater than 2, the groups represented by R1 can be the same or different from each other.

[0153] In Formulas 2-1 to 2-5, Ar3 and Ar4 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0154] In Equations 2-1 to 2-5, * represents the binding site with an adjacent atom.

[0155] When A in Formula 1 is represented by Formula 2-4 or Formula 2-5, in Formula 1, n can be 1 and Ar2 can be a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0156] In this embodiment, the amine compound may be a monoamine compound. In this embodiment, the amine compound may contain a heteroaryl group containing N.

[0157] In the embodiments, the monoamine compound represented by Formula 1 may not contain substituents containing N.

[0158] In the embodiments, Ar3 and / or Ar4 in Formulas 2-1 to 2-5 may be substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms.

[0159] In the embodiments, Ar3 and / or Ar4 in Formulas 2-1 to 2-5 may be substituted or unsubstituted phenyl groups.

[0160] In the embodiments, when Ar1 and / or Ar2 in Formula 1 are substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms, Ar1 and / or Ar2 can be represented by Formula 5.

[0161] [Formula 5]

[0162]

[0163] In Equation 5, X can be O or S.

[0164] In Formula 5, R3 can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0165] In Equation 5, b can be an integer from 0 to 7, and when b is 2 or greater than 2, the groups represented by R3 can be the same or different from each other.

[0166] In Equation 5, * represents the binding site with an adjacent atom.

[0167] In the implementation scheme, n in Equation 1 can be 0 or 1.

[0168] In the embodiments, L in Formula 1 can be a substituted or unsubstituted aryl group having 6 to 15 cyclic carbon atoms. L in Formula 1 can be an unsubstituted aryl group having 6 to 15 cyclic carbon atoms.

[0169] In the implementation scheme, L in Formula 1 can be a straight bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0170] In the implementation scheme, Equation 1 can be represented by one of Equations 6-1 to 6-4.

[0171] [Equation 6-1]

[0172]

[0173] [Equation 6-2]

[0174]

[0175] [Equation 6-3]

[0176]

[0177] [Equation 6-4]

[0178]

[0179] In Formulas 6-1 to 6-4, R2 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0180] In Equations 6-1 to 6-4, a can be an integer from 0 to 4, and when a is 2 or greater than 2, the groups represented by R2 can be the same or different from each other.

[0181] In Equations 6-1 to 6-4, A, Ar1, and Ar2 can be the same as those defined in Equation 1.

[0182] In the implementation scheme, R1 in Formula 1 can be a hydrogen atom or a deuterium atom.

[0183] In the implementation scheme, Equation 1 can be represented by one of Equations 3-1 to 3-3.

[0184] [Equation 3-1]

[0185]

[0186] [Equation 3-2]

[0187]

[0188] [Equation 3-3]

[0189]

[0190] In Formulas 3-1 to 3-3, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0191] In Equations 3-1 to 3-3, m can be an integer from 0 to 4, and when m is 2 or greater than 2, the groups represented by R1 can be the same or different from each other.

[0192] In Formulas 3-1 to 3-3, Ar3 and Ar4 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0193] In Equations 3-1 to 3-3, Ar1, Ar2, L, and n can be the same as those defined in Equation 1.

[0194] In the implementation scheme, Equation 1 can be represented by Equation 4-1 or Equation 4-2.

[0195] [Equation 4-1]

[0196]

[0197] [Equation 4-2]

[0198]

[0199] In Formula 4-2 and Formula 4-2, Ar2 can be a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0200] In Formulas 4-1 and 4-2, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0201] In Equations 4-1 and 4-2, m can be an integer from 0 to 4, and when m is 2 or greater than 2, the groups represented by R1 can be the same or different from each other.

[0202] In Formulas 4-1 and 4-2, Ar3 and Ar4 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0203] In Equations 4-1 and 4-2, Ar1 and L can be the same as those defined in Equation 1.

[0204] In the embodiments, Ar2 in Formula 4-1 and Formula 4-2 may be a substituted or unsubstituted heteroaryl group having 2 to 15 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 12 cyclic carbon atoms.

[0205] In the implementation scheme, Ar2 in Equations 4-1 and 4-2 can be represented by Equation 5.

[0206] [Formula 5]

[0207]

[0208] In Equation 5, X can be O or S.

[0209] In Formula 5, R3 can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0210] In Equation 5, b can be an integer from 0 to 7, and when b is 2 or greater than 2, the groups represented by R3 can be the same or different from each other.

[0211] In Equation 5, * represents the binding site with an adjacent atom.

[0212] In the implementation scheme, Equation 3-1 can be represented by one of Equations 3-1-1 to 3-1-3.

[0213] [Equation 3-1-1]

[0214]

[0215] [Equation 3-1-2]

[0216]

[0217] [Equation 3-1-3]

[0218]

[0219] In Equations 3-1-1 to 3-1-3, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 3-1.

[0220] In the implementation scheme, Equation 3-2 can be represented by one of Equations 3-2-1 to 3-2-3.

[0221] [Equation 3-2-1]

[0222]

[0223] [Equation 3-2-2]

[0224]

[0225] [Equation 3-2-3]

[0226]

[0227] In Equations 3-2-1 to 3-2-3, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 3-2.

[0228] In the implementation scheme, Equation 3-3 can be represented by one of Equations 3-3-1 to 3-3-3.

[0229] [Equation 3-3-1]

[0230]

[0231] [Equation 3-3-2]

[0232]

[0233] [Equation 3-3-3]

[0234]

[0235] In Equations 3-3-1 to 3-3-3, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 3-3.

[0236] In the implementation scheme, Equation 4-1 can be represented by Equation 4-1-1 or Equation 4-1-2.

[0237] [Equation 4-1-1]

[0238]

[0239] [Equation 4-1-2]

[0240]

[0241] In Equations 4-1-1 and 4-1-2, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 4-1.

[0242] In the implementation scheme, Equation 4-2 can be represented by Equation 4-2-1 or Equation 4-2-2.

[0243] [Equation 4-2-1]

[0244]

[0245] [Equation 4-2-2]

[0246]

[0247] In Equations 4-2-1 and 4-2-2, Ar1 to Ar4, R1 and m can be the same as those defined in Equation 4-2.

[0248] The amine compound represented by Formula 1 in an embodiment of the present invention may be one of the compounds selected from groups 1 to 4 of compounds. However, embodiments of the present invention are not limited thereto.

[0249] [Compound Group 1]

[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]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333] [Compound Group 2]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414] [Compound Group 3]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467] [Compound Group 4]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510]

[0511]

[0512]

[0513]

[0514]

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539]

[0540]

[0541]

[0542]

[0543]

[0544] Reference Figures 1 to 3 An organic electroluminescent device according to an embodiment of the present invention is described.

[0545] As described above, the hole transport region HTR contains an amine compound as described above according to an embodiment of the present invention. For example, the hole transport region HTR may contain an amine compound represented by Formula 1.

[0546] When the hole transport region HTR is a multilayer structure, any one of the layers may contain an amine compound represented by Formula 1. For example, the hole transport region HTR may include a hole injection layer HIL disposed on the first electrode EL1 and a hole transport layer HTL disposed on the hole injection layer HIL, wherein the hole transport layer HTL may contain an amine compound represented by Formula 1. However, the embodiments are not limited thereto. For example, the hole injection layer HIL may contain an amine compound represented by Formula 1.

[0547] The hole transport region (HTR) may contain one or more amine compounds represented by Formula 1. For example, the hole transport region (HTR) may contain at least one compound selected from groups 1 to 4 of compounds as described above.

[0548] Hole transport regions (HTRs) can be formed using various methods, such as vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0549] However, the hole transport region (HTR) can further contain the following materials in each layer.

[0550] Hole injection layer HIL may contain, for example, phthalocyanine compounds (e.g., copper phthalocyanine); N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-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,N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4 Poly(4-styrene sulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate, dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN), etc.

[0551] Hole transport layer (HTL) may comprise common materials known in the art. Hole transport layer (HTL) may further comprise, for example, carbazole derivatives (e.g., N-phenylcarbazole and polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (e.g., 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0552] The electron blocking layer (EBL) may contain, for example, carbazole derivatives (e.g., N-phenylcarbazole and polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (e.g., 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), 4,4'-cyclohexylbis[N,N] [-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), 1,3-bis(N-carbazolyl)benzene (mCP), 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mCDP), etc.

[0553] The thickness of the hole transport region (HTR) can be approximately to approximately For example, the thickness of the hole transport region (HTR) can be approximately to approximately The thickness of the hole injection layer (HIL) can be approximately to approximately Furthermore, the thickness of the hole transport layer (HTL) can be approximately... to approximately For example, the thickness of the electron blocking layer EBL can be approximately to approximately If the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the ranges described above, satisfactory hole transport properties can be achieved without a significant increase in driving voltage.

[0554] In addition to the materials described above, the hole transport region (HTR) may further include a charge-generating material to increase conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-doper. The p-doper may be at least one selected from quinone derivatives, metal oxides, and compounds containing cyano groups, but embodiments of the present invention are not limited thereto. For example, non-limiting examples of p-dopers may include, but are not limited to, quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal halides (e.g., MgF2, CuI, RbI), and metal oxides (e.g., tungsten oxide and molybdenum oxide).

[0555] As described above, the hole transport region (HTR) may further include at least one selected from a hole buffer layer and an electron blocking layer (EBL). The hole buffer layer can compensate for the resonant distance to increase light emission efficiency based on the wavelength of light emitted from the emitter layer (EML). Materials that can be included in the hole transport region (HTR) can be used as materials that can be included in the hole buffer layer. The electron blocking layer (EBL) is a layer used to prevent electrons from being injected from the electron transport region (ETR) into the hole transport region (HTR).

[0556] An emitter layer EML is provided on the hole transport region (HTR). The thickness of the emitter layer EML can be approximately... to approximately For example, the thickness of the emitter layer EML can be approximately to approximately The emitter layer (EML) can have a single layer made of a single material, a single layer made of different materials, or a multilayer structure with multiple layers made of different materials.

[0557] As the material for the emitter layer EML, known materials can be used, and the known materials can be selected from fluoranthene derivatives, pyrene derivatives, arylaceyne derivatives, anthracene derivatives, fluorene derivatives, perylene derivatives, etc. One of the derivatives, etc., but not limited thereto. The host material may include pyrene derivatives, perylene derivatives, and anthracene derivatives. For example, an anthracene derivative represented by Formula 10 may be used as the host material for the emitter layer EML.

[0558] [Formula 10]

[0559]

[0560] In Formula 10, W1 to W4 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring, m1 and m2 are each independently an integer from 0 to 4, and m3 and m4 are each independently an integer from 0 to 5.

[0561] If m1 is 1, W1 can be a non-hydrogen atom; if m2 is 1, W2 can be a non-hydrogen atom; if m3 is 1, W3 can be a non-hydrogen atom; and if m4 is 1, W4 can be a non-hydrogen atom.

[0562] If m1 is 2 or greater than 2, the groups represented by W1 can be the same or different. If m2 is 2 or greater than 2, the groups represented by W2 can be the same or different. If m3 is 2 or greater than 2, the groups represented by W3 can be the same or different. If m4 is 2 or greater than 2, the groups represented by W4 can be the same or different.

[0563] Compounds represented by Formula 10 may include, for example, compounds represented by the following structures. However, compounds represented by Formula 10 are not limited thereto.

[0564]

[0565] The emitter layer (EML) can contain dopants, and known materials can be used as dopants. For example, styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB), and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVB) At least one of Bi), perylene and its derivatives (e.g., 2,5,8,11-tetratert-butylperylene (TBPe)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene and 1,6-bis(N,N-diphenylamino)pyrene), or 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi) can be used as a dopant, but is not limited thereto.

[0566] The emitter layer EML can contain a host material. For example, the emitter layer EML can contain, but is not limited to, tris(8-hydroxyquinoline)aluminum (Alq3), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 3-tert-butyl-9,10-di At least one of the following is used as the host material: (naphthyl-2-yl)anthracene (TBADN), stilbeneyl arylene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH-2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), or 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi).

[0567] When the emitting layer EML emits red light, the emitting layer EML may further contain, for example, a fluorescent material, including tris(dibenzoylmethane)phenanthroline europium (PBD:Eu(DBM)3(Phen)) or perylene. When the emitting layer EML emits red light, the dopants contained in the emitting layer EML may be, for example, metal complexes or organometallic complexes (e.g., iridium bis(1-phenylisoquinoline)acetylacetonate (PIQIr(acac)), iridium bis(1-phenylquinoline)acetylacetonate (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr) and octaethylporphyrin platinum (PtOEP)), rubrene and its derivatives, and 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) and its derivatives.

[0568] When the emitting layer EML emits green light, the emitting layer EML may further contain, for example, a fluorescent material, including tris(8-hydroxyquinoline)aluminum (Alq3). When the emitting layer EML emits green light, the dopant contained in the emitting layer EML may be selected, for example, from metal complexes or organometallic complexes (e.g., planar-tris(2-phenylpyridine)iridium (Ir(ppy)3)) and coumarin and its derivatives.

[0569] When the emitting layer EML emits blue light, the emitting layer EML may further comprise, for example, a fluorescent material, including any one selected from the group consisting of spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene-arylene (DSA), polyfluorene-based polymers (PFO), and poly(p-phenylenevinylene) (PPV)-based polymers. When the emitting layer EML emits blue light, the dopant contained in the emitting layer EML may be, for example, selected from metal complexes (e.g., (4,6-F₂ppy)₂Irpic) or organometallic complexes, perylene, and their derivatives.

[0570] The electron transport region (ETR) is disposed on the emitter layer (EML). The electron transport region (ETR) may include, but is not limited to, at least one of the hole blocking layer (HBL), the electron transport layer (ETL), or the electron injection layer (EIL).

[0571] The electron transport region (ETR) can have a single layer made of a single material, a single layer made of different materials, or a multi-layer structure including multiple layers made of different materials.

[0572] For example, the electron transport region (ETR) can have a single-layer structure of either the electron injection layer (EIL) or the electron transport layer (ETL), and can have a single-layer structure formed of an electron injection material and an electron transport material. The ETR can have a single-layer structure formed of different materials, or it can have a structure in which the electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are stacked sequentially from the emitter layer (EML), but is not limited thereto. The thickness of the ETR can be approximately... to approximately

[0573] Electron transport regions (ETRs) can be formed using various methods, such as vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser-induced thermal imaging (LITI), etc.

[0574] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETL may contain an anthracene-based compound. However, embodiments of the present invention are not limited thereto, and the ETL may contain, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline. (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-oline)aluminum (BAlq), bis(benzoquinoline-10-oline)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), or mixtures thereof. The thickness of the electron transport layer (ETL) can be approximately to approximately For example, the thickness of the electron transport layer (ETL) can be approximately to approximately If the thickness of the electron transport layer (ETL) meets the range described above, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.

[0575] If the electron transport region (ETR) includes an electron injection layer (EIL), the EIL can be formed using metal halides (e.g., LiF, NaCl, CsF, RbCl, and RbI), lanthanides (e.g., Yb), metal oxides (e.g., Li₂O and BaO), or lithium 8-hydroxyquinoline (LiQ), but embodiments of the present invention are not limited thereto. The EIL can also be formed from a mixture of an electron injection material and an insulating organometallic salt. The organometallic salt can be a material having a band gap of about 4 eV or greater. The organometallic salt can include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, or metal stearates. The thickness of the EIL can be approximately... to approximately For example, the thickness of the electron-injected layer (EIL) can be approximately to approximately If the thickness of the electron injection layer (EIL) meets the range described above, satisfactory electron injection properties can be obtained without a significant increase in driving voltage.

[0576] The electron transport region (ETR) may include a hole blocking layer (HBL) as described above. The hole blocking layer (HBL) may contain, but is not limited to, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO), or 4,7-diphenyl-1,10-phenanthroline (Bphen).

[0577] A second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode or a negative electrode. The second electrode EL2 can be a transmission electrode, a semi-transmissive reflective electrode, or a reflective electrode. When the second electrode EL2 is a transmission electrode, the second electrode EL2 can be formed of a transparent metal oxide (e.g., ITO, IZO, ZnO, ITZO, etc.).

[0578] When the second electrode EL2 is a semi-transparent reflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, their compounds or mixtures thereof (e.g., a mixture of Ag and Mg). For example, the first electrode EL1 may have a multilayer structure, which includes a reflective layer or a semi-transparent reflective layer formed of the materials described above, and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc.

[0579] Although not shown, the second electrode EL2 can be connected to the auxiliary electrode. Connecting the second electrode EL2 to the auxiliary electrode can reduce the resistance of the second electrode EL2.

[0580] refer to Figure 4 The organic electroluminescent device 10 according to the embodiment may further include a capping layer CPL disposed on the second electrode EL2. The capping layer CPL may include multiple layers or a single layer.

[0581] In the implementation, the capping layer CPL may include at least one organic layer and / or at least one inorganic layer. For example, the capping layer CPL may have a structure in which an organic layer / inorganic layer is alternately disposed at least once, or in which an inorganic layer / organic layer is alternately disposed.

[0582] When the capping layer CPL contains inorganic materials, the inorganic materials may include alkali metal compounds (e.g., LiF), alkaline earth metal compounds (e.g., MgF2), SiON, and SiN. x SiOy wait.

[0583] When the capping layer CPL contains organic materials, it may contain α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), etc. For example, it may contain epoxy resin or acrylate (e.g., methacrylate). However, embodiments of the present invention are not limited thereto, and the organic materials may also include compounds P1 to P5.

[0584]

[0585] In one implementation, the capping layer CPL may have a refractive index equal to or greater than about 1.6, measured at about 589 nm. The capping layer CPL may also have a refractive index equal to or less than about 2.0, measured at about 589 nm.

[0586] In the organic electroluminescent device 10, when voltages are applied to the first electrode EL1 and the second electrode EL2, holes injected from the first electrode EL1 move through the hole transport region HTR to the emitter layer EML, and electrons injected from the second electrode EL2 move through the electron transport region ETR to the emitter layer EML. Electrons and holes recombine in the emitter layer EML to generate excitons, and light is emitted when the excitons return from the excited state to the ground state.

[0587] When the organic electroluminescent device 10 is a front-emitting type, the first electrode EL1 can be a reflective electrode, and the second electrode EL2 can be a transmissive electrode or a semi-transmissive reflective electrode. When the organic electroluminescent device 10 is a rear-emitting type, the first electrode EL1 can be a transmissive electrode or a semi-transmissive reflective electrode, and the second electrode EL2 can be a reflective electrode.

[0588] The organic electroluminescent device 10 according to an embodiment of the present invention comprises an amine compound represented by Formula 1, thereby achieving high efficiency and long service life. Low driving voltage can be achieved.

[0589] The present disclosure will be described in more detail below with reference to embodiments and comparative examples. These embodiments are merely examples to aid in understanding the inventive concept, and the scope of the inventive concept is not limited thereto.

[0590] [Synthesis example]

[0591] The amine compounds according to embodiments of the present invention can be synthesized, for example, as follows. However, the methods for synthesizing amine compounds according to embodiments of the present invention are not limited thereto.

[0592] 1. Synthesis of compound 3-Al-38

[0593] (Synthesis of compound B)

[0594]

[0595] DCM solvent (100 mL) was added to naphthylene compound A (12.2 g, 41.2 mmol), and pyridine (6.7 mL) and Tf₂O (10 mL) were added dropwise to the reaction solution at 0 °C. The reaction solution was stirred at room temperature for 12 hours and neutralized with a saturated aqueous solution of NaHCO₃. The reaction solution was extracted with CH₂Cl₂, washed with H₂O and brine, and dried over Mg₂SO₄. The obtained solution was concentrated and purified by silica gel column chromatography to obtain compound B (14 g, 35 mmol, 85%, m / z 428.1).

[0596] (Synthesis of compound C1)

[0597]

[0598] Toluene / EtOH / H2O (v / v / v = 4 / 2 / 1, 1000 mL) was added to the obtained compound B (20.4 g, 48 mmol), boric acid B2 (12 g, 72 mmol), and K3PO4 (20 g, 95 mmol), and the mixture was degassed. Under an argon atmosphere, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (2.0 g, 4.8 mmol) and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (2.8 g, 2.4 mmol) were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound C1 (11 g, 28 mmol, 59%, m / z 390.1).

[0599] (Synthesis of compound 3-A1-38)

[0600]

[0601] Toluene (350 mL) was added to compound C1 (7.8 g, 20 mmol), amine D (3.1 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. tA 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g (1.0 mmol) of Pd2(dba)3 were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 3-A1-38 (6.2 g, 9 mmol, 44%, m / z 699.3).

[0602] 2. Synthesis of compound 3-A1-93

[0603]

[0604] Toluene (350 mL) was added to compound C1 (7.8 g, 20 mmol), amine E (8.4 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. t A 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g (1.0 mmol) of Pd2(dba)3 were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand and cooled to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 3-A1-93 (7.5 g, 9.0 mmol, 45%, m / z 831.3).

[0605] 3. Synthesis of compound 1-A1-93

[0606]

[0607] Toluene (350 mL) was added to compound C2 (7.8 g, 20 mmol, CAS No. 1383673-32-2), amine E (8.4 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. t A 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g (1.0 mmol) of Pd2(dba)3 were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 1-A1-93 (6.0 g, 9.5 mmol, 48%, m / z 831.3).

[0608] 4. Synthesis of compound 2-A1-93

[0609] (Synthesis of compound A3)

[0610]

[0611] Toluene / EtOH / H2O (v / v / v = 4 / 2 / 1, 250 mL) was added to compound A2 (6.9 g, 20 mmol), boric acid B2 (4.1 g, 20 mmol), and K3PO4 (8.5 g, 40 mmol), and the mixture was degassed. Under an argon atmosphere, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.6 g, 4.0 mmol) and tetrakis(triphenylphosphine)palladium (1.6 g, 1.0 mmol) were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound A3 (5.8 g, 18 mmol, 90%, m / z 330.1).

[0612] (Synthesis of compound B3)

[0613]

[0614] Naphthylene derivative A3 (13.6 g, 41.2 mmol) and pyridine (6.7 mL) were added to DCM solvent (100 mL), and Tf₂O (10 mL) was added dropwise to the reaction solution at 0 °C. The reaction solution was stirred at room temperature for 12 hours and neutralized with a saturated aqueous solution of NaHCO₃. The reaction solution was extracted with CH₂Cl₂, washed with H₂O and brine, and dried over Mg₂SO₄. The obtained solution was concentrated and purified by silica gel column chromatography to obtain compound B3 (15.6 g, 34 mmol, 82%, m / z 462.0).

[0615] (Synthesis of compound C3)

[0616]

[0617] Toluene / EtOH / H2O (v / v / v = 4 / 2 / 1, 250 mL) was added to compound B3 (9.3 g, 20 mmol), phenylboronic acid (2.4 g, 20 mmol), and K3PO4 (8.5 g, 40 mmol), and the mixture was degassed. Under an argon atmosphere, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.6 g, 4.0 mmol) and tetrakis(triphenylphosphine)palladium (1.6 g, 1.0 mmol) were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound C3 (5.6 g, 14 mmol, 72%, m / z 390.1).

[0618] (Synthesis of compound 2-A1-93)

[0619]

[0620] Toluene (350 mL) was added to the aryl chloride C3 (7.8 g, 20 mmol), amine E (8.4 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. t A 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g of Pd2(dba)3 (1.0 mmol) were added to the mixture, and it was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 2-A1-93 (10 g, 12 mmol, 60%, m / z 831.3).

[0621] 5. Synthesis of compound 4-A1-31

[0622]

[0623] Toluene (350 mL) was added to the aryl chloride C4 (7.8 g, 20 mmol), amine E (8.4 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. tA 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g of Pd2(dba)3 (1.0 mmol) were added to the mixture, and it was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 4-A1-31 (13 g, 16 mmol, 78%, m / z 831.3).

[0624] 6. Synthesis of compound 5-A1-31

[0625]

[0626] Toluene (350 mL) was added to the aryl chloride C5 (7.8 g, 20 mmol), amine E (8.4 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. t A 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g (1.0 mmol) of Pd2(dba)3 were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 5-A1-31 (13 g, 15 mmol, 75%, m / z 831.3).

[0627] 7. Synthesis of compound 3-C1-93

[0628]

[0629] Toluene (350 mL) was added to compound B1 (8.6 g, 20 mmol), amine E (8.4 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. t A 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g of Pd2(dba)3 (1.0 mmol) were added to the mixture, and it was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 3-C1-93 (6.0 g, 8 mmol, 40%, m / z 755.3).

[0630] 8. Synthesis of compound 3-A1-98

[0631]

[0632] Toluene (350 mL) was added to compound C1 (7.8 g, 20 mmol), amine F (7.6 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. t A 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g (1.0 mmol) of Pd2(dba)3 were added, and the mixture was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 3-A1-98 (7.4 g, 9.0 mmol, 51%, m / z 735.2).

[0633] 9. Synthesis of compound 5-A1-36

[0634]

[0635] Toluene (350 mL) was added to compound C5 (7.8 g, 20 mmol), amine F (7.6 g, 20 mmol), and NaO. t Bu (4.2 g, 20 mmol), and degassed. Under an argon atmosphere, 2.0 M P(O) was added. t A 1.0 mL solution of Bu(dba)3 in toluene and 0.6 g of Pd2(dba)3 (1.0 mmol) were added to the mixture, and it was heated and stirred at 85 °C for 6 hours. The reaction solution was allowed to stand to cool to room temperature, extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The obtained solution was concentrated and purified by column chromatography to obtain compound 5-A1-36 (8.5 g, 12 mmol, 58%, m / z 735.2).

[0636] (Device Manufacturing Example)

[0637] Organic electroluminescent devices were fabricated using the compounds of the following examples and comparative examples as hole transport region materials.

[0638] [Example Compounds]

[0639]

[0640] [Comparative Compounds]

[0641]

[0642] The organic electroluminescent devices of the examples and comparative examples were fabricated using the following method: A 150 nm thick layer of ITO was patterned on a glass substrate, and the glass substrate was washed with ultrapure water and treated with UV and ozone for about 10 minutes to form a first electrode. 2-TNATA was deposited on it to a thickness of about 60 nm, and a hole transport layer of about 30 nm thickness was formed using either the example compound or the comparative example compound. TBP was doped into ADN at 3% to form an emitter layer of about 25 nm thickness, an Alq3 layer of about 25 nm thickness was formed on the emitter layer, and a LiF layer of about 1 nm thickness was formed to form an electron transport region. A second electrode of about 100 nm thickness was formed using aluminum (Al). A 70 nm thick capping layer was formed on the second electrode. Each layer was formed by vacuum deposition.

[0643] The light emission efficiency of the organic electroluminescent devices according to Examples 1 to 9 and Comparative Examples 1 to 5 was measured. The results are shown in Table 1.

[0644] [Table 1]

[0645]

[0646]

[0647] Referring to Table 1, it can be confirmed that all of Examples 1 to 9 have achieved high efficiency compared to Comparative Examples 1 to 5.

[0648] The compound in the examples was found to have three aryl groups at specific positions on a benzene ring near the nitrogen atom, and thus the electrons in a benzene ring of naphthalene become abundant, thereby increasing the device efficiency.

[0649] When comparing the compounds of Example 1 and Comparative Example 1, in structures where the aryl amine group is substituted at the 2-position of the naphthyl group, the device of Example 1 containing the compound of Example 1, where the aryl group is substituted at the 1- and 3-positions of the naphthyl group, shows a greater increase in efficiency than the device of Comparative Example 1 containing the compound of Comparative Example 1, where the aryl group is substituted at the 1- and 4-positions of the naphthyl group. This suggests that the electronic effect varies depending on the substitution position of the aryl group, and that the electronic effect is more effectively exhibited when the aryl group is substituted at the 1- and 3-positions.

[0650] The compounds of Examples 2 to 3 and Example 8 are embodiments in which the arylamine group is substituted at the 2-position of the naphthyl group, and the aryl group is substituted at the 1- and 3-positions, so that electronic effects caused by the substituents can be expected (as in Example 1), and it can be confirmed that the efficiency of the device is increased compared to the comparative example.

[0651] The compound of Example 5 is an embodiment in which the arylamine group is substituted at the 1-position of the naphthyl group, and the aryl group is substituted at the 2- and 4-positions, so that electronic effects caused by the substituents can be expected (as in Example 1), and it can be confirmed that the efficiency of the device is increased compared to the comparative example.

[0652] When comparing the compounds of Comparative Example 6 and Comparative Example 2, when the arylamine group is substituted at the 1-position of the naphthyl group, there is no aryl group at the position adjacent to the arylamine group, and the electronic effect may be less effective. Therefore, it was found that the heteroaryl group is substituted at the Ar1 or Ar2 position bonded to the nitrogen atom, and the aryl group is a linker between the naphthyl group and the nitrogen atom, thereby effectively exhibiting an electron-donating effect.

[0653] When comparing the compounds of Example 6 and Comparative Example 3, it was found that the aryl group was disclosed as a linker between the naphthyl group and the nitrogen atom, thereby effectively exhibiting an electron-donating effect with the naphthyl group.

[0654] When comparing the compounds of Examples 8 to 9 and Comparative Examples 3 to 5, these are embodiments in which the substituents Ar1 and / or Ar2 of the nitrogen atom are heteroaryl groups, and it was found that the electrons of the naphthyl group are enriched by the electron-donating effect of the heteroaryl group, thereby increasing the efficiency of the device.

[0655] The organic electroluminescent device according to an embodiment of the present invention uses an amine compound according to the embodiment, thereby achieving low driving voltage, high efficiency and long service life.

[0656] Because of the improved orientation properties through steric factors and the improved electronic properties through delocalization, the amine compounds according to embodiments of the present invention can have improved characteristics in hole injection and hole transport processes.

[0657] The organic electroluminescent device according to the embodiment of the present invention can have excellent efficiency.

[0658] The amine compounds of the present invention can be used as materials for the hole transport region of an organic electroluminescent device, thereby enabling the organic electroluminescent device to have improved efficiency.

[0659] Although embodiments of the inventive concept have been described, those skilled in the art will understand that this disclosure can be implemented in other forms without altering the technical concept or essential characteristics. Therefore, the disclosed embodiments should be considered illustrative rather than restrictive.

Claims

1. An organic electroluminescent device, comprising: First electrode; A hole transport region disposed on the first electrode; An emission layer disposed on the hole transmission region; An electron transmission area is disposed on the emission layer; as well as The second electrode is disposed on the electron transport region. The hole transport region therein comprises an amine compound represented by Formula 1: [Formula 1] In Equation 1, L is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. n is an integer from 0 to 2. Ar1 and Ar2 are each independently an aryl group having 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group having 2 to 30 cyclic carbon atoms. A is represented by one of equations 2-1 to 2-5: [Equation 2-1] [Equation 2-2] [Equation 2-3] [Equation 2-4] [Equation 2-5] Among them, in equations 2-1 to 2-5, R1 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. m is an integer from 0 to 4. Ar3 and Ar4 are each independently an aryl group with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group with 2 to 30 cyclic carbon atoms. * indicates a binding site with adjacent atoms, and When A in equation 1 is represented by equation 2-4 or equation 2-5: In Formula 1, n is 1 and Ar2 is a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

2. The organic electroluminescent device as claimed in claim 1, wherein formula 1 is represented by one of formulas 3-1 to 3-3: [Equation 3-1] [Equation 3-2] [Equation 3-3] Among them, in equations 3-1 to 3-3, R1 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. m is an integer from 0 to 4. Ar3 and Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar1, Ar2, L, and n are the same as those defined in Equation 1.

3. The organic electroluminescent device as claimed in claim 1, wherein formula 1 is represented by formula 4-1 or formula 4-2: [Equation 4-1] [Equation 4-2] In equations 4-1 and 4-2, Ar2 is a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R1 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. m is an integer from 0 to 4. Ar3 and Ar4 are each independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and Ar1 and L are the same as those defined in Equation 1.

4. The organic electroluminescent device as claimed in claim 3, wherein Ar2 is represented by formula 5: [Formula 5] In Equation 5, X is O or S. R3 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. b is an integer from 0 to 7, and * indicates a binding site with an adjacent atom.

5. The organic electroluminescent device as claimed in claim 2, wherein formula 3-1 is represented by one of formulas 3-1-1 to 3-1-3: [Equation 3-1-1] [Equation 3-1-2] [Equation 3-1-3] Among them, in equations 3-1-1 to 3-1-3, Ar1 to Ar4, R1 and m are the same as those defined in Equation 3-1.

6. The organic electroluminescent device as claimed in claim 2, wherein formula 3-2 is represented by one of formulas 3-2-1 to 3-2-3: [Equation 3-2-1] [Equation 3-2-2] [Equation 3-2-3] Among them, in equations 3-2-1 to 3-2-3, Ar1 to Ar4, R1 and m are the same as those defined in Equation 3-2.

7. The organic electroluminescent device as claimed in claim 2, wherein formula 3-3 is represented by one of formulas 3-3-1 to 3-3-3: [Equation 3-3-1] [Equation 3-3-2] [Equation 3-3-3] Among them, in equations 3-3-1 to 3-3-3, Ar1 to Ar4, R1 and m are the same as those defined in Equation 3-3.

8. The organic electroluminescent device as claimed in claim 3, wherein formula 4-1 is represented by formula 4-1-1 or formula 4-1-2: [Equation 4-1-1] [Equation 4-1-2] In Equations 4-1-1 and 4-1-2, Ar1 to Ar4, R1 and m are the same as those defined in Equation 4-1.

9. The organic electroluminescent device as claimed in claim 3, wherein formula 4-2 is represented by formula 4-2-1 or formula 4-2-2: [Equation 4-2-1] [Equation 4-2-2] In equations 4-2-1 and 4-2-2, Ar1 to Ar4, R1 and m are the same as those defined in Equation 4-2.

10. The organic electroluminescent device of claim 1, wherein L in Formula 1 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

11. The organic electroluminescent device as claimed in claim 1, wherein formula 1 is represented by one of formulas 6-1 to 6-4: [Equation 6-1] [Equation 6-2] [Equation 6-3] [Equation 6-4] in, In equations 6-1 to 6-4, R2 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. a is an integer from 0 to 4, and A, Ar1, and Ar2 are the same as those defined in Equation 1.

12. The organic electroluminescent device as claimed in claim 1, wherein... The hole transport region includes: A hole injection layer disposed on the first electrode; as well as A hole transport layer disposed on the hole injection layer, and The hole transport layer contains the amine compound represented by Formula 1.

13. The organic electroluminescent device of claim 12, wherein... The hole transport layer further comprises a p-dopant, and The p-doper is selected from at least one of quinone derivatives, metal oxides, and compounds containing cyano groups.

14. The organic electroluminescent device of claim 1, further comprising a capping layer disposed on the second electrode and having a refractive index equal to or greater than 1.

6.

15. The organic electroluminescent device of claim 14, wherein the capping layer comprises at least one organic layer or at least one inorganic layer.

16. Amine compounds represented by Formula 1: [Formula 1] In Equation 1, L is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. n is an integer from 0 to 2. Ar1 and Ar2 are each independently an aryl group having 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group having 2 to 30 cyclic carbon atoms. A is represented by one of equations 2-1 to 2-5: [Equation 2-1] [Equation 2-2] [Equation 2-3] [Equation 2-4] [Equation 2-5] Among them, in equations 2-1 to 2-5, R1 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. m is an integer from 0 to 4. Ar3 and Ar4 are each independently an aryl group with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group with 2 to 30 cyclic carbon atoms. * indicates a binding site with adjacent atoms, and When A in equation 1 is represented by equation 2-4 or equation 2-5: In Formula 1, n is 1 and Ar2 is a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

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