Organic electroluminescence device and monoamine compound for organic electroluminescence device

Abstract

An organic electroluminescent device of one embodiment comprises a first electrode, a second electrode disposed on the first electrode, and an intermediate layer disposed between the first electrode and the second electrode, wherein the organic layer comprises a monoamine compound comprising a heterocompound with three condensed rings and a heterocompound with four condensed rings as substituents, and the heterocompound with four condensed rings may exhibit high luminescence efficiency by including two atoms of at least one of an oxygen atom and a sulfur atom.

Description

Technology Field

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

[0002] Recently, there has been active development of organic electroluminescence displays as image display devices. Unlike liquid crystal displays, organic electroluminescence displays are so-called self-emissive display devices that realize a display by causing a light-emitting material containing an organic compound in the light-emitting layer to emit light by recombining holes and electrons injected from a first electrode and a second electrode in the light-emitting layer.

[0003] In applying organic light-emitting diodes to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan of the devices, and there is a continuous demand for the development of materials for organic light-emitting diodes that can stably realize these requirements. The problem to be solved

[0004] One objective of the present invention is to provide an organic electroluminescent device and an amine compound for an organic electroluminescent device, and more specifically, to provide a high-efficiency organic electroluminescent device and an amine compound included in the hole transport region of an organic electroluminescent device. means of solving the problem

[0005] An organic electroluminescent device according to one embodiment of the present invention comprises a first electrode, a second electrode disposed on the first electrode, and an intermediate layer disposed between the first electrode and the second electrode. The organic layer comprises a monoamine compound having a three-ring condensed heterocompound and a four-ring condensed heterocompound as substituents. The four-ring condensed heterocompound comprises two atoms, at least one of an oxygen atom and a sulfur atom.

[0006] The heterocompound formed by the condensation of the three rings above may include any one of a nitrogen atom, a sulfur atom, and an oxygen atom.

[0007] The above heterocompounds may each independently bond to the amine group through a linker or bond directly.

[0008] The organic layer may include a hole transport region disposed on the first electrode, a light-emitting layer disposed on the hole transport region, and an electron transport region disposed on the light-emitting layer. The hole transport region may include the monoamine compound.

[0009] The hole transport region may include a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer. The hole injection layer or the hole transport layer may include the monoamine compound.

[0010] The above monoamine compound can be represented by the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above Chemical Formula 1, X is NAr1, S, or O; A and B are each independently O or S; Ar1 ​​and Ar2 are each independently a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms; R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms; L1 and L2 are directly bonded, substituted or unsubstituted cyclic arylene groups having 6 to 30 carbon atoms, or substituted or unsubstituted cyclic heteroaryl groups having 2 to 30 carbon atoms; a and b are integers from 0 to 4; and c and d is an integer between 0 and 3 inclusive, and m and n are integers between 0 and 2 inclusive.

[0014] The above chemical formula 1 can be represented by the following chemical formula 2 or chemical formula 3.

[0015] [Chemical Formula 2]

[0016]

[0017] [Chemical Formula 3]

[0018]

[0019] In the above chemical formulas 2 and 3, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1.

[0020] The above chemical formula 1 can be represented by the following chemical formula 4 or chemical formula 5.

[0021] [Chemical Formula 4]

[0022]

[0023] [Chemical Formula 5]

[0024]

[0025] In the above chemical formulas 4 and 5, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1.

[0026] The above m and n are each independently 0 or 1, and the above L1 and L2 may each independently be a ring-forming arylene group having 6 or more and 12 or fewer carbon atoms that is directly bonded, substituted, or unsubstituted.

[0027] The above Ar1 may be a substituted or unsubstituted cyclic aryl group with 6 to 18 carbon atoms.

[0028] The above chemical formula 1 can be represented by the following chemical formula 6.

[0029] [Chemical Formula 6]

[0030]

[0031] In the above chemical formula 6, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1.

[0032] An organic electroluminescent device according to one embodiment of the present invention comprises a first electrode, a second electrode disposed on the first electrode, and an organic layer disposed between the first electrode and the second electrode. The organic layer comprises a monoamine compound represented by Formula 1.

[0033] The organic layer may include a hole transport region disposed on the first electrode, a light-emitting layer disposed on the hole transport region, and an electron transport region disposed on the light-emitting layer. The hole transport region may include a monoamine compound represented by Formula 1. Effects of the invention

[0034] An organic electroluminescent device according to one embodiment of the present invention has excellent efficiency.

[0035] A monoamine compound according to one embodiment of the present invention can be used as a material for the hole transport region of an organic electroluminescent device, and by using it, the efficiency of the organic electroluminescent device can be improved.

[0036] A monoamine compound according to one embodiment of the present invention can be used as a material for the hole transport region of an organic electroluminescent device, and by using it, there is an effect of improving the efficiency of the organic electroluminescent device. Brief explanation of the drawing

[0037] FIG. 1 is a schematic cross-sectional view of an organic electroluminescent device according to one embodiment of the present invention. FIG. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIG. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. FIG. 4 is a cross-sectional view schematically showing an organic electroluminescent device according to one embodiment of the present invention. Specific details for implementing the invention

[0038] The above objects, other objects, features, and advantages of the present invention will be readily understood through 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 to ensure that the disclosed content is thorough and complete, and to ensure that the spirit of the invention is sufficiently conveyed to a person skilled in the art.

[0039] In describing each drawing, similar reference numerals have been used for similar components. In the attached drawings, the dimensions of the structures are depicted enlarged from their actual size for clarity of the invention. Terms such as "first," "second," etc., may be used to describe various components, but said components should not be limited by said terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the invention, the first component may be named the second component, and similarly, the second component may be named the first component. A singular expression includes a plural expression unless the context clearly indicates otherwise.

[0040] In this specification, terms such as "comprising" or "having" are intended to specify the existence of the features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, actions, components, parts, or combinations thereof. Furthermore, when a part such as a layer, film, region, or plate is described as being "on" another part, this includes not only the case where it is "immediately above" the other part, but also the case where there is another part in between. Conversely, when a part such as a layer, film, region, or plate is described as being "below" another part, this includes not only the case where it is "immediately below" the other part, but also the case where there is another part in between.

[0041] First, an organic electroluminescent device according to one embodiment of the present invention will be described with reference to FIGS. 1 to 3.

[0042] FIG. 1 is a schematic cross-sectional view of an organic electroluminescent device according to one embodiment of the present invention. FIG. 2 is a schematic cross-sectional view of an organic electroluminescent device according to one embodiment of the present invention. FIG. 3 is a schematic cross-sectional view of an organic electroluminescent device according to one embodiment of the present invention.

[0043] Referring to FIG. 1, an organic electroluminescent device (10) according to one embodiment of the present invention includes a first electrode (EL1), an organic layer (OL), and a second electrode (EL2). The first electrode (EL1) and the second electrode (EL2) are arranged facing each other, and an organic layer (OL) may be arranged between the first electrode (EL1) and the second electrode (EL2).

[0044] Meanwhile, FIG. 2 shows a cross-sectional view of an organic electroluminescent device (10) of one embodiment in which the organic layer (OL) includes a hole transport region (HTR), a light-emitting layer (EML), and an electron transport region (ETR), compared with FIG. 1.

[0045] In addition, FIG. 3 shows a cross-sectional view of an organic electroluminescent device (10) of one embodiment in which, compared to FIG. 2, the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL).

[0046] In addition, FIG. 4 shows a cross-sectional view of an organic electroluminescent device (10) of one embodiment in which, compared with FIG. 2, the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), and the electron transport region (ETR) includes a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL).

[0048] The organic layer (OL) comprises a monoamine compound according to one embodiment of the present invention. Hereinafter, the monoamine compound according to one embodiment of the present invention will be described in detail, and then each layer of the organic electroluminescent device (10) will be described.

[0049] In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, silyl groups, boron groups, phosphine groups, alkyl groups, alkenyl groups, aryl groups, and heterocyclic groups. Additionally, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or as a phenyl group substituted with a phenyl group.

[0050] In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0051] In this specification, the alkyl group may be straight-chain, branched-chain, or cyclic. The number of carbon atoms in the alkyl group is 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 4 or less. Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group, n-hexyl group, 1-methylhexyl group, 2-ethylhexyl 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, adamantyl 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, n-heptadecyl group, n-octadecyl group, Examples include, but are not limited to, n-nonadecyl groups, n-icosyl groups, 2-ethylicosyl groups, 2-butylicosyl groups, 2-hexylicosyl groups, 2-octylicosyl groups, n-henicosyl groups, n-docosyl groups, n-tricosyl groups, n-tetracosyl groups, n-pentacosyl groups, n-hexacosyl groups, n-heptacosyl groups, n-octacosyl groups, n-nonacosyl groups, and n-triacontyl groups.

[0052] In this specification, an 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-forming carbon atoms in the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 12 or less. Examples of aryl groups may include, but are not limited to, phenyl groups, naphthyl groups, fluorenyl groups, anthracenyl groups, phenanthryl groups, biphenyl groups, terphenyl groups, quarterphenyl groups, quinkphenyl groups, sexphenyl groups, biphenylene groups, triphenylene groups, pyrenyl groups, benzofluoranthenyl groups, crisenyl groups, etc.

[0053] In this specification, the fluorenyl group may be substituted, and two substituents may be combined to form a spiro structure. Examples of cases where the fluorenyl group is substituted are as follows. However, it is not limited thereto.

[0054]

[0055] In this specification, the heteroaryl group may be a heteroaryl group comprising one or more of O, N, P, Si, and S as heteroatoms. If the heteroaryl group comprises two heteroatoms, the two heteroatoms may be identical or different. The ring-forming carbon number of the heteroaryl group is 2 or more and 30 or less, or 5 or more and 12 or less. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The polycyclic heteroaryl group may have, for example, a two-ring or three-ring structure. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acryl group, pyridazine group, pyrazinyl group, quinoline group, quinazolin group, quinoxaline group, phenoxazine group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, thienothiophene group. Benzofuran group, phenanthroline group, thiazole group, isooxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzosilol group and dibenzofuran group, etc., are included but are not limited to these.

[0056] In this specification, silyl groups include alkyl silyl groups and aryl silyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.

[0057] In this specification, the description of the aryl group described above applies except that the arylene group is a divalent group.

[0058] In this specification, the description of the aforementioned heteroaryl group applies except that the heteroarylen group is a divalent group.

[0059] In one embodiment, the monoamine compound comprises a heterocompound with three condensed rings and a heterocompound with four condensed rings as substituents, and the heterocompound with four condensed rings comprises two atoms of at least one of an oxygen atom and a sulfur atom. For example, the heterocompound with four condensed rings included in the monoamine compound may comprise two oxygen atoms. Alternatively, the heterocompound with four condensed rings included in the monoamine compound may comprise two sulfur atoms. Alternatively, the heterocompound with four condensed rings included in the monoamine compound may comprise one oxygen atom and one sulfur atom.

[0060] A heterocompound in which three rings are condensed and included in a monoamine compound may contain any one of a nitrogen atom, a sulfur atom, and an oxygen atom.

[0061] In one embodiment, the heterocompound in which three rings included in the monoamine compound are condensed may be bonded to the amine group through a linker or directly bonded to the amine group.

[0062] In one embodiment, the heterocompound in which four rings included in the monoamine compound are condensed may be bonded to the amine group through a linker or directly bonded to the amine group.

[0063] A monoamine compound according to one embodiment is represented by the following chemical formula 1.

[0064] [Chemical Formula 1]

[0065]

[0066] In Chemical Formula 1, X is NAr1, S, or O.

[0067] In Chemical Formula 1, A and B are each independently O or S.

[0068] In Chemical Formula 1, Ar1 and Ar2 are each independently a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0069] In Chemical Formula 1, R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms.

[0070] In Chemical Formula 1, L1 and L2 are directly bonded, substituted or unsubstituted ring-forming arylene groups having 6 to 30 carbon atoms, or substituted or unsubstituted ring-forming heteroarylene groups having 2 to 30 carbon atoms.

[0071] In Chemical Formula 1, a and b are integers from 0 to 4. Meanwhile, if a is 2 or greater, multiple R1s are identical or different from each other, and if b is 2 or greater, multiple R2s are identical or different from each other.

[0072] In Chemical Formula 1, c and d are integers from 0 to 3. Meanwhile, if c is 2 or greater, multiple R3s are identical or different from each other, and if d is 2 or greater, multiple R4s are identical or different from each other.

[0073] In Chemical Formula 1, m and n are integers from 0 to 2. Meanwhile, when m is 2 or greater, multiple L1s are identical or different from each other, and when n is 2 or greater, multiple L2s are identical or different from each other.

[0074] In one embodiment, m and n of Formula 1 may each be independently 0, and L1 and L2 may each be independently direct bonds.

[0075] In one embodiment, m and n of Formula 1 are each independently 1, and L1 and L2 may each be independently substituted or unsubstituted arylene groups having 6 to 12 carbon atoms. L1 and L2 may each be, for example, independently substituted or unsubstituted phenylene groups or substituted or unsubstituted biphenylene groups. However, it is not limited thereto.

[0076] In one embodiment, Ar1 of Formula 1 may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. For example, Ar1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group. However, it is not limited thereto.

[0077] In one embodiment, A and B of Formula 1 may be the same atom. In this case, Formula 1 may be represented by the following Formula 2 or Formula 3.

[0078] [Chemical Formula 2]

[0079]

[0080] [Chemical Formula 3]

[0081]

[0082] In Chemical Formulas 2 and 3, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in Chemical Formula 1.

[0083] In one embodiment, A and B of Formula 1 may be different atoms. In this case, Formula 1 may be represented by the following Formula 4 or Formula 5.

[0084] [Chemical Formula 4]

[0085]

[0086] [Chemical Formula 5]

[0087]

[0088] In Chemical Formulas 4 and 5, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in Chemical Formula 1.

[0089] In one embodiment, Chemical Formula 1 can be represented by the following Chemical Formula 6.

[0090] [Chemical Formula 6]

[0091]

[0092] In Chemical Formula 6, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in Chemical Formula 1.

[0093] A monoamine compound represented by Formula 1 according to one embodiment of the invention may be at least one selected from the compounds listed in Compound Group 1 below. However, it is not limited thereto.

[0094] [Compound Group 1]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] Referring again to FIGS. 1 to 3, an organic electroluminescent device according to one embodiment of the present invention will be described. The organic layer (OL) comprises a monoamine compound according to one embodiment of the present invention described above. For example, the organic layer (OL) comprises a monoamine compound represented by Chemical Formula 1.

[0103] The following description focuses specifically on the differences from the monoamine compound according to the embodiment of the present invention described above, and any parts not described are based on the monoamine compound according to the embodiment of the present invention described above.

[0104] The first electrode (EL1) has conductivity. The first electrode (EL1) may be a pixel electrode or an anode. The first electrode (EL1) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. If the first electrode (EL1) is a transmissive electrode, the first electrode (EL1) may include a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode (EL1) is a semitransmissive electrode or a reflective electrode, the first electrode (EL1) 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 (for example, a mixture of Ag and Mg). Alternatively, it may be a plurality of layer structures including a reflective film or a semipermeable film formed of the above material and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the first electrode (EL1) may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0105] The thickness of the first electrode (EL1) may be about 1000 Å to about 10000 Å, for example, about 1000 Å to about 3000 Å.

[0106] An organic layer (OL) is disposed on a first electrode (EL1). The organic layer (OL) may include a hole transport region (HTR), an emitting layer (EML), and an electron transport region (ETR). When the organic layer (OL) includes a hole transport region (HTR), an emitting layer (EML), and an electron transport region (ETR), at least one of these layers may include a monoamine compound according to one embodiment.

[0107] A hole transport region (HTR) is disposed on the first electrode (EL1). The hole transport region (HTR) 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).

[0108] The hole transport region (HTR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0110] For example, the hole transport region (HTR) may have a single-layer structure of a hole injection layer (HIL) or a hole transport layer (HTL), or it may have a single-layer structure composed of a hole injection material and a hole transport material. Additionally, the hole transport region (HTR) may have a single-layer structure composed of multiple different materials, or it may have a structure of a hole injection layer (HIL) / hole transport layer (HTL), a hole injection layer (HIL) / hole transport layer (HTL) / hole buffer layer, a hole injection layer (HIL) / hole buffer layer, a hole transport layer (HTL) / hole buffer layer, or a hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) stacked sequentially from the first electrode (EL1), but is not limited thereto.

[0111] In one embodiment, the hole transport region (HTR) may include a monoamine compound according to one embodiment of the present invention. The hole transport region (HTR) may have a multilayer structure having a plurality of layers, and any one of the plurality of layers may include a monoamine compound represented by Formula 1. For example, the hole transport region (HTR) may include a hole injection layer (HIL) disposed on a first electrode (EL1) and a hole transport layer (HTL) disposed on the hole injection layer (HIL), and the hole transport layer (HTL) may include a monoamine compound represented by Formula 1. However, it is not limited thereto, and for example, the hole injection layer (HIL) may include a monoamine compound of one embodiment.

[0112] The hole transport region (HTR) may include one or more monoamine compounds of one embodiment. For example, the hole transport region (HTR) may include at least one selected from the compounds listed in the aforementioned compound group 1.

[0113] Hole transport regions (HTRs) can be formed using various methods such as vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0114] However, the hole transport area may additionally include the following materials for each layer.

[0115] The hole injection layer (HIL) is a phthalocyanine compound, for example, 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), PANI / CSA(Polyaniline / Camphor sulfonicacid), PANI / PSS((Polyaniline) / Poly(4-styrenesulfonate)), It may include NPD (N,N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), polyetherketone containing triphenylamine (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium Tetrakis(pentafluorophenyl)borate, HAT-CN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile), etc.

[0116] As described above, the hole transport layer (HTL) may include the monoamine compound of one embodiment. However, it is not limited thereto and may include general materials known in the art. For example, it may include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorine derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and 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]), and HMTPD (4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl).

[0117] The electron blocking layer (EBL) may include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorine derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), 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.

[0118] The thickness of the hole transport region (HTR) may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 5,000 Å. The thickness of the hole injection layer (HIL) may be, for example, about 30 Å to about 1,000 Å, and the thickness of the hole transport layer (HTL) may be about 30 Å to about 1,000 Å. For example, the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1,000 Å. When the thicknesses of the hole transport region (HTR), the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0119] In addition to the aforementioned materials, the hole transport region (HTR) may further include a charge-generating material to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto. For example, non-limiting examples of p-dopants include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, but are not limited thereto.

[0120] The hole transport region (HTR) may further include at least one of a hole buffer layer and an electron blocking layer (EBL). The hole buffer layer can increase light emission efficiency by compensating for the resonance distance according to the wavelength of light emitted from the light-emitting layer (EML). The material included in the hole buffer layer may be a material that can be included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that serves to prevent electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0121] The emitting layer (EML) is disposed on the hole transport region (HTR). The emitting layer (EML) may have a thickness of, for example, about 100 Å to about 1000 Å or about 100 Å to about 600 Å. The emitting layer (EML) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0122] As a material for the light-emitting layer (EML), known light-emitting materials may be used, and are not particularly limited but are selected from fluoranthene derivatives, pyrene derivatives, arylacetylene derivatives, anthracene derivatives, fluorene derivatives, perylene derivatives, chrysene derivatives, etc. Preferably, pyrene derivatives, perylene derivatives, and anthracene derivatives may be used. For example, as a host material for the light-emitting layer (EML), an anthracene derivative represented by the following chemical formula 7 may be used.

[0123] [Chemical Formula 7]

[0124]

[0125] In Chemical Formula 7, W1 to W4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or can form a ring by bonding with adjacent groups, and m1 and m2 are each independently integers from 0 to 4, and m3 and m4 are each independently integers from 0 to 5.

[0126] If m1 is 1, W1 may not be a hydrogen atom, if m2 is 1, W2 may not be a hydrogen atom, if m3 is 1, W3 may not be a hydrogen atom, and if m4 is 1, W4 may not be a hydrogen atom.

[0127] If m1 is 2 or more, multiple W1s are identical or different from each other. If m2 is 2 or more, multiple W2s are identical or different from each other. If m3 is 2 or more, multiple W3s are identical or different from each other. If m4 is 2 or more, multiple W4s are identical or different from each other.

[0128] As an example of a compound represented by Chemical Formula 7, a compound represented by the following structural formula may be cited. However, the compound represented by Chemical Formula 7 is not limited to the following.

[0129]

[0130] The light-emitting layer (EML) may include a fluorescent material selected from the group consisting of, for example, spiro-DPVBi, 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).

[0131] 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., 2,5,8,11-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), TPBi(1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), etc. can be used as dopants.

[0132] The emitting layer (EML) is, 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(1-phenyl-1H-benzo[d]imidazol-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 It may contain PPF (2,8-Bis(diphenylphosphoryl)dibenzofuran), etc.

[0133] An electron transport region (ETR) is disposed on the light-emitting layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but is not limited thereto.

[0134] The electron transport region (ETR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0136] 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 composed of an electron injection material and an electron transport material. Additionally, the electron transport region (ETR) may have a single-layer structure composed of multiple different materials, or may have an electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) structure stacked sequentially from the emitting layer (EML), but is not limited thereto. The thickness of the electron transport region (ETR) may be, for example, about 100 Å to about 1500 Å.

[0137] The electron transport region (ETR) can be formed using various methods such as vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0138] When the electron transport region (ETR) includes an electron transport layer (ETL), the electron transport region (ETR) is 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(1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq2(berylliumbis(benzoquinolin-10-olate), ADN(9,10-di(naphthalene-2-yl)anthracene) or mixtures thereof may be included, but are not limited thereto. The thickness of the electron transport layers (ETLs) is approximately It can be 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å.If the thickness of the electron transport layers (ETLs) satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0139] When the electron transport region (ETR) includes an electron injection layer (EIL), the electron transport region (ETR) may use lanthanide metals such as LiF, LiQ (Lithium quinolate), Li2O, BaO, NaCl, CsF, and Yb, or halide metals such as RbCl and RbI, but is not limited thereto. The electron injection layer (EIL) may also be composed of a material in which an electron transport material and an insulating organometal salt are mixed. The organometal salt may be a material with an energy band gap of approximately 4 eV or more. Specifically, for example, the organometal salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. The thickness of the electron injection layers (EILs) can be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layers (EILs) satisfies the ranges described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0140] As previously mentioned, the electron transport region (ETR) may include a hole blocking layer (HBL). The hole blocking layer (HBL) may include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), or DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), but is not limited thereto.

[0141] The second electrode (EL2) is placed on the electron transport region (ETR). The second electrode (EL2) may be a common electrode or a cathode. The second electrode (EL2) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. If the second electrode (EL2) is a transmissive electrode, the second electrode (EL2) may be made of a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc.

[0142] When the second electrode (EL2) is a semi-transparent electrode or a reflective electrode, the second electrode (EL2) 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 containing these (e.g., a mixture of Ag and Mg). Alternatively, it may be a plurality of layer structures including a reflective film or a semi-transparent film formed of the above material and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc.

[0143] Although not illustrated, the second electrode (EL2) can be connected to an auxiliary electrode. When the second electrode (EL2) is connected to an auxiliary electrode, the resistance of the second electrode (EL2) can be reduced.

[0144] In an organic electroluminescent device (10), as voltage is applied to the first electrode (EL1) and the second electrode (EL2), holes injected from the first electrode (EL1) move through the hole transport region (HTR) to the light-emitting layer (EML), and electrons injected from the second electrode (EL2) move through the electron transport region (ETR) to the light-emitting layer (EML). The electrons and holes recombine in the light-emitting layer (EML) to generate excitons, and light is emitted as the excitons fall from the excited state to the ground state.

[0145] When the organic electroluminescent device (10) is of the front-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 of the back-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.

[0146] An organic electroluminescent device (10) according to one embodiment of the present invention is characterized by including a monoamine compound of one embodiment, thereby enabling high efficiency and a long lifespan. In addition, there is also an effect of low driving voltage.

[0147] The present invention will be explained in more detail below through specific embodiments and comparative examples. The following embodiments are merely examples to aid in understanding the present invention and do not limit the scope of the present invention.

[0148] (Synthetic Example)

[0149] A monoamine compound according to one embodiment of the present invention can be synthesized, for example, as follows. However, the method of synthesizing the monoamine compound according to one embodiment of the present invention is not limited thereto.

[0150] 1. Synthesis of Compound 5

[0151] (1) Synthesis of Compound A

[0152]

[0153] A-1 (1.1g), 2,3-dibromo-2,3-dihydrobenzofuran (2.5g), Pd(PPh3)4 (0.5g), and K2CO3 (3.1g) were dissolved in THF (50 ml) and stirred at 80°C for 10 hours. After lowering the temperature of the reaction mixture to room temperature, the reaction was terminated with water and extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and the residue obtained by vacuum distillation was separated and purified by column chromatography to obtain intermediate A-2 (2.6g, yield: 65%).

[0154] Intermediate A-2 (2.6 g) and K2CO3 (3.7) were dissolved in THF (50) and stirred at 80°C for 3 hours. After lowering the temperature of the reaction mixture to room temperature, the reaction was terminated with water and extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and the residue obtained by vacuum distillation was separated and purified by column chromatography to obtain intermediate A-3 (1.5 g, yield: 80%).

[0155] Br2 (1.24g) dissolved in dichloromethane (30 ml) was added to intermediate A-3 (1.5g), and the mixture was stirred at room temperature for 3 hours. The reaction was terminated with water, an aqueous solution of Na2S2O3 (100 ml) was added, and the mixture was extracted three times with dichloromethane and water. The separated organic layer was dried with anhydrous magnesium sulfate and the residue obtained by vacuum distillation was separated and purified by recrystallization to obtain compound A (1.43g, yield: 70%).

[0156] (2) Synthesis of Compound 5

[0157]

[0158] Reactant 5-1 (1.6 g) was dissolved in toluene (50 mL) along with 3-iodo-9-phenyl-9H-carbazole (4.6 g), Pd2(dba)3 (0.5 g), PtBu3 (0.2 ml), and KOtBu3 (2.8 g), and stirred at 85°C for 1 hour. The reaction mixture was cooled to room temperature, the reaction was terminated with water, and the mixture was extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and subjected to vacuum distillation; the resulting residue was separated and purified by column chromatography to obtain intermediate 5-2 (2.6 g, yield: 65%).

[0159] Compound 5 (2.8g, yield: 80%) was obtained by proceeding in the same manner as the synthesis method of intermediate 5-2, except that compound A (2.2g) was used instead of intermediate 5-2 (2.6g) and 3-iodo-9-phenyl-9H-carbazole.

[0161] 2. Synthesis of Compound 24

[0162]

[0163] Reactant 24-1 (1.1g), 2-(4-bromophenyl)dibenzo[b,d]thiophene (3.3g), Pd2(dba)3 (0.5g), PtBu3 (0.2ml), and KOtBu (2.8g) were dissolved in toluene (50mL) and stirred at 85°C for 1 hour. After lowering the temperature of the reaction mixture to room temperature, the reaction was terminated with water and extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and the residue obtained by vacuum distillation was separated and purified by column chromatography to obtain intermediate 24-2 (2.5g, yield: 75%).

[0164] Compound 24 (2.2g, yield: 70%) was obtained by proceeding in the same manner as the synthesis method of intermediate 24-2, except that A (2.2g) was used instead of intermediate 24-2 (2.5g) and 2-(4-bromophenyl)dibenzo[b,d]thiophene.

[0166] 3. Synthesis of Compound 32

[0167] (1) Synthesis of reactant C

[0168]

[0169] Compound B-1 (2.4g) was obtained by proceeding in the same manner as the synthesis method of intermediate A-2, except that 2,3-dibromo-2,3-dihydrobenzo[b]thiophene (2.6g) was used instead of 2,3-dibromo-2,3-dihydrobenzofuran. Compound B-2 (1.6g, yield: 80%) was obtained by proceeding with intermediate B-1 (2.4g) in the same manner as the synthesis method of compound A-3.

[0170] Compound C (1.5g, yield: 70%) was obtained by proceeding with intermediate B-2 (1.6g) in the same manner as the synthesis method for compound A.

[0171] (2) Synthesis of Compound 32

[0172]

[0173] 5-1 (2.0 g), 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.3 g), Pd2(dba)3 (0.5 g), PtBu3 (0.2 ml), and KOtBu (2.8 g) were dissolved in toluene (50 mL) and stirred at 85°C for 1 hour. After cooling the reaction mixture to room temperature, the reaction was terminated with water and extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and subjected to vacuum distillation; the resulting residue was separated and purified by column chromatography to obtain intermediate 32-1 (3.5 g, yield 1 80%).

[0174] Compound 32 (2.5g, yield: 70%) was obtained by proceeding in the same manner as the synthesis method for intermediate 32-1, except that C (2.3g) was used instead of intermediate 32-1 (3.5g) and 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.3g).

[0176] 4. Synthesis of Compound 59

[0177] (1) Synthesis of Compound D

[0178]

[0179] Br2 (1.24g) dissolved in dichloromethane (30 ml) was added to D-1 (1.7g), and the mixture was stirred at room temperature for 3 hours. The reaction was terminated with water, an aqueous solution of Na2S2O3 (100 ml) was added, and the mixture was extracted three times with dichloromethane and water. The separated organic layer was dried with anhydrous magnesium sulfate and the residue obtained by vacuum distillation was separated and purified by recrystallization to obtain compound D (1.6g, yield: 70%).

[0180] (2) Synthesis of Compound 59

[0181]

[0182] Reactant 24-1 (1.2 g), 3-iodo-9-phenyl-9H-carbazole (3.4 g), Pd2(dba)3 (0.5 g), PtBu3 (0.2 ml), and KOtBu (2.7 g) were dissolved in toluene (50 mL) and stirred at 85°C for 1 hour. After cooling the reaction mixture to room temperature, the reaction was terminated with water and extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and subjected to vacuum distillation; the resulting residue was separated and purified by column chromatography to obtain intermediate 59-1 (2.2 g, yield: 65%).

[0183] Compound 59 (2.4g, yield: 75%) was obtained by proceeding in the same manner as the synthesis method of intermediate 59-1, except that D (2.2g) was used instead of intermediate 59-1 (2.2g) and 3-iodo-9-phenyl-9H-carbazole.

[0185] 5. Synthesis of Compound 67

[0186]

[0187] Intermediate 24-1 (1.2 g), 2-(4-bromophenyl)dibenzo[b,d]furan (3.0 g), Pd2(dba)3 (0.5 g), PtBu3 (0.2 ml), and KOtBu (2.5 g) were dissolved in toluene (50 mL) and stirred at 85°C for 1 hour. After cooling the reaction mixture to room temperature, the reaction was terminated with water and extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and the residue obtained by vacuum distillation was separated and purified by column chromatography to obtain intermediate 67-1 (2.1 g, yield: 66%).

[0188] Compound 67 (3.6 g, yield: 80%) was obtained in the same manner as 67-1 using intermediate 67-1 (2.1 g) and D (2.3 g) instead of 2-(4-bromophenyl)dibenzo[b,d]furan.

[0190] 6. Synthesis of Compound 75

[0191] (1) Synthesis of Compound B

[0192]

[0193] Compound B-1 (2.4g) was obtained in the same manner as intermediate A-2, except that intermediate B-1 (1.1g) was obtained using 2,3-dibromo-2,3-dihydrobenzo[b]thiophene (2.6g) instead of 2,3-dibromo-2,3-dihydrobenzofuran.

[0194] Compound B-2 (1.6g, yield: 80%) was obtained from intermediate B-1 (2.4g) in the same way as compound A-3.

[0195] Intermediate B-2 (1.6g) was used to obtain B (1.5g, yield: 70%) in the same way as compound A.

[0196] (2) Synthesis of Compound 75

[0197]

[0198] Intermediate 75-1 (1.8 g) was dissolved in toluene (mL) along with 3-iodo-9-phenyl-9H-carbazole (3.9 g), Pd2(dba)3 (0.5 g), PtBu3 (0.2 ml), and KOtBu3 (2.7 g), and the mixture was stirred at 85°C for 1 hour. The reaction mixture was cooled to room temperature, the reaction was terminated with water, and the mixture was extracted three times with ethyl ether. The separated organic layer was dried with anhydrous magnesium sulfate and subjected to vacuum distillation; the resulting residue was separated and purified by column chromatography to obtain intermediate 75-2 (2.0 g, yield: 60%).

[0199] Compound 75 (2.5g, yield: 79%) was obtained by using intermediate 75-2 (2.0g) and B (2.2g) in the same way as with 75-2.

[0201] (Example of device creation)

[0202] Organic electroluminescent devices of Examples 1 to 6 were fabricated using the aforementioned compounds 5, 24, 32, 59, 67, and 75 as hole transport region materials.

[0203] [Example Compound]

[0204]

[0205] Organic electroluminescent devices of Comparative Examples 1 to 4 were fabricated using the following Comparative Example compounds R-1 to R-4 as hole transport regions.

[0206] [Comparative Example Compound]

[0207]

[0208]

[0209] The organic electroluminescent devices of the examples and comparative examples were prepared by the following method. The anode was Corning 15 Ω / cm 2 A (1200 Å) ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, then cleaned by irradiating with ultraviolet light for 30 minutes and exposing to ozone, and then installed in a vacuum deposition apparatus. On the upper surface of the substrate, a known material, 2-TNATA, was first vacuum deposited to form a hole injection layer with a thickness of 600 Å, and then a hole transport layer was formed by vacuum depositing a compound from an example or comparative example to a thickness of 300 Å as a hole transport compound.

[0210] A light-emitting layer with a thickness of 300 Å was formed by simultaneously depositing 9,10-di(naphthalen-2-yl)anthracene (hereinafter, DNA) as a known blue fluorescent host and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter, DPAVBi), a known compound, as a blue fluorescent dopant in a weight ratio of 98:2 on the upper surface of the hole transport layer.

[0211] Subsequently, an organic electroluminescent device was fabricated by depositing Alq3 as an electron transport layer with a thickness of 300 Å on top of the light-emitting layer, depositing LiF, an alkali metal halide, as an electron injection layer with a thickness of 10 Å on top of the electron transport layer, and vacuum depositing Al with a thickness of 3000 Å (cathode electrode) to form a LiF / Al electrode. Each layer was formed by vacuum deposition.

[0212] [Sensor-forming compounds]

[0213]

[0214] The organic electroluminescence efficiencies according to Examples 1 to 6 and Comparative Examples 1 to 4 are shown in Table 1 below. The luminescence efficiency is 50 mA / cm² 2 The value was measured at, and the half-life is 1.0 mA / Cm 2 This is the test result from.

[0215] Precision transport layer Voltage (V) Luminance (cd / m²) 2 ) Efficiency (cd / A) Lifespan (h) Example 1 Example Compound 5 4.89 3410 6.82 412 Example 2 Example Compound 24 4.87 3435 6.87 406 Example 3 Example Compound 32 4.64 3385 6.77 419 Example 4 Example Compound 59 4.56 3460 6.92 423 Example 5 Example Compound 67 4.67 3475 6.95 410 Example 6 Example Compound 75 4.87 3300 6.60 405 Comparative Example 1 Comparative Example Compound R-1 5.9 2645 5.29 258 Comparative Example 2 Comparative Example Compound R-2 5.7 3121 5.4 298 Comparative Example 3 Comparative Example Compound R-3 6.8 2854 5.2 235 Comparative Example 4 Comparative Example Compound R-4 7.0 2587 5.5 260

[0216] Referring to Table 1 above, it can be confirmed that Examples 1 to 6 all achieve lower voltage, longer lifespan, and higher efficiency compared to Comparative Examples 1 to 4. In particular, it can be confirmed that the lifespan is significantly improved compared to the Comparative Examples due to the effect of improving the device's lifespan. It is determined that the monoamine compound according to the present invention has a shallow HOMO (Highest Occupied Molecular Orbital) compared to the materials of the Comparative Examples, and that the charge balance between holes and electrons is improved through the control of the charge injection rate, thereby improving the efficiency and lifespan of the device.

[0217] A monoamine compound according to one embodiment of the present invention is used in the hole transport region to contribute to lower driving voltage, higher efficiency, and longer lifespan of an organic electroluminescent device.

[0218] Although embodiments of the present invention have been described above, those skilled in the art will understand that the present invention may be implemented in other specific forms without changing its technical concept or essential features. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. Explanation of the symbols

[0219] 10: Organic electroluminescent device EL1: First electrode HTR: Hole transport zone HIL: Hole injection layer HTL: Hole transport layer EML: Emissive layer ETR: Electronic Transport Area ETL: Electronic Transport Layer EIL: Electron Injection Layer EL2: Second Electrode

Claims

Claim 1 An organic electroluminescent device comprising: a first electrode; a second electrode disposed on the first electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer comprises a monoamine compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, X is NAr2, S, or O, A and B are each independently O or S, Ar1 and Ar2 are each independently a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R 1, R2 and R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, R3 is an unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, L1 and L2 are directly bonded, substituted or unsubstituted cyclic arylene groups having 6 to 30 carbon atoms, or substituted or unsubstituted cyclic heteroarylene groups having 2 to 30 carbon atoms, a and b are integers from 0 to 4, c is an integer from 1 to 3, d is an integer from 0 to 3, and m and n are integers from 0 to 2. Claim 2 In claim 1, the intermediate layer comprises a hole transport region disposed on the first electrode; a light-emitting layer disposed on the hole transport region; and an electron transport region disposed on the light-emitting layer, wherein the hole transport region comprises the monoamine compound, forming an organic electroluminescent device. Claim 3 In paragraph 2, the hole transport region comprises a hole injection layer disposed on the first electrode; and a hole transport layer disposed on the hole injection layer, and the hole injection layer or the hole transport layer comprises the monoamine compound, forming an organic electroluminescent device. Claim 4 An organic electroluminescent device according to claim 1, wherein the above chemical formula 1 is represented by the following chemical formula 2 or chemical formula 3: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1. Claim 5 An organic electroluminescent device according to claim 1, wherein the above chemical formula 1 is represented by the following chemical formula 4 or chemical formula 5: [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 4 and 5, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1. Claim 6 An organic electroluminescent device according to claim 1, wherein m is 1 or 2, and L1 is a substituted or unsubstituted ring-forming arylene group having 6 or more and 12 or fewer carbon atoms. Claim 7 An organic electroluminescent device according to claim 1, wherein Ar1 is a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms. Claim 8 An organic electroluminescent device according to claim 1, wherein the above chemical formula 1 is represented by the following chemical formula 6: [Chemical Formula 6] In the above chemical formula 6, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1. Claim 9 Monoamine compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, X is NAr2, S, or O, A and B are each independently O or S, Ar1 and Ar2 are each independently a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R 1, R2 and R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, R3 is an unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, L1 and L2 are directly bonded, substituted or unsubstituted cyclic arylene groups having 6 to 30 carbon atoms, or substituted or unsubstituted cyclic heteroarylene groups having 2 to 30 carbon atoms, a and b are integers from 0 to 4, c is an integer from 1 to 3, d is an integer from 0 to 3, and m and n are integers from 0 to 2. Claim 10 In claim 9, the monoamine compound wherein Chemical Formula 1 is represented by the following Chemical Formula 2 or Chemical Formula 3: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1. Claim 11 In claim 9, the monoamine compound wherein Chemical Formula 1 is represented by Chemical Formula 4 or Chemical Formula 5: [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 4 and 5, X, Ar1, R1 to R4, L1, L2, a to d, m, and n are the same as defined in chemical formula 1. Claim 12 A monoamine compound according to claim 9, wherein m is 1 or 2, and L1 is a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms. Claim 13 In claim 9, the above Ar1 is a monoamine compound in which the aryl group is a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms.

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