Organic electroluminescent device and amine compound for organic electroluminescent device

Abstract

To provide: an organic electroluminescent element with improved luminous efficiency and element life; and an amine compound capable of improving the luminous efficiency and element life of the organic electroluminescent element.SOLUTION: An amine compound is represented by the following chemical formula 1.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an organic electroluminescent device and an amine compound used therein, and more particularly to an amine compound used as a light-emitting material and an organic electroluminescent device containing the same. [Background technology]

[0002] Recently, organic electroluminescence displays (OLEDs) have been actively developed as image display devices. Unlike liquid crystal displays, OLEDs are so-called self-luminous displays that realize display by recombining holes and electrons injected from a first electrode and a second electrode in a light-emitting layer to cause a light-emitting material containing an organic compound in the light-emitting layer to emit light.

[0003] In order to apply organic electroluminescent devices to display devices, there is a demand for lower driving voltages, higher luminous efficiency, and longer life for the organic electroluminescent devices, and there is a continuous demand for the development of materials for organic electroluminescent devices that can stably achieve these demands.

[0004] Furthermore, in order to realize highly efficient organic electroluminescent devices, development of materials for the hole transport layer is underway. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2003-004231 A [Patent Document 2] Korean Patent No. 10-1973030 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide an organic electroluminescent device having improved luminous efficiency and device life.

[0007] Another object of the present invention is to provide an amine compound capable of improving the luminous efficiency and device life of an organic electroluminescent device. [Means for solving the problem]

[0008] According to an embodiment of the present invention, an organic electroluminescent device includes a first electrode, a second electrode facing the first electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes an amine compound, the amine compound includes an amino group and a tetraphenylethenyl group substituted on the amino group, and the amino group is bonded to one phenyl group included in the tetraphenylethenyl group.

[0009] The tetraphenylethenyl group may be attached to the amino group via a linker or directly.

[0010] The organic layer may include a hole transport region disposed on the first electrode, a light emitting layer disposed on the hole transport region, and an electron transport region disposed on the light emitting layer. The hole transport region may include the amine compound.

[0011] The hole transport region may include a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer. The hole transport region may include the amine compound.

[0012] The hole transport region includes a plurality of organic layers, and an organic layer adjacent to the light emitting layer among the plurality of organic layers may include the amine compound.

[0013] According to an embodiment of the present invention, there is provided an organic electroluminescent device including a first electrode, a second electrode facing the first electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes an amine compound represented by Chemical Formula 1 below: [ka] ...(chemical formula 1) In the above formula 1, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; L 1 is a single bond (direct linkage), a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; R 1 ~R 4 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms; 1 ~n 3 are each independently an integer of 0 to 5, 4 is an integer between 0 and 4 inclusive.

[0014] The amine compound represented by Chemical Formula 1 may be a monoamine compound.

[0015] The amine compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 2-1 or 2-2. [ka] ...(chemical formula 2-1) [ka] ...(chemical formula 2-2) In the above Chemical Formula 2-1 and Chemical Formula 2-2, R 5is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, 5 is an integer of 0 to 4. In Chemical Formula 2-1 and Chemical Formula 2-2, Ar 1 and Ar 2 , R 1 ~R 4 , and n 1 ~n 4 The same explanation as defined in Chemical Formula 1 applies to the above.

[0016] The amine compound represented by Chemical Formula 1 may be represented by any one of Chemical Formulas 3-1 to 3-3 below. [ka] ...(chemical formula 3-1) [ka] ...(chemical formula 3-2) [ka] ...(chemical formula 3-3) In the above Chemical Formula 3-1 to Chemical Formula 3-3, Ar 1 and Ar 2 , R 1 ~R 4 , and n 1~ n 4 The same explanation as defined in Chemical Formula 1 applies to the above.

[0017] The Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0018] The Ar 1 and Ar 2 may be different from each other.

[0019] The Ar 1 is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, 2 may be a substituted or unsubstituted aryl group in which two or more rings are fused, or a substituted or unsubstituted heteroaryl group in which two or more rings are fused.

[0020] The amine compound according to one embodiment of the present invention is represented by Formula 1. Effect of the Invention

[0021] The organic electroluminescent device according to one embodiment exhibits improved device characteristics, such as low driving voltage, high efficiency, and long life.

[0022] The amine compound according to an embodiment is contained in a hole transport region of an organic electroluminescent device, and contributes to improving the efficiency and extending the life of the organic electroluminescent device. [Brief description of the drawings]

[0023] [Figure 1] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. [Diagram 2] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. [Diagram 3] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. [Figure 4] 1 is a cross-sectional view illustrating an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0024] Since the present invention can be modified in various ways and can have various forms, specific embodiments are illustrated in the drawings and described in detail in the text, but it is not intended to limit the present invention to the specific disclosed forms, but it should be understood that the present invention includes all modifications, equivalents, and alternatives included in the spirit and technical scope of the present invention.

[0025] As used herein, when a component (or region, layer, portion, etc.) is referred to as being "on," "coupled," or "bonded" to another component, it means that it may be directly disposed, coupled, or bonded to the other component, or that a third component may be disposed therebetween.

[0026] The same reference numerals refer to the same components. Also, in the drawings, thicknesses, proportions and dimensions of the components are exaggerated for the purpose of effectively explaining the technical contents.

[0027] "And / or" includes all combinations of one or more of the associated construct.

[0028] Terms such as first and second are used to describe various components, but the components are not limited to the terms. The terms are used only to distinguish one structural element from another. For example, a first component may be referred to as a second component, and similarly, a second component may be referred to as a first component, without departing from the scope of the present invention. A singular expression includes a plural expression, unless the context clearly indicates otherwise.

[0029] In addition, terms such as "under", "below", "up" and "above" are used to describe the relationship between components shown in the drawings. The terms are relative concepts and are described based on the directions shown in the drawings.

[0030] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Furthermore, terms such as those defined in commonly used dictionaries should be interpreted to have a meaning consistent with the meaning in the context of the relevant art, and are expressly defined herein, unless interpreted in an idealized or overly formal sense.

[0031] It should be understood that the terms "comprise" or "have" specify the presence of any feature, numeral, step, operation, component, part, or combination thereof described hereinabove in the specification, but do not preclude the presence or additional possibility of one or more other features, numerals, steps, operations, components, parts, or combinations thereof.

[0032] In this specification, "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boryl group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. Each of the above-mentioned exemplary substituents may be substituted or unsubstituted. For example, a biphenylyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0033] In this specification, "adjacent groups bond together to form a ring" means adjacent groups bond together to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The ring formed by bonding adjacent groups together is a monocycle or polycycle. In addition, the ring formed by bonding together may be bonded to another ring to form a spiro structure.

[0034] In the present specification, the term "adjacent group" refers to a substituent substituted on an atom directly bonded to the atom on which the corresponding substituent is substituted, another substituent substituted on an atom on which the corresponding substituent is substituted, or a substituent structurally most adjacent to the corresponding substituent. For example, two methyl groups in 1,2-dimethylbenzene are interpreted as "adjacent groups" to each other, and two ethyl groups in 1,1-diethylcyclopentene are interpreted as "adjacent groups" to each other.

[0035] As used herein, a direct bond is a single bond. In this specification, examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0036] In this specification, an alkyl group is linear, branched, or cyclic. The number of carbon atoms in an alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl ...3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, i-pentyl, Hexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl n-butyldecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl , n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, 2-hexylicosyl group, 2-octylicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group, but are not limited to these.

[0037] In this specification, the term "hydrocarbon ring" includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The term "heterocycle" includes an aliphatic heterocycle and an aromatic heterocycle. The hydrocarbon ring and the heterocycle may be monocyclic or polycyclic.

[0038] In the present specification, the term "hydrocarbon ring group" refers to any functional group or substituent derived from an aliphatic hydrocarbon ring, or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of ring carbon atoms in the hydrocarbon ring group is 5 to 60.

[0039] In this specification, a heterocyclic group is any functional group or substituent derived from a heterocycle containing at least one heteroatom as a ring-forming atom. The heterocyclic group contains one or more of B, O, N, P, Si, and S as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept including a heteroaryl group. The number of ring-forming carbon atoms of the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.

[0040] In this specification, the aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group is a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group is 6 to 30, 6 to 20, or 6 to 15. Examples of the aryl group include, but are not limited to, a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenylyl group, a terphenylyl group, a quaterphenylyl group, a quinquephenylyl group, a sexiphenylyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthenyl group, and a chrysenyl group.

[0041] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of fluorenyl groups that may be substituted include, but are not limited to, the following: [ka]

[0042] In this specification, the heteroaryl group includes one or more of B, O, N, P, Si, and S as a heteroatom. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group is a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms of the heteroaryl group is 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl group include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxanyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, an N-aryl group, Examples of such an alkyl group include, but are not limited to, an alkylcarbazolyl group, an N-heteroarylcarbazolyl group, an N-alkylcarbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a thienothiophenyl group, a benzofuranyl group, a phenanthrolinyl group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a phenothiazinyl group, a dibenzosilolyl group, and a dibenzofuranyl group.

[0043] In this specification, the above explanation of the aryl group applies to the arylene group, except that the arylene group is a divalent group. The above explanation of the heteroaryl group applies to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0044] In this specification, the alkenyl group is a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of the alkenyl group include, but are not limited to, a vinyl group, a 1-butenyl group, a 1-pentenyl group, a 1,3-butadienylaryl group, a styrenyl group, and a styrylvinyl group.

[0045] In this specification, the silyl group includes an alkylsilyl group and an arylsilyl group. Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.

[0046] In this specification, the boryl group includes an alkylboryl group and an arylboryl group. Examples of the boryl group include, but are not limited to, a trimethylboryl group, a triethylboryl group, a t-butyldimethylboryl group, a triphenylboryl group, a diphenylboryl group, and a phenylboryl group.

[0047] In this specification, the number of carbon atoms of the amino group is not particularly limited, but is from 1 to 30. The amino group includes an alkylamino group and an arylamino group. Examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamino group, a 9-methyl-anthracenylamino group, and a triphenylamino group.

[0048] Hereinafter, an organic electroluminescent device according to an embodiment of the present invention will be described with reference to the drawings.

[0049] 1 to 4 are cross-sectional views each showing a schematic configuration of an organic electroluminescent device according to an embodiment of the present invention. Referring to FIG. 1 to FIG. 4, in an organic electroluminescent device 10 according to an embodiment of the present invention, a first electrode EL1 and a second electrode EL2 are disposed opposite each other, and a plurality of organic layers are disposed between the first electrode EL1 and the second electrode EL2. The plurality of organic layers include a hole transport region HTR, an emission layer EML, and an electron transport region ETR. That is, the organic electroluminescent device 10 according to an embodiment of the present invention includes a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2, which are sequentially stacked. A capping layer CPL may be further disposed on the second electrode EL2.

[0050] The organic electroluminescent device 10 according to an embodiment includes an amine compound according to an embodiment described below in at least one organic layer among a plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2. For example, the organic electroluminescent device 10 according to an embodiment includes an amine compound according to an embodiment described below in an emission layer EML disposed between the first electrode EL1 and the second electrode EL2. However, the embodiment of the present invention is not limited thereto. The organic electroluminescent device 10 according to an embodiment may include an amine compound according to an embodiment described below in at least one organic layer included in the hole transport region HTR and the electron transport region ETR, which are a plurality of organic layers disposed between the first electrode EL1 and the second electrode EL2, in addition to the emission layer EML, or may include an amine compound according to an embodiment described below in a capping layer CPL disposed on the second electrode EL2.

[0051] Meanwhile, Fig. 2 is a cross-sectional view of an organic electroluminescent device 10 according to an embodiment, in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL, unlike Fig. 1. Fig. 3 is a cross-sectional view of an organic electroluminescent device 10 according to an embodiment, in which 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, unlike Fig. 1. Fig. 4 is a cross-sectional view of an organic electroluminescent device 10 according to an embodiment, in which a capping layer CPL is disposed on the second electrode EL2, unlike Fig. 2.

[0052] Next, in the description of the organic electroluminescent device 10 according to one embodiment, it is described that the hole transport region HTR contains an amine compound according to one embodiment described later, but the embodiment of the present invention is not limited thereto, and the amine compound according to one embodiment described later may be contained in the emission layer EML or the electron transport region ETR.

[0053] The first electrode EL1 has conductivity. The first electrode EL1 is made of a metal alloy or a conductive compound. The first electrode EL1 is an anode. Also, the first electrode EL1 is a pixel electrode. The first electrode EL1 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, the first electrode EL1 includes a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode EL1 is a semi-transmissive electrode or a reflective electrode, the first electrode EL1 includes Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, or a compound or mixture thereof (for example, an alloy of Ag and Mg). The first electrode EL1 may have a multi-layer structure including a reflective film or semi-transparent film made of the above-mentioned material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a triple-layer structure of ITO / Ag / ITO, but is not limited thereto. The thickness of the first electrode EL1 is about 100 nm to about 1000 nm, for example, about 100 nm to about 300 nm.

[0054] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR includes at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 5 nm to about 150 nm.

[0055] The hole transport region HTR may have a single layer of a single material, a single layer of a plurality of different materials, or a multi-layer structure having a plurality of layers of a plurality of different materials.

[0056] 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 a single layer structure of a hole injection material and a hole transport material. The hole transport region HTR may have a single layer structure of a plurality of different materials, or a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer (not shown), a hole injection layer HIL / hole buffer layer (not shown), a hole transport layer HTL / hole buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, which are stacked in order from the first electrode EL1, but the present embodiment is not limited thereto.

[0057] The hole transport region HTR can be formed using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and Laser Induced Thermal Imaging (LITI).

[0058] In the organic electroluminescent device 10 of one embodiment, the hole transport region HTR includes an amine compound according to one embodiment.

[0059] An amine compound according to an embodiment includes a tetraphenylethenyl group as a substituent. An amine compound according to an embodiment includes an amino group and includes a tetraphenylethenyl group substituted with the amino group. The tetraphenylethenyl group has a structure in which two phenyl groups are substituted on each of two carbons of ethane at the center. The amino group has a structure in which one phenyl group included in the tetraphenylethenyl group is bonded to the amino group. The tetraphenylethenyl group included in the amine compound is bonded directly to the amino group or via a linker.

[0060] In one embodiment, the amine compound is a monoamine compound, which contains one amino group within the compound structure.

[0061] The amine compound according to one embodiment is represented by the following chemical formula 1. [ka] ...(chemical formula 1)

[0062] In Chemical Formula 1, Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group. 1 and Ar 2 may be different from each other. 1 is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, Ar 2 may be a substituted or unsubstituted aryl group having two or more fused rings, or a substituted or unsubstituted heteroaryl group having two or more fused rings. An example of the substituted or unsubstituted aryl group having two or more fused rings may be a substituted or unsubstituted fluorenyl group. An example of the substituted or unsubstituted heteroaryl group having two or more fused rings may be a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group. In one embodiment, Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted naphthyl group; Ar 2 may be a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0063] In Chemical Formula 1, L 1is a single bond, a substituted or unsubstituted arylene group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having from 2 to 30 ring carbon atoms. 1 is a single bond or a substituted or unsubstituted phenylene group. For example, L 1 may be a single bond or an unsubstituted phenylene group.

[0064] In Chemical Formula 1, R 1 ~R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms. 1~ R 4 Each of them is not bonded to the adjacent group to form a ring. That is, in the amine compound represented by Chemical Formula 1, the tetraphenylethenyl moiety does not form any further rings other than the four benzene rings. In one embodiment, R 1 ~R 4 may each be a hydrogen atom.

[0065] In Chemical Formula 1, n 1 ~n 3 are each independently an integer of 0 to 5, 4 is an integer of 0 to 4. In Chemical Formula 1, n 1 is 0, the tetraphenylethenyl group in the amine compound according to one embodiment is R 1 In Chemical Formula 1, n 1 is 5 and R 1 If both are hydrogen atoms, then in formula 1, n 1 is 0. In Chemical Formula 1, n 1 If is 2 or more, multiple R 1 are the same as or different from each other. 2 is 0, the tetraphenylethenyl group in the amine compound according to one embodiment is R 2In Chemical Formula 1, n 2 is 5 and R 2 If both are hydrogen atoms, then in formula 1, n 2 is 0. In Chemical Formula 1, n 2 If is 2 or more, multiple R 2 are the same as or different from each other. 3 is 0, the tetraphenylethenyl group in the amine compound according to one embodiment is R 3 In Chemical Formula 1, n 3 is 5 and R 3 If both are hydrogen atoms, then in formula 1, n 3 is 0. In Chemical Formula 1, n 3 If is 2 or more, multiple R 3 are the same as or different from each other. 4 is 0, the tetraphenylethenyl group in the amine compound according to one embodiment is R 4 In Chemical Formula 1, n 4 is 4 and R 4 If both are hydrogen atoms, then in formula 1, n 4 is 0. In Chemical Formula 1, n 4 If is 2 or more, multiple R 4 are the same as each other or different from each other.

[0066] The amine compound according to an embodiment includes a tetraphenylethenyl group as a substituent bonded to the amine. More specifically, the amine compound includes a tetraphenylethenyl group having no additional ring as a substituent. The amine compound according to an embodiment includes a tetraphenylethenyl group as a substituent, and thus the compound structure is stabilized, thereby improving the intermolecular hole transport ability. Thus, an organic electroluminescent device including the amine compound according to an embodiment as a hole transport material has a long life because damage to the material caused by excess charge is prevented, and further has high luminous efficiency, low driving voltage, and high brightness.

[0067] The amine compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2-1 or 2-2. [ka] ...(chemical formula 2-1) [ka] ...(chemical formula 2-2)

[0068] Chemical formula 2-1 is the same as that of Chemical formula 1 except that L 1 is the case of a single junction. Chemical formula 2-2 is the same as Chemical formula 1 except that L 1 is a substituted or unsubstituted phenylene group.

[0069] In Chemical Formula 2-2, R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms. 5 does not join adjacent groups to form a ring. 5 may be a hydrogen atom.

[0070] In Chemical Formula 2-2, n 5 is an integer of 0 to 4. In Chemical Formula 2-2, n 5 is 0, the phenylene group as a linker in the amine compound according to one embodiment is R 5 In Chemical Formula 2-2, n 5 is 4 and R 5 If all are hydrogen atoms, then in chemical formula 2-2, n 5 is 0. In Chemical Formula 2-2, n 5 If is 2 or more, multiple R 5 are the same as each other or different from each other.

[0071] On the other hand, in Chemical Formula 2-1 and Chemical Formula 2-2, Ar1 and Ar 2 , R 1 ~R 4 , and n 1 ~n 4 The same applies as described above for Chemical Formula 1.

[0072] The amine compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-3. [ka] ...(chemical formula 3-1) [ka] ...(chemical formula 3-2) [ka] ...(chemical formula 3-3)

[0073] Chemical formula 3-1 is a case where one phenyl group contained in the tetraphenylethenyl group in Chemical Formula 1 is bonded to an amino group at the para position of the phenyl group. Chemical formula 3-2 is a case where one phenyl group contained in the tetraphenylethenyl group in Chemical Formula 1 is bonded to an amino group at the meta position of the phenyl group. Chemical formula 3-3 is a case where one phenyl group contained in the tetraphenylethenyl group in Chemical Formula 1 is bonded to an amino group at the ortho position of the phenyl group.

[0074] On the other hand, in Chemical Formula 3-1 to Chemical Formula 3-3, Ar 1 and Ar 2 , R 1 ~R 4 , and n 1 ~n 4 The same applies as described above for Chemical Formula 1.

[0075] The amine compound represented by Chemical Formula 2-2 is represented by any one of the following Chemical Formulas 4-1 to 4-3. [ka] ...(Chemical formula 4-1) [ka] ...(Chemical formula 4-2) [ka] ...(Chemical formula 4-3)

[0076] Chemical formula 4-1 is a case where an amino group and a tetraphenylethenyl group are bonded to the para position of the phenylene linker in chemical formula 2-2. Chemical formula 4-2 is a case where an amino group and a tetraphenylethenyl group are bonded to the meta position of the phenylene linker in chemical formula 2-2. Chemical formula 4-3 is a case where an amino group and a tetraphenylethenyl group are bonded to the ortho position of the phenylene linker in chemical formula 2-2.

[0077] On the other hand, in Chemical Formula 4-1 to Chemical Formula 4-3, Ar 1 and Ar 2 , R 1 ~R 5 , and n 1 ~n 5 The same applies as described above for Chemical Formula 1 and Chemical Formula 2-2.

[0078] The amine compound according to an embodiment may be any one of the compounds shown in the first compound group below. The organic electroluminescent device 10 according to an embodiment includes at least one amine compound among the compounds shown in the first compound group in the electron transport region HTR. For example, the organic electroluminescent device 10 according to an embodiment includes at least one amine compound among the compounds shown in the first compound group in the hole transport layer HTL. [First compound group] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0079] In the organic electroluminescent device 10 according to one embodiment, the hole transport region HTR may further include a known material.

[0080] The hole injection layer HTL may be, for example, a phthalocyanine compound such as copper phthalocyanine, DNTPD (N,N'-diphenyl-N,N'-bis-[4-phenyl-m-tolylamino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine), TDATA (4,4',4"-tris(N,N-diphenylamino)triphenylamine), 2-TNATA (4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonyl)sulfonyl) phonate), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), polyether ketone with triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile), and the like.

[0081] The hole transport layer HTL may further include, for example, a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorene derivative, a triphenylamine derivative such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) or TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), or mCP (1,3-bis(N-carbazolyl)benzene).

[0082] The thickness of the hole transport region HTR may be about 5 nm to about 1000 nm, for example, about 10 nm to about 500 nm. The thickness of the hole injection layer HIL may be, for example, about 3 nm to about 100 nm, and the thickness of the hole transport layer HTL may be, for example, about 3 nm to about 100 nm. When the hole transport region HTR includes an electron blocking layer EBL, the thickness of the electron blocking layer EBL may be, for example, about 1 nm to about 100 nm. When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above-mentioned ranges, sufficient hole transport properties can be obtained without a substantial increase in driving voltage.

[0083] In addition to the above-mentioned materials, the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material is uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material is, for example, a p-dopant. The p-dopant may be one of, but is not limited to, a quinone derivative, a metal oxide, and a cyano group-containing compound. For example, the p-dopant may be, but is not limited to, a quinone derivative such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), a metal oxide such as tungsten oxide and molybdenum oxide, and the like.

[0084] As described above, the hole transport region HTR may further include at least one of a hole buffer layer (not shown) and an electron blocking layer EBL in addition to the hole transport layer HTL and the hole injection layer HIL. The hole buffer layer (not shown) compensates for the resonance distance according to the wavelength of light emitted from the emission layer EML to increase light emission efficiency. The material included in the hole buffer layer (not shown) is a material that can be included in the hole transport region HTR. The electron blocking layer EBL is a layer that serves to prevent the injection of electrons from the electron transport region ETR to 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 adjacent to the emission layer EML, the amine compound according to an embodiment may be included in the hole buffer layer and / or the electron blocking layer adjacent to the emission layer EML.

[0085] The light-emitting layer EML is provided on the hole transport region HTR. The light-emitting layer EML has a thickness of, for example, about 10 nm to about 100 nm, or about 10 nm to about 30 nm. The light-emitting layer EML has a multilayer structure having a single layer made of a single material, a single layer made of a plurality of different materials, or a plurality of layers made of a plurality of different materials.

[0086] In addition, the emission layer EML of the organic electroluminescent device 10 emits blue light. For example, the emission layer EML of the organic electroluminescent device 10 in one embodiment may emit blue light in a region of 490 nm or more. However, the present embodiment is not limited thereto, and the emission layer EML may emit green light or red light.

[0087] Although not shown, the organic electroluminescent device 10 according to an embodiment may include a plurality of light-emitting layers. The plurality of light-emitting layers may be stacked in sequence. For example, the organic electroluminescent device 10 including the plurality of light-emitting layers may emit white light. The organic electroluminescent device 10 including the plurality of light-emitting layers is an organic electroluminescent device having a tandem structure.

[0088] In one embodiment, the emitting layer EML is a delayed fluorescent emitting layer, a fluorescent emitting layer, a phosphorescent emitting layer, etc., and the emitting layer MEL includes a known host material and a dopant. For example, the emitting layer EML may emit thermally activated delayed fluorescence (TADF).

[0089] The host material of the light-emitting layer EML may be a known material, and is not particularly limited, and may be selected from fluoranthene derivatives, pyrene derivatives, arylacetylene derivatives, anthracene derivatives, fluorene derivatives, perylene derivatives, chrysene derivatives, etc. Preferred are pyrene derivatives, perylene derivatives, and anthracene derivatives. For example, an anthracene derivative represented by the following chemical formula 5 may be used as the host material of the light-emitting layer EML. [ka] ...(chemical formula 5)

[0090] In Chemical Formula 5, R 31 ~R 40 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 31 ~R 40 R may combine with adjacent groups to form a ring. 31 ~R 40 may be bonded to adjacent groups to form a saturated or unsaturated hydrocarbon ring.

[0091] In Chemical Formula 5, c and d each independently represent an integer of 0 or more and 5 or less.

[0092] Chemical formula 5 may be any one of the following compounds 5-1 to 5-16. [ka] [ka] [ka] [ka] [ka] [ka]

[0093] In one embodiment, the emitting layer EML contains Alq as a host material. 3 (tris(8-hydroxyquinolino)aluminum), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), PVK (poly(n-vinylcarbazole), ADN (9,10-di(naphthalen-2-yl)anthracene), TCTA (4,4',4"-tris(carbazol-9-yl)-triphenylamine), TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), TBADN (3-tert-butyl 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN (2-methyl-9,10-bis(naphthalen-2-yl)anthracene), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), CP1 (hexaphenylcyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO 3 (Hexaphenylcyclotrisiloxane), DPSiO 4(octaphenylcyclotetrasiloxane), or PPF (2,8-bis(diphenylphosphoryl)dibenzofuran), mCBP (3,3'-bis(N-carbazolyl)-1,1'-biphenyl), mCP (1,3-bis(N-carbazolyl)benzene), DNA (9,10-di(naphthalene-2-yl)anthracene), etc. However, the present embodiment is not limited thereto, and may include a known delayed fluorescent host material other than the presented host material.

[0094] In one embodiment, the light-emitting layer MEL includes, as a dopant, a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc., such as 2,5,8,11-tetra-t-butylperylene (TBP)).

[0095] In one embodiment, the emission layer EML may include two dopant materials having different lowest triplet excitation energy levels (T1 levels). In the organic electroluminescent device 10 according to one embodiment, the emission layer EML includes a host 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.

[0096] In the organic electroluminescent device 10 according to an embodiment, in which the emission layer EML includes a host, a first dopant, and a second dopant, the first dopant is a delayed fluorescent dopant, and the second dopant is a fluorescent dopant.

[0097] For example, when the emission layer EML of the organic electroluminescent device 10 according to the embodiment includes a plurality of dopants, the emission layer EML may include a first dopant and a second dopant that are different from each other. For example, when the emission layer EML emits blue light, the emission layer EML may further include, as the second dopant, any one selected from the group consisting of spiro-DPVBi, spiro-6P, DSB (distyryl-benzene), DSA (distyryl-arylene), PFO (polyfluorene)-based polymers, and PPV (poly(p-phenylenevinylene)-based polymers. In addition, as the second dopant, (4,6-F 2 ppy) 2 Metal complexes or organometallic complexes such as Irpic, perlene, and derivatives thereof may also be used.

[0098] 1 to 4, the electron transport region ETR is provided on the emission layer EML. The electron transport region ETR includes at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the present embodiment is not limited thereto.

[0099] The electron transport region ETR has a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

[0100] For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single layer structure made of an electron injection material and an electron transport material. The electron transport region ETR may have a single layer structure made of a plurality of different materials, or may have a structure of an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL stacked in order from the light emitting layer EML, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 100 nm to about 150 nm.

[0101] The electron transport region ETR can be formed using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0102] When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR may include an anthracene-based compound. However, the electron transport region is not limited thereto, and may include, for example, Alq 3 (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl), BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bph en (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), Bebq 2 (beryllium bis(benzoquinoline-10-olate), ADN (9,10-di(naphthalene-2-yl)anthracene), and a mixture thereof. The electron transport layer ETL may have a thickness of about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thickness of the electron transport layer HTL satisfies the above-mentioned range, sufficient electron transport properties can be obtained without a substantial increase in driving voltage.

[0103] When the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may be a metal halide such as LiF, NaCl, CsF, RbCl, RbI, or CuI, a lanthanide metal such as Yb, or a Li 2 Metal oxides such as O, BaO, or LiQ (lithium quinolate) may be used, but are not limited thereto. The electron injection layer EIL may also be made of a material in which an electron transport material and an insulating organo metal salt are mixed. The organo metal salt is a material having an energy band gap of about 4 eV or more. In detail, for example, the organo metal salt includes metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. The thickness of the electron injection layer EIL is about 0.1 nm to about 10 nm, or about 0.3 nm to about 9 nm. When the thickness of the electron injection layer EIL satisfies the above-mentioned range, sufficient electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0104] The electron transport region ETR may include a hole blocking layer HBL as described above. The hole blocking layer HBL may include at least one of, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline), but is not limited thereto.

[0105] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 is a common electrode or a negative electrode. The second electrode EL2 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 is made of a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.

[0106] If the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 contains Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, or a compound or mixture containing these (for example, an alloy of Ag and Mg). The second electrode EL2 may have a multi-layer structure including a reflective film or semi-transmissive film made of the above material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, or the like.

[0107] Although not shown, the second electrode EL2 may be connected to an auxiliary electrode, If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0108] Meanwhile, although not shown, the organic electroluminescent device 10 according to an embodiment may further include a buffer layer between the emission layer EML and the electron transport region ETR. The buffer layer adjusts the concentration of excitons generated from the emission layer EML. For example, the buffer layer includes a part of the material of the emission layer EML. The buffer layer may include a host material of the material of the emission layer EML. The lowest triplet excitation energy level of the material of the buffer layer is adjusted to be equal to or higher than the lowest triplet excitation energy level of the second dopant or lower than the lowest triplet excitation energy level, depending on the combination of the host and dopant materials included in the emission layer EML.

[0109] Meanwhile, a capping layer CPL may be further disposed on the second electrode EL2 of the organic electroluminescent device 10 according to the embodiment. The capping layer CPL may be, for example, α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4"-tris(carbazolesol-9-yl)triphenylamine), and the like.

[0110] The organic electroluminescent device 10 according to one embodiment of the present invention exhibits high luminous efficiency and long device life characteristics by including the amine compound according to the embodiment described above in the hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2.

[0111] Meanwhile, the amine compound according to the embodiment described above may be included in an organic layer other than the hole transport region HTR as a material for the organic electroluminescent device 10. For example, the organic electroluminescent device 10 according to an embodiment of the present invention may include the amine compound described above 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.

[0112] The amine compound according to the embodiment described above includes a tetraphenylethenyl group bonded to an amino group, and thus has improved intermolecular hole transport capability compared to conventional compounds. Therefore, when the amine compound according to the embodiment is used as a hole transport material for an organic electroluminescent device, it is possible to realize a long life and high efficiency of the organic electroluminescent device. EXAMPLES

[0113] Hereinafter, an amine compound according to an embodiment of the present invention and an organic electroluminescent device according to an embodiment of the present invention will be described in detail with reference to examples and comparative examples. Note that the following examples are merely illustrative for the purpose of helping to understand the present invention, and the scope of the present invention is not limited thereto.

[0114] [Synthesis example] 1. Synthesis of amine compounds First, the synthesis method of the amine compounds according to the present embodiment will be specifically described by taking as examples the synthesis methods of compounds 1, 3, 6, 30, 43, 82, and 83. The synthesis method of the amine compounds described below is merely an example, and the synthesis method of the amine compounds according to the embodiment of the present invention is not limited to the following synthesis example.

[0115] (1) Synthesis of Compound 1 Compound 1 according to one embodiment is synthesized, for example, by the following reaction. [Reaction Scheme 1-1] [ka]

[0116] 1-Bromo-3-(1,2,2-triphenylethenyl)benzene (12.5 g), NH 3 (5 ml), CuI (5.7 g), acetylacetone (1.8 g), and Cs 2 CO 3 (1.0 g) was dissolved in DMF (300 ml) and stirred at 120° C. for 24 hours. The reaction solution was cooled to room temperature, and the reaction was terminated with water and extracted three times with ethyl ether. The separated organic phase was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue, which was separated and purified by column chromatography to obtain intermediate A (7.0 g, yield: 68%).

[0117] [Reaction Scheme 1-2] [ka]

[0118] Reactants Compound A (6.2 g) and bromobenzene (2.3 g), Pd 2 (dba) 3 (0.68g), P( t -Bu) 3 (0.30 g), and NaO t Bu (4.32 g) was dissolved in toluene (200 ml) and stirred at 90° C. for 2 hours. The reaction solution was cooled to room temperature, and the reaction was terminated with water and extracted three times with ethyl ether. The separated organic phase was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue, which was separated and purified by column chromatography to obtain intermediate 1-1 (3.8 g, yield: 63%).

[0119] Compound 1 (2.6 g, yield: 54%) was obtained in the same manner as intermediate 1-1 synthesis, except that intermediate 1-1 (3.38 g) and 3-bromo-9,9-dimethyl-9H-fluorene (2.7 g) were used instead of bromobenzene. The molecular weight of compound 1 measured by FAB-MS was 615. From the results, it was confirmed that the obtained compound was compound 1.

[0120] (2) Synthesis of compound 6 Compound 6 according to one embodiment is synthesized, for example, by the following reaction. [Reaction Scheme 2] [ka]

[0121] Compound 6 (2.5 g, yield: 48%) was obtained by synthesizing compound 6 in the same manner as compound 1, except that 3-bromo-9,9-dimethyl-9H-fluorene was replaced with 3-bromo-9-phenyl-9H-carbazole (3.0 g). The molecular weight of compound 6 measured by FAB-MS was 664. From the results, it was confirmed that the obtained compound was compound 6.

[0122] (3) Synthesis of Compound 3 Compound 3 according to one embodiment is synthesized, for example, by the following reaction. [Reaction Scheme 3] [ka]

[0123] Compound 3 (2.3 g, yield: 49%) was obtained by synthesizing compound 3 in the same manner as compound 1, except that 2-bromodibenzo[b,d]furan (2.4 g) was used instead of 3-bromo-9,9-dimethyl-9H-fluorene. The molecular weight of compound 3 measured by FAB-MS was 664. From the results, it was confirmed that the obtained compound was compound 3.

[0124] (4) Synthesis of compound 30 Compound 30 according to one embodiment is synthesized, for example, by the following reaction: [Reaction Scheme 4] [ka]

[0125] Compound 30 (2.8 g, yield: 52%) was obtained in the same manner as in the synthesis of compound 1, except that intermediate B was used instead of intermediate A, 4-bromo-1,1'-biphenyl was used instead of bromobenzene, and 2-bromo-9,9-dimethyl-9H-fluorene (2.6 g) was used instead of 3-bromo-9,9-dimethyl-9H-fluorene. The molecular weight of compound 30 measured by FAB-MS measurement was 692. From this result, it was confirmed that the obtained compound was compound 30. Intermediate B can be synthesized in the same manner as in the synthesis of intermediate A, except that 1-bromo-4-(1,2,2-triphenylethenyl)benzene was used instead of 1-bromo-3-(1,2,2-triphenylethenyl)benzene.

[0126] (5) Synthesis of compound 43 Compound 43 according to one embodiment is synthesized, for example, by the following reaction. [Reaction Scheme 5] [ka]

[0127] Compound 43 (2.5 g, yield: 48%) was obtained in the same manner as compound 30, except that 2-bromo-9,9-dimethyl-9H-fluorene was replaced with 2-bromo-9-phenyl-9H-carbazole (3.0 g). The molecular weight of compound 43 measured by FAB-MS was 741. From the results, it was confirmed that the obtained compound was compound 43.

[0128] (6) Synthesis of Compound 82 Compound 82 according to one embodiment is synthesized, for example, by the following reaction: [Reaction Scheme 6-1] [ka]

[0129] 4-(1,2,2-triphenylethenyl)phenylboronic acid (11.2 g) and 1-bromo-4-iodobenzene (8.48 g), Pd(PPh 3 ) 4 (1.6g), K 2 CO 3 (11g), THF(150ml), H 2 The mixture was dissolved in 150 ml of ethyl acetate and stirred at 90° C. for 2 hours. The reaction mixture was cooled to room temperature, and the reaction was terminated with water and extracted three times with ethyl ether. The separated organic phase was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue, which was separated and purified by column chromatography to obtain intermediate C (8.1 g, yield: 56%).

[0130] [Reaction Scheme 6-2] [ka]

[0131] Intermediate C (7.3 g) and aniline (1.6 g), Pd 2 (dba) 3 (0.68g), P( t -Bu) 3 (0.30 g), and NaO tBu (4.32 g) was dissolved in toluene (200 ml) and stirred at 90° C. for 2 hours. The reaction solution was cooled to room temperature, and the reaction was terminated with water and extracted with ethyl ether three times. The separated organic phase was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue, which was separated and purified by column chromatography to obtain intermediate 82-1 (4.0 g, yield: 54%). Compound 82 (2.6 g, yield: 48%) was obtained in the same manner as in the synthesis of intermediate 82-1, except that 2-bromo-9,9-dimethylfluorene (2.6 g) was used instead of intermediate 82-1 (4.0 g) and aniline. The molecular weight of compound 82 measured by FAB-MS was 692. It was confirmed from the results that the obtained compound was compound 82.

[0132] (7) Synthesis of Compound 83 Compound 83 according to one embodiment is synthesized, for example, by the following reaction: [Reaction Scheme 7] [ka]

[0133] Compound 83 (2.2 g, yield: 44%) was obtained in the same manner as compound 82, except that 4-bromobiphenyl (2.2 g) was used instead of 2-bromo-9,9-dimethylfluorene. The molecular weight of compound 83 measured by FAB-MS was 652. From the results, it was confirmed that the obtained compound was compound 83.

[0134] 2. Structures of Example Compounds and Comparative Compounds The structures of Example compounds 1, 3, 6, 30, 43, 82, and 83 and Comparative Example compounds C1 to C4 are as follows. [ka] [ka]

[0135] 3. Fabrication and evaluation of organic electroluminescent devices containing amine compounds (Fabrication of Organic Electroluminescent Device) An organic electroluminescence device of an embodiment containing an amine compound according to an embodiment in a hole transport layer was produced by the following method. The amine compounds of the above-mentioned example compounds, Compound 1, Compound 3, Compound 6, Compound 30, Compound 43, Compound 82, and Compound 83, were used as hole transport layer materials to produce organic electroluminescence devices of Examples 1 to 7. Comparative Examples 1 to 4 correspond to organic electroluminescence devices produced using Comparative Examples C1 to C4 as hole transport layer materials.

[0136] Corning 15Ω / cm 2 A (120 nm) ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, washed with isopropyl alcohol and ultrapure water, and ultrasonically cleaned for 5 minutes, then irradiated with UV for 30 minutes and then treated with ozone. Next, 2-TNATA (4,4',4"-tris{N,-2(-naphthyl)-N-phenylamino}-triphenylamine) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then the example compound or comparative example compound was vacuum-deposited to a thickness of 30 nm to form a hole transport layer.

[0137] A blue fluorescent host DNA (9,10-di(naphthalen-2-yl)anthracene) and DPAVBi (4,4'-bis[2-(4-N,N-diphenylamino)phenyl)vinyl]biphenyl) were co-evaporated in a ratio of 98:2 on the hole transport layer to form a 30 nm-thick light-emitting layer.

[0138] Alq on the light-emitting layer 3 A 30 nm-thick electron transport layer was formed using (tris(8-hydroxyquinolino)aluminum), and then 1 nm of LiF was evaporated to form an electron injection layer. A 300 nm-thick second electrode was formed using aluminum (Al) on the electron injection layer.

[0139] The compounds used in the preparation of the organic electroluminescent devices of the Examples and Comparative Examples are shown below. [ka]

[0140] (Evaluation of the characteristics of organic electroluminescent devices) Table 1 shows the evaluation results of the organic electroluminescent devices of Examples 1 to 7 and Comparative Examples 1 to 4. Table 1 shows a comparison of the driving voltage, luminance, luminous efficiency, and half-life of the fabricated organic electroluminescent devices.

[0141] In the results of the characteristic evaluation of the examples and comparative examples shown in Table 1, the voltage and current density were measured using a source meter (Keithley Instrument, 2400 series), and the external quantum efficiency (EQE) was measured using an external quantum efficiency measurement device C9920-12 manufactured by Hamamatsu Photonics. The luminous efficiency was measured at a current density of 50 mA / cm. 2 The current efficiency values ​​for [Table 1]

[0142] Referring to the results in Table 1, it can be seen that the organic electroluminescent device using the amine compound according to one embodiment of the present invention as a hole transport layer material emits the same blue light as the comparative example, but exhibits a lower driving voltage value, relatively high luminance, luminous efficiency, and high external quantum efficiency.

[0143] In the case of the example compounds, the amine compounds have high stability due to the tetraphenylethenyl group substituted on the amino group in the arylamine-based hole transport material. Therefore, the organic electroluminescent device of the example has high hole transport properties compared to the comparative example compounds, and therefore exhibits improved luminous efficiency and long life compared to the organic electroluminescent device of the comparative example. In particular, the organic electroluminescent device according to an embodiment includes the amine compound according to an embodiment as a hole transport material, thereby realizing high luminous efficiency and long life in the blue light wavelength region.

[0144] In the case of the comparative compound C1, it contains a diamine compound but does not contain a tetraphenylethenyl group substituted with an amino group, and the stability and hole transport properties are reduced compared to the amine compounds of the examples, and therefore the device of Comparative Example 1 has a reduced luminous efficiency and lifespan and a higher driving voltage compared to the devices of the examples. In the case of the comparative compounds C2 and C4, it contains a similar structure to the tetraphenylethenyl group substituted with an amino group, but has a shape in which the tetraphenylethenyl group forms an additional ring, and therefore the stability and hole transport properties are reduced compared to the amine compounds of the examples, and therefore the devices of Comparative Examples 2 and 4 have a reduced luminous efficiency and lifespan and a higher driving voltage compared to the devices of the examples. In the case of the comparative compound C3, it contains a tetraphenylethenyl group substituted with an amino group, but is a diamine compound, and the stability and hole transport properties are reduced compared to the compounds of the examples, and therefore the device of Comparative Example 3 has a reduced luminous efficiency and lifespan and a higher driving voltage compared to the devices of the examples.

[0145] Although the present invention has been described above with reference to preferred embodiments thereof, it will be understood by those skilled in the art or those having ordinary knowledge in the art that various modifications and variations of the present invention can be made without departing from the spirit and technical scope of the present invention as set forth in the claims below.

[0146] Therefore, the technical scope of the present invention should be determined not by the contents described in the detailed description of the specification, but by the claims. [Explanation of symbols]

[0147] 10: Organic electroluminescent element EL1: First electrode EL2: second electrode HTR: hole transport region EML: Light-emitting layer ETR: Electron transport region

Claims

1. An amine compound represented by any one of the following chemical formulas 3-1 to 3-3. 【Chemistry 1】 ...(Chemical formula 3-1) 【Chemistry 2】 ...(Chemical formula 3-2) 【Chemistry 3】 ...(Chemical formula 3-3) (In the above Chemical Formula 3-1 to Chemical Formula 3-3, Ar １ and Ar ２ each independently represents a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, L １ represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, R １ ~R ４ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, n １ ~n ３ are each independently an integer of 0 to 5, n ４ is an integer between 0 and 4, When the amine compound is represented by the above formula 3-1, said Ar 1 and Ar 2 are not bonded to each other, said Ar 1 and Ar 2 are not substituted with a carbazolyl group and a fluorenyl group, and said Ar 1 and Ar 2 are not a benzothiadiazolyl group; The R 3 is not a triazinyl group, The L 1 is not a single bond, The partial structure constituted by NAr 1 Ar 2 and L 1 does not have a structure represented by the following structural formula: 【Chemistry 4】 In the above structural formula, R' is a hydrogen atom or an alkyl group; n is a natural number between 1 and 10.)

2. The amine compound according to claim 1 , wherein the amine compound represented by Chemical Formula 1 is a monoamine compound.

3. In the above Chemical Formula 3-1 to Chemical Formula 3-3, The Ar １ and Ar ２ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.

4. In the above Chemical Formula 3-1 to Chemical Formula 3-3, The Ar １ and Ar ２ The amine compound according to claim 1 , wherein:

5. The Ar １ represents a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, The Ar ２ The amine compound according to claim 1, wherein is a substituted or unsubstituted aryl group having two or more condensed rings, or a substituted or unsubstituted heteroaryl group having two or more condensed rings.

6. An amine compound comprising at least one compound selected from the following first compound group: 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】

7. A first electrode; a second electrode facing the first electrode; a plurality of organic layers disposed between the first electrode and the second electrode; 7. An organic electroluminescent device, comprising: at least one organic layer of the plurality of organic layers, the at least one organic layer of the plurality of organic layers comprising the amine compound according to claim 1.

8. The organic layer is a hole transport region disposed over the first electrode; a light-emitting layer disposed over the hole transport region; an electron transport region disposed over the light emitting layer; The organic electroluminescent device according to claim 7 , wherein the hole transport region comprises the amine compound.

9. The hole transport region is a hole injection layer disposed over the first electrode; a hole transport layer disposed on the hole injection layer; The organic electroluminescent device according to claim 8 , wherein the hole transport layer comprises the amine compound.

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