Organic electroluminescent device and monoamine compound for organic electroluminescent device

Abstract

To provide an organic electroluminescent element and an amine compound for organic electroluminescent element, more specifically a highly efficient organic electroluminescent element and an amine compound contained in a positive pore transportation region of the organic electroluminescent element.SOLUTION: An organic electroluminescent element 10 contains a first electrode EL1, a positive pore transportation region HTR arranged on the first electrode, a luminescent layer EML arranged on the positive pore transportation region, an electron transportation region ETR arranged on the luminescent layer, and a second electrode EL2 arranged on the electron transportation region, in which the positive pore transportation region contains a monoamine compound represented by the chemical formula 1 and can exhibit high luminous efficiency.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to an organic electroluminescent device and a monoamine compound for the organic electroluminescent device. [Background technology]

[0002] Recently, organic electroluminescence displays (OLEDs) have been actively developed as image display devices. Unlike liquid crystal displays (LCDs), OLEDs are self-emissive displays that display images by causing luminescent materials containing organic compounds in the emissive layer to emit light as holes and electrons injected from the first and second electrodes are recombined in the emissive layer.

[0003] In applying organic electroluminescent elements to display devices, there is a demand for lower driving voltages, higher luminous efficiency, and longer lifespans of the organic electroluminescent elements, and there is a continuous demand for the development of materials for organic electroluminescent elements that can stably achieve these goals. Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide an organic electroluminescent device and an amine compound for the organic electroluminescent device, and more specifically, to provide a highly efficient organic electroluminescent device and an amine compound contained in the hole transport region of the organic electroluminescent device. [Means for solving the problem]

[0005] One embodiment of the present invention provides an organic electroluminescent device comprising a first electrode, a hole transport region provided on the first electrode, an emitting layer provided on the hole transport region, an electron transport region provided on the emitting layer, and a second electrode provided on the electron transport region, wherein the hole transport region comprises a monoamine compound represented by the following Chemical Formula 1:

[0006] [ka]

[0007] In Chemical Formula 1, Ar1 and Ar2 are each independently a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, 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 is 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; R1 is a hydrogen atom, a heavy R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms; R2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms; a is an integer of from 0 to 3; m is an integer of from 0 to 1; and n is an integer of from 0 to 6; The case where either one of Ar1 and Ar2 is a 3-dibenzofuranyl group and the remaining one is a 9-phenanthryl group is excluded.

[0008] The hole transport region may have a multilayer structure having a plurality of layers, and one of the plurality of layers that is in contact with the light-emitting layer may contain the monoamine compound according to one embodiment of the present invention.

[0009] The hole transport region may include a hole injection layer disposed on the first electrode, a hole transport layer disposed on the hole injection layer, and an electron blocking layer disposed on the hole transport layer, and the electron blocking layer may contain the monoamine compound according to one embodiment of the present invention described above.

[0010] The electron transport region may include a hole blocking layer provided on the light-emitting layer, an electron transport layer provided on the hole blocking layer, and an electron injection layer provided on the electron transport layer.

[0011] Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 8 below.

[0012] [ka]

[0013] [ka]

[0014] [ka]

[0015] [ka]

[0016] [ka]

[0017] [ka]

[0018] [ka]

[0019] In Chemical Formulas 2 to 8, Ar1, Ar2, L, R1, R2, a, m, and n are the same as defined in Chemical Formula 1.

[0020] L may be a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[0021] L may be a substituted or unsubstituted phenylene group.

[0022] Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0023] Ar1 and Ar2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0024] Ar1 and Ar2 may each independently be a substituted or unsubstituted heteroaryl group having 5 to 12 ring carbon atoms.

[0025] Ar1 and Ar2 may each independently be a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0026] Ar 1 and Ar 2 At least one of may be a substituted or unsubstituted 4-dibenzofuranyl group.

[0027] The monoamine compound represented by Chemical Formula 1 may be represented by Chemical Formula 9 below. [ka] In Chemical Formula 9, R 3 may be 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 cycloalkyl group having from 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, p may be an integer of from 0 to 7, Ar 2 , L, R 1 、R 2 , a, m, and n are the same as defined in Chemical Formula 1.

[0028] One embodiment of the present invention provides a monoamine compound represented by the above formula 1. [Effects of the Invention]

[0029] The organic electroluminescent device according to one embodiment of the present invention has excellent efficiency.

[0030] The monoamine compound according to one embodiment of the present invention may be used as a material for the hole transport region of an organic electroluminescent device, and by using the monoamine compound, the efficiency and life span of the organic electroluminescent device can be improved.

[0031] The monoamine compound according to one embodiment of the present invention may be used as a material for the hole transport region of an organic electroluminescent device, and by using this, it is possible to reduce the driving voltage of the organic electroluminescent device. [Brief explanation of the drawings]

[0032] [Figure 1] 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention. [Figure 2] 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention. [Figure 3] 1 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0033] The above and other objects, features, and advantages of the present invention will be easily understood from the accompanying drawings and the following preferred embodiments. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms. Rather, the embodiments introduced herein are provided so that the disclosed content will be thorough and complete, and so that the concept of the present invention will be fully conveyed to those skilled in the art.

[0034] In describing the various drawings, like reference numerals are used for like elements. In the accompanying drawings, the dimensions of structures are exaggerated for clarity. Terms such as "first," "second," etc. are used to describe various elements, but these elements should not be limited by these terms. These terms are used only to distinguish one element from another. For example, a first element may be called a "second element," and similarly, a second element may be called a "first element," without departing from the scope of the present invention. A singular term includes a plural term unless the context clearly dictates otherwise.

[0035] As used herein, terms such as "comprise" or "have" are intended to specify the presence of a feature, numeral, step, operation, component, part, or combination thereof as described in the specification, but should not be understood to preclude the presence or addition of one or more other features, numerals, steps, operations, components, parts, or combinations thereof. Furthermore, when a layer, film, region, plate, or other part is referred to as being "on" another part, it includes not only the case where it is "directly on" the other part, but also the case where there is another part between them. Conversely, when a layer, film, region, plate, or other part is referred to as being "under" the other part, it includes not only the case where it is "directly under" the other part, but also the case where there is another part between them.

[0036] First, an organic electroluminescent device according to one embodiment of the present invention will be described with reference to FIGS.

[0037] Fig. 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention, Fig. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention, and Fig. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.

[0038] 1 to 3, an organic electroluminescent device 10 according to one embodiment of the present invention includes a first electrode EL1, a hole transporting region HTR, an emitting layer EML, an electron transporting region ETR, and a second electrode EL2.

[0039] The hole transport region HTR includes a monoamine compound according to an embodiment of the present invention. Hereinafter, the monoamine compound according to an embodiment of the present invention will be described in detail, followed by a description of each layer of the organic electroluminescent device 10.

[0040] As used herein, "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, a silyl group, a boron group, a phosphine group, an alkyl group, an alkenyl group, an aryl group, and a heterocyclic group, or is unsubstituted. Each of the exemplified 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.

[0041] In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0042] In this specification, an alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is 1 to 30, 1 to 20, 1 to 10, or 1 to 4. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group, an i-butyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, an n-pentyl group, an i-pentyl group, a neopentyl group, a t-pentyl group, a cyclopentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a 2-ethylpentyl group, a 4-methyl-2-pentyl group, an n-hexyl group, a 1-methylhexyl group, a 2-ethylbutyl group, a 4-methyl-2-pentyl group, a 4-methyl-2-pentyl group, a 4-methylhex ... Hexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adaman ethyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, Examples of such alkyl groups include, but are not limited to, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl, 2-ethylicosyl, 2-butylicosyl, 2-hexylicosyl, 2-octylicosyl, n-henicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, and n-triaconityl groups.

[0043] As used herein, the term "aryl group" refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 12. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenylyl, terphenylyl, quaterphenylyl, quinquephenylyl, sexiphenylyl, biphenylenyl, triphenylenyl, pyrenyl, benzofluoranthenyl, and chrysenyl.

[0044] 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 are shown below. However, the present invention is not limited to these.

[0045] [ka]

[0046] In this specification, the heteroaryl group may be a heteroaryl group containing one or more heteroatoms selected from O, N, P, Si and S. When two heteroatoms are contained, the two heteroatoms may be the same or different. The number of ring carbon atoms in the heteroaryl group is 2 to 30 or 5 to 12. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The polycyclic heteroaryl group may have, for example, a bicyclic or tricyclic structure. Examples of heteroaryl groups 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 pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a butalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, and an indolyl group. , carbazolyl group, N-arylcarbazolyl group, N-heteroarylcarbazolyl group, N-alkylcarbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, thienothiophenyl group, benzofuranyl group, phenanthrolinyl group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzosilolyl group, and dibenzofuranyl group.

[0047] As used herein, the term "silyl group" includes alkylsilyl groups and arylsilyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0048] As used herein, the term "boron group" includes alkylboron groups and arylboron groups. Examples of boron groups include, but are not limited to, trimethylboron groups, triethylboron groups, t-butyldimethylboron groups, triphenylboron groups, diphenylboron groups, and phenylboron groups.

[0049] In this specification, the alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but may 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-phenthenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.

[0050] In this specification, the above description of the aryl group applies to the arylene group, except that the arylene group is a divalent group.

[0051] In this specification, the above description of the heteroaryl group applies to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0052] The monoamine compound according to one embodiment of the present invention is represented by the following Chemical Formula 1:

[0053] [ka]

[0054] In Chemical Formula 1, Ar1 and Ar2 each independently represent a substituted or unsubstituted carbon atom. a substituted or unsubstituted alkyl group having from 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, 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.

[0055] In Chemical Formula 1, L is 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.

[0056] In Chemical Formula 1, R1 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 cycloalkyl group having from 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms.

[0057] In Chemical Formula 1, R2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms. On the other hand, R2 is not an aryl group or a heteroaryl group. When R2 is an aryl group or a heteroaryl group, the HOMO (Highest Occupied Molecular Orbital) is largely distributed on the naphthalene skeleton side, which relatively reduces the electron density on the amino group side, making it difficult to maintain the properties of the amino group that induce a long lifetime, and may shorten the lifetime of the organic electroluminescent device. The phrase "R2 is not an aryl group or a heteroaryl group" includes both cases where R2 is not an aryl group or a heteroaryl group and cases where R2 is not substituted with an aryl group or a heteroaryl group.

[0058] In Chemical Formula 1, a is an integer of 0 or more and 3 or less. On the other hand, when a is 2 or more, the multiple Ls may be the same or different.

[0059] In Chemical Formula 1, m is an integer of 0 or more and 1 or less.

[0060] In Chemical Formula 1, n is an integer of 0 to 6. On the other hand, when n is 2 or greater, multiple R2s may be the same or different.

[0061] In Chemical Formula 1, when one of Ar1 and Ar2 is a 3-dibenzofuranyl group, the remaining one is a 9-phenanthryl group, except for the case where Ar1 is a 3-dibenzofuranyl group, Ar2 is not a 9-phenanthryl group, and when Ar2 is a 3-dibenzofuranyl group, Ar1 is not a 9-phenanthryl group, except for the case where a 3-dibenzofuranyl group and a 9-phenanthryl group are simultaneously substituted on a nitrogen atom. When a 3-dibenzofuranyl group and a 9-phenanthryl group are simultaneously substituted on a nitrogen atom, thermal decomposition may occur due to strong molecular stacking and high deposition temperatures, which may result in degradation of the properties of the organic electroluminescent device.

[0062] In one embodiment, Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 8 below.

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] In Chemical Formulas 2 to 8, Ar1, Ar2, L, R1, R2, a, m, and n are the same as defined in Chemical Formula 1.

[0071] In Chemical Formula 1, m is 1, and L may be a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. L may be, for example, a substituted or unsubstituted phenylene group, although it is not limited thereto.

[0072] In Chemical Formula 1, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. For example, Ar1 and Ar2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenylene group. However, the present invention is not limited to this.

[0073] In Chemical Formula 1, Ar1 and Ar2 may each independently be a substituted or unsubstituted heteroaryl group having 5 to 12 ring carbon atoms. For example, Ar1 and Ar2 may each independently be a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group. However, they are not limited thereto. Ar 1 and Ar 2 At least one of may be a substituted or unsubstituted 4-dibenzofuranyl group. For example, Ar 1 and Ar 2 All of Ar may be unsubstituted 4-dibenzofuranyl groups. 1 may be an unsubstituted 4-dibenzofuranyl group, and Ar 2 However, Ar may be an unsubstituted m-terphenyl group. 1 may be an unsubstituted 4-dibenzofuranyl group, and Ar 2 However, it may also be an unsubstituted 4-naphthylphenyl group.

[0074] The monoamine compound represented by Chemical Formula 1 may be represented by Chemical Formula 9 below. [ka] In Chemical Formula 9, R 3 may be 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 cycloalkyl group having from 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms. For example, R 3 may be a hydrogen atom or a deuterium atom. p may be an integer of 0 to 7. When p is an integer of 2 or more, a plurality of R 3 may be the same or different from each other.

[0075] In Chemical Formula 1, R2 may be a hydrogen atom or a deuterium atom.

[0076] The monoamine compound represented by Chemical Formula 1 according to one embodiment of the present invention may be any one selected from the compounds represented by the following Compound Groups 1 to 7, but is not limited thereto.

[0077] [Compound group 1] [ka] JPEG0007813090000021.jpg102153JPEG0007813090000022.jpg114153 JPEG0007813090000023.jpg102149 JPEG0007813090000024.jpg123153 JPEG0007813090000025.jpg195149JPEG0007813090000026.jpg186144JPEG0007813090000027.jpg217142

[0078] [Compound group 2] [ka] JPEG0007813090000029.jpg125159JPEG0007813090000030.jpg119155JPEG0007813090000031.jpg115160JPEG00078130900 00032.jpg113157JPEG0007813090000033.jpg183154JPEG0007813090000034.jpg188162JPEG0007813090000035.jpg215154

[0079] [Compound group 3]

change

[0080] [Compound Group 4]

change

[0081] [Compound Group 5]

change

[0082] [Compound Group 6] [ka] JPEG0007813090000061.jpg115155JPEG0007813090000062.jpg122155JPEG0007813090000063.jpg114154JPEG0007813090000064.jpg118148 JPEG0007813090000065.jpg217128 JPEG0007813090000066.jpg217140JPEG0007813090000067.jpg217135

[0083] [Compound group 7] [ka] JPEG0007813090000069.jpg104153JPEG0007813090000070.jpg116153JPEG0007813090000071.jpg103153JPEG0007813090000072.jpg112151 JPEG0007813090000073.jpg217151JPEG0007813090000074.jpg206153JPEG0007813090000075.jpg217138

[0084] The monoamine compound according to one embodiment of the present invention includes a fused ring and a phenylnaphthyl group having high heat resistance and charge resistance, which can contribute to extending the life of organic electroluminescent devices when applied to the device. The volume of the phenylnaphthyl group reduces molecular symmetry, suppressing crystallization, thereby improving film quality and contributing to higher efficiency.

[0085] An organic electroluminescent device according to one embodiment of the present invention will now be described with reference to Figures 1 to 3. The organic electroluminescent device according to one embodiment of the present invention includes the monoamine compound according to one embodiment of the present invention described above. For example, the hole transport region HTR includes a monoamine compound represented by Chemical Formula 1.

[0086] Hereinafter, differences from the monoamine compound according to one embodiment of the present invention will be mainly described in detail, and the parts not described will be in accordance with the monoamine compound according to one embodiment of the present invention.

[0087] The first electrode EL1 is conductive. The first electrode EL1 may be a pixel electrode or a positive electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, it may include a transparent metal oxide such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), or ITZO (indium tin zinc oxide). When the first electrode EL1 is a semi-transmissive electrode or a reflective electrode, it may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof (e.g., a mixture of Ag and Mg). Alternatively, the first electrode EL1 may have a multi-layer structure including a reflective film or semi-transmissive film made of the above materials and a transparent conductive film made of ITO, IZO, ZnO, ITZO, or the like. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited to this.

[0088] The thickness of the first electrode EL1 may be about 100 nm to about 1000 nm, for example, about 100 nm to about 300 nm.

[0089] The hole transport region HTR is provided on the first electrode EL1 and may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer EBL.

[0090] The hole transport region HTR comprises a monoamine compound according to one embodiment of the present invention, as described above.

[0091] The hole transport region HTR may be 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.

[0092] 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 composed of a hole injection material and a hole transport material. The hole transport region HTR may also have a single layer structure composed of multiple different materials, or a structure stacked in order from the first electrode EL1, such as hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, but is not limited to these.

[0093] As described above, the hole transport region HTR may have a multilayer structure having multiple layers, and a layer of the multiple layers in contact with the emitting layer EML may contain the monoamine compound represented by Chemical Formula 1. For example, the hole transport region HTR may include a hole injection layer HIL disposed on the first electrode EL1, a hole transport layer HTL disposed on the hole injection layer HIL, and an electron blocking layer EBL disposed on the hole transport layer HTL, and the electron blocking layer EBL may contain the monoamine compound represented by Chemical Formula 1. However, without being limited thereto, for example, the hole transport region HTR may include a hole injection layer HIL and a hole transport layer HTL, and the hole transport layer HTL may contain the monoamine compound represented by Chemical Formula 1.

[0094] The hole transport region HTR may contain one or more monoamine compounds represented by Chemical Formula 1. For example, the hole transport region HTR may contain at least one compound selected from the compounds represented by Compound Group 1 to Compound Group 7 described above.

[0095] The hole transport region HTR may 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).

[0096] However, the hole transport region may further contain the following materials for each layer.

[0097] The hole injection layer HIL may be formed of, for example, a phthalocyanine compound such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4''-tris(3-methylphenylphenylamino)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-styrenesulfonate)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), acid), PANI / CSA (Polyaniline / Camphor sulfonic acid), PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)), NPD (N,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), triphenylamine-containing polyether ketone (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.

[0098] The hole transport layer HTL may contain, for example, a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorine 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), NPD (N,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), or HMTPD (4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl).

[0099] As described above, the electron blocking layer EBL may include a monoamine compound represented by Chemical Formula 1. However, the electron blocking layer EBL is not limited thereto, and may include any common material known in the art. The electron blocking layer (EBL) may contain, for example, a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorine 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), NPD (N,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD (4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), or mCP.

[0100] The thickness of the hole transport region HTR may be about 10 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 about 3 nm to about 100 nm. For example, the thickness of the electron blocking layer EBL may be about 1 nm to about 100 nm. When the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL satisfy the above-mentioned ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0101] In addition to the above-mentioned materials, the hole transport region HTR may further include a charge generation material to improve conductivity. The charge generation material may be uniformly or non-uniformly dispersed within the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may be one of, but is not limited to, a quinone derivative, a metal oxide, or a cyano group-containing compound. Non-limiting examples of p-dopants include, but are not limited to, quinone derivatives such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), and metal oxides such as tungsten oxide and molybdenum oxide.

[0102] As described above, 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 may compensate for the resonance distance according to the wavelength of light emitted from the emitting layer EML, thereby increasing light emission efficiency. The material contained in the hole buffer layer may be the same as that contained in the hole transport region HTR. The electron blocking layer EBL serves to prevent electron injection from the electron transport region ETR to the hole transport region HTR.

[0103] The emitting layer EML is provided on the hole transport region HTR. The emitting layer EML may have a thickness of, for example, about 10 nm to about 100 nm, or about 10 nm to about 60 nm. The emitting layer EML may be a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure having multiple layers made of multiple different materials.

[0104] The material for the emitting layer EML may be a known emitting 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 examples include pyrene derivatives, perylene derivatives, and anthracene derivatives. For example, an anthracene derivative represented by the following chemical formula 10 can be used as the host material for the emitting layer EML.

[0105] [ka]

[0106] In Chemical Formula 10, W1 to W4 each independently represent 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 20 carbon atoms, 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, or can be bonded to adjacent groups to form a ring; m1 and m2 each independently represent an integer of from 0 to 4, and m3 and m4 each independently represent an integer of from 0 to 5.

[0107] When m1 is 1, W1 may not be a hydrogen atom; when m2 is 1, W2 may not be a hydrogen atom; when m3 is 1, W3 may not be a hydrogen atom; and when m4 is 1, W4 may not be a hydrogen atom.

[0108] When m1 is 2 or more, multiple W1s may be the same or different from each other. When m2 is 2 or more, multiple W2s may be the same or different from each other. When m3 is 2 or more, multiple W3s may be the same or different from each other. When m4 is 2 or more, multiple W4s may be the same or different from each other.

[0109] An example of the compound represented by Chemical Formula 10 is a compound represented by the following structural formula: However, the compound represented by Chemical Formula 10 is not limited to the following.

[0110] [ka]

[0111] The emitting layer EML may contain a fluorescent material including any one selected from the group consisting of spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P, 2,2',7,7'-tetrakis(biphenyl-4-yl)-9,9'-spirobifluorene(spiro-sexiphenyl)), DSB (distyryl-benzene), DSA (distyryl-arylene), PFO (polyfluorene)-based polymers, and PPV (poly(p-phenylene vinylene))-based polymers.

[0112] The light-emitting layer EML may further include a dopant, and the dopant may be a known material. For example, styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)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, Examples of usable dopants include 8,11-tetra-t-butylperylene (TBPe), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-Bis(N,N-Diphenylamino)pyrene, 1,6-Bis(N,N-Diphenylamino)pyrene), 2,5,8,11-Tetra-t-butylperylene (TBP), and TPBi (2,4,6-tris(N-phenylbenzimidazole-2-yl)benzene).

[0113] The light-emitting layer EML includes, for example, Alq3 (tris(8-hydroxyquinolino)aluminum), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl), PVK(poly(N-vinylcarbazole), ADN (9,10-di(naphthalene-2-yl)anthracene), TCTA (4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1,3,5-tris(N-phenylbenzim idazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(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 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO3 (Hexaphenylcyclotrisiloxane), DPSiO4 (Octaphenylcyclotetra siloxane), or PPF (2,8-Bis(diphenylphosphoryl)dibenzofuran).

[0114] The electron transport region ETR is provided on the light emitting layer EML and may include, but is not limited to, at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL.

[0115] The electron transport region ETR may be a single layer of a single material, a single layer of multiple different materials, or a multilayer structure having multiple layers of multiple different materials.

[0116] 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 a single layer structure consisting of an electron injection material and an electron transport material. The electron transport region ETR may also have a single layer structure consisting of multiple different materials, or a structure stacked in this order from the emitting layer EML, such as an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 10 nm to about 150 nm.

[0117] The electron transport region ETR may be formed by using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser thermal transfer.

[0118] When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR is made of Alq3 (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, DPEPO (bis[2-(diphenylphosphino)phenyl]ether), oxide), 2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene, TPBi(2,4,6-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl), BCP(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroli ne), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenyl)-4-phenyl-5-tert-butylphe nyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4- The electron transport layer ETL may include, but is not limited to, Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), BAlq (berylliumbis(benzoquinolin-10-olate)), ADN (9,10-di(naphthalene-2-yl)anthracene), and mixtures thereof. The thickness of the electron transport layer ETL may be about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thickness of the electron transport layer ETL satisfies the above-mentioned range, satisfactory electron transport properties can be obtained without a substantial increase in driving voltage.

[0119] When the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may be made of, but is not limited to, lanthanoid metals such as LiF, LiQ (lithium quinolate), Li2O, BaO, NaCl, CsF, and Yb, or metal halides such as RbCl and RbI. The electron injection layer EIL may also be made of a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may have an energy bandgap of about 4 eV or more. Specifically, the organometallic salt may include, for example, metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. The thickness of the electron injection layer EIL may be about 0.1 to about 10 nm, or about 0.3 to about 9 nm. When the thickness of the electron injection layer EIL satisfies the above range, a satisfactory level of electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0120] The electron transport region ETR may include a hole-blocking layer HBL as described above. The hole-blocking layer HBL may include, for example, but is not limited to, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO).

[0121] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode or a negative electrode. The second electrode EL2 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be made of a transparent metal oxide, such as ITO, IZO, ZnO, or ITZO.

[0122] When the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture containing these (e.g., a mixture of Ag and Mg). Alternatively, the second electrode EL2 may have a multi-layer structure including a reflective film or semi-transmissive film made of the above materials and a transparent conductive film made of ITO, IZO, ZnO, ITZO, or the like.

[0123] Although not shown, the second electrode EL2 may be connected to an auxiliary electrode, which can reduce the resistance of the second electrode EL2.

[0124] In the organic electroluminescent device 10, when a voltage is applied to the first electrode EL1 and the second electrode EL2, holes injected from the first electrode EL1 move to the emission layer EML via the hole transport region HTR, and electrons injected from the second electrode EL2 move to the emission layer EML via the electron transport region ETR. The electrons and holes recombine in the emission layer EML to generate excitons, which then emit light as they fall from the excited state to the ground state.

[0125] When the organic electroluminescent device 10 is a top-emitting type, the first electrode EL1 may be a reflective electrode, and the second electrode EL2 may be a transmissive electrode or a semi-transmissive electrode. When the organic electroluminescent device 10 is a bottom-emitting type, the first electrode EL1 may be a transmissive electrode or a semi-transmissive electrode, and the second electrode EL2 may be a reflective electrode.

[0126] The organic electroluminescent device 10 according to one embodiment of the present invention is characterized by containing a monoamine compound represented by Chemical Formula 1, which can achieve high efficiency and long life, and also has the effect of lowering the driving voltage. [Example]

[0127] The present invention will be described in more detail with reference to the following specific examples and comparative examples. The following examples are merely illustrative examples to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0128] (Synthesis example) The monoamine compound according to an embodiment of the present invention can be synthesized, for example, as follows: However, the method for synthesizing the monoamine compound according to an embodiment of the present invention is not limited thereto.

[0129] 1. Synthesis of Compound A4 Compound A4, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0130] (Synthesis of intermediate IM-1) [ka]

[0131] In an Ar atmosphere, 25.00 g (75.1 mmol) of 7-bromo-1-iodonaphthalene and phenylboronic acid were placed in a 1 L three-neck flask. 10.07 g (1.1 equiv, 82.6 mmol), 1.13 g (3.0 equiv, 225.2 mmol) of K2CO3, 4.34 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added sequentially and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene for the developing layer) to obtain intermediate IM-1 (15.95 g, 75% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 283, confirming intermediate IM-1.

[0132] (Synthesis of intermediate IM-2) [ka]

[0133] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-1, 7.90 g (1.1 equiv, 50.5 mmol), 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-2 (11.71 g, 81% yield). FAB-MS was measured and a molecular ion peak was observed at mass number m / z=314, confirming the intermediate IM-2.

[0134] (Synthesis of intermediate IM-3) [ka]

[0135] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-2, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 3.05 g (1.0 equiv, 31.8 mmol) of NaOtBu, 159 mL of toluene, 8.57 g (1.1 equiv, 34.9 mmol) of 3,5-diphenylaniline, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer, and the organic layer was further extracted. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was removed by filtration and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound IM-3 (13.81 g, 83% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 523, confirming the identity of compound IM-3.

[0136] (Synthesis of Compound A4) [ka]

[0137] Under an Ar atmosphere, 8.00 g (15.3 mmol) of IM-3, 0.26 g (0.03 equiv, 0.5 mmol) of Pd(dba)2, 2.94 g (2.0 equiv, 30.6 mmol) of NaOtBu, 76 mL of toluene, 2.64 g (1.1 equiv, 16.8 mmol) of bromobenzene, and 0.31 g (0.1 equiv, 1.5 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound A4 (7.79 g, yield 85%).

[0138] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=599, confirming that the compound was A4.

[0139] 2. Synthesis of Compound A17 Compound A17, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0140] (Synthesis of intermediate IM-4) [ka]

[0141] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-2, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 3.05 g (1.0 equiv, 31.8 mmol) of NaOtBu, 159 mL of toluene, 5.91 g (1.1 equiv, 34.9 mmol) of p-biphenylamine, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer, and the organic layer was further extracted. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was removed by filtration and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound IM-4 (11.37 g, 80% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 447, confirming the compound IM-4.

[0142] (Synthesis of Compound A17) [ka]

[0143] Under an Ar atmosphere, 8.00 g (17.9 mmol) of IM-4, 0.31 g (0.03 equiv, 0.5 mmol) of Pd(dba)2, 3.44 g (2.0 equiv, 35.7 mmol) of NaOtBu, 89 mL of toluene, 6.33 g (1.1 equiv, 19.7 mmol) of 3-bromo-9-phenyl-9H-carbazole, and 0.36 g (0.1 equiv, 1.8 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer, and the organic layer was further extracted. The combined organic layers were washed with brine and then dried over MgSO4. The MgSO4 was removed by filtration and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound A17 (9.23 g, 75% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 688, confirming the identity of compound A17.

[0144] 3. Synthesis of Compound B13 Compound B13, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0145] (Synthesis of intermediate IM-5) [ka]

[0146] Under an Ar atmosphere, 25.00 g (75.1 mmol) of 7-bromo-2-iodonaphthalene, 10.07 g (1.1 equiv, 82.6 mmol) of phenylboronic acid, 1.13 g (3.0 equiv, 225.2 mmol) of K2CO3, 44.34 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain intermediate IM-5 (15.31 g, 72% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 283, confirming that this was intermediate IM-5.

[0147] (Synthesis of intermediate IM-6) [ka]

[0148] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-5, 7.90 g (1.1 equiv, 50.5 mmol), 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-6 (11.27 g, 78% yield). FAB-MS was measured and a molecular ion peak was observed at mass number m / z=314, confirming the intermediate IM-6.

[0149] (Synthesis of intermediate IM-7) [ka]

[0150] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-6, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 3.05 g (1.0 equiv, 31.8 mmol) of NaOtBu, 159 mL of toluene, 7.66 g (1.1 equiv, 34.9 mmol) of 4-(naphthalen-2-yl)aniline, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer, and the organic layer was further extracted. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was removed by filtration and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound IM-7 (12.65 g, 80% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 497, confirming the identity of compound IM-7.

[0151] (Synthesis of Compound B13) [ka]

[0152] Under an Ar atmosphere, 8.00 g (16.1 mmol) of IM-7, 0.27 g (0.03 equiv, 0.5 mmol) of Pd(dba)2, 3.09 g (2.0 equiv, 32.2 mmol) of NaOtBu, 80 mL of toluene, 7.35 g (1.1 equiv, 17.7 mmol) of 1-bromo-4-triphenylsilylbenzene, and 0.33 g (0.1 equiv, 1.6 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound B13 (9.90 g, 74% yield). FAB-MS analysis revealed that a molecular ion peak at m / z = 832 was observed, confirming that this was compound B13.

[0153] 4. Synthesis of Compound B20 Compound B20, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0154] (Synthesis of intermediate IM-8) [ka]

[0155] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-6, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 3.05 g (1.0 equiv, 31.8 mmol) of NaOtBu, 159 mL of toluene, 3.25 g (1.1 equiv, 34.9 mmol) of aniline, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was removed by filtration and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound IM-8 (8.38 g, 71% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 371, confirming the identity of compound IM-8.

[0156] (Synthesis of Compound B20) [ka]

[0157] Under an Ar atmosphere, 8.00 g (21.5 mmol) of IM-8, 0.37 g (0.03 equiv, 0.6 mmol) of Pd(dba)2, 4.14 g (2.0 equiv, 43.1 mmol) of NaOtBu, 108 mL of toluene, 9.41 g (1.1 equiv, 23.7 mmol) of 9(4-bromophenyl)-9-phenyl-9H-fluorene, and 0.44 g (0.1 equiv, 2.1 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound B20 (11.41 g, 77% yield). FAB-MS analysis revealed that a molecular ion peak at m / z = 687 was observed, confirming that this was compound B20.

[0158] 5. Synthesis of Compound B40 Compound B40, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0159] (Synthesis of Compound B40) [ka]

[0160] Under an Ar atmosphere, 8.00 g (21.5 mmol) of IM-8, 0.37 g (0.03 equiv, 0.6 mmol) of Pd(dba)2, 4.14 g (2.0 equiv, 43.1 mmol) of NaOtBu, 108 mL of toluene, 9.41 g (1.1 equiv, 23.7 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene, and 0.44 g (0.1 equiv, 2.1 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer, and the organic layer was further extracted. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound B40 (11.42 g, 75% yield). FAB-MS analysis revealed that a molecular ion peak at m / z = 687 was observed, confirming that this was compound B40.

[0161] 6. Synthesis of Compound C25 Compound C25, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0162] (Synthesis of intermediate IM-9) [ka]

[0163] Under an Ar atmosphere, 25.00 g (75.1 mmol) of 2-bromo-6-iodonaphthalene, 16.35 g (1.1 equiv, 82.6 mmol) of 2-biphenylboronic acid, 1.13 g (3.0 equiv, 225.2 mmol) of K2CO3, 44.34 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain intermediate IM-9 (18.61 g, 69% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 359, confirming that this was intermediate IM-9.

[0164] (Synthesis of intermediate IM-10) [ka]

[0165] Under an Ar atmosphere, 15.00 g (41.8 mmol) of IM-9, 7.18 g (1.1 equiv, 45.9 mmol), 17.31 g (3.0 equiv, 125.3 mmol) of K2CO3, 42.41 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-10 (12.24 g, 75% yield). FAB-MS was measured and a molecular ion peak was observed at mass number m / z=390, confirming the intermediate IM-10.

[0166] (Synthesis of Compound C25) [ka]

[0167] Under an Ar atmosphere, 10.00 g (25.6 mmol) of IM-10, 0.44 g (0.03 equiv, 0.6 mmol) of Pd(dba)2, 4.92 g (2.0 equiv, 51.2 mmol) of NaOtBu, 128 mL of toluene, 9.04 g (1.1 equiv, 28.1 mmol) of bis(4-biphenyl)amine, and 0.52 g (0.1 equiv, 2.6 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was removed by filtration and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound C25 (13.83 g, 80% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 675, confirming the identity of compound C25.

[0168] 7. Synthesis of Compound C51 Compound C51, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0169] (Synthesis of intermediate IM-11) [ka]

[0170] Under an Ar atmosphere, 25.00 g (75.1 mmol) of 2-bromo-6-iodonaphthalene, 10.07 g (1.1 equiv, 82.6 mmol) of phenylboronic acid, 1.13 g (3.0 equiv, 225.2 mmol) of K2CO3, 44.34 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain intermediate IM-11 (15.31 g, 72% yield). FAB-MS analysis revealed a molecular ion peak at m / z = 283, confirming that this was intermediate IM-11.

[0171] (Synthesis of intermediate IM-12) [ka]

[0172] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-11, 7.90 g (1.1 equiv, 50.5 mmol), 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-12 (11.42 g, 79% yield).

[0173] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=314, confirming the intermediate IM-12.

[0174] (Synthesis of Compound C51) [ka]

[0175] Under an Ar atmosphere, 8.00 g (25.4 mmol) of IM-12, 0.44 g (0.03 equiv, 0.8 mmol) of Pd(dba)2, 4.88 g (2.0 equiv, 50.8 mmol) of NaOtBu, 128 mL of toluene, 9.82 g (1.1 equiv, 28.0 mmol) of N-([1,1'-biphenyl]-4-yl)dibenzothiophen-4-amine, and 0.51 g (0.1 equiv, 2.5 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound C51 (13.28 g, 83% yield). FAB-MS analysis revealed that a molecular ion peak at m / z = 629 was observed, confirming the identity of compound C51.

[0176] 8. Synthesis of Compound D12 Compound D12, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0177] (Synthesis of intermediate IM-13) [ka]

[0178] Under an Ar atmosphere, 25.00 g (75.1 mmol) of 2-bromo-5-iodonaphthalene, 10.07 g (1.1 equiv, 82.6 mmol) of phenylboronic acid, 1.13 g (3.0 equiv, 225.2 mmol) of K2CO3, 44.34 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain intermediate IM-13 (15.95 g, 75% yield).

[0179] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=283, confirming the intermediate IM-13.

[0180] (Synthesis of intermediate IM-14) [ka]

[0181] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-13, 7.90 g (1.1 equiv, 50.5 mmol) of 4-chlorophenylboronic acid, 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-14 (11.71 g, 81% yield). FAB-MS was measured and a molecular ion peak was observed at mass number m / z=314, confirming the intermediate IM-14.

[0182] (Synthesis of Compound D12) [ka]

[0183] Under an Ar atmosphere, 9.35 g (2.2 equiv, 29.7 mmol) of IM-14, 0.23 g (0.03 equiv, 0.4 mmol) of Pd(dba)2, 2.59 g (2.0 equiv, 27.0 mmol) of NaOtBu, 67 mL of toluene, 1.5 g (13.5 mmol) of 4-fluoroaniline, and 0.27 g (0.1 equiv, 1.3 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound D12 (7.48 g, yield 83%).

[0184] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=667, confirming that the compound was D12.

[0185] 9. Synthesis of Compound D22 Compound D22, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0186] (Synthesis of Compound D22) [ka]

[0187] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-14, 10.10 g (1.1 equiv, 34.9 mmol) of (4-(diphenylamino)phenyl)boronic acid, 13.17 g (3.0 equiv, 95.3 mmol) of K2CO3, 1.84 g (0.05 equiv, 1.6 mmol) of Pd(PPh3)4, and 222 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound D22 (10.98 g, yield 66%).

[0188] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=523, confirming that the compound was D22.

[0189] 10. Synthesis of Compound E3 Compound E3, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0190] (Synthesis of intermediate IM-15) [ka]

[0191] Under an Ar atmosphere, 25.00 g (75.1 mmol) of 3-bromo-1-iodonaphthalene, 10.07 g (1.1 equiv, 82.6 mmol) of phenylboronic acid, 1.13 g (3.0 equiv, 225.2 mmol) of K2CO3, 44.34 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain intermediate IM-15 (15.52 g, yield 73%).

[0192] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=283, confirming the intermediate IM-15.

[0193] (Synthesis of intermediate IM-16) [ka]

[0194] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-15, 7.90 g (1.1 equiv, 50.5 mmol), 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-16 (12.57 g, 87% yield).

[0195] FAB-MS was measured and a molecular ion peak at mass number m / z=314 was observed, confirming the intermediate IM-16.

[0196] (Synthesis of intermediate IM-17) [ka]

[0197] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-16, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 3.05 g (1.0 equiv, 31.8 mmol) of NaOtBu, 159 mL of toluene, 5.00 g (1.1 equiv, 34.9 mmol) of 1-naphthylamine, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layers were washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound IM-17 (9.37 g, yield 70%).

[0198] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=421, confirming the compound IM-17.

[0199] (Synthesis of Compound E3) [ka]

[0200] Under an Ar atmosphere, 8.00 g (19.0 mmol) of IM-17, 0.33 g (0.03 equiv, 0.6 mmol) of Pd(dba)2, 3.65 g (2.0 equiv, 38.0 mmol) of NaOtBu, 95 mL of toluene, 4.87 g (1.1 equiv, 20.9 mmol) of 2-bromobiphenyl, and 0.39 g (0.1 equiv, 1.9 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to give compound E3 (7.40 g, yield: 68%).

[0201] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=573, confirming the compound E3.

[0202] 11. Synthesis of Compound E32 Compound E32, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0203] (Synthesis of intermediate IM-18) [ka]

[0204] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-15, 7.90 g (1.1 equiv, 50.5 mmol), 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-18 (11.42 g, 79% yield).

[0205] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=314, confirming the intermediate IM-18.

[0206] (Synthesis of Compound E32) [ka]

[0207] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-18, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 6.11 g (2.0 equiv, 63.5 mmol) of NaOtBu, 158 mL of toluene, 14.73 g (1.1 equiv, 34.9 mmol) of bis(4-(naphthalen-1-yl)phenyl)amine, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated, and the resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound E32 (18.23 g, yield 82%).

[0208] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=699, confirming that the compound was E32.

[0209] 12. Synthesis of Compound F46 Compound F46, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0210] (Synthesis of intermediate IM-19) [ka]

[0211] Under an Ar atmosphere, 25.00 g (87.4 mmol) of 2,3-dibromonaphthalene, 11.73 g (1.1 equiv, 96.2 mmol) of phenylboronic acid, 36.2 g (3.0 equiv, 262.3 mmol) of K2CO3, 45.05 g (0.05 equiv, 3.4 mmol) of Pd(PPh3), and 612 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain intermediate IM-19 (19.31 g, 78% yield).

[0212] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=283, confirming the intermediate IM-19.

[0213] (Synthesis of intermediate IM-20) [ka]

[0214] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-19, 7.90 g (1.1 equiv, 50.5 mmol), 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-20 (12.00 g, 83% yield).

[0215] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=314, confirming the intermediate IM-20.

[0216] (Synthesis of intermediate IM-21) [ka]

[0217] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-20, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 3.05 g (1.0 equiv, 31.8 mmol) of NaOtBu, 159 mL of toluene, 7.66 g (1.1 equiv, 34.9 mmol) of 4-(naphthalen-1-yl)aniline, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated, and the resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound IM-21 (10.31 g, yield 77%).

[0218] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=421, confirming that the compound was IM-21.

[0219] (Synthesis of compound F46) [ka]

[0220] Under an Ar atmosphere, 8.00 g (19.0 mmol) of IM-21, 0.33 g (0.03 equiv, 0.6 mmol) of Pd(dba)2, 3.65 g (2.0 equiv, 38.0 mmol) of NaOtBu, 95 mL of toluene, 5.49 g (1.1 equiv, 20.9 mmol) of 3-bromo-dibenzothiophen, and 0.39 g (0.1 equiv, 1.9 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound F46 (11.61 g, yield 90%).

[0221] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=679, confirming that the compound was F46.

[0222] 13. Synthesis of Compound F53 Compound F53, which is a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0223] (Synthesis of compound F53) [ka]

[0224] Under an Ar atmosphere, 8.00 g (23.4 mmol) of IM-20, 0.40 g (0.03 equiv, 0.7 mmol) of Pd(dba)2, 4.50 g (2.0 equiv, 46.8 mmol) of NaOtBu, 117 mL of toluene, 9.82 g (1.1 equiv, 25.7 mmol) of bis(dibenzothiophen-4-yl)amine, and 0.47 g (0.1 equiv, 2.3 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated, and the resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound F53 (13.44 g, yield 87%).

[0225] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=659, confirming that the compound was F53.

[0226] 14. Synthesis of Compound G54 Compound G54, a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0227] (Synthesis of intermediate IM-22) [ka]

[0228] Under an Ar atmosphere, 25.00 g (75.1 mmol) of 2-bromo-1-iodo-naphthalene, 10.07 g (1.1 equiv, 82.6 mmol) of phenylboronic acid, 1.1 g (3.0 equiv, 225.2 mmol) of K2CO3, 44.34 g (0.05 equiv, 3.8 mmol) of Pd(PPh3), and 525 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order, and the mixture was heated and stirred at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain intermediate IM-22 (16.16 g, 76% yield).

[0229] FAB-MS was measured and a molecular ion peak at mass number m / z=283 was observed, confirming the intermediate IM-22.

[0230] (Synthesis of intermediate IM-23) [ka]

[0231] Under an Ar atmosphere, 13.00 g (45.9 mmol) of IM-22, 7.90 g (1.1 equiv, 50.5 mmol), 19.04 g (3.0 equiv, 60.7 mmol) of K2CO3, 42.65 g (0.05 equiv, 2.3 mmol) of Pd(PPh3), and 321 mL of a mixed solution of toluene / EtOH / HO (4 / 2 / 1) were added to a 1 L three-neck flask in this order and heated with stirring at 80 °C. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed, and the organic layer was washed with saturated brine and then dried over MgSO4. The MgSO4 was removed by filtration, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene as the developing layer) to obtain intermediate IM-23 (10.55 g, 73% yield).

[0232] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=314, confirming the intermediate IM-23.

[0233] (Synthesis of Compound G54) [ka]

[0234] Under an Ar atmosphere, 8.00 g (25.4 mmol) of IM-23, 0.44 g (0.03 equiv, 0.8 mmol) of Pd(dba)2, 4.88 g (2.0 equiv, 50.8 mmol) of NaOtBu, 127 mL of toluene, 9.77 g (1.1 equiv, 28.0 mmol) of bis(dibenzofuran-3-yl)amine, and 0.51 g (0.1 equiv, 2.5 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound G54 (14.4 g, yield 90%).

[0235] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=627, confirming that the compound was G54.

[0236] 15. Synthesis of Compound G58 Compound G58, a monoamine compound according to one embodiment of the present invention, can be synthesized, for example, by the following reaction.

[0237] (Synthesis of intermediate IM-24) [ka]

[0238] Under an Ar atmosphere, 10.00 g (31.8 mmol) of IM-23, 0.55 g (0.03 equiv, 1.0 mmol) of Pd(dba)2, 3.05 g (1.0 equiv, 31.8 mmol) of NaOtBu, 159 mL of toluene, 3.25 g (1.1 equiv, 34.9 mmol) of aniline, and 0.64 g (0.1 equiv, 3.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated, and the resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound IM-24 (9.56 g, yield 81%).

[0239] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=371, confirming the compound IM-24.

[0240] (Synthesis of Compound G58) [ka]

[0241] Under an Ar atmosphere, 8.00 g (21.5 mmol) of IM-24, 0.37 g (0.03 equiv, 0.6 mmol) of Pd(dba)2, 4.14 g (2.0 equiv, 43.1 mmol) of NaOtBu, 108 mL of toluene, 9.36 g (1.1 equiv, 23.7 mmol) of 4-bromo-9,9'-spirobifluorene, and 0.44 g (0.1 equiv, 2.2 mmol) of tBu3P were added to a 300 mL three-neck flask in this order, and the mixture was heated to reflux with stirring. After air-cooling to room temperature, water was added to the reaction solvent and the organic layer was separated. Toluene was added to the aqueous layer to further extract the organic layer. The combined organic layer was washed with brine and then dried over MgSO4. The MgSO4 was filtered off and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography (a mixed solvent of hexane and toluene was used for the developing layer) to obtain compound G58 (10.63 g, yield 72%).

[0242] FAB-MS was measured and a molecular ion peak was observed at mass number m / z=685, confirming that the compound was G58.

[0243] (Element creation example) The organic electroluminescent devices of Examples 1 to 15 were fabricated using the above-mentioned compounds A4, A17, B13, B20, B40, C25, C51, D12, D22, E3, E32, F46, F53, G54 and G58 as materials for the electron blocking layer.

[0244] [Example Compounds] [ka] JPEG0007813090000118.jpg37116 JPEG0007813090000119.jpg42149 JPEG0007813090000120.jpg42113 JPEG0007813090000121.jpg39126JPEG0007813090000122.jpg36108

[0245] The following comparative compounds R-1 to R-8 were used as materials for the electron blocking layer to fabricate organic electroluminescent devices of comparative examples 1 to 8.

[0246] [Comparative Example Compound] [ka] JPEG0007813090000124.jpg42136 JPEG0007813090000125.jpg45149

[0247] The organic electroluminescent devices of Examples 1 to 15 and Comparative Examples 1 to 8 each comprised a 150 nm first electrode formed from ITO, a 10 nm hole injection layer formed from HT1 doped with 2% HIL-M, a 120 nm hole transport layer formed from HT1, a 10 nm electron blocking layer formed from an example compound or a comparative compound, a 30 nm emissive layer formed from BH doped with 2% BD, a 10 nm hole blocking layer formed from ET1, a 20 nm electron transport layer formed from ET2, a 1 nm electron injection layer formed from LiF, and a 120 nm second electrode formed by co-evaporating magnesium (Mg) and silver (Ag) in a 9:1 (volume ratio). All layers were formed by vacuum deposition.

[0248] [ka]

[0249] Table 1 shows the voltage, half-life, luminous efficiency and color coordinates of the organic electroluminescent devices according to Examples 1 to 15 and Comparative Examples 1 to 8.

[0250] [Table 1]

[0251] The luminous efficiency is 10mA / cm 2 The half-life is 1.0 mA / cm 2 is the value at

[0252] Referring to Table 1 above, Examples 1 to 15 exhibited lower driving voltages, longer life spans, and higher efficiency than Comparative Examples 1 to 8. The monoamine compound according to one embodiment of the present invention achieved lower driving voltages, longer life spans, and higher efficiency by including a substituted β-phenylnaphthyl group. The introduction of a naphthyl group, which has excellent resistance to heat and electric charges, enabled the device to have a longer life span while maintaining the properties of the amine. Furthermore, the substitution of a phenyl group for the naphthyl group increased the volume, reduced molecular symmetry, and suppressed crystallization, resulting in improved film quality and improved efficiency.

[0253] Examples 1, 2, 8 to 11, 14, and 15 showed improved device life and efficiency. Compounds A4, A17, D12, D22, E3, E32, G54, and G58 contain a substituent at the α-position of the naphthyl group, and stereoelectronic repulsion occurs between the substituent bonded to the α-position and the hydrogen atom substituted at the other α'-position. This causes the phenyl group substituted on the naphthyl group and the naphthyl group skeleton to twist relative to each other, reducing the planarity of the entire molecule and suppressing crystallinity, while improving hole transportability and increasing the probability of recombination of holes and electrons in the light-emitting layer.

[0254] The lifetime and efficiency of the devices were improved in Examples 3 to 7, 12, and 13. Compounds B13, B20, B40, C25, C51, F46, and F53 each contain a substituent at the β-position of the naphthyl group, and the substituent bonded to the β-position and the naphthyl group form a nearly planar three-dimensional structure, which delocalizes the conjugation around the amine and stabilizes the radical state, thereby improving the lifetime.

[0255] Comparative Example 1 showed results that were particularly short in device lifetime compared to Examples. Similar to an Example of the present invention, R1 has an amino group bonded to the β-position of the naphthyl group via a linker, but two phenyl groups are substituted on the naphthyl group, which results in a large distribution of HOMO orbitals on the naphthyl group, resulting in a relatively small electron density on the amino group side, making it difficult to maintain the amine properties that induce a long lifetime.

[0256] Comparative Example 2 is an amine compound containing a naphthyl group, but does not contain a phenylnaphthyl group, and therefore has low charge resistance and insufficient film quality, resulting in a short device life and low efficiency.

[0257] Comparative Examples 3 and 4 are compounds similar to an example of the present invention, in which an amino group is bonded to the β-position of a naphthyl group via a linker. However, a polycyclic aromatic group, not a phenyl group, is bonded to the naphthyl group. It is believed that the polycyclic aromatic group causes very strong molecular stacking, and the deposition temperature is high, which makes thermal decomposition easy to occur. As a result, the luminous efficiency and lifetime are both lower than those of the example.

[0258] Comparative Example 6 is a compound similar to one example of the present invention, in which an amino group is attached to the β-position of a naphthyl group via a linker. However, since the phenyl group contains two substituents, molecular stacking is very strong, and thermal decomposition easily occurs due to the high deposition temperature, resulting in lower luminous efficiency and lifetime compared to the examples.

[0259] The comparative examples 5 and 7 showed results in which the luminous efficiency was particularly reduced compared to the examples. It is considered that the carrier balance was disrupted because the comparative example compound R5 has a dibenzofuran ring, which is a heterocyclic ring, substituted on the naphthyl-substituted phenyl group, and the comparative example compound R7 is a diamine compound.

[0260] Comparative Example 8 showed results showing reduced luminous efficiency and lifetime compared to the Examples. It is believed that Comparative Example Compound R8 easily underwent thermal decomposition due to the simultaneous attachment of a 3-dibenzofuranly group and a 9-phenanthryl group to the nitrogen atom. That is, the 9-phenanthryl group, which can significantly strengthen molecular stacking, was attached to the nitrogen, and the 3-dibenzofuranly group, which increases the planarity of the entire molecule, was also attached, strengthening molecular stacking. As the deposition temperature increased, thermal decomposition of the molecules readily occurred, resulting in reduced device efficiency and lifetime.

[0261] The monoamine compound according to an embodiment of the present invention is used in the hole transport region, and contributes to lowering the driving voltage, increasing the efficiency, and extending the life of the organic electroluminescent device.

[0262] Although the embodiments of the present invention have been described above, those skilled in the art will understand that the present invention can be embodied in other specific forms without changing the technical spirit or essential characteristics thereof. Therefore, it should be understood that the embodiments described above are illustrative in all respects and are not limiting. [Explanation of symbols]

[0263] 10 Organic electroluminescent device EL1 First electrode HTR hole transport region HIL hole injection layer HTL hole transport layer EML Light Emitting Layer ETR electron transport region ETL electron transport layer EIL electron injection layer EL2 2nd electrode

Claims

1. A monoamine compound represented by the following chemical formula 1. 【Chemistry 1】 In the above Chemical Formula 1, Ar １ and Ar ２ each independently represents an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted 9,9-diphenylfluorenyl group, a phenyl group substituted with fluorine, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group, L is an unsubstituted phenylene group; R １ 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 cycloalkyl group having from 3 to 20 ring carbon atoms, or an unsubstituted phenyl group, R ２ represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, a is an integer of 0 to 3, m is an integer of 0 to 1, n is an integer of 0 to 6.

2. It is preferable that the chemical formula 1 is represented by any one of the following chemical formulas 2 to 8. The monoamine compound according to claim 1, 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 In the above chemical formulas 2 to 8, Ar １ , Ar ２ , L, R １ , R ２ , a, m, and n are the same as defined in Chemical Formula 1.

3. R ２ The monoamine compound according to claim 1, wherein is a hydrogen atom or a deuterium atom.

4. A monoamine compound which is at least one selected from the compounds represented by the following compound groups 1 to 7. [Compound group 1] 【Chemistry 10】 【change】 【change】 【change】 [Compound group 2] 【Chemistry 11】 【change】 【change】 【change】 [Compound group 3] 【Chemistry 12】 【change】 【change】 【change】 [Compound group 4] 【Chemistry 13】 【change】 【change】 【change】 [Compound group 5] 【Chemistry 14】 【change】 【change】 【change】 [Compound group 6] 【Chemistry 15】 【change】 【change】 【change】 [Compound group 7] 【Chemistry 16】 【change】 【change】

5. A first electrode; a hole transport region provided on the first electrode; a light-emitting layer provided on the hole transport region; an electron transport region provided on the light-emitting layer; a second electrode provided on the electron transport region; 10. An organic electroluminescent device, wherein the hole transport region contains any one of the monoamine compounds according to claim 1 to 4.

6. the hole transport region comprises a multilayer structure having a plurality of layers; 6. The organic electroluminescent device according to claim 5, wherein one of the plurality of layers that is in contact with the light-emitting layer contains the monoamine compound.

7. The hole transport region is a hole injection layer disposed on the first electrode; a hole transport layer disposed on the hole injection layer; an electron blocking layer disposed on the hole transport layer; 6. The organic electroluminescent device according to claim 5, wherein the electron blocking layer contains the monoamine compound.

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