Organic compound and electroluminescent device comprising the same

Abstract

The present invention relates to a novel organic compound represented by [Chemical Formula I] that can be employed in an organic layer, such as a hole transport layer, within an organic light-emitting device to realize light-emitting characteristics such as low voltage driving of the device and excellent light-emitting efficiency, and to an organic light-emitting device containing the same. [Chemical Formula I]

Description

Technology Field

[0001] The present invention relates to a compound employed in an organic light-emitting diode, and more specifically, to an organic compound characterized by being employed as an organic layer material within an organic light-emitting diode, and to an organic light-emitting diode in which the light-emitting characteristics, such as low-voltage operation of the device and excellent light-emitting efficiency, are significantly improved by employing the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs) can be formed on transparent substrates, and compared to plasma display panels or inorganic light-emitting diode (EL) displays, they have the advantages of being able to operate at a low voltage of 10 V or less, consuming relatively little power, and having excellent color quality, and can display three colors of green, blue, and red, so they have recently become the subject of much interest as next-generation display devices.

[0003] However, for such organic light-emitting diodes to exhibit the characteristics described above, it is necessary for the materials forming the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials—to be supported by stable and efficient materials; yet, the development of stable and efficient organic layer materials for organic light-emitting diodes has not yet been sufficiently achieved.

[0004] Therefore, in order to realize more stable organic light-emitting diodes and to achieve high efficiency, long lifespan, and large scale, further improvements in efficiency and lifespan characteristics are required; in particular, there is an urgent need for the development of materials constituting each organic layer of the organic light-emitting diode.

[0005] In this regard, research has recently been actively conducted on the hole transport layer material of the aforementioned organic light-emitting diode structure to improve the mobility of existing organic materials. The problem to be solved

[0006] Accordingly, the present invention aims to provide a novel organic compound that can be employed in an organic layer, such as a hole transport layer, within an organic light-emitting device to realize excellent luminescence characteristics, such as low-voltage driving of the device and improved luminescence efficiency, and an organic light-emitting device containing the same. means of solving the problem

[0007] To solve the above problem, the present invention provides an organic compound represented by the following [Chemical Formula I] and an organic light-emitting device that includes the same in an organic layer such as a hole transport layer within the device.

[0008] [Chemical Formula I]

[0009]

[0010] The characteristic structure of the above [Chemical Formula I] and the definitions of the compounds realized by it, Np, L, Ar1, Ar2 and R1 to R3 will be described later. Effects of the invention

[0011] When the organic compound according to the present invention is adopted as an organic layer material, such as a hole transport layer in an organic light-emitting diode, light-emitting characteristics such as low voltage driving of the device and excellent luminous efficiency can be realized, making it useful for various display devices. Specific details for implementing the invention

[0012] The present invention will be described in more detail below.

[0013] The present invention relates to a compound employed in an organic layer within an organic light-emitting diode that can achieve light-emitting characteristics such as low voltage driving of the device and excellent luminous efficiency, characterized by including at least one cyano group (CN) at a specific position in the compound core, and is represented by the following [Chemical Formula I].

[0014] [Chemical Formula I]

[0015]

[0016] In the above [Chemical Formula I], Np is represented by the following [Structural Formula 1] or [Structural Formula 2].

[0017] [Structural Formula 1]

[0018]

[0019] [Structural Formula 2]

[0020]

[0021] In the above [Chemical Formula I], [Structural Formula 1] and [Structural Formula 2],

[0022] L is a single bond, or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and m is an integer from 0 to 3, and if m is 2 or more, a plurality of Ls are identical or different from each other.

[0023] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0024] R1 to R3 are identical or different from each other and are each independently selected from hydrogen, deuterium, halogen group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted amine group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heteroaryl group and substituted or unsubstituted silyl group, o is an integer from 0 to 4, and p and q are integers from 0 to 6, and if o, p and q are 2 or more, a plurality of R1 to R3 are each identical or different from each other.

[0025] CN is a cyano group, and n is 1 or 2.

[0027] Meanwhile, in the definitions of L, Ar1, Ar2 and R1 to R3 above, "substituted or unsubstituted" means that L, Ar1, Ar2 and R1 to R3 are each substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, nitro group, hydroxyl group, alkyl group, halogenated alkyl group, deuteriumated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuteriumated alkoxy group, amine group, aryl group, heteroaryl group, alkylsilyl group, and arylsilyl group, or are substituted with a substituent in which two or more of the said substituents are connected, or have no substituents.

[0028] For example, the term substituted aryl group means that the phenyl group, biphenyl group, naphthalene group, fluorenyl group, pyrenyl group, phenanthrenyl group, perylene group, tetracenyl group, anthracenyl group, etc., are substituted with other substituents.

[0029] In addition, the term substituted heteroaryl group means that pyridyl group, thiophenyl group, triazine group, quinoline group, phenanthroline group, imidazole group, thiazole group, oxazole group, carbazole group and their condensed heterocyclic groups, such as benzquinoline group, benzimidazole group, benzoxazole group, benzthiazole group, benzcarbazole group, dibenzothiophenyl group, dibenzofuran group, etc., are substituted with other substituents.

[0031] In the present invention, examples of the substituents are described in detail below, but are not limited thereto.

[0032] In the present invention, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohectylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, There are, but are not limited to, 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups, etc.

[0033] In the present invention, the alkoxy group may be a straight chain or a branched chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferably 1 to 20, which is within the range that does not cause steric interference. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0034] In addition, in the present invention, the alkyl group or alkoxy group may be substituted with deuterium or / and a halogen group to be a deuterated alkyl group or alkoxy group, or a halogenated alkyl group or alkoxy group.

[0035] In the present invention, the aryl group may be monocyclic or polycyclic, and although the number of carbon atoms is not particularly limited, it is preferably 6 to 30. Additionally, it includes a polycyclic aryl group structure fused with cycloalkyl, etc. Examples of monocyclic aryl groups include phenyl groups, biphenyl groups, terphenyl groups, stilbene groups, etc. Examples of polycyclic aryl groups include naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups, perylenyl groups, tetracenyl groups, chrysenyl groups, fluorenyl groups, acenaphthacenyl groups, triphenylene groups, fluoranthrene groups, etc., but the scope of the present invention is not limited only to these examples.

[0036] In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, examples include , , There are others.

[0037] In the present invention, the fluorenyl group comprises a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which the connection of one ring compound is broken in a structure in which two ring organic compounds are connected through one atom, examples include , There are others.

[0038] In addition, the carbon atoms of the above ring may be substituted with one or more heteroatoms selected from N, S, and O, examples include , , , There are others.

[0039] In the present invention, the heteroaryl group is a heterocyclic group comprising O, N, or S as a heteroatom, and although the number of carbon atoms is not particularly limited, it is preferably 2 to 30 carbon atoms, and comprises a polycyclic heteroaryl group structure fused with cycloalkyl or heterocycloalkyl, etc. Specific examples thereof in the present invention include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, an acryl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazolin group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, Benzooxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazoyl group, thiadiazolyl group, benzothiazoyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., are included, but are not limited to these.

[0040] In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc. Specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., but are not limited thereto.

[0041] Specific examples of halogen groups used as substituents in the present invention include fluorine (F), chlorine (Cl), bromine (Br), etc.

[0042] In the present invention, the cycloalkyl group refers to a monocyclic, polycyclic, and spiroalkyl radical, and includes the same, preferably containing a cyclic carbon atom having 3 to 20 carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicycloheptyl, spirodecyl, spirondecyl, adamantyl, etc., and the cycloalkyl group may be optionally substituted.

[0043] In the present invention, the heterocycloalkyl group refers to an aromatic and non-aromatic cyclic radical containing one or more heteroatoms, and includes the above, wherein one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, N or S, and specifically, when N is included, may be aziridine, pyrrolidine, piperidine, azephan, azocan, etc.

[0044] In the present invention, the amine group may be -NH2, an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., and the arylamine group refers to an amine substituted with an aryl group, the alkylamine group refers to an amine substituted with an alkyl group, and the arylheteroarylamine group refers to an amine substituted with an aryl and a heteroaryl group. Examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group and heteroaryl group among the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group, a polycyclic heteroaryl group. The arylamine group and arylheteroarylamine group comprising two or more aryl groups and heteroaryl groups may be a monocyclic aryl group (heteroaryl group). It may include a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (heteroaryl group) and a polycyclic aryl group (heteroaryl group) simultaneously. Additionally, the aryl group and heteroaryl group among the arylamine group and the arylheteroarylamine group may be selected from the examples of aryl groups and heteroaryl groups described above.

[0046] The organic compound according to the present invention represented by [Chemical Formula I] above can be used in various organic layers within an organic light-emitting diode due to its structural specificity, and preferably can be used in a hole transport layer.

[0047] Preferred embodiments of the organic compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited thereto.

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0073] As such, the organic compound according to the present invention can be synthesized to have various properties by utilizing a characteristic framework that exhibits unique properties and a moiety having unique properties introduced therein. As a result, the organic compound according to the present invention can be applied as various organic layer materials such as an emissive layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer, and preferably, as a hole transport material, it can further improve luminescence characteristics such as the luminescence efficiency of a device.

[0075] In addition, the compound of the present invention can be applied to a device according to a general method for manufacturing an organic light-emitting device, and an organic light-emitting device according to one embodiment of the present invention may be formed with a structure including a first electrode, a second electrode, and an organic layer disposed between them, and may be manufactured using a conventional method and materials for manufacturing a device, except that the organic compound according to the present invention is used in the organic layer of the device.

[0076] The organic layer of the organic light-emitting diode according to the present invention may be formed as a single layer structure, but may be formed as a multilayer structure in which two or more organic layers are stacked. For example, it may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc., and may have a structure including a light efficiency improvement layer (Capping layer) provided in the organic light-emitting diode, but is not limited thereto and may include a smaller or larger number of organic layers.

[0077] The structure of the organic layer of a preferred organic light-emitting diode according to the present invention will be explained in more detail in the embodiments described below.

[0079] In addition, the organic light-emitting diode according to the present invention can be manufactured by using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

[0080] In addition to the above method, an organic light-emitting diode can also be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, an emitting layer, and an electron transport layer, but is not limited thereto and may have a single-layer structure. Furthermore, the organic layer can be manufactured with fewer layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0081] As for the anode material, a material with a large work function is generally preferred so that hole injection into the organic layer can be smooth. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metal and oxide such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited to these.

[0082] The above-mentioned cathode material is preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0083] The hole injection material is a material capable of effectively receiving holes from the anode at low voltage, and it is desirable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited to these.

[0084] As a hole transport material, a material capable of receiving holes from an anode or a hole injection layer and transferring them to an emissive layer is suitable if it has high hole mobility. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions; however, by using the organic compound according to the present invention, the low-voltage driving characteristics, luminous efficiency, and lifespan characteristics of the device can be further improved.

[0085] As for the luminescent material, it is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material with good quantum efficiency for fluorescence or phosphorescence is preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, etc., but are not limited to these.

[0086] As an electron transport material, it is a material that can effectively receive electrons from the cathode and transfer them to the emissive layer, and a material with high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavone-metal complexes, but are not limited to these.

[0088] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0089] In addition, the organic light-emitting compound according to the present invention can also function in organic electronic devices, including organic solar cells, organic photosensitive materials, and organic transistors, on a principle similar to that applied to organic light-emitting devices.

[0091] The present invention will be described in more detail below with reference to preferred embodiments. However, these embodiments are intended to explain the invention more specifically, and the scope of the invention is not limited by them. It will be obvious to those skilled in the art that various changes and modifications are possible within the scope and spirit of the invention.

[0093] Synthetic example 1 : Synthesis of Compound 2

[0094] (1) Preparation Example 1 : Synthesis of intermediate 2-1

[0095]

[0096] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to 1-Bromo-4-chloronaphthalene (10.0 g, 0.041 mol), 4-Cyanophenylboronic acid (7.3 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), and Pd(PPh3)4 (1.0 g, 0.82 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.2 g (yield 75.1%) of <Intermediate 2-1>.

[0098] (2) Preparation Example 2 : Synthesis of Compound 2

[0099]

[0100] 150 mL of Xylene was added to intermediate 2-1 (10.0 g, 0.038 mol), Bis(4-biphenylyl)amine (18.3 g, 0.057 mol), NaOtBu (10.9 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 14.1 g (yield 67.8%) of <Compound 2>.

[0101] LC / MS: m / z=548[(M) + ]

[0103] Synthetic example 2: Synthesis of Compound 14

[0104] (1) Preparation Example 1 : Synthesis of intermediate 14-1

[0105]

[0106] 150 mL of toluene was added to 2-Bromo-9,9'-spirobi[9H-fluorene] (10.0 g, 0.025 mol), 2-Aminobiphenyl (6.4 g, 0.038 mol), NaOtBu (7.3 g, 0.076 mol), Pd(dba)2 (0.6 g, 1.0 mmol), and t-Bu3P (0.4 g, 2.0 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.6 g (yield 70.3%) of <Intermediate 14-1>.

[0108] (2) Preparation Example 2: Synthesis of Compound 14

[0109]

[0110] 150 mL of Xylene was added to intermediate 2-1 (10.0 g, 0.038 mol), intermediate 14-1 (27.5 g, 0.057 mol), NaOtBu (10.9 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 18.6 g (yield 69.0%) of <Compound 14>.

[0111] LC / MS: m / z=710[(M) + ]

[0113] Synthetic example 3: Synthesis of Compound 39

[0114] (1) Preparation Example 1 : Synthesis of intermediate 39-1

[0115]

[0116] 200 mL of Dioxane was added to intermediate 2-1 (10.0 g, 0.038 mol), Bis(pinacolato)diboron (26.1 g, 0.046 mol), CH3COOK (7.4 g, 0.076 mol), Pd(dppf)Cl2 (0.8 g, 1.14 mmol), and X-phos (0.7 g, 1.38 mmol), and the mixture was reacted with stirring at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 9.5 g (yield 70.5%) of <intermediate 39-1>.

[0118] (2) Preparation Example 2 : Synthesis of intermediate 39-2

[0119]

[0120] 1-Bromo-4-chlorobenzene (10.0 g, 0.052 mol), intermediate 39-1 (22.3 g, 0.062 mol), K2CO3 (21.7 g, 0.156 mol), and Pd(PPh3)4 (1.2 g, 1.04 mmol) were mixed with 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O and reacted at 100 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted, concentrated, and then column-coated to obtain 13.3 g (yield 74.9%) of <intermediate 39-2>.

[0122] (3) Preparation Example 3 : Synthesis of intermediate 39-3

[0123]

[0124] 150 mL of toluene was added to 3-Bromodibenzothiophene (10.0 g, 0.038 mol), 2-Aminobiphenyl (9.7 g, 0.057 mol), NaOtBu (11.0 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.4 g (yield 70.4%) of <intermediate 39-3>.

[0126] (4) Preparation Example 4: Synthesis of Compound 39

[0127]

[0128] 150 mL of Xylene was added to intermediate 39-2 (10.0 g, 0.029 mol), intermediate 39-3 (15.5 g, 0.044 mol), NaOtBu (8.5 g, 0.088 mol), Pd(dba)2 (0.7 g, 1.16 mmol), and t-Bu3P (0.5 g, 2.32 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.7 g (yield 65.9%) of <Compound 39>.

[0129] LC / MS: m / z=654[(M) + ]

[0131] Synthetic example 4: Synthesis of Compound 56

[0132] (1) Preparation Example 1 : Synthesis of intermediate 56-1

[0133]

[0134] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to 1-Bromo-4-chloronaphthalene (10.0 g, 0.041 mol), 3-Cyanophenylboronic acid (7.3 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), and Pd(PPh3)4 (1.0 g, 0.82 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.9 g (yield 72.4%) of <Intermediate 56-1>.

[0136] (2) Preparation Example 2: Synthesis of Compound 56

[0137]

[0138] 150 mL of Xylene was added to intermediate 56-1 (10.0 g, 0.038 mol), N-Biphenyl-4-yl-3-dibenzofuranamine (19.1 g, 0.057 mol), NaOtBu (10.9 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 14.2 g (yield 66.6%) of <Compound 56>.

[0139] LC / MS: m / z=562[(M) + ]

[0141] Synthetic example 5: Synthesis of Compound 80

[0142] (1) Preparation Example 1 : Synthesis of intermediate 80-1

[0143]

[0144] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to 1-Bromo-4-chloronaphthalene (10.0 g, 0.041 mol), 3,5-Dicyanophenylboronic acid (8.5 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), and Pd(PPh3)4 (1.0 g, 0.82 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.7 g (yield 72.8%) of <intermediate 80-1>.

[0146] (2) Preparation Example 2: Synthesis of Compound 80

[0147]

[0148] 150 mL of Xylene was added to intermediate 80-1 (10.0 g, 0.035 mol), 2-(4-Biphenylyl)amino-9,9-dimethylfluorene (18.8 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 13.9 g (yield 65.4%) of <Compound 80>.

[0149] LC / MS: m / z=613[(M) + ]

[0151] Synthetic example 6: Synthesis of Compound 89

[0152] (1) Preparation Example 1: Synthesis of Compound 89

[0153]

[0154] 150 mL of Xylene was added to intermediate 80-1 (10.0 g, 0.035 mol), Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)amine (25.2 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 17.1 g (yield 66.9%) of <Compound 89>.

[0155] LC / MS: m / z=737[(M) + ]

[0157] Synthetic example 7: Synthesis of Compound 95

[0158] (1) Preparation Example 1: Synthesis of Compound 95

[0159]

[0160] 150 mL of Xylene was added to intermediate 80-1 (10.0 g, 0.035 mol), N-(Biphenyl-2-yl)dibenzo[b,d]furan-3-amine (17.4 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.8 g (yield 62.9%) of <Compound 95>.

[0161] LC / MS: m / z=587[(M) + ]

[0163] Synthetic example 8: Synthesis of Compound 103

[0164] (1) Preparation Example 1 : Synthesis of intermediate 103-1

[0165]

[0166] 150 mL of toluene was added to 3-Bromodibenzofuran (10.0 g, 0.041 mol), 2-Amino-9,9-dimethylfluorene (12.7 g, 0.062 mol), NaOtBu (11.7 g, 0.124 mol), Pd(dba)2 (0.9 g, 1.64 mmol), and t-Bu3P (0.7 g, 3.28 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 10.8 g (yield 71.1%) of <intermediate 103-1>.

[0168] (2) Preparation Example 2: Synthesis of Compound 103

[0169]

[0170] 150 mL of Xylene was added to intermediate 80-1 (10.0 g, 0.035 mol), intermediate 103-1 (19.5 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 14.5 g (yield 66.7%) of <compound 103>.

[0171] LC / MS: m / z=627[(M) + ]

[0173] Synthetic example 9: Synthesis of Compound 161

[0174] (1) Preparation Example 1 : Synthesis of intermediate 161-1

[0175]

[0176] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to 2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), 4-Cyanophenylboronic acid (7.3 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), and Pd(PPh3)4 (1.0 g, 0.82 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.4 g (yield 76.9%) of <Intermediate 161-1>.

[0178] (2) Preparation Example 2: Synthesis of Compound 161

[0179]

[0180] 150 mL of Xylene was added to intermediate 161-1 (10.0 g, 0.038 mol), N-(3,5-Diphenylphenyl)-9,9-dimethylfluoren-2-amine (24.9 g, 0.057 mol), NaOtBu (10.9 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 16.7 g (yield 66.2%) of <Compound 161>.

[0181] LC / MS: m / z=664[(M) + ]

[0183] Synthetic example 10: Synthesis of Compound 172

[0184] (1) Preparation Example 1: Synthesis of Compound 172

[0185]

[0186] 150 mL of Xylene was added to intermediate 161-1 (10.0 g, 0.038 mol), N-Biphenyl-4-yl-3-dibenzofuranamine (19.1 g, 0.057 mol), NaOtBu (10.9 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 15.2 g (yield 71.2%) of <Compound 172>.

[0187] LC / MS: m / z=562[(M) + ]

[0189] Synthetic example 11: Synthesis of Compound 212

[0190] (1) Preparation Example 1 : Synthesis of intermediate 212-1

[0191]

[0192] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to 2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), 2-Cyanophenylboronic acid (7.3 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), and Pd(PPh3)4 (1.0 g, 0.82 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.9 g (yield 72.4%) of <Intermediate 212-1>.

[0194] (2) Preparation Example 2: Synthesis of Compound 212

[0195]

[0196] 150 mL of Xylene was added to intermediate 212-1 (10.0 g, 0.038 mol), N-[1,1'-Biphenyl]-2-yl-9,9-dimethyl-9H-fluoren-4-amine (20.6 g, 0.057 mol), NaOtBu (10.9 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 14.1 g (yield 63.2%) of <compound 212>.

[0197] LC / MS: m / z=588[(M) + ]

[0199] Synthetic example 12: Synthesis of Compound 233

[0200] (1) Preparation Example 1 : Synthesis of intermediate 233-1

[0201]

[0202] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to 2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), 3,5-Dicyanophenylboronic acid (8.5 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), and Pd(PPh3)4 (1.0 g, 0.82 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.5 g (yield 71.1%) of <Intermediate 233-1>.

[0204] (2) Preparation Example 2: Synthesis of Compound 233

[0205]

[0206] 150 mL of Xylene was added to intermediate 233-1 (10.0 g, 0.035 mol), 2-(4-Biphenylyl)amino-9,9-dimethylfluorene (18.8 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 14.8 g (yield 69.6%) of <Compound 233>.

[0207] LC / MS: m / z=613[(M) + ]

[0209] Synthetic example 13: Synthesis of Compound 242

[0210] (1) Preparation Example 1: Synthesis of Compound 242

[0211]

[0212] 150 mL of Xylene was added to intermediate 233-1 (10.0 g, 0.035 mol), Bis(9,9-dimethyl-9H-fluoren-2-yl)amine (20.9 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 15.0 g (yield 66.2%) of <Compound 242>.

[0213] LC / MS: m / z=653[(M) + ]

[0215] Synthetic example 14: Synthesis of Compound 248

[0216] (1) Preparation Example 1 : Synthesis of intermediate 248-1

[0217]

[0218] 150 mL of toluene was added to 2-Bromo-9,9'-spirobi[9H-fluorene] (10.0 g, 0.025 mol), 4-Aminobiphenyl (6.4 g, 0.038 mol), NaOtBu (7.3 g, 0.076 mol), Pd(dba)2 (0.6 g, 1.0 mmol), and t-Bu3P (0.4 g, 2.0 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.8 g (yield 71.9%) of <intermediate 248-1>.

[0220] (2) Preparation Example 2: Synthesis of Compound 248

[0221]

[0222] 150 mL of Xylene was added to intermediate 233-1 (10.0 g, 0.035 mol), intermediate 248-1 (25.1 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 15.3 g (yield 60.0%) of <compound 248>.

[0223] LC / MS: m / z=735[(M) + ]

[0225] Synthetic example 15: Synthesis of Compound 254

[0226] (1) Preparation Example 1 : Synthesis of intermediate 254-1

[0227]

[0228] 150 mL of toluene was added to 2-Bromo-9,9'-spirobi[9H-fluorene] (10.0 g, 0.025 mol), 2-Amino-9,9-dimethylfluorene (7.9 g, 0.038 mol), NaOtBu (7.3 g, 0.076 mol), Pd(dba)2 (0.6 g, 1.0 mmol), and t-Bu3P (0.4 g, 2.0 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.6 g (yield 72.5%) of <intermediate 254-1>.

[0230] (2) Preparation Example 2: Synthesis of Compound 254

[0231]

[0232] 150 mL of Xylene was added to intermediate 233-1 (10.0 g, 0.035 mol), intermediate 254-1 (27.2 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 16.2 g (yield 60.3%) of <compound 254>.

[0233] LC / MS: m / z=775[(M) + ]

[0235] Synthetic example 16: Synthesis of Compound 258

[0236] (1) Preparation Example 1 : Synthesis of intermediate 258-1

[0237]

[0238] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to 1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), phenyl-d5-boronic acid (11.3 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), and Pd(PPh3)4 (0.9 g, 0.74 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 7.6 g (yield 74.8%) of <intermediate 258-1>.

[0240] (2) Preparation Example 2 : Synthesis of intermediate 258-2

[0241]

[0242] 150 mL of Xylene was added to intermediate 258-1 (10.0 g, 0.036 mol), 3-Dibenzofuranamine (10.0 g, 0.054 mol), NaOtBu (10.5 g, 0.108 mol), Pd(dba)2 (0.8 g, 1.44 mmol), and t-Bu3P (0.6 g, 2.88 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.7 g (yield 63.2%) of <intermediate 258-2>.

[0244] (3) Preparation Example 3: Synthesis of Compound 258

[0245]

[0246] 150 mL of Xylene was added to intermediate 233-1 (10.0 g, 0.035 mol), intermediate 258-2 (21.9 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 15.9 g (yield 68.1%) of <compound 258>.

[0247] LC / MS: m / z=673[(M) + ]

[0249] Synthetic example 17: Synthesis of Compound 262

[0250] (1) Preparation Example 1 : Synthesis of intermediate 262-1

[0251]

[0252] 150 mL of toluene was added to 4-(4-Bromophenyl)-6-phenyldibenzo[b,d]furan (10.0 g, 0.025 mol), 4-Aminobiphenyl (6.4 g, 0.038 mol), NaOtBu (7.2 g, 0.076 mol), Pd(dba)2 (0.6 g, 1.0 mmol), and t-Bu3P (0.4 g, 2.0 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.3 g (yield 76.2%) of <Intermediate 262-1>.

[0254] (2) Preparation Example 2: Synthesis of Compound 262

[0255]

[0256] 150 mL of Xylene was added to intermediate 233-1 (10.0 g, 0.035 mol), intermediate 262-1 (25.3 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 16.4 g (yield 64.0%) of <compound 262>.

[0257] LC / MS: m / z=739[(M) + ]

[0259] Synthetic example 18: Synthesis of Compound 263

[0260] (1) Preparation Example 1: Synthesis of Compound 263

[0261]

[0262] 150 mL of Xylene was added to intermediate 233-1 (10.0 g, 0.035 mol), Bis(dibenzo[b,d]furan-3-yl)amine (18.2 g, 0.053 mol), NaOtBu (10.0 g, 0.106 mol), Pd(dba)2 (0.8 g, 1.4 mmol), and t-Bu3P (0.6 g, 2.8 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 14.3 g (yield 68.6%) of <Compound 263>.

[0263] LC / MS: m / z=604[(M) + ]

[0265] Synthetic example 19: Synthesis of Compound 281

[0266] (1) Preparation Example 1 : Synthesis of intermediate 281-1

[0267]

[0268] 200 mL of Dioxane was added to intermediate 233-1 (10.0 g, 0.035 mol), Bis(pinacolato)diboron (23.8 g, 0.042 mol), CH3COOK (6.8 g, 0.070 mol), Pd(dppf)Cl2 (0.8 g, 1.05 mmol), and X-phos (0.6 g, 1.26 mmol), and the mixture was reacted with stirring at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8.4 g (yield 63.8%) of <intermediate 281-1>.

[0270] (2) Preparation Example 2 : Synthesis of intermediate 281-2

[0271]

[0272] 1-Bromo-4-chlorobenzene (10.0 g, 0.052 mol), intermediate 281-1 (23.8 g, 0.062 mol), K2CO3 (21.7 g, 0.156 mol), and Pd(PPh3)4 (1.2 g, 1.04 mmol) were mixed with 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O and reacted at 100 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted, concentrated, and then column-coated to obtain 14.3 g (yield 75.0%) of <intermediate 281-2>.

[0274] (3) Preparation Example 3 : Synthesis of intermediate 281-3

[0275]

[0276] 150 mL of toluene was added to 3-Bromodibenzothiophene (10.0 g, 0.038 mol), 3,5-Diphenylaniline (14.0 g, 0.057 mol), NaOtBu (11.0 g, 0.114 mol), Pd(dba)2 (0.9 g, 1.52 mmol), and t-Bu3P (0.6 g, 3.04 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 11.1 g (yield 68.3%) of <intermediate 281-3>.

[0278] (4) Preparation Example 4: Synthesis of Compound 281

[0279]

[0280] 150 mL of Xylene was added to intermediate 281-2 (10.0 g, 0.027 mol), intermediate 281-3 (17.6 g, 0.041 mol), NaOtBu (7.9 g, 0.082 mol), Pd(dba)2 (0.6 g, 1.08 mmol), and t-Bu3P (0.4 g, 2.16 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.8 g (yield 61.8%) of <Compound 281>.

[0281] LC / MS: m / z=755[(M) + ]

[0283] Synthetic example 20: Synthesis of Compound 285

[0284] (1) Preparation Example 1 : Synthesis of intermediate 285-1

[0285]

[0286] 2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), intermediate 281-1 (18.9 g, 0.049 mol), K2CO3 (17.2 g, 0.123 mol), and Pd(PPh3)4 (1.0 g, 0.82 mmol) were mixed with 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O and reacted at 100 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.7 g (yield 73.9%) of <intermediate 285-1>.

[0288] (2) Preparation Example 2: Synthesis of Compound 285

[0289]

[0290] 150 mL of Xylene was added to intermediate 285-1 (10.0 g, 0.024 mol), Bis(9,9-dimethyl-9H-fluoren-2-yl)amine (14.5 g, 0.036 mol), NaOtBu (7.0 g, 0.072 mol), Pd(dba)2 (0.6 g, 0.96 mmol), and t-Bu3P (0.4 g, 1.92 mmol), and the mixture was reacted with stirring at 70 °C for 4 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.3 g (yield 65.4%) of <Compound 285>.

[0291] LC / MS: m / z=779[(M) + ]

[0293] device Examples ( HTL )

[0294] In an embodiment according to the present invention, an ITO transparent electrode was patterned on a 25 mm × 25 mm × 0.7 mm glass substrate using an ITO glass substrate with an attached ITO transparent electrode to have a light-emitting area of ​​2 mm × 2 mm, and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 -6 After making the torr, the organic material and metal were deposited on the above ITO in the following structure.

[0296] device Examples 1 to 72

[0297] A compound implemented according to the present invention was employed in a hole transport layer to fabricate an organic light-emitting diode having the device structure as described below, and then the luminescence and driving characteristics of the compound implemented according to the present invention were measured.

[0299] ITO / Hole injection layer (HAT-CN, 5 nm) / Hole transport layer (100 nm) / Electron blocking layer (EB1, 10 nm) / Emitting layer (20 nm) / Electron transport layer (ET1:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

[0301] After forming a hole injection layer by depositing [HAT-CN] to a thickness of 5 nm on top of an ITO transparent electrode, a hole transport layer was formed by depositing a compound according to the present invention described in [Table 1] below to a thickness of 100 nm. Subsequently, an electron blocking layer was formed by depositing [EB1] to a thickness of 10 nm, and a light-emitting layer was formed by co-depositing [BH1] as the host compound and [BD1] as the dopant compound to a thickness of 20 nm. Afterward, an electron transport layer (50% doping of the [ET1] compound below with Liq) was deposited to a thickness of 30 nm, and then an electron injection layer was formed by depositing LiF to a thickness of 1 nm. Subsequently, an organic light-emitting diode was fabricated by depositing Al to a thickness of 100 nm.

[0303] device Comparative example 1

[0304] The organic light-emitting device for Comparative Example 1 was fabricated in the same manner as the device structure of the above example, except that the following [α-NPB] was used in the hole transport layer instead of the compound according to the present invention.

[0306] device Comparative example 2

[0307] The organic light-emitting diode for device Comparison Example 2 was fabricated in the same manner as the device structure of the above example, except that the following [HT1] was used in the hole transport layer instead of the compound according to the present invention.

[0309] Experimental Example 1 : Element Examples Luminescence characteristics of 1 to 72

[0310] The driving voltage, current efficiency, and color coordinates of the organic light-emitting diodes manufactured according to the above examples and comparative examples were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the results based on 1,000 nit are as shown in [Table 1] below.

[0311] Examples The transport layer of the air force V cd / A CIEx CIEy 1 Chemical formula 2 4.26 7.78 0.1339 0.1357 2 Chemical formula 3 4.32 7.25 0.1335 0.1364 3 Chemical formula 5 4.06 7.27 0.1353 0.1370 4 Chemical formula 7 4.19 7.36 0.1377 0.1246 5 Chemical formula 10 4.45 7.55 0.1376 0.1399 6 Chemical formula 14 4.27 7.41 0.1368 0.1250 7 Chemical formula 16 4.20 7.48 0.1355 0.1252 8 Chemical formula 17 4.50 7.08 0.1400 0.1254 9 Chemical formula 24 4.11 7.30 0.1369 0.1263 10 Chemical formula 25 4.05 7.47 0.1387 0.1216 11 Chemical formula 28 4.23 7.40 0.1385 0.1386 12 Chemical formula 30 4.52 7.45 0.1390 0.1386 13 Chemical formula 31 4.17 7.46 0.1365 0.1247 14 Chemical formula 32 4.36 7.85 0.1353 0.1397 15 Chemical formula 33 4.26 7.59 0.1346 0.1259 16 Chemical formula 39 4.31 7.40 0.1365 0.1356 17 Chemical formula 40 4.16 7.15 0.1376 0.1356 18 Chemical formula 41 3.98 7.56 0.1355 0.1415 19 Chemical formula 44 4.41 7.64 0.1382 0.1415 20 Chemical formula 50 4.08 7.37 0.1345 0.1417 21 Chemical formula 56 4.15 7.39 0.1355 0.1394 22 Chemical formula 52 4.29 7.05 0.1334 0.1395 23 Chemical formula 53 4.48 7.24 0.1353 0.1395 24 Chemical formula 61 4.23 7.72 0.1327 0.1415 25 Chemical formula 65 4.16 7.35 0.1351 0.1440 26 Chemical formula 71 4.22 7.15 0.1350 0.1400 27 Chemical formula 74 4.11 7.95 0.1348 0.1402 28 Chemical formula 75 4.39 7.57 0.1350 0.1403 29 Chemical formula 79 4.45 7.67 0.1354 0.1291 30 Chemical formula 80 4.14 7.62 0.1355 0.1297 31 Chemical formula 81 4.11 7.40 0.1371 0.1418 32 Chemical formula 82 4.08 7.12 0.1356 0.1386 33 Chemical formula 84 4.24 7.28 0.1363 0.1309 34 Chemical formula 88 4.43 7.61 0.1335 0.1313 35 Chemical formula 89 4.09 7.06 0.1407 0.1399 36 Chemical formula 95 4.06 7.14 0.1377 0.1265 37 Chemical formula 103 4.43 7.58 0.1386 0.1265 38 Chemical formula 119 4.14 7.72 0.1385 0.1269 39 Chemical formula 134 4.33 7.66 0.1415 0.1374 40 Chemical formula 158 4.11 7.59 0.1345 0.1431 41 Chemical formula 160 4.47 7.15 0.1429 0.1433 42 Chemical formula 161 4.22 7.31 0.1427 0.1434 43 Chemical formula 164 4.07 7.19 0.1436 0.1436 44 Chemical formula 166 4.28 7.56 0.1356 0.1386 45 Chemical formula 169 4.01 7.54 0.1344 0.1411 46 Chemical formula 172 4.38 7.61 0.1367 0.1411 47 Chemical formula 173 4.13 7.40 0.1415 0.1350 48 Chemical formula 176 4.08 7.39 0.1423 0.1350 49 Chemical formula 185 4.29 7.58 0.1336 0.1371 50 Chemical formula 194 4.38 7.15 0.1357 0.1409 51 Chemical formula 202 4.36 7.29 0.1338 0.1419 52 Chemical formula 210 4.54 7.35 0.1355 0.1413 53 Chemical formula 212 4.18 7.27 0.1359 0.1397 54 Chemical formula 221 4.39 7.15 0.1337 0.1399 55 Chemical formula 230 4.17 7.77 0.1335 0.1371 56 Chemical formula 233 3.92 7.13 0.1402 0.1414 57 Chemical formula 234 4.22 7.55 0.1356 0.1386 58 Chemical formula 242 4.19 7.51 0.1355 0.1381 59 Chemical formula 248 4.23 7.38 0.1351 0.1384 60 Chemical formula 250 4.34 7.18 0.1349 0.1385 61 Chemical formula 251 4.16 7.75 0.1375 0.1403 62 Chemical formula 254 4.57 7.07 0.1353 0.1408 63 Chemical formula 255 4.29 7.19 0.1326 0.1383 64 Chemical formula 256 3.94 7.41 0.1371 0.1419 65 Chemical formula 257 4.09 7.40 0.1336 0.1421 66 Chemical formula 258 4.57 7.37 0.1340 0.1421 67 Chemical formula 262 4.38 7.16 0.1337 0.1424 68 Chemical formula 263 4.47 7.64 0.1344 0.1425 69 Chemical formula 266 4.01 7.55 0.1343 0.1427 70 Chemical formula 272 4.30 7.20 0.1384 0.1427 71 Chemical formula 281 4.06 7.36 0.1323 0.1429 72 Chemical formula 285 4.27 7.94 0.1343 0.1398 Comparative Example 1 α-NPB 4.67 6.65 0.1353 0.1517 Comparative Example 2 HT1 5.09 7.02 0.1312 0.1422

[0312] Looking at the results shown in [Table 1] above, it can be confirmed that in the case of an organic light-emitting device in which the compound according to the present invention is employed in the hole transport layer within the device, the driving voltage is reduced and the current efficiency is improved compared to devices (Comparative Examples 1 and 2) in which the compound used as a conventional hole transport material and the compound having a structure contrasting with the characteristic structure of the compound according to the present invention are employed.

[0313]

[0314] [HAT_CN] [α-NPB] [BH1] [BD1] [ET1]

[0315]

[0316] [EB1] [HT1]

Claims

Claim 1 Compounds represented by the following [Chemical Formula I]: [Chemical Formula I] In the above [Chemical Formula I], Np is represented by the following [Structural Formula 1] or [Structural Formula 2], and [Structural Formula 1] [Structural Formula 2] L is a single bond, or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; m is an integer from 0 to 3, and if m is 2 or more, a plurality of Ls are identical or different from each other; Ar1 ​​and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; R1 to R3 are identical or different from each other and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 3 to 30 carbon atoms. Any one selected from heteroaryl groups and substituted or unsubstituted silyl groups, o is an integer from 0 to 4, p and q are integers from 0 to 6, and if o, p, and q are 2 or more, a plurality of R1 to R3 are each identical or different from each other, CN is a cyano group, and n is 1 or 2, and in the definitions of L, Ar1, Ar2, and R1 to R3, "substituted or unsubstituted" means that L, Ar1, Ar2, and R1 to R3 are each selected from the group consisting of deuterium, cyano group, alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, deuterated alkoxy group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, carbazoleyl group, dibenzofuranyl group, dibenzothiophenyl group, alkylsilyl group, and arylsilyl group. It means being substituted with one or more substituents, being substituted with two or more of the said substituents connected to a substituent, or having no substituents at all. Claim 2 delete Claim 3 A compound according to claim 1, characterized in that [Chemical Formula I] is any one selected from [Compound 1] to [Compound 308] below: Claim 4 An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by [Chemical Formula I] according to claim 1. Claim 5 An organic light-emitting device according to claim 4, wherein the organic layer comprises one or more layers selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer, and a light-emitting layer, and wherein one or more of the layers comprises a compound represented by [Chemical Formula I]. Claim 6 An organic light-emitting device according to claim 5, characterized in that any one of the hole transport layer, the hole injection layer, and the layer that performs both hole transport and hole injection functions includes a compound represented by [Chemical Formula I].

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