Organic electroluminescence device and amine compound for organic electroluminescence device

Abstract

The present application provides an organic electroluminescence device and an amine compound for the same, the organic electroluminescence device including a first electrode and a second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the plurality of organic layers includes an amine compound represented by Formula 1, thereby exhibiting improved emission efficiency.[Formula 1]

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0138279, filed on October 23, 2020, the entire contents of which are incorporated herein by reference. Background Technology

[0003] One or more aspects of embodiments of this disclosure relate to organic electroluminescent devices and amine compounds therein, and for example, to amine compounds used as luminescent materials and organic electroluminescent devices comprising them. Technical Field

[0004] Organic electroluminescent displays (OLEDs) are being actively developed as image displays. Unlike liquid crystal displays (LCDs), OLEDs are so-called self-emissive displays, in which holes and electrons injected from the first and second electrodes recombine in the emitting layer, causing the luminescent material, which contains organic compounds, in the emitting layer to emit light and thus achieve display.

[0005] When organic electroluminescent devices are used in displays, it is desirable to reduce the driving voltage of the organic electroluminescent devices and increase the emission efficiency and / or lifetime (e.g., lifespan), and it is desirable to develop materials that can provide these properties for organic electroluminescent devices.

[0006] To realize highly efficient organic electroluminescent devices, materials for hole transport layers are being developed. Summary of the Invention

[0007] One or more aspects of embodiments of this disclosure relate to organic electroluminescent devices having improved emission efficiency and / or device lifetime.

[0008] One or more aspects of embodiments of this disclosure relate to amine compounds capable of improving the emission efficiency and / or device lifespan (lifetime) of organic electroluminescent devices.

[0009] One or more embodiments of this disclosure provide an organic electroluminescent device comprising: a first electrode, a second electrode opposite to the first electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the plurality of organic layers comprises an amine compound comprising an amino group (e.g., an amine functional group) and three aromatic ring substituents substituted at the amino group (e.g., at the nitrogen atom of the amine functional group), and the three aromatic ring substituents comprising carbazole and benzo[b]fluorene.

[0010] In embodiments, each of the carbazoyl and benzo[b]fluorenyl groups may be linked to an amino group via a linker or directly linked to an amino group.

[0011] In one embodiment, the plurality of organic layers may include a hole transport region disposed on the first electrode, an emitter layer disposed on the hole transport region, and an electron transport region disposed on the emitter layer, wherein the hole transport region may include an amine compound.

[0012] 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, and the hole transport layer may include an amine compound.

[0013] In one embodiment, the hole transport region may include multiple organic hole transport layers, and the organic hole transport layer adjacent to the emitter layer may include an amine compound.

[0014] One or more embodiments of this disclosure provide an organic electroluminescent device comprising: a first electrode, a second electrode opposite to the first electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the plurality of organic layers comprises an amine compound represented by Formula 1.

[0015] [Formula 1]

[0016]

[0017] In Formula 1, Ar1 to Ar4 are each independently an aryl group with 6 to 30 cyclic carbon atoms, substituted or unsubstituted, or a heteroaryl group with 2 to 30 cyclic carbon atoms; L1 and L2 are each independently a directly linked, substituted or unsubstituted, arylene group with 6 to 30 cyclic carbon atoms, or a heteroarylene group with 2 to 30 cyclic carbon atoms; R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group with 1 to 20 cyclic carbon atoms, a aryl group with 6 to 60 cyclic carbon atoms, or a heteroaryl group with 2 to 60 cyclic carbon atoms, substituted or unsubstituted; "n1" is an integer selected from 0 to 4; "n2" and "n3" are each independently integers selected from 0 to 3; and "n4" is an integer selected from 0 to 6.

[0018] In an embodiment, the amine compound represented by Formula 1 may be a monoamine compound (e.g., may include only one amine functional group).

[0019] In an embodiment, the amine compound represented by Formula 1 may be represented by any one of Formulas 2-1 to 2-3.

[0020] [Equation 2-1]

[0021]

[0022] [Equation 2-2]

[0023]

[0024] [Equation 2-3]

[0025]

[0026] In Equations 2-1 to 2-3, Ar1, Ar2, Ar3, Ar4, L1, L2, R1, R2, R3, R4, “n1”, “n2”, “n3” and “n4” are each independently identical to those defined in Equation 1.

[0027] In the embodiments, the amine compound represented by Formula 1 may be represented by Formula 3-1 or Formula 3-2.

[0028] [Equation 3-1]

[0029]

[0030] [Equation 3-2]

[0031]

[0032] In Equations 3-1 and 3-2, Ar1, Ar2, Ar3, Ar4, L1, L2, R1, R2, R3, R4, “n1”, “n2”, “n3” and “n4” are each independently identical to those defined in Equation 1.

[0033] In the embodiments, the amine compound represented by Formula 1 may be represented by Formula 4-1 or Formula 4-2.

[0034] [Equation 4-1]

[0035]

[0036] [Equation 4-2]

[0037]

[0038] In Formulas 4-1 and 4-2, R5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms, "n5" is an integer selected from 0 to 4, and Ar1, Ar2, Ar3, Ar4, L1, R1, R2, R3, R4, "n1", "n2", "n3" and "n4" are each independently the same as those defined in Formula 1 above.

[0039] In embodiments, the amine compound represented by Formula 1 may be represented by Formula 5-1 or Formula 5-2.

[0040] [Equation 5-1]

[0041]

[0042] [Equation 5-2]

[0043]

[0044] In Formulas 5-1 and 5-2, R6 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms, "n6" is an integer selected from 0 to 4, and Ar1, Ar2, Ar3, Ar4, L2, R1, R2, R3, R4, "n1", "n2", "n3" and "n4" are each independently the same as those defined in Formula 1.

[0045] In the embodiments, Ar1 to Ar4 may each be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0046] In an implementation, R1 to R4 may each (e.g., all at the same time) be a hydrogen atom.

[0047] One or more embodiments of this disclosure provide amine compounds represented by Formula 1. Attached Figure Description

[0048] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the disclosure and, together with the description, serve to explain the principles of the disclosure. In the drawings:

[0049] Figure 1 A plan view of a display device according to an embodiment of the present disclosure is provided.

[0050] Figure 2 A cross-sectional view of a display device according to an embodiment of the present disclosure is provided.

[0051] Figure 3 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes.

[0052] Figure 4 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes.

[0053] Figure 5 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes.

[0054] Figure 6 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown schematically; and

[0055] Figure 7 and Figure 8 A cross-sectional view of a display device according to an embodiment is shown. Detailed Implementation

[0056] This disclosure may have various suitable modifications and may be embodied in different forms, and embodiments will be explained in more detail with reference to the accompanying drawings. However, this disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, all modifications, equivalents, and substitutions within the spirit and scope of this disclosure should be included herein.

[0057] In this description, it will be understood that when an element (or area, layer, component, etc.) is referred to as being “on”, “connected to”, or “linked to” another element, it can be directly on, directly connected to, or directly linked to the other element, or a third intermediary element may be present. When an element is referred to as being “directly” on, “directly connected to”, or “directly linked to” another element, no intermediary element is present.

[0058] The same reference numerals always refer to the same elements, and repeated descriptions of them are not required. In the drawings, the thickness, proportions, and dimensions of the constituent elements may be exaggerated for the purpose of effectively interpreting the technical content.

[0059] The term “and / or” includes any and all combinations of one or more of the related listed elements. As used herein, expressions such as “at least one of…”, “one of…”, and “selected from” when placed before / after the list of elements modify the entire list of elements, not individual elements of the list. As used herein, the singular forms “a(a)”, “an(an)”, and “the” are intended to also include the plural forms, unless the context clearly indicates otherwise. Furthermore, the use of “may” in describing embodiments of this disclosure means “one or more embodiments of this disclosure”.

[0060] It will be understood that while 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. Therefore, without departing from the teachings of this disclosure, a first element may be referred to as a second element. Similarly, a second element may alternatively be referred to as a first element.

[0061] In some implementations, the terms "below," "under," "above," and "above" are used to explain the spatial relationship of the elements shown in the figures. These terms are relative concepts and may be based on the orientation shown in the figures.

[0062] Unless otherwise specified, all terms used herein (including technical and scientific terms) shall 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 common dictionaries, shall be interpreted as having meanings consistent with their meanings in the context of the relevant field, and not as idealized or overly formal, unless expressly defined herein.

[0063] It will be further understood that when the terms “includes,” “including,” “comprises,” and / or “comprising” are used in this specification, they indicate the presence of the stated features, figures, steps, operations, elements, components, or combinations thereof, but do not exclude the presence or addition of one or more other features, figures, steps, operations, elements, components, or combinations thereof.

[0064] In this description, the term "substituted or unsubstituted" means that 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, cycloalkyl, aryl, and heterocyclic. In some embodiments, each of the substituents may be further substituted or unsubstituted. For example, biphenyl can be interpreted as aryl, or a phenyl group substituted with a phenyl group.

[0065] In this description, the terms "to form a ring by bonding with an adjacent group," "to form a ring by bonding with an adjacent group," and similar terms may refer to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle when bonded (e.g., connected) with an adjacent group. The term "hydrocarbon ring" includes aliphatic hydrocarbon rings and aromatic hydrocarbon rings. The term "heterocycle" includes aliphatic heterocycles and aromatic heterocycles. The ring formed by bonding with an adjacent group may be monocyclic or polycyclic. In some embodiments, the ring formed by bonding with an adjacent group may bond with another ring to form a spirostructure.

[0066] In this description, the term "adjacent group" can refer to a substituent on the same atom or point, a substituent directly attached to an atom of the base atom or point, or a substituent located spatially closest to the corresponding substituent (e.g., within the intramolecular bonding distance). For example, in 1,2-dimethylbenzene, the two methyl groups can be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentane, the two ethyl groups can be interpreted as "adjacent groups" to each other.

[0067] In this description, the halogen atom may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0068] In this description, the alkyl group may be straight-chain, branched, or cyclic. 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 alkyl groups 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, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-Hexyldecyl, 2-Octydecyl, undecyl, dodecyl, 2-Ethyldodecyl, 2-Butyldodecyl, 2-Hexyldodecyl, 2-Octydecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-Ethylhexadecyl, 2-Butylhexadecyl, 2-Hexylhexadecyl, 2-Octydecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-Ethyleicosyl, 2-Butyleicosyl, 2-Hexyleicosyl, 2-Octydecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, octadecyl, nonadecanyl, triadecyl, etc., without limitation.

[0069] In this description, the hydrocarbon ring may be any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring may be a saturated hydrocarbon ring with 5 to 20 cyclic carbon atoms.

[0070] In this description, the term "aryl" refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be monocyclic or polycyclic. The number of carbons in the aryl group used to form the ring can be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrene, benzofluoranthracene, 1,2-benzophenanthryl, etc.

[0071] In this description, the fluorene group may be substituted (e.g., at the 9H position), and two substituents may combine with each other to form a spirostructure. Examples of substituted fluorene groups are given below. However, embodiments of this disclosure are not limited thereto.

[0072]

[0073] In this description, the term "heterocyclic group" refers to an optional functional group or substituent derived from a ring comprising one or more of boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), and sulfur (S) as heteroatoms. Heterocyclic groups can include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl. Aliphatic and aromatic heterocyclic groups can be monocyclic or polycyclic.

[0074] In this description, the heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group and has the concept of including a heteroaryl group. The number of carbon atoms in the ring of the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.

[0075] In this description, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. The ring used to form the aliphatic heterocyclic group may have 2 to 30, 2 to 20, or 2 to 10 carbon atoms. Examples of aliphatic heterocyclic groups may include, but are not limited to, ethylene oxide, thiopropylcycloyl, pyrrolyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thiaalkyl, tetrahydropyranyl, 1,4-dioxane, etc.

[0076] In this description, a heteroaryl group may include one or more of B, O, N, P, Si, and S as heteroatoms. When a heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of carbons in the heteroaryl group for forming the ring may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include thienyl, furanyl, pyrrolyl, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, N-arylcarbazoleyl, N-heteroarylcarbazoleyl, N-alkylcarbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothiaryl, dibenzofuranyl, etc., without limitation.

[0077] In this description, the interpretation of aryl can be similarly applied to arylene, except that arylene is a divalent group. The interpretation of heteroaryl can be similarly applied to heteroarylene, except that heteroarylene is a divalent group.

[0078] In this description, the term "silyl" includes alkylsilyl and arylsilyl. Examples of silyl compounds may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc. However, embodiments of this disclosure are not limited thereto.

[0079] In this description, there is no specific limitation on the number of carbon atoms in the carbonyl group, but the number of carbon atoms can be from 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group can have any of the following structures, but is not limited thereto.

[0080]

[0081] In this description, there is no specific limitation on the number of carbon atoms in the sulfinyl and sulfonyl groups, but they can be from 1 to 30. The term "sulfinyl" can include alkylsulfinyl and arylsulfinyl. The term "sulfonyl" can include alkylsulfonyl and arylsulfonyl.

[0082] In this description, the term "thio group" may include alkylthio and arylthio groups. A thio group may include the aforementioned alkyl or aryl groups bonded to a sulfur atom. Examples of thio groups include, but are not limited to, methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, naphthio, etc.

[0083] In this description, the term "oxygen group" may refer to an alkyl or aryl group as defined above, bonded to an oxygen atom. Oxide groups may include alkoxy and aryloxy groups. Alkoxy groups may be straight-chain, branched, or cyclic. There is no specific limitation on the number of carbon atoms in an alkoxy group, but it may be, for example, 1 to 20 or 1 to 10. Examples of oxygen groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, benzyloxy, etc. However, embodiments of this disclosure are not limited thereto.

[0084] In this description, the term "boronyl" may refer to an alkyl or aryl group as defined above, bonded to a boron atom. Boronyl groups include alkylboronyl and arylboronyl groups. Examples of boronyl groups include, but are not limited to, dimethylboronyl, diethylboronyl, tert-butylmethylboronyl, diphenylboronyl, phenylboronyl, etc.

[0085] In this description, the term "alkenyl" can be straight-chain or branched. There is no specific limitation on the number of carbon atoms in an alkenyl group, but it can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc.

[0086] In this description, there is no specific limitation on the number of carbon atoms in the amino group, but it can be from 1 to 30. The term "amino group" can include alkylamino and arylamino groups. Examples of amino groups include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, etc., without limitation.

[0087] In this description, each of the alkyl groups (alkylthio, alkylsulfonyl, alkylaryl, alkylboronyl, alkylsilyl, and alkylamine) may be substantially the same as the examples of the alkyl groups described above.

[0088] In this description, each of the aryl groups, including aryloxy, arylthio, arylsulfonyl, arylamino, arylboryl, and arylsilyl, may be substantially the same as the examples of the aryl groups described above.

[0089] In this description, the term "direct link" may refer to a single key.

[0090] In this description, The symbol "--*" indicates the location to be connected.

[0091] The embodiments of this disclosure will be explained below with reference to the accompanying drawings.

[0092] Figure 1 A plan view illustrating an embodiment of the display device DD. Figure 2 This is a cross-sectional view of the display device DD. Figure 2 To show along Figure 1 A cross-sectional view of a portion of the line I-I' in the diagram.

[0093] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting devices ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP and may control or reduce the reflection of external light by the display panel DP. The optical layer PP may include, for example, a polarizing layer or a color filter layer. In some embodiments, the optical layer PP may not be provided in the display device DD of the embodiment. In some embodiments, a blocking layer may be further included between the optical layer PP and the display panel DP. The blocking layer may include, for example, at least one of a silicone polymer resin and an acrylic polymer resin.

[0094] The display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining layer PDL, light-emitting devices ED-1, ED-2, and ED-3 disposed in the pixel defining layer PDL, and an encapsulation layer TFE disposed on the light-emitting devices ED-1, ED-2, and ED-3.

[0095] The substrate layer BS can be a component providing a substrate surface, on which the display device layer DP-ED is disposed. The substrate layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments disclosed herein are not limited to these, and the substrate layer BS can be an inorganic layer, an organic layer, or a composite material layer.

[0096] In this embodiment, the circuit layer DP-CL is disposed on the substrate layer BS, and the circuit layer DP-CL may include multiple transistors. Each of the multiple transistors may 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 devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0097] Each of the light-emitting devices ED-1, ED-2, and ED-3 may have according to Figures 3 to 6 The structure of any one of the light-emitting devices ED will be explained later. Each of the light-emitting devices ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, an emitter layer EML-R, EML-G and EML-B, an electron transport region ETR, and a second electrode EL2.

[0098] exist Figure 2 The present invention illustrates an embodiment in which the emitting layers EML-R, EML-G, and EML-B of light-emitting devices ED-1, ED-2, and ED-3 are disposed within an opening OH defined in a pixel-defining layer PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as a common layer in all light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto. In some embodiments, the hole transport region HTR and the electron transport region ETR may be patterned and deposited within the opening OH defined in the pixel-defining layer PDL. For example, in an embodiment, the hole transport region HTR, the emitting layers EML-R, EML-G, and EML-B, and the electron transport region ETR of light-emitting devices ED-1, ED-2, and ED-3 may be patterned and deposited using an inkjet printing method.

[0099] The encapsulation layer TFE may cover the light-emitting devices ED-1, ED-2, and ED-3. The encapsulation layer TFE may encapsulate the display device layer DP-ED. The encapsulation layer TFE may be a thin-film encapsulation layer. The encapsulation layer TFE may be a single layer or a stack of multiple layers. The encapsulation layer TFE includes at least one insulating layer. According to embodiments, the encapsulation layer TFE may include at least one inorganic layer (hereinafter, encapsulated inorganic layer). In some embodiments, the encapsulation layer TFE according to embodiments may include at least one organic layer (hereinafter, encapsulated organic layer) and at least one encapsulated inorganic layer.

[0100] The encapsulation inorganic layer protects the display device layer (DP-ED) from moisture and oxygen, while the encapsulation organic layer protects the DP-ED from foreign matter (such as dust particles). The encapsulation inorganic layer may include silicon nitride, silicon oxynitride, silicon oxide, titanium dioxide, and / or aluminum oxide, without specific limitations. The encapsulation organic layer may include acrylic compounds, epoxy compounds, etc. The encapsulation organic layer may include photopolymerizable organic materials, without specific limitations.

[0101] The encapsulation layer TFE can be disposed on the second electrode EL2 and can be disposed at the same time as filling the opening portion OH.

[0102] The top substrate layer BL can be a component providing a substrate surface, on which the optical layer PP is disposed. The top substrate layer BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of this disclosure are not limited to these, and the top substrate layer BL can be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, the top substrate layer BL may not be provided. When the top substrate layer BL is omitted, the optical layer PP can be directly provided on the encapsulation layer TFE.

[0103] refer to Figure 1 and Figure 2 The display device DD may include a non-emitting region NPXA and emitting regions PXA-R, PXA-G, and PXA-B. The emitting regions PXA-R, PXA-G, and PXA-B may be regions that emit light generated from light-emitting devices ED-1, ED-2, and ED-3, respectively. The emitting regions PXA-R, PXA-G, and PXA-B may be separated from each other on a plane.

[0104] The light-emitting regions PXA-R, PXA-G, and PXA-B can be separated by the pixel-defining layer PDL. The non-light-emitting region NPXA can be located between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and can correspond to the pixel-defining layer PDL. In some embodiments, each of the light-emitting regions PXA-R, PXA-G, and PXA-B can correspond to a single pixel. The pixel-defining layer PDL can divide (e.g., spatially divide) the light-emitting devices ED-1, ED-2, and ED-3. The emitting layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 can be disposed and divided within an opening OH defined in the pixel-defining layer PDL.

[0105] The luminescent regions PXA-R, PXA-G, and PXA-B can be grouped according to the color of the light produced by the luminescent devices ED-1, ED-2, and ED-3. Figure 1 and Figure 2In the display device DD of the illustrated embodiment, three light-emitting regions PXA-R, PXA-G, and PXA-B, which respectively emit red, green, and blue light, are shown as an embodiment. For example, the display device DD of the embodiment may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are separated from each other.

[0106] In the display device DD according to an embodiment, a plurality of light-emitting devices ED-1, ED-2, and ED-3 can emit light with different wavelengths. For example, in an embodiment, the display device DD may include a first light-emitting device ED-1 that emits red light, a second light-emitting device ED-2 that emits green light, and a third light-emitting device ED-3 that emits blue light. For example, each of the red emitting regions PXA-R, the green emitting regions PXA-G, and the blue emitting regions PXA-B may correspond to the first light-emitting device ED-1, the second light-emitting device ED-2, and the third light-emitting device ED-3.

[0107] However, the embodiments disclosed herein are not limited thereto, and the first to third light-emitting devices ED-1, ED-2, and ED-3 may emit light in the same wavelength region, or at least one of them may emit light in different wavelength regions. For example, all of the first to third light-emitting devices ED-1, ED-2, and ED-3 may emit blue light.

[0108] According to the embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern. (Reference) Figure 1 Multiple red emitting regions PXA-R, multiple green emitting regions PXA-G, and multiple blue emitting regions PXA-B can be arranged along the second direction axis DR2. In some embodiments, the red emitting regions PXA-R, green emitting regions PXA-G, and blue emitting regions PXA-B can be arranged alternately along the first direction axis DR1 (e.g., they can be arranged alternately).

[0109] exist Figure 1 and Figure 2 In the illustration, the areas of the emitting regions PXA-R, PXA-G, and PXA-B are shown to be the same, but the embodiments of this disclosure are not limited thereto. Depending on the wavelength region of the emitted light, the areas of the emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. In some embodiments, the areas of the emitting regions PXA-R, PXA-G, and PXA-B may refer to the areas on the plane defined by the first directional axis DR1 and the second directional axis DR2.

[0110] In some embodiments, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1The configuration shown, and the arrangement order of the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B, can be provided in various suitable combinations depending on the nature of the display quality required by the display device DD. For example, the arrangement of the emitting areas PXA-R, PXA-G, and PXA-B can be as follows: Arrangement, or diamond arrangement.

[0111] In some embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one 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 of this disclosure are not limited thereto.

[0112] Figures 3 to 6 A cross-sectional view of an organic electroluminescent device according to an embodiment of the present disclosure is shown for illustrative purposes. Reference Figures 3 to 6 In the light-emitting device ED of the embodiment, a first electrode EL1 and a second electrode EL2 may be disposed opposite to each other, and a plurality of organic layers may be disposed between the first electrode EL1 and the second electrode EL2. The plurality of organic layers may include a hole transport region (HTR), an emitter layer (EML), and an electron transport region (ETR). For example, the light-emitting device ED according to the embodiment may include a first electrode, a hole transport region (HTR), an emitter layer (EML), an electron transport region (ETR), and a second electrode EL2 stacked in sequence. A capping layer (CPL) may be further disposed on the second electrode EL2.

[0113] The light-emitting device ED of the embodiments may include the amine compound of the embodiments in at least one of the plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2, which will be explained later. For example, the light-emitting device ED of the embodiments may include the amine compound of the embodiments in the hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2, which will be explained later. However, the embodiments of this disclosure are not limited thereto, and the light-emitting device ED of the embodiments may include the amine compound of the embodiments in at least one of the plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2 (including the emission layer EML and the electron transport region ETR in addition to the hole transport region HTR), which will be explained later; or may include the amine compound of the embodiments in the capping layer CPL disposed on the second electrode EL2, which will be explained later.

[0114] and Figure 3 Compare, Figure 4 A cross-sectional view of the light-emitting device ED 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 the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 Compare, Figure 5 A cross-sectional view of the light-emitting device ED 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 the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 Compare, Figure 6 A cross-sectional view of a light-emitting device ED including a capping layer CPL disposed on a second electrode EL2 is shown.

[0115] In the following explanation of the light-emitting device ED according to the embodiments, the amine compound according to the embodiments (which will be explained later) is included in the hole transport region HTR, but the embodiments of this disclosure are not limited thereto, and the amine compound according to the embodiments may be included in the emission layer EML or the electron transport region ETR.

[0116] The first electrode EL1 is conductive. The first electrode EL1 may be formed using a metal alloy and / or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, embodiments of this disclosure are not limited thereto. In some embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). When the first electrode EL1 is a transmissive / reflective electrode or a reflective electrode, the first electrode EL1 may include silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF, molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), zinc (Zn), tin (Sn), their compounds, mixtures thereof (e.g., a mixture of Ag and Mg), or one or more oxides thereof, or materials with a multilayer structure such as LiF / calcium (Ca) or LiF / aluminum (Al). Furthermore, the first electrode EL1 may have a structure comprising multiple layers, including a reflective or transmissive layer formed using the above materials and a transmissive conductive layer formed using ITO, IZO, ZnO, or ITZO. For example, the first electrode EL1 may include a three-layer structure of ITO / Ag / ITO. However, embodiments of this disclosure are not limited thereto. The thickness of the first electrode EL1 may be approximately... to approximately For example, the thickness of the first electrode EL1 can be approximately to approximately

[0117] A hole transport region (HTR) is provided on the first electrode EL1. The HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer, an emitter assist layer, and an electron blocking layer (EBL). The thickness of the HTR may be approximately [missing information]. to approximately

[0118] The hole transport region (HTR) may have a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure including multiple layers formed using multiple different materials.

[0119] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it may have a single-layer structure formed using a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR may have a single-layer structure formed using multiple different materials, or a structure of 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 EBL stacked from the first electrode EL1, without limitation.

[0120] Hole transport regions (HTRs) can be formed using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0121] In the light-emitting device ED of the embodiment, the hole transport region HTR may include the amine compound of the embodiment.

[0122] The amine compounds of the embodiments include carbazoyl and benzo[b]fluoreneyl as substituents. For example, the amine compounds of the embodiments include an amino group and three aromatic ring substituents substituted at the amino group, and the three aromatic ring substituents include carbazoyl and benzo[b]fluoreneyl. The benzo[b]fluoreneyl is a substituent in which the benzene ring is further fused with the fluoreneyl group, and may have the structure of formula a.

[0123] [Formula a]

[0124]

[0125] In equation a, Ar a and Ar b Each can be 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, either substituted or unsubstituted. For example, Ar... a and Ar bEach can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.

[0126] In equation a, R a and R b Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms. For example, R a and R b It can be (for example, both are) hydrogen atoms.

[0127] In formula a, “——*” indicates the position where the benzo[b]fluorene substituent is attached to the amino group.

[0128] In equation a, n a It can be an integer selected from 0 to 3, and n b It can be an integer selected from 0 to 6. In equation a, when n a When the value is 0, the benzo[b]fluorene substituent in the embodiment may not be R. a Effective substitution. For example, where n a =3 and all R a Formula a, where n is a hydrogen atom, can be combined with n. a The expression 'a' that is 0 is essentially the same. In expression 'a', when n... a When R is an integer of 2 or greater, multiple R a The functional groups can be the same or different. In formula a, when n b When the value is 0, the benzo[b]fluorene substituent in the embodiment may not be R. b Effective substitution. For example, where n b =3 and all R b Formula a, where n is a hydrogen atom, can be combined with n. b The expression 'a' that is 0 is essentially the same. In expression 'a', when n... b When R is an integer of 2 or greater, multiple R b The functional groups can be the same or different.

[0129] The amino group is linked to the fluorene moiety of the benzo[b]fluorene group. Within the fluorene moiety of the benzo[b]fluorene group, the amino group is linked to the benzene ring, without any additional fusion of the benzene ring with it. Each of the carbazolyl and benzo[b]fluorene groups included in the amine compound may be directly or via a linker to the amino group. In embodiments, the linker connecting each of the carbazolyl and benzo[b]fluorene groups to the amino group may be a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0130] The amine compound used in the embodiments may be a monoamine compound. An amine compound may include an amine group in its compound structure.

[0131] The amine compound used in the embodiments can be represented by Formula 1.

[0132] [Formula 1]

[0133]

[0134] In Formula 1, Ar1 to Ar4 can each independently be a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. In embodiments, Ar1 to Ar4 can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted aryl group with two or more cyclic rings fused together, or a substituted or unsubstituted heteroaryl group with two or more cyclic rings fused together. Ar1 to Ar4 can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group. Ar1 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted o-phenyl, a substituted or unsubstituted meta-phenyl, a substituted or unsubstituted para-phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene. Ar2 can be a substituted or unsubstituted phenyl, a substituted or unsubstituted o-phenyl, a substituted or unsubstituted meta-phenyl, a substituted or unsubstituted para-phenyl, or a substituted or unsubstituted naphthyl. Ar3 and Ar4 can each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted o-phenyl, a substituted or unsubstituted meta-phenyl, a substituted or unsubstituted para-phenyl, or a substituted or unsubstituted naphthyl.

[0135] In Formula 1, L1 and L2 can each independently be a directly linked, substituted, or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. In embodiments, L1 and L2 can each independently be a directly linked, substituted, or unsubstituted phenylene. For example, L1 and L2 can each independently be a directly linked or unsubstituted phenylene. L1 and L2 can each independently be a directly linked, unsubstituted ortho-phenylene, unsubstituted meta-phenylene, or unsubstituted para-phenylene.

[0136] In Formula 1, R1 to R4 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. In Formula 1, the possibility that R1 to R4 are individually bonded to adjacent groups to form a ring can be excluded. For example, in amine compounds represented by Formula 1, the carbazoyl and benzo[b]fluorenyl groups may not form additional rings other than the carbazoyl and benzo[b]fluorenyl moieties. In embodiments, each of R1 to R4 can be a hydrogen atom.

[0137] In Formula 1, "n1" can be an integer selected from 0 to 4, "n2" and "n3" can each be independently an integer selected from 0 to 3, and "n4" can be an integer selected from 0 to 6. In Formula 1, when n1 is 0, the amine compound of the embodiment may not be effectively substituted by R1. For example, Formula 1 where n1 is 4 and all R1 are hydrogen atoms can be substantially the same as Formula 1 where n1 is 0. In Formula 1, when n1 is 2 or a larger integer, the plurality of R1 groups may be the same or different. In Formula 1, when "n2" is 0, the amine compound of the embodiment may not be substituted by R2. For example, Formula 1 where n2 is 3 and all R2 are hydrogen atoms can be substantially the same as Formula 1 where n2 is 0. In Formula 1, when n2 is 2 or a larger integer, the plurality of R2 groups may be the same or different. In Formula 1, when n3 is 0, the amine compound of the embodiment may not be substituted by R3. For example, Formula 1 where n3 is 3 and all R3 are hydrogen atoms can be substantially the same as Formula 1 where n3 is 0. In Formula 1, when n3 is 2 or a larger integer, the plurality of R3 groups can be the same or different. In Formula 1, when n4 is 0, the amine compound of the embodiment may not be effectively substituted by R4. Formula 1 where n4 is 6 and all R4 are hydrogen atoms can be substantially the same as Formula 1 where n4 is 0. In Formula 1, when n4 is 2 or a larger integer, the plurality of R4 groups can be the same or different.

[0138] The amine compounds of the embodiments include carbazole and benzo[b]fluorene as substituents attached to the nitrogen atom of the amine group. Because the amine compounds of the embodiments include carbazole and benzo[b]fluorene as substituents, the intermolecular hole transport capability can be improved through the stability of the compound structure. Therefore, organic electroluminescent devices including the amine compounds of the embodiments as hole transport materials can have increased lifetime due to preventing or reducing damage to the material by excess charge, and can achieve high emission efficiency, low driving voltage, and / or high brightness.

[0139] The amine compound represented by Formula 1 can be represented by any one of Formulas 2-1 to 2-3.

[0140] [Equation 2-1]

[0141]

[0142] [Equation 2-2]

[0143]

[0144] [Equation 2-3]

[0145]

[0146] Formulas 2-1 to 2-3 are the structures of Formula 1, wherein the carbon positions of the benzo[b]fluorene moiety are specified to bond with the central nitrogen atom of the amine compound via L2.

[0147] According to Formula 2-1, in the amine compound of the embodiment, the benzo[b]fluorenyl group can be connected to the central nitrogen atom of the amine group at the carbon 2 position via L2. According to Formula 2-2, in the amine compound of the embodiment, the benzo[b]fluorenyl group can be connected to the central nitrogen atom of the amine group at the carbon 3 position via L2. According to Formula 2-3, in the amine compound of the embodiment, the benzo[b]fluorenyl group can be connected to the central nitrogen atom of the amine group at the carbon 4 position via L2.

[0148] In Equations 2-1 to 2-3, the same interpretations of Ar1, Ar2, Ar3, Ar4, L1, L2, R1, R2, R3, R4, “n1”, “n2”, “n3” and “n4” in Equation 1 can be applied.

[0149] Amine compounds represented by Formula 1 can be represented by Formula 3-1 or Formula 3-2.

[0150] [Equation 3-1]

[0151]

[0152] [Equation 3-2]

[0153]

[0154] Formulas 3-1 and 3-2 are structures of Formula 1, wherein the carbon positions of the carbazolyl moiety are specified to be bonded to the central nitrogen atom of the amine compound via L1.

[0155] According to Formula 3-1, in the amine compound of the embodiment, the carbazoyl group can be connected to the central nitrogen atom of the amine group at the carbon 2 position via L1. According to Formula 3-2, in the amine compound of the embodiment, the carbazoyl group can be connected to the central nitrogen atom of the amine group at the carbon 3 position via L1.

[0156] In Equations 3-1 and 3-2, the same interpretations of Ar1, Ar2, Ar3, Ar4, L1, L2, R1, R2, R3, R4, “n1”, “n2”, “n3” and “n4” in Equation 1 can be applied.

[0157] Amine compounds represented by Formula 1 can be represented by Formula 4-1 or Formula 4-2.

[0158] [Equation 4-1]

[0159]

[0160] [Equation 4-2]

[0161]

[0162] Formulas 4-1 and 4-2 are structures of Formula 1 in which L2 is specified as a particular structure. Formula 4-1 is a directly linked Formula 1. Formula 4-2 is a Formula 1 in which L2 is a substituted or unsubstituted phenylene oxide.

[0163] In Formula 4-2, R5 may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms. In an embodiment, R5 may be a hydrogen atom.

[0164] In Formula 4-2, "n5" can be an integer selected from 0 to 4. In Formula 4-2, when n5 is 0, the amine compound of the embodiment may not be substituted with R5. For example, Formula 4-2 in which n5 is 4 and all R5 are hydrogen atoms can be substantially the same as Formula 4-2 in which n5 is 0. In Formula 4-2, when n5 is 2 or a larger integer, the plurality of R5 groups may be the same or different.

[0165] In Equations 4-1 and 4-2, the same interpretations of Ar1, Ar2, Ar3, Ar4, L1, R1, R2, R3, R4, “n1”, “n2”, “n3” and “n4” in Equation 1 can be applied.

[0166] Amine compounds represented by Formula 1 can be represented by Formula 5-1 or Formula 5-2.

[0167] [Equation 5-1]

[0168]

[0169] [Equation 5-2]

[0170]

[0171] Formulas 5-1 and 5-2 are structures of Formula 1 in which L1 is specified as a particular structure. Formula 5-1 corresponds to Formula 1 in which L1 is directly linked. Formula 5-2 corresponds to Formula 1 in which L1 is a substituted or unsubstituted phenylene oxide.

[0172] In Formula 5-2, R6 may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms. In an embodiment, R6 may be a hydrogen atom.

[0173] In Formula 5-2, "n6" can be an integer selected from 0 to 4. In Formula 5-2, when n6 is 0, the amine compound of the embodiment may not be substituted with R6. For example, Formula 5-2 in which n6 is 4 and all R6 groups are hydrogen atoms can be substantially the same as Formula 5-2 in which n6 is 0. In Formula 5-2, when n6 is 2 or a larger integer, the plurality of R6 groups may be the same or different.

[0174] In some implementations, the same interpretation of Ar1, Ar2, Ar3, Ar4, L2, R1, R2, R3, R4, “n1”, “n2”, “n3” and “n4” of reference Equation 1 can be applied in Equations 5-1 and 5-2.

[0175] The amine compound in the embodiments may be at least one of the compounds represented in compound group 1. In some embodiments, the light-emitting device ED of the embodiments may include at least one amine compound represented in compound group 1 in the hole transport region HTR. In some embodiments, the light-emitting device ED of the embodiments may include at least one amine compound represented in compound group 1 in the hole transport layer HTL.

[0176] [Compound Group 1]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] In some embodiments, the hole transport region (HTR) in the light-emitting device (ED) of the embodiment may further include a suitable material.

[0185] Hole transport region (HTR) may include, for example, phthalocyanine compounds (such as copper phthalocyanine), N 1 N 1 ′-([1,1′-biphenyl]-4,4′-diyl)bis(N 1 -Phenyl-N 4 N 4 -di-m-tolylphenyl-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 (P ANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N′-di(naphthyl-1-yl)-N,N′-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4′-methyldiphenyliodonium [tetra(pentafluorophenyl)borate] and dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN).

[0186] Hole transport regions (HTRs) may include, for example, carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), triphenylamine derivatives (such as 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA)), N,N′-bis(naphthyl-1-yl)-N,N′-diphenyl-benzidine (NPB), 4,4′-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0187] In some implementations, the hole transport region (HTR) may include, for example, 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-carbazole-9-yl)benzene (mDCP), etc.

[0188] The hole transport region HTR may include the aforementioned compound of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0189] The thickness of the hole transport region (HTR) can be approximately to approximately For example, about to approximately The thickness of the hole injection layer (HIL) can be, for example, approximately... to approximately Furthermore, the thickness of the hole transport layer (HTL) can be approximately [missing information]. to approximately For example, the thickness of the electron blocking layer (EBL) can be approximately to approximately When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the above-mentioned ranges, satisfactory hole transport properties can be achieved without a significant increase in driving voltage.

[0190] 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 substantially uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may include at least one of quinone derivatives, metal oxides, metal halides, and cyano-containing compounds, without limitation. For example, non-limiting examples of p-dopers may include quinone derivatives (such as tetracyanoquinone dimethyl (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7′,8,8′-tetracyanoquinone dimethyl (F4-TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide), metal halides (such as CuI and / or RbI), cyano-containing compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile), etc., without limitation.

[0191] 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 hole buffer layer and an electron blocking layer EBL. The hole buffer layer can compensate for the optical resonant distance of the wavelength of light emitted from the emitter layer EML, and thus can increase the light emission efficiency. Materials that can be included in the hole transport region HTR may be included in the hole buffer layer. The electron blocking layer EBL can prevent or reduce the injection of electrons from the electron transport region ETR into the hole transport region HTR. When the hole transport region HTR includes at least one of a hole buffer layer and an electron blocking layer EBL adjacent to the emitter layer EML, the amine compound according to the embodiment may be included in the hole buffer layer and / or the electron blocking layer EBL adjacent to the emitter layer EML.

[0192] The emitter layer EML is provided on the hole transport region HTR. The emitter layer EML may, for example, have approximately to approximately or about to approximately The thickness of the emitter layer (EML) can be a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure having multiple layers formed using multiple different materials.

[0193] In some embodiments, the emitting layer EML of the light-emitting device ED can emit blue light. For example, the emitting layer EML of the light-emitting device ED in the embodiment can emit blue light in the region of about 490 nm or larger. However, the embodiments of this disclosure are not limited to this, and the emitting layer EML can also emit green or red light.

[0194] In some embodiments, the light-emitting device ED may include multiple emitting layers EML. The multiple emitting layers EML may be stacked sequentially. For example, a light-emitting device ED including multiple emitting layers EML may emit white light. An organic electroluminescent device including multiple emitting layers EML may be an organic electroluminescent device with a series structure.

[0195] In the light-emitting device ED of the embodiments, the emitting layer EML may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-benzophenanthrene derivatives, dihydrobenzanthene derivatives, and / or triphenylene derivatives. For example, the emitting layer EML may include anthracene derivatives and / or pyrene derivatives.

[0196] exist Figures 3 to 6 In the light-emitting device ED of the embodiment shown, the emitting layer EML may include a host and a dopant, and the emitting 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.

[0197] [Equation E-1]

[0198]

[0199] In equation E-1, R 31 To R 40 Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or combined with adjacent groups to form a ring. In some embodiments, R 31 To R 40 It can combine with adjacent groups to form saturated or unsaturated hydrocarbon rings.

[0200] In E-1, “c” and “d” can each be an integer selected from 0 to 5 independently.

[0201] Formula E-1 can be represented by any of compounds E1 to E18.

[0202]

[0203]

[0204] In an embodiment, the emitting layer EML may include a compound represented by formula E-2a or formula E-2b. The compound represented by formula E-2a or formula E-2b may be used as a phosphorescent host material.

[0205] [Equation E-2a]

[0206]

[0207] In equation E-2a, L a It can be an arylene group consisting of 6 to 30 cyclic carbon atoms, either directly linked, substituted, or unsubstituted. In some embodiments, in formula E-2a, A1 to A5 can each independently be N or CRi. a To R i Each group may 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 with 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, or may combine with adjacent groups to form a ring. R a To R i Each can independently combine with adjacent groups to form a hydrocarbon ring or a heterocycle including N, O, S, etc. as cyclic atoms.

[0208] In some embodiments, in formula E-2a, two or three selected from A1 to A5 may be N, and the remaining groups may be CR. i .

[0209] [Equation E-2b]

[0210]

[0211] In formula E-2b, Cbz1 and Cbz2 can each be an unsubstituted carbazole group or a carbazole group substituted with aryl groups of 6 to 30 cyclic carbon atoms. b It can be a directly linked, or substituted or unsubstituted aryl group consisting of 6 to 30 cyclic carbon atoms.

[0212] The compound represented by formula E-2a or E-2b may be represented by any of the compounds in compound group E-2. However, the compounds shown in compound group E-2 are for illustrative purposes only, and the compounds represented by formula E-2a or E-2b are not limited to the compounds represented in compound group E-2.

[0213] [Compound Group E-2]

[0214]

[0215]

[0216] The emitter layer EML may further comprise any suitable host material in the art. For example, the emitter layer EML may comprise at least one of bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 2,8-bis(diphenylphospho)dibenzo[b,d]furan (PPF), 4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA), and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi) as the host material. However, embodiments of this disclosure are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq3), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthalene-2-yl)benzene, etc., may be used as the host material. 1,3,5-Tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbene aromatic hydrocarbons (DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphosphoyl)dibenzo[b,d]furan (PPF) and other similar materials can be used as host materials.

[0217] The emitter layer (EML) may include compounds represented by the formula Ma or Mb. Compounds represented by the formula Ma or Mb can be used as phosphorescent dopant materials.

[0218] [Formula Ma]

[0219]

[0220] In formula Ma, Y1 to Y4 and Z1 to Z4 can each independently be CR1 or N, and R1 to R4 can 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 with 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or can be combined with adjacent groups to form a ring. In formula Ma, "m" can be 0 or 1, and "n" can be 2 or 3. In formula Ma, when "m" is 0, "n" is 3, and when "m" is 1, "n" is 2.

[0221] Compounds represented by the formula Ma can be used as red or green phosphorescent dopants.

[0222] The compound represented by formula Ma can be represented by any one of compounds M-a1 to M-a6. However, compounds M-a1 to M-a6 are for illustrative purposes, and the compound represented by formula Ma is not limited to the compounds represented by compounds M-a1 to M-a6.

[0223]

[0224]

[0225] Compounds M-a1 and / or M-a2 can be used as red dopant materials, and compounds M-a3 and / or M-a4 can be used as green dopant materials.

[0226] [Formula Mb]

[0227]

[0228] In formula Mb, Q1 to Q4 can each be independently C or N, and C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring with 5 to 30 cyclic carbon atoms or a substituted or unsubstituted heterocycle with 2 to 30 cyclic carbon atoms. L 21 To L 24 Each can be independently connected directly. The substituted or unsubstituted divalent alkyl group with 1 to 20 carbon atoms, the substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or the substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, wherein “e1” to “e4” may each be 0 or 1 independently. R 31 To R 39 Each of the following groups may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or combined with adjacent groups to form a ring, and "d1" to "d4" may each be independently an integer selected from 0 to 4.

[0229] Compounds represented by the formula Mb can be used as blue or green phosphorescent dopants.

[0230] The compound represented by formula Mb can be represented by any of these compounds. However, these compounds are for illustrative purposes, and the compound represented by formula Mb is not limited to those compounds.

[0231]

[0232] The emitter layer (EML) may include a compound represented by any one of the formulas Fa to Fc. Compounds represented by formulas Fa to Fc can be used as fluorescent dopant materials.

[0233] [Form Fa]

[0234]

[0235] In the formula Fa, the formula is selected from R. a To R j The two values ​​in R can be independently replaced by *-NAr1Ar2. a To R j The remaining unsubstituted groups in *-NAr1Ar2 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 alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. In *-NAr1Ar2, Ar1 and Ar2 can each independently be a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. For example, at least one of Ar1 and Ar2 can be a heteroaryl group including O or S as a cyclic atom.

[0236] [Formula Fb]

[0237]

[0238] In equation Fb, R a and R b Each of Ar1 to Ar4 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms. U and V can each be independently a substituted or unsubstituted hydrocarbon ring with 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle with 2 to 30 cyclic carbon atoms.

[0239] In formula Fb, the number of rings represented by U and V can each be independently 0 or 1. For example, in formula Fb, when the number of U or V is 1, a ring forms a fused ring at the portion specified by U or V, and when the number of U or V is 0, no ring exists at the portion specified by U or V. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with a fluorene core in formula Fb can be a cyclic compound with four rings. In some embodiments, when the number of both U and V is 0 (e.g., simultaneously), the fused ring with a fluorene core in formula Fb can be a cyclic compound with three rings. In some embodiments, when the number of both U and V is 1 (e.g., simultaneously), the fused ring with a fluorene core in formula Fb can be a cyclic compound with five rings.

[0240] [Formula Fc]

[0241]

[0242] In equation Fc, A1 and A2 can each be independently O, S, Se, or NR. m And R m It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. R1 to R 11 Each of the following groups may be independently 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 oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or combined with adjacent groups to form a ring.

[0243] In formula Fc, A1 and A2 can each independently combine with substituents of adjacent rings to form fused rings. For example, when A1 and A2 are each independently NR m In some embodiments, A1 can be combined with R4 or R5 to form a ring. A2 can be combined with R7 or R8 to form a ring.

[0244] In embodiments, the emitter layer EML may include 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), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and / or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and / or its derivatives (e.g., 1,1′-dipyrene, 1,4-dipyrenebenzene, and 1,4-bis(N,N-diphenylamino)pyrene) as suitable dopant materials.

[0245] The emitter layer (EML) may comprise any suitable phosphorescent dopant material. For example, phosphorescent dopant may utilize metal complexes comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). For instance, bis(4,6-difluorophenylpyridine-N,C2')pyridinecarboxylated iridium(III) (FIrpic), bis(2,4-difluorophenylpyridine)-tetra(1-pyrazolyl)boronate iridium(III) (FIr6), and / or octaethylporphyrin platinum (PtOEP) may be used as phosphorescent dopant. However, embodiments of this disclosure are not limited thereto.

[0246] The emitter layer (EML) may include quantum dot materials. The core of the quantum dots may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0247] Group II-VI compounds may be selected from the group consisting of: binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and mixtures thereof; and compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnT. Ternary compounds selected from the group consisting of e, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0248] Group III-VI compounds may include binary compounds (such as In2S3 and / or In2Se3), ternary compounds (such as InGaS3 and / or InGaSe3), and / or one or more optional combinations thereof.

[0249] Group I-III-VI compounds may be selected from: ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; or quaternary compounds (such as AgInGaS2 and / or CuInGaS2).

[0250] Group III-V compounds may be selected from the group consisting of: binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, InAsP, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. In some embodiments, Group III-V compounds may further include Group II metals. For example, InZnP and the like can be selected as group III-II-V compounds.

[0251] Group IV-VI compounds may be selected from the following groups: binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0252] In this case, binary, ternary, or quaternary compounds can exist in the particles at substantially uniform concentrations, or they can exist in the same particle with partially different concentration distributions. In some embodiments, a core / shell structure in which one quantum dot encloses another quantum dot is possible. The core-shell interface can have a concentration gradient in which the concentration of the element present in the shell decreases toward the center (e.g., toward the core).

[0253] In some embodiments, the quantum dot may have the aforementioned core / shell structure, comprising a core containing nanocrystals and a shell enclosing the core. The shell of the quantum dot may serve as a protective layer to prevent or reduce chemical deformation of the core to maintain its semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be single-layered or multi-layered. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases towards the center. Non-limiting examples of the shell of a quantum dot may include metal or non-metal oxides, semiconductor compounds, and / or one or more combinations thereof.

[0254] For example, metal or non-metal oxides may include binary compounds (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO), or ternary compounds (such as MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4), but the embodiments of this disclosure are not limited thereto.

[0255] In addition, the semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiments disclosed herein are not limited thereto.

[0256] Quantum dots may have a full width at half maximum (FWHM) of their emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less. Within these ranges, color purity and / or color reproducibility can be improved. In some embodiments, light emitted through quantum dots is emitted in all directions, and thus optical viewing angle properties can be improved.

[0257] The shape of quantum dots can be any suitable shape in the art, without specific limitations. For example, spherical, conical, multi-armed and / or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplate particle shapes, etc., can be utilized.

[0258] Quantum dots can control or determine the color of the emitted light based on their particle size, and therefore, quantum dots can have one or more suitable emission colors (such as blue, red, and green).

[0259] In some embodiments, the emitter layer EML may include two dopant materials with different lowest triplet excitation energy levels (T1). In the light-emitting device ED of the embodiment, the emitter layer EML may include a body having a first lowest triplet excitation energy level, a first dopant having a second lowest triplet excitation energy level lower than the first lowest triplet excitation energy level, and a second dopant having a third lowest triplet excitation energy level lower than the second lowest triplet excitation energy level.

[0260] In a light-emitting device ED comprising a body in an emitter layer EML, a first dopant, and a second dopant, the first dopant may be a delayed fluorescence dopant, and the second dopant may be a fluorescent dopant.

[0261] For example, when the emitting layer EML of the light-emitting device ED in an embodiment includes multiple dopants, the emitting layer EML may include a first dopant and a second dopant that are different from each other. For example, when the emitting layer EML emits blue light, the emitting layer EML may further include any one selected from the group consisting of: spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene aromatic hydrocarbons (DSA), polyfluorene (PFO) polymers, and poly(p-phenylenevinylene) (PPV) polymers. In some embodiments, metal complexes or organometallic complexes such as (4,6-F2ppy)2Irpic, perylene and / or their derivatives may be used as the second dopant.

[0262] In such Figures 3 to 6 In the light-emitting device ED of the embodiment shown, the electron transport region ETR is provided on the emitter layer EML. The electron transport region ETR may include at least one of the hole blocking layer HBL, the electron transport layer ETL, and the electron injection layer EIL. However, the embodiments of this disclosure are not limited thereto.

[0263] The electronic transport region (ETR) can have a single layer formed using a single material, a single layer formed using multiple different materials, or a multilayer structure with multiple layers formed using multiple different materials.

[0264] 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), or a single-layer structure formed using an electron injection material and an electron transport material. Furthermore, the ETR can have: a single-layer structure with multiple different materials, or a structure of electron transport layer (ETL) / electron injection layer (EIL), or a structure of hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) stacked from the emitter layer (EML), without limitation. The thickness of the ETR can be, for example, approximately [missing information - likely a number]. to approximately

[0265] The electron transport region (ETR) can be formed using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0266] For example, an electron transport layer (ETL) may include a compound represented by formula ET-1.

[0267] [Formula ET-1]

[0268]

[0269] In formula ET-1, at least one of X1 to X3 is N, and the remaining groups are CR. a R a Ar1 to Ar3 can each be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0270] In formula ET-1, L1 to L3 can each be independently an arylene group with 6 to 30 cyclic carbon atoms directly connected, substituted or unsubstituted, or a heteroarylene group with 2 to 30 cyclic carbon atoms.

[0271] The electron transport region (ETR) may include anthracene compounds. However, embodiments of this disclosure are not limited thereto, and the ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzyl-3-yl]benzene, 2,4,6-tris(3′-(pyridyl-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-benzimidazol-2-yl)- 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 hydroxy-N1,O8)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB) and / or one or more mixtures thereof, without limitation.

[0272] In some embodiments, the electron transport region (ETR) may include metal halides (such as LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI), lanthanides (such as Yb), or co-deposited materials of metal halides and lanthanides. For example, the ETR may include KI:Yb, RbI:Yb, etc., as co-deposited materials. In some embodiments, the ETR may utilize metal oxides (such as Li₂O and / or BaO), or lithium 8-hydroxyquinoline (Liq). However, embodiments of this disclosure are not limited thereto. The electron injection layer (EIL) may be formed using a mixture of an electron injection material and an insulating organometallic salt. The insulating organometallic salt may be a material having a band gap of about 4 eV. For example, the insulating organometallic salt may include metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.

[0273] In addition to the materials described above, the electron transport region (ETR) may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, embodiments of this disclosure are not limited thereto.

[0274] The electron transport region ETR may include the aforementioned compound of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0275] When the electron transport region (ETR) includes the electron transport layer (ETL), the thickness of the ETL can be approximately [missing information]. to approximately For example, about to approximately When the thickness of the electron transport layer (ETL) meets the above range, satisfactory electron transport properties can be obtained without a significant increase in driving voltage.

[0276] When the electron transport region (ETR) includes the electron injection layer (EIL), the thickness of the EIL can be approximately [missing information]. to approximately For example, about to approximately When the thickness of the electron injection layer (EIL) meets the above range, satisfactory electron injection properties can be obtained without a significant increase in driving voltage.

[0277] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiments of this disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.

[0278] The second electrode EL2 can be a transmission electrode, a transmission-reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, it can be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.

[0279] When the second electrode EL2 is a transmissive or reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, In, Zn, Sn, one or more of their compounds, one or more of their mixtures (e.g., a mixture of Ag and / or Mg), and / or one or more of their oxides, or materials with a multilayer structure such as LiF / Ca or LiF / Al. The second electrode EL2 may have a multilayer structure, which includes a reflective or transmissive layer formed using the above-mentioned materials and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc.

[0280] In some embodiments, the second electrode EL2 may be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0281] In some embodiments, the light-emitting device ED may further include a buffer layer between the emitter layer EML and the electron transport region ETR. The buffer layer can control the concentration of excitons generated in the emitter layer EML. For example, the buffer layer may include a portion of the material used for the emitter layer EML (e.g., the same material in the emitter layer EML). The buffer layer may include the host material in the material used for the emitter layer EML. Depending on the combination of host and dopant materials included in the emitter layer EML, the lowest triplet excitation energy level of the material used for the buffer layer may be controlled or selected to be the lowest triplet excitation energy level of the second dopant or higher, or the lowest triplet excitation energy level of the second dopant or lower.

[0282] In some embodiments, in the light-emitting device ED of the embodiment, a capping layer CPL may be further disposed on the second electrode EL2. The capping layer CPL may include multiple layers or a single layer.

[0283] In this embodiment, the capping layer CPL can be an organic layer or an inorganic layer. For example, when the capping layer CPL includes an inorganic material, the inorganic material may include alkali metal compounds (such as LiF) and / or alkaline earth metal compounds (such as MgF2), SiON, SiN. x SiO y wait.

[0284] For example, when the capping layer CPL comprises an organic material, the organic material may include 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (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), epoxy resins, and / or acrylates (such as methacrylates), etc. In some embodiments, the capping layer CPL may include at least one of compounds P1 to P5, but embodiments of this disclosure are not limited thereto.

[0285]

[0286]

[0287] In some implementations, the refractive index of the capping layer CPL may be about 1.6 or greater. For example, the refractive index of the capping layer CPL may be about 1.6 or greater relative to light in the wavelength region from about 550 nm to about 660 nm.

[0288] The light-emitting device ED according to the embodiments of the present disclosure may include the amine compound of the embodiments in the hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2, and may exhibit high emission efficiency and long device life characteristics.

[0289] In some embodiments, the amine compound of the embodiment may be included as a material for the light-emitting device ED in an organic layer other than the hole transport region HTR. For example, the light-emitting device ED according to embodiments of the present disclosure may include an amine compound in at least one organic layer disposed between the first electrode EL1 and the second electrode EL2 or in a capping layer CPL disposed on the second electrode EL2.

[0290] The amine compounds of the embodiments include carbazole and benzo[b]fluorenyl groups linked to an amine group, and exhibit improved intermolecular hole transport capabilities compared to conventional compounds; and when used as hole transport materials in organic electroluminescent devices, they can achieve long lifetimes and / or high efficiency in organic electroluminescent devices.

[0291] Figure 7 and Figure 8 This is a cross-sectional view of a display device according to an embodiment. Figure 7 and Figure 8 In the explanation of display devices, the previous explanations will no longer be provided. Figures 1 to 6 The section described in the text will explain the main differences in features.

[0292] refer to Figure 7 According to the embodiments, the display device DD may include: a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

[0293] exist Figure 7 In the embodiment shown, the display panel DP includes a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light-emitting device ED.

[0294] The light-emitting device ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emitter layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emitter layer EML, and a second electrode EL2 disposed on the electron transport region ETR. In some embodiments, Figures 3 to 6 The same structure of the light-emitting device ED can be applied to Figure 7 The structure of the light-emitting device ED shown is illustrated.

[0295] refer to Figure 7 The emitting layer EML can be disposed in the opening portion OH defined in the pixel defining layer PDL. For example, the emitting layer EML provided in each of the light-emitting regions PXA-R, PXA-G, and PXA-B, as defined by the pixel defining layer PDL, can emit light in the same wavelength range. In the display device DD of the embodiment, the emitting layer EML can emit blue light. In some embodiments, the emitting layer EML can be provided as a common layer for all light-emitting regions PXA-R, PXA-G, and PXA-B.

[0296] A light control layer (CCL) may be disposed on a display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be or include quantum dots and / or phosphors. The light converter converts the wavelength of the supplied light and then emits the converted light. For example, the light control layer (CCL) may be a layer including quantum dots or a layer including phosphors.

[0297] The optical control layer (CCL) may include multiple optical control components CCP1, CCP2, and CCP3. The optical control components CCP1, CCP2, and CCP3 may be separated from each other along a first direction DR1.

[0298] refer to Figure 7 The separator pattern BMP can be disposed between the separate light control components CCP1, CCP2, and CCP3, but the embodiments disclosed herein are not limited thereto. Figure 7 In this embodiment, the separator pattern BMP is shown as not overlapping with the light control components CCP1, CCP2 and CCP3, but in some embodiments, at least a portion of the edges of the light control components CCP1, CCP2 and CCP3 may overlap with the separator pattern BMP.

[0299] The light control layer CCL may include: a first light control component CCP1, which includes a first quantum dot QD1 that converts a first color light provided by the light-emitting device ED into a second color light; a second light control component CCP2, which includes a second quantum dot QD2 that converts the first color light into a third color light; and a third light control component CCP3 that transmits the first color light.

[0300] In this embodiment, the first light control component CCP1 can provide red light as the second color light, and the second light control component CCP2 can provide green light as the third color light. The third light control component CCP3 can transmit and provide blue light as the first color light provided from the light-emitting device ED. For example, the first quantum dot QD1 can be a red quantum dot, and the second quantum dot QD2 can be a green quantum dot. The same explanation as above can be applied to quantum dots QD1 and QD2.

[0301] In some embodiments, the optical control layer CCL may further include a scatterer SP. The first optical control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control component CCP3 may include a scatterer SP instead of a quantum dot.

[0302] The scatterer SP can be inorganic particles. For example, the scatterer SP may include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP may include one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may be a mixture of two or more materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0303] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may each comprise a base resin BR1, BR2, and BR3, respectively, dispersing quantum dots QD1 and QD2 and a scatterer SP. In an embodiment, the first light control component CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in the first base resin BR1, the second light control component CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in the second base resin BR2, and the third light control component CCP3 may include the scatterer SP dispersed in the third base resin BR3. The base resins BR1, BR2, and BR3 are the media in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed, and may be composed of various suitable resin compositions, which are generally referred to as binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 may be transparent resins. In the implementation, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.

[0304] The light control layer CCL may include an insulating layer BFL1. The insulating layer BFL1 serves to block or reduce the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The insulating layer BFL1 may be disposed on the light control components CCP1, CCP2, and CCP3 to block or reduce the exposure of the light control components CCP1, CCP2, and CCP3 to moisture / oxygen. In some embodiments, the insulating layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In some embodiments, the insulating layer BFL2 may be provided between the color filter layer CFL and each of the light control components CCP1, CCP2, and CCP3.

[0305] The isolation layers BFL1 and BFL2 may include at least one inorganic layer. For example, the isolation layers BFL1 and BFL2 may be formed by including inorganic materials. For example, the isolation layers BFL1 and BFL2 may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide and / or silicon oxynitride, or a metal thin film that ensures light transmittance. In some embodiments, the isolation layers BFL1 and BFL2 may further include an organic layer. The isolation layers BFL1 and BFL2 may each consist of a single layer or multiple layers.

[0306] In the display device DD of this embodiment, the color filter layer CFL can be disposed on the light control layer CCL. For example, the color filter layer CFL can be disposed directly on the light control layer CCL. In this case, the isolation layer BFL2 may not be provided.

[0307] The color filter layer CFL may include a light-blocking component BM and color filters CF1, CF2, and CF3. The color filter layer CFL may include a first color filter CF1 that transmits a second color of light, a second color filter CF2 that transmits a third color of light, and a third color filter CF3 that transmits a first color of light. For example, the first color filter CF1 may be a red color filter, the second color filter CF2 may be a green color filter, and the third color filter CF3 may be a blue color filter. Each of the color filters CF1, CF2, and CF3 may include a polymeric photosensitive resin and a pigment or dye. The first color filter CF1 may include a red pigment or dye, the second color filter CF2 may include a green pigment or dye, and the third color filter CF3 may include a blue pigment or dye. In some embodiments, the embodiments of this disclosure are not limited thereto, and the third color filter CF3 may not include a pigment or dye. The third color filter CF3 may include a polymeric photosensitive resin and does not include a pigment or dye. The third color filter CF3 may be transparent. The third color filter CF3 may be formed using a transparent photosensitive resin.

[0308] In some embodiments, the first color filter CF1 and the second color filter CF2 may be yellow color filters. The first color filter CF1 and the second color filter CF2 may be provided indistinguishably in a single body.

[0309] The light-blocking component BM can be a black matrix. The light-blocking component BM can be formed from organic or inorganic light-blocking materials comprising black pigments or dyes. The light-blocking component BM prevents or reduces light leakage and defines the boundaries between adjacent color filters CF1, CF2, and CF3. In some embodiments, the light-blocking component BM can be formed as a blue color filter.

[0310] The first to third color filters CF1, CF2 and CF3 can be set to correspond to the red emitting area PXA-R, the green emitting area PXA-G and the blue emitting area PXA-B, respectively.

[0311] The substrate BL can be disposed on the color filter layer CFL. The substrate BL can be a component providing a substrate surface, on which the color filter layer CFL, light control layer CCL, etc., are disposed. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of this disclosure are not limited to these, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, the substrate BL may not be provided.

[0312] Figure 8 This is a cross-sectional view showing a portion of a display device according to an embodiment. In the display device DD-TD of the embodiment, the light-emitting device ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting device ED-BT may include a first electrode EL1 and a second electrode EL2 disposed opposite to each other, and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include an emission layer EML (Emitting Layer, Emulsion ... Figure 7 ), and an emission layer EML is set in between. Figure 7 The hole transport region (HTR) and electron transport region (ETR) of the electron transport region.

[0313] For example, the light-emitting device ED-BT included in the display device DD-TD in the embodiment may be a light-emitting device with a series structure including multiple emission layers EML.

[0314] exist Figure 8 In the embodiments shown, the light emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 can all be blue light. However, the embodiments of this disclosure are not limited to this, and the wavelength regions of the light emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 can be different from each other. For example, a light-emitting device ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 emitting light in different wavelength regions can emit white light.

[0315] Charge generation layers CGL1 and CGL2 may be disposed between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 may include p-type charge generation layers and / or n-type charge generation layers.

[0316] The following description, with reference to embodiments and comparative examples, will explain in more detail the compounds according to the embodiments and the organic electroluminescent devices according to the embodiments of this disclosure. The following examples are for illustrative purposes only and are not intended to aid in understanding this disclosure, nor are they limited thereto.

[0317] [Example]

[0318] 1. Synthesis of amine compounds

[0319] First, an example synthesis method for amine compounds according to embodiments of the present disclosure will be explained by describing the synthesis methods of compounds 1, 2, 3, 17, 21, 27, 33, 34, 35, 49, 53, and 59. The synthesis methods of amine compounds explained below are examples, and the embodiments of the present disclosure are not limited to these embodiments.

[0320] (1) Synthesis of compound 1

[0321] According to the embodiments, amine compound 1 can be synthesized by, for example, the following reaction.

[0322] [Reaction 1-1]

[0323]

[0324] (Synthetic intermediate compound 1-1)

[0325] 2.07 g (10 mmol) of 2-bromonaphthalene was dissolved in 30 mL of THF, and n-butyllithium (4 mL, 2.5 M in hexane) was added at approximately -78 °C. After 1 hour at the same temperature, 2.04 mL (10 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added. After stirring at room temperature for approximately 5 hours, water was added, and the resulting solution was washed three times with diethyl ether (30 mL). The washed diethyl ether layer was dried over MgSO4 and under reduced pressure to obtain the product. The product was then separated by column chromatography to obtain 1.78 g of intermediate compound 1-1. The resulting compound was identified by LC-MS. 16 H 19 BO2: M+254.1.

[0326] [Reaction 1-2]

[0327]

[0328] (Synthetic intermediate compounds 1-2)

[0329] 2.54 g (10.0 mmol) of intermediate compound 1-1, 3.75 g (11.0 mmol) of methyl 5-bromo-2-iodobenzoate, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of a THF / H2O (2 / 1) mixture and stirred at approximately 80 °C for approximately 16 hours. After cooling the reaction solution to room temperature, it was extracted three times with 60 mL of water and 60 mL of diethyl ether. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated. The crude product was separated by silica gel column chromatography to obtain 2.39 g (70% yield) of intermediate compound 1-2. The resulting compound was identified by LC-MS. 18 H 13 BrO2: M+340.0.

[0330] [Reactions 1-3]

[0331]

[0332] (Synthetic intermediate compounds 1-3)

[0333] To a flask containing 3.41 g (10 mmol) of intermediate compounds 1-2 dissolved in THF (20 mL), magnesium phenyl bromide (8.4 mL, 3.0 M in diethyl ether) was slowly added at approximately 0 °C, followed by stirring at room temperature for approximately 2 hours. The reaction solution was extracted three times with 60 mL of water and 60 mL of diethyl ether. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated. The crude product was separated by silica gel column chromatography to obtain 2.79 g (60% yield) of intermediate compounds 1-3. The resulting compounds were identified by LC-MS. 29 H 21 BrO: M+464.1.

[0334] [Reactions 1-4]

[0335]

[0336] (Synthetic intermediate compounds 1-4)

[0337] 4.65 g (10 mmol) of intermediate compounds 1-3 were dissolved in 20 mL of acetic acid / HCl (4 / 1) and stirred at approximately 60 °C for about 6 hours. After cooling the reaction solution to room temperature, 10 g of sodium hydroxide was dissolved in 20 mL of water, and the solution was added to the solution. The mixture was then extracted three times with 60 mL of water and 60 mL of dichloromethane. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated. The crude product was separated by silica gel column chromatography to obtain 3.35 g (75% yield) of intermediate compounds 1-4. The resulting compounds were identified by LC-MS. 29 H 19 Br: M+446.1.

[0338] [Reactions 1-5]

[0339]

[0340] (Synthetic intermediate compounds 1-5)

[0341] 4.46 g (10 mmol) of intermediate compounds 1-4, 1.40 g (15 mmol) of aniline, 0.46 g (0.5 mmol) of tris(dibenzylacetone)dipalladium(O)(Pd2(dba)3), 2.88 g (30 mmol) of sodium tert-butoxide, and 0.24 g (1 mmol) of tritert-butylphosphine (P(t-Bu)3) were dissolved in 60 mL of toluene and stirred at approximately 80 °C for about 3 hours. After cooling the reaction solution to room temperature, 40 mL of water was added, and the mixture was extracted three times with 50 mL of diethyl ether. The resulting organic layers were dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 3.21 g (70% yield) of intermediate compounds 1-5. The resulting compounds were identified by LC-MS. 35 H 25 N:M+459.2.

[0342] [Reactions 1-6]

[0343]

[0344] (Synthetic compound 1)

[0345] 4.59 g (10 mmol) of intermediate compounds 1-5, 3.54 g (11 mmol) of 2-bromo-9-phenyl-9H-carbazole, 0.46 g (0.5 mmol) of tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3), 2.88 g (30 mmol) of sodium tert-butoxide, and 0.24 g (1 mmol) of tritert-butylphosphine (P(t-Bu)3) were dissolved in 60 mL of toluene, and the mixture was stirred at about 80 °C for about 3 hours. After cooling the reaction solution to room temperature, 40 mL of water was added, and the mixture was extracted three times with 50 mL of diethyl ether. The resulting organic layers were dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 4.91 g (70% yield) of compound 1. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0346] (2) Synthesis of compound 2

[0347] According to the embodiments, amine compound 2 can be synthesized, for example, by the following reaction.

[0348] [Reaction 2-1]

[0349]

[0350] (Synthetic intermediate compound 2-1)

[0351] Intermediate compound 2-1 was synthesized using the same synthetic method as intermediate compounds 1-5, except that naphthalene-1-amine was used instead of aniline.

[0352] [Reaction 2-2]

[0353]

[0354] (Synthetic compound 2)

[0355] Compound 2 was synthesized using the same synthetic method as compound 1, except that intermediate compound 2-1 was used instead of intermediate compounds 1-5. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0356] (3) Synthesis of compound 3

[0357] According to the embodiments, amine compound 3 can be synthesized, for example, by the following reaction.

[0358] [Reaction 3-1]

[0359]

[0360] (Synthetic intermediate compound 3-1)

[0361] Intermediate compound 3-1 was synthesized using the same synthetic method as intermediate compounds 1-5, except that naphthalene-2-amine was used instead of aniline.

[0362] [Reaction 3-2]

[0363]

[0364] (Synthetic compound 3)

[0365] Compound 3 was synthesized using the same synthetic method as compound 1, except that intermediate compound 3-1 was used instead of intermediate compounds 1-5. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0366] (4) Synthetic compound 17

[0367] The amine compound 17 according to the embodiments can be synthesized, for example, by the following reaction.

[0368] [Reaction 4-1]

[0369]

[0370] (Synthetic intermediate compound 17-1)

[0371] 2.46 g (10.0 mmol) of 2-bromo-9H-carbazole, 3.11 g (15.0 mmol) of 2-bromonaphthalene, 0.1 g (0.5 mmol) of CuI, 0.09 g (0.5 mmol) of 1,10-phenanthroline, and 4.14 g (30.0 mmol) of K₂CO₃ were dissolved in 60 mL of DMF, and then stirred at approximately 150 °C for approximately 16 hours. After cooling the reaction solution to room temperature, it was extracted three times with 60 mL of water and 60 mL of diethyl ether. The resulting organic layer was dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 2.05 g (55% yield) of intermediate compound 17-1. The resulting compound was identified by LC-MS. 22 H 14 BrN: M+371.0.

[0372] [Reaction 4-2]

[0373]

[0374] (Synthetic compound 17)

[0375] 4.08 g (11 mmol) of intermediate compound 17-1, 4.59 g (10 mmol) of intermediate compound 1-5, 0.46 g (0.5 mmol) of tris(dibenzylacetone)dipalladium(0) (Pd2(dba)3), 2.88 g (30 mmol) of sodium tert-butoxide, and 0.24 g (1 mmol) of tritert-butylphosphine (P(t-Bu)3) were dissolved in 60 mL of toluene and stirred at about 80 °C for about 3 hours. After cooling the reaction solution to room temperature, 40 mL of water was added, and the mixture was extracted three times with 50 mL of diethyl ether. The resulting organic layers were dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 5.26 g (70% yield) of compound 17. The obtained compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0376] (5) Synthetic compound 21

[0377] According to the embodiments, amine compound 21 can be synthesized, for example, by the following reaction.

[0378] [Reaction 5-1]

[0379]

[0380] (Synthetic intermediate compound 21-1)

[0381] 3.22 g (10.0 mmol) of 2-bromo-9-phenyl-9H-carbazole, 1.56 g (10.0 mmol) of (4-chlorophenyl)boric acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of a THF / H2O (2 / 1) mixture, and then stirred at about 80 °C for about 16 hours. After cooling the reaction solution to room temperature, it was extracted three times with 60 mL of water and 60 mL of diethyl ether. The resulting organic layer was dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 2.12 g (60% yield) of intermediate compound 21. The obtained compound was identified by LC-MS. 24 H 16 ClN: M+353.1.

[0382] [Reaction 5-2]

[0383]

[0384] (Synthetic compound 21)

[0385] 3.89 g (11 mmol) of intermediate compound 21-1, 4.59 g (10 mmol) of intermediate compounds 1-5, 0.46 g (0.5 mmol) of tris(dibenzylacetone)dipalladium(O)(Pd2(dba)3), 2.88 g (30 mmol) of sodium tert-butoxide, and 0.24 g (1 mmol) of tritert-butylphosphine (P(t-Bu)3) were dissolved in 60 mL of toluene, and then stirred at about 80 °C for about 3 hours. After cooling the reaction solution to room temperature, 40 mL of water was added, and the mixture was extracted three times with 50 mL of diethyl ether. The resulting organic layers were dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 5.44 g (70% yield) of compound 21. The obtained compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0386] (6) Synthetic compound 27

[0387] The amine compound 27 according to the embodiments can be synthesized, for example, by the following reaction.

[0388] [Reaction 6-1]

[0389]

[0390] (Synthetic intermediate compound 27-1)

[0391] 3.17 g (10.0 mmol) of 2-bromo-4-chloro-1-iodobenzene, 1.72 g (10.0 mmol) of naphth-2-ylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of a THF / H2O (2 / 1) mixture, and then stirred at about 80 °C for about 16 hours. After cooling the reaction solution to room temperature, it was extracted three times with 60 mL of water and 60 mL of diethyl ether. The resulting organic layer was dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to give 1.91 g (60% yield) of intermediate compound 27-1. The obtained compound was identified by LC-MS. 16 H 10 BrCl: M+315.9.

[0392] [Reaction 6-2]

[0393]

[0394] (Synthetic intermediate compound 27)

[0395] 2.61 g (10.0 mmol) of 3-bromobenzophenone, 1.46 g (12.0 mmol) of phenylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.14 g (30.0 mmol) of K2CO3 were dissolved in 60 mL of a THF / H2O (2 / 1) mixture, and then stirred at about 80 °C for about 16 hours. After cooling the reaction solution to room temperature, it was extracted three times with 60 mL of water and 60 mL of diethyl ether. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated. The crude product was then separated by silica gel column chromatography to give 2.19 g (85% yield) of intermediate compound 27-2. The obtained compound was identified by LC-MS. 19 H 14 O:M+258.1.

[0396] [Reaction 6-3]

[0397]

[0398] (Synthetic intermediate compound 27-3)

[0399] 3.18 g (10 mmol) of intermediate compound 27-1 was dissolved in 30 mL of THF, and n-butyllithium (4 mL, 2.5 M in hexane) was added at approximately -78 °C. After 1 hour at the same temperature, 2.58 g of intermediate compound 27-2 was dissolved in 30 mL of THF and then added. After stirring at room temperature for approximately 5 hours, water was added, and the resulting solution was washed three times with diethyl ether (30 mL). The washed diethyl ether layer was dried over MgSO4 and under reduced pressure to obtain the crude product. The crude product was separated by silica gel column chromatography to obtain 3.73 g of intermediate compound 27-3. The resulting compounds were identified by LC-MS. 35 H 25 ClO: M+496.1.

[0400] [Reaction 6-4]

[0401]

[0402] (Synthetic intermediate compound 27-4)

[0403] 4.97 g (10 mmol) of intermediate compound 27-3 was dissolved in 20 mL of acetic acid / HCl (4 / 1) and stirred at approximately 60 °C for about 6 hours. After cooling the reaction solution to room temperature, 10 g of sodium hydroxide was dissolved in 20 mL of water, and the solution was added to the solution. The mixture was then extracted three times with 60 mL of water and 60 mL of dichloromethane. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated. The crude product was separated by silica gel column chromatography to obtain 3.35 g (70% yield) of intermediate compound 27-4. The resulting compound was identified by LC-MS. 35 H 23 Clr: M+478.1.

[0404] [Reaction 6-5]

[0405]

[0406] (Synthetic intermediate compound 27-5)

[0407] 4.79 g (10 mmol) of intermediate compound 27-4, 1.40 g (15 mmol) of aniline, 0.46 g (0.5 mmol) of tris(dibenzylacetone)dipalladium(O)(Pd2(dba)3), 2.88 g (30 mmol) of sodium tert-butoxide, and 0.24 g (1 mmol) of tritert-butylphosphine (P(t-Bu)3) were dissolved in 60 mL of toluene and stirred at about 80 °C for about 3 hours. After cooling the reaction solution to room temperature, 40 mL of water was added, and the mixture was extracted three times with 50 mL of diethyl ether. The resulting organic layers were dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 3.51 g (77% yield) of intermediate compound 27-5. The resulting compound was identified by LC-MS. 35 H 25 N:M+535.2.

[0408] [Reaction 6-6]

[0409]

[0410] (Compound 27)

[0411] 5.35 g (10 mmol) of intermediate compound 27-5, 3.54 g (11 mmol) of 2-bromo-9-phenyl-9H-carbazole, 0.46 g (0.5 mmol) of tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3), 2.88 g (30 mmol) of sodium tert-butoxide, and 0.24 g (1 mmol) of tritert-butylphosphine (P(t-Bu)3) were dissolved in 60 mL of toluene, and the mixture was stirred at about 80 °C for about 3 hours. After cooling the reaction solution to room temperature, 40 mL of water was added, and the mixture was extracted three times with 50 mL of diethyl ether. The resulting organic layers were dried over magnesium sulfate, the solvent was evaporated, and the crude product was separated by silica gel column chromatography to obtain 5.44 g (70% yield) of compound 27. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0412] (7) Synthesis of compound 33

[0413] The amine compound 33 according to the embodiments can be synthesized, for example, by the following reaction.

[0414] [Reaction 7]

[0415]

[0416] (Synthetic compound 33)

[0417] Compound 33 was synthesized using the same synthetic method as compound 1, except that 3-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-9-phenyl-9H-carbazole. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0418] (8) Synthesize compound 34

[0419] The amine compound 34 according to the embodiments can be synthesized, for example, by the following reaction.

[0420] [Reaction 8]

[0421]

[0422] (Synthetic compound 34)

[0423] Compound 34 was synthesized using the same synthetic method as compound 33, except that intermediate compound 2-1 was used instead of intermediate compounds 1-5. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0424] (9) Synthesize compound 35

[0425] The amine compound 35 according to the embodiments can be synthesized, for example, by the following reaction.

[0426] [Reaction 9]

[0427]

[0428] (Synthetic compound 35)

[0429] Compound 35 was synthesized using the same synthetic method as compound 33, except that intermediate compound 3-1 was used instead of intermediate compounds 1-5. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0430] (10) Synthetic compound 49

[0431] The amine compound 49 according to the embodiments can be synthesized, for example, by the following reaction.

[0432] [Reaction 10-1]

[0433]

[0434] (Synthetic intermediate compound 49-1)

[0435] Intermediate compound 49-1 was synthesized using the same synthetic method as intermediate compound 17-1, except that 3-bromo-9H-carbazole was used instead of 2-bromo-9H-carbazole. The resulting compound was identified by LC-MS. 22 H 14 BrN: M+371.0.

[0436] [Reaction 10-2]

[0437]

[0438] (Compound 49)

[0439] Compound 49 was synthesized using the same synthetic method as compound 17, except that intermediate compound 49-1 was used instead of intermediate compound 17-1. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0440] (11) Synthesis of compound 53

[0441] The amine compound 53 according to the embodiments can be synthesized, for example, by the following reaction.

[0442] [Reaction 11-1]

[0443]

[0444] (Synthetic intermediate compound 53-1)

[0445] Intermediate compound 53-1 was synthesized using the same synthetic method as intermediate compound 21-1, except that 3-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-9-phenyl-9H-carbazole. The resulting compound was identified by LC-MS. 24 H 16 ClN: M+353.1.

[0446] [Reaction 11-2]

[0447]

[0448] (Synthetic compound 53)

[0449] Compound 53 was synthesized using the same synthetic method as compound 21, except that intermediate compound 53-1 was used instead of intermediate compound 21-1. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0450] (12) Synthetic compound 59

[0451] The amine compound 59 according to the embodiments can be synthesized, for example, by the following reaction.

[0452] [Reaction 12]

[0453]

[0454] (Synthetic compound 59)

[0455] Compound 59 was synthesized using the same synthetic method as compound 27, except that 3-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-9-phenyl-9H-carbazole. The resulting compound was analyzed by MS / FAB and... 1 Identification was performed using H NMR.

[0456] Table 1 below shows the compounds of the examples. 1 H NMR and MS / FAB results.

[0457] [Table 1]

[0458]

[0459]

[0460] 2. Fabrication and evaluation of organic electroluminescent devices including amine compounds

[0461] (Manufacturing organic electroluminescent devices)

[0462] The organic electroluminescent devices of the embodiments comprising the amine compounds of the embodiments in the hole transport layer are manufactured by the method described below. The organic electroluminescent devices of Examples 1 to 12 are manufactured using amine compounds of compounds 1, 2, 3, 17, 21, 27, 33, 34, 35, 49, 53, and 59 (which are the compounds of the above examples) as materials for the hole transport layer. Comparative Examples 1 to 6 correspond to organic electroluminescent devices manufactured using comparative compounds C1 to C6 as materials for the hole transport layer.

[0463] As the first electrode, Corning's 15Ω / cm 2 The ITO glass substrate was cut to a size of 50mm x 50mm x 0.7mm and rinsed with isopropanol and pure water, exposed to ultrasound for about 5 minutes and UV for about 30 minutes, and then treated with ozone. Afterwards, 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA) was deposited in a vacuum to approximately [size missing]. The thickness is such that a hole injection layer is formed, and the example compound or comparative compound is deposited in a vacuum to approximately [amount missing]. The thickness is sufficient to form a hole transport layer.

[0464] On the hole transport layer, the blue fluorescent host 9,10-bis(naphthyl-2-yl)anthracene (DNA) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) were co-deposited at a ratio of 98:2 (e.g., by weight) to form a layer with a thickness of approximately The emission layer.

[0465] On the emitter layer, a layer with a thickness of approximately [thickness missing] is formed using tris(8-hydroxyquinoline)aluminum (Alq3). An electron transport layer is formed, and then LiF is deposited to approximately [amount missing]. To form an electron injection layer. On the electron injection layer, an aluminum (Al) layer with a thickness of approximately... The second electrode.

[0466] Compounds for manufacturing organic electroluminescent devices of the examples and comparative examples are shown.

[0467]

[0468]

[0469] (Evaluating the properties of organic electroluminescent devices)

[0470] Table 2 shows the evaluation results of the organic electroluminescent devices of Examples 1 to 12 and Comparative Examples 1 to 6. Table 2 compares and shows the driving voltage, brightness, emission efficiency, and half-life of the organic electroluminescent devices thus manufactured.

[0471] In the evaluation results of the embodiments and comparative examples shown in Table 2, voltage and current density were measured using the V7000 OLED IVL testing system (Polaronix). The values ​​were approximately 50 mA / cm². 2 The emission efficiency was measured at a current density of approximately 100 mA / cm². 2 The half-life value was measured at a current density.

[0472] [Table 2]

[0473]

[0474]

[0475] Referring to the results in Table 2, it can be observed that, compared with the comparative examples, each of the embodiments of the organic electroluminescent device utilizing the amine compound according to the embodiments of this disclosure as the material for the hole transport layer emits the same blue light and exhibits low driving voltage values ​​and relatively high brightness, emission efficiency, and device lifetime (lifetime). In the case of comparative compound C1, carbazole and benzo[b]fluorene groups substituted at the amine group are not included, and when applied to an organic electroluminescent device, compared with the example compounds, the driving voltage increases, brightness and emission efficiency decrease, and the half-life decreases. In the cases of comparative compounds C2 and C3, carbazole and benzo[c]fluorene groups substituted at the amine group are included, but comparative compound C2 includes benzo[a]fluorene and comparative compound C3 includes benzo[c]fluorene, and when applied to an organic electroluminescent device, compared with the example compounds, they exhibit high driving voltage, low brightness and emission efficiency, and short half-life. In the cases of comparative compounds C4 and C6, only one of carbazoyl and benzo[b]fluoreneyl is included, and when applied to an organic electroluminescent device, it exhibits a high driving voltage, low brightness and emission efficiency, and a short half-life compared to the example compounds. In the case of comparative compound C5, both (e.g., simultaneously) carbazoyl and benzo[b]fluoreneyl are included, but the benzo[b]fluoreneyl is substituted at the nitrogen atom of the carbazoyl group instead of at the amino group, and it can be confirmed that when applied to an organic electroluminescent device, it exhibits a high driving voltage, low brightness and emission efficiency, and a short half-life compared to the example compounds.

[0476] In the case of the compound in the examples, among the aromatic amine hole transport materials, the amine compound of the embodiments exhibits high stability due to the carbazole group and benzo[b]fluorene group substituted at the amino group. Therefore, when compared with comparative compounds C1 to C5, higher hole transport properties can be achieved, and thus, when compared with the organic electroluminescent device of the comparative examples, the organic electroluminescent device of the embodiments can exhibit improved emission efficiency and longer lifetime. For example, the organic electroluminescent device of the embodiments includes the amine compound of the embodiments as a hole transport material, and can achieve high emission efficiency and / or long lifetime in the blue wavelength region.

[0477] The organic electroluminescent devices of the embodiments can exhibit improved device properties such as low driving voltage, high efficiency, and / or long lifespan.

[0478] The amine compound in the embodiment is included in the hole transport region of the organic electroluminescent device and can help increase the efficiency and lifespan (lifetime) of the organic electroluminescent device.

[0479] As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation, not as terms of degree, and are intended to describe the inherent biases of measured or calculated values ​​that would be recognized by one of ordinary skill in the art. As used herein, “about” or “about” includes stated values ​​and means within an acceptable range of deviation for a particular value, determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.

[0480] Any numerical range described herein is intended to include all subranges containing the same numerical precision within the stated range. For example, the range “1.0 to 10.0” is intended to include all subranges between (and including) the minimum value of 1.0 and the maximum value of 10.0, i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly describe any subranges contained within the range expressly described herein.

[0481] Although embodiments of the present disclosure have been described, it is to be understood that the present disclosure should not be limited to these embodiments, and various appropriate changes and modifications can be made by those skilled in the art within the spirit and scope of the present disclosure as described in the appended claims and their equivalents.

Claims

1. An amine compound represented by Formula 1: [Formula 1] In Equation 1, Ar1 to Ar4 are each independently an unsubstituted phenyl, an unsubstituted biphenyl, or an unsubstituted naphthyl group. L1 and L2 are each independently an arylene group consisting of 6 to 30 cyclic carbon atoms that are directly linked or unsubstituted. R1 to R4 are each independently a hydrogen atom, a deuterium atom, or a halogen atom. n1 is an integer selected from 0 to 4. n2 and n3 are each independent integers selected from 0 to 3, and n4 is an integer selected from 0 to 6.

2. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by any one of formulas 2-1 to 2-3: [Equation 2-1] [Equation 2-2] [Equation 2-3] and In equations 2-1 to 2-3, Ar1, Ar2, Ar3, Ar4, L1, L2, R1, R2, R3, R4, n1, n2, n3, and n4 are each independently identical to those defined in Equation 1.

3. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by formula 3-1 or formula 3-2: [Equation 3-1] [Equation 3-2] and In Equations 3-1 and 3-2, Ar1, Ar2, Ar3, Ar4, L1, L2, R1, R2, R3, R4, n1, n2, n3, and n4 are each independently identical to those defined in Equation 1.

4. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by formula 4-1 or formula 4-2: [Equation 4-1] [Equation 4-2] and In equations 4-1 and 4-2, R5 is a hydrogen atom. n5 is an integer selected from 0 to 4, and Ar1, Ar2, Ar3, Ar4, L1, R1, R2, R3, R4, n1, n2, n3, and n4 are each independently identical to those defined in Equation 1.

5. The amine compound of claim 1, wherein the amine compound represented by formula 1 is represented by formula 5-1 or formula 5-2: [Equation 5-1] [Equation 5-2] and In Equations 5-1 and 5-2, R6 is a hydrogen atom. n6 is an integer selected from 0 to 4, and Ar1, Ar2, Ar3, Ar4, L2, R1, R2, R3, R4, n1, n2, n3, and n4 are each independently identical to those defined in Equation 1.

6. The amine compound of claim 1, wherein R1 to R4 are hydrogen atoms.

7. The amine compound of claim 1, wherein the amine compound represented by formula 1 is a monoamine compound.

8. The amine compound of claim 1, wherein the amine compound is at least one selected from the compounds represented in group 1: [Compound Group 1] 9. An organic electroluminescent device, comprising: First electrode; The second electrode facing the first electrode; as well as Multiple organic layers between the first electrode and the second electrode At least one of the plurality of organic layers comprises an amine compound according to any one of claims 1 to 8.

10. The organic electroluminescent device of claim 9, wherein the plurality of organic layers comprises: Hole transport region on the first electrode; The emission layer on the hole transport region; and In the electron transport region on the emission layer, and The hole transport region therein includes the amine compound.

11. The organic electroluminescent device of claim 10, wherein the hole transport region comprises: Hole injection layer on the first electrode; and A hole transport layer on the hole injection layer, and The hole transport layer therein includes the amine compound.

12. The organic electroluminescent device of claim 10, wherein the hole transport region comprises a plurality of organic hole transport layers. The organic hole transport layer adjacent to the emitter layer in the plurality of organic hole transport layers includes the amine compound.

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