KR20230031455A - Organic compound and electroluminescent device comprising the same - Google Patents

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 in an organic light emitting device to implement low voltage driving of the device and luminous properties such as excellent luminous efficiency, and an organic light emitting device including the same.

Description

Organic compound and organic light emitting device comprising the same {Organic compound and electroluminescent device comprising the same}

The present invention relates to a compound used in an organic light emitting device, and more particularly, an organic compound characterized in that it is employed as an organic layer material in an organic light emitting device, and luminous properties such as low voltage driving and excellent luminous efficiency of the device by employing the same It relates to a remarkably improved organic light emitting device.

Organic light emitting devices can not only be formed on a transparent substrate, but also can be driven at a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. , It has the advantage of being excellent in color, and can show three colors of green, blue, and red, so it has recently become a subject of much interest as a next-generation display device.

However, in order for the organic light emitting device to exhibit the above characteristics, the materials constituting the organic layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, and electron injection materials, are supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic light emitting devices has not yet been sufficiently accomplished.

Therefore, in order to implement a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, further improvement in terms of efficiency and lifespan characteristics is required, and in particular, development of materials forming each organic layer of the organic light emitting device is required. It is desperately needed.

In this regard, studies have recently been actively conducted to improve the mobility of existing organic materials for the hole transport layer material in the structure of the organic light emitting device.

Accordingly, an object of the present invention is to provide a novel organic compound that can be employed in an organic layer such as a hole transport layer in an organic light emitting device to implement excellent light emitting characteristics such as low voltage driving and improved light emitting efficiency of the device, and an organic light emitting device including the same.

In order to solve the above problems, the present invention provides an organic light emitting device including an organic compound represented by [Chemical Formula I] and an organic layer such as a hole transport layer in the device.

[Formula I]

The characteristic structure of [Formula 1] and the definitions of the compounds implemented thereby, Np, L, Ar ₁ , Ar ₂ and R ₁ to R ₃ will be described later.

When the organic compound according to the present invention is used as a material for an organic layer such as a hole transport layer in an organic light emitting device, low voltage driving of the device and luminous properties such as excellent luminous efficiency can be implemented, so that it can be usefully used in various display devices.

Hereinafter, the present invention will be described in more detail.

The present invention relates to a compound used for an organic layer in an organic light emitting device capable of achieving light emitting characteristics such as low voltage driving of the device and excellent luminous efficiency, and includes at least one cyano group (CN) at a specific position in the compound core It is characterized in that, and characterized in that it is represented by the following [Formula I].

[Formula I]

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

[Structural Formula 1]

[Structural Formula 2]

In [Formula I], [Structural Formula 1] and [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 of 0 to 3, wherein m is 2 or more In this case, a plurality of L's are the same as or different from each other.

Ar ₁ and Ar ₂ 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.

R ₁ to R ₃ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted It is selected from a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted silyl group, and o is an integer of 0 to 4 And, p and q are integers from 0 to 6, and when o, p and q are 2 or more, a plurality of R ₁ to R ₃ are the same as or different from each other.

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

Meanwhile, in the definition of L, Ar ₁ , Ar ₂ and R ₁ to R ₃ , 'substituted or unsubstituted' means that L, Ar ₁ , Ar ₂ and R ₁ to R ₃ are deuterium and halogen groups, respectively. , Cyano group, nitro group, hydroxyl group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, amine group, aryl group, heteroaryl group , It means that it is substituted with one or two or more substituents selected from the group consisting of an alkylsilyl group and an arylsilyl group, is substituted with a substituent in which two or more substituents are connected, or does not have any substituent.

For example, a substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, and the like are substituted with other substituents. do.

In addition, the substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group, and condensed heterocyclic groups thereof, such as a benzquinoline group. , It means that a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other substituents.

In the present invention, examples of the substituents will be described in detail below, but are not limited thereto.

In the present invention, the alkyl group may be straight or branched, 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, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but is not limited thereto.

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

Further, in the present invention, the alkyl group or alkoxy group may be a deuterium or alkoxy group substituted with deuterium or/and a halogen group, or a halogenated alkyl or alkoxy group.

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

,

,

등이 있다.In the present invention, the fluorenyl group is a structure in which two ring organic compounds are linked through one atom, for example

,

,

etc.

,

등이 있다.In the present invention, the fluorenyl group includes the structure of an open fluorenyl group, where the open fluorenyl group is a structure in which one ring compound is disconnected from a structure in which two ring organic compounds are connected through one atom. , for example

,

etc.

,

,

,

등이 있다.In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example

,

,

,

etc.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and is a polycyclic group in which cycloalkyl or heterocycloalkyl is fused. It includes a heteroaryl group structure, and 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, and a bipyridyl group. , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., but only these It is not limited.

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., and specific examples of such a silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but are not limited thereto.

Specific examples of the substituent halogen group used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).

In the present invention, the cycloalkyl group refers to and includes monocyclic, polycyclic and spiroalkyl radicals, preferably containing ring carbon atoms of 3 to 20 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirundecyl, adamantyl, and the like, and the cycloalkyl group may be optionally substituted.

In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, one or more heteroatoms being O, S, N, P, B, Si, and Se , Preferably selected from O, N or S, specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., the arylamine group refers to an amine substituted with an aryl, and the alkylamine group refers to an amine substituted with an alkyl. The arylheteroarylamine group refers to an amine substituted with aryl and heteroaryl groups, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted diarylamine group. There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group or a monocyclic heteroaryl group, or may be a polycyclic aryl group or a polycyclic heteroaryl group. And, the aryl group and heteroaryl group including two or more arylamine groups and arylheteroarylamine groups are monocyclic aryl groups (heteroaryl groups), polycyclic aryl groups (heteroaryl groups), or monocyclic aryl groups (heteroaryl groups). aryl group) and polycyclic aryl group (heteroaryl group) may be included at the same time. In addition, the aryl group and heteroaryl group of the arylamine group and the arylheteroarylamine group may be selected from examples of the aryl group and heteroaryl group described above.

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

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

As described above, the organic compound according to the present invention can synthesize organic compounds having various properties by using a characteristic backbone that exhibits unique properties and a moiety having unique properties introduced thereto, and as a result The organic compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. can make it

In addition, the compound of the present invention can be applied to a device according to a general organic light emitting device manufacturing method, and an organic light emitting device according to an embodiment of the present invention includes a first electrode and a second electrode and an organic layer disposed therebetween. It can be made of a structure, and can be manufactured using conventional device manufacturing methods and materials, except that the organic compound according to the present invention is used in the organic layer of the device.

The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer 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, and the like, and a structure including a light efficiency improvement layer (capping layer) provided in an organic light emitting device. However, it is not limited thereto and may include fewer or more organic layers.

An organic layer structure of a preferred organic light emitting device according to the present invention will be described in more detail in Examples to be described later.

In addition, the organic light emitting device according to the present invention uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It can be manufactured by depositing an anode, 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.

In addition to this method, an organic light emitting device may be manufactured 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, a light emitting layer and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed by using various polymer materials and using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. Can be made in layers.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , but conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al. structural materials, etc., but are not limited thereto.

The hole injection material is a material capable of receiving holes well from the anode at a low voltage, and the hole injection material preferably has a highest occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high hole mobility is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts. can be further improved.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazoles, benzthiazoles, and Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited thereto.

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq ₃ organic radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

In addition, the organic light emitting compound according to the present invention may act in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like, on a principle similar to that applied to organic light emitting devices.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to explain the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those who have knowledge.

synthesis example 1: Synthesis of Compound 2

(One) manufacturing example 1: Synthesis of Intermediate 2-1

1-Bromo-4-chloronaphthalene (10.0 g, 0.041 mol), 4-Cyanophenylboronic acid (7.3 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 8.2 g (yield: 75.1%) of <Intermediate 2-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: synthesis of compound 2

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), t 150 mL of Xylene was added to -Bu ₃ P (0.6 g, 3.04 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 14.1 g (yield 67.8%) of <Compound 2> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=548 [(M) ⁺ ]

synthesis example 2: synthesis of compound 14

(One) manufacturing example 1: synthesis of intermediate 14-1

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-Bu ₃ P (0.4 g, 2.0 mmol) were added with 150 mL of Toluene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 8.6 g (yield 70.3%) of <Intermediate 14-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: synthesis of compound 14

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), t-Bu ₃ 150 mL of Xylene was added to P (0.6 g, 3.04 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 18.6 g (yield: 69.0%) of <Compound 14> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z = 710 [(M) ⁺ ]

synthesis example 3: synthesis of compound 39

(One) manufacturing example 1: synthesis of intermediate 39-1

Intermediate 2-1 (10.0 g, 0.038 mol), Bis(pinacolato)diboron (26.1 g, 0.046 mol), CH ₃ COOK (7.4 g, 0.076 mol), Pd(dppf)Cl ₂ (0.8 g, 1.14 mmol), 200 mL of Dioxane was added to X-phos (0.7 g, 1.38 mmol), followed by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 9.5 g of <Intermediate 39-1> (yield: 70.5%).

(2) manufacturing example 2: synthesis of intermediate 39-2

1-Bromo-4-chlorobenzene (10.0 g, 0.052 mol), intermediate 39-1 (22.3 g, 0.062 mol), K ₂ CO ₃ (21.7 g, 0.156 mol), Pd(PPh ₃ ) ₄ (1.2 g, 1.04 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 13.3 g of <Intermediate 39-2> (yield: 74.9%).

(3) manufacturing example 3: synthesis of intermediate 39-3

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), t-Bu ₃ P ( 0.6 g, 3.04 mmol) into 150 mL of Toluene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 9.4 g (yield 70.4%) of <Intermediate 39-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) manufacturing example 4: synthesis of compound 39

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), t-Bu ₃ 150 mL of Xylene was added to P (0.5 g, 2.32 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 12.7 g (yield 65.9%) of <Compound 39> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=654 [(M) ⁺ ]

synthesis example 4: synthesis of compound 56

(One) manufacturing example 1: synthesis of intermediate 56-1

1-Bromo-4-chloronaphthalene (10.0 g, 0.041 mol), 3-Cyanophenylboronic acid (7.3 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 7.9 g (yield 72.4%) of <Intermediate 56-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: synthesis of compound 56

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-Bu ₃ P (0.6 g, 3.04 mmol) into 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 14.2 g (yield: 66.6%) of <Compound 56> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z = 562 [(M) ⁺ ]

synthesis example 5: synthesis of compound 80

(One) manufacturing example 1: synthesis of intermediate 80-1

1-Bromo-4-chloronaphthalene (10.0 g, 0.041 mol), 3,5-Dicyanophenylboronic acid (8.5 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g , 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 8.7 g (yield 72.8%) of <Intermediate 80-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: synthesis of compound 80

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-Bu ₃ P (0.6 g, 2.8 mmol) were added with 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 13.9 g (yield 65.4%) of <Compound 80> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=613 [(M) ⁺ ]

synthesis example 6: synthesis of compound 89

(One) manufacturing example 1: Synthesis of Compound 89

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), 150 mL of Xylene was added to Pd(dba) ₂ (0.8 g, 1.4 mmol) and t-Bu ₃ P (0.6 g, 2.8 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 17.1 g (yield 66.9%) of <Compound 89> was obtained by extraction, concentration, column and recrystallization.

LC/MS: m/z=737 [(M) ⁺ ]

synthesis example 7: synthesis of compound 95

(One) manufacturing example 1: Synthesis of Compound 95

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 150 mL of Xylene was added to (dba) ₂ (0.8 g, 1.4 mmol) and t-Bu ₃ P (0.6 g, 2.8 mmol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, 12.8 g (yield: 62.9%) of <Compound 95> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=587 [(M) ⁺ ]

synthesis example 8: synthesis of compound 103

(One) manufacturing example 1: synthesis of intermediate 103-1

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), 150 mL of Toluene was added to t-Bu ₃ P (0.7 g, 3.28 mmol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, 10.8 g (yield: 71.1%) of <Intermediate 103-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of Compound 103

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), t-Bu ₃ 150 mL of Xylene was added to P (0.6 g, 2.8 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 14.5 g of <Compound 103> (yield: 66.7%).

LC/MS: m/z=627 [(M) ⁺ ]

synthesis example 9: synthesis of compound 161

(One) manufacturing example 1: synthesis of intermediate 161-1

2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), 4-Cyanophenylboronic acid (7.3 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 8.4 g (yield 76.9%) of <Intermediate 161-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of Compound 161

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 ( 150 mL of Xylene was added to dba) ₂ (0.9 g, 1.52 mmol) and t-Bu ₃ P (0.6 g, 3.04 mmol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, 16.7 g (yield 66.2%) of <Compound 161> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=664 [(M) ⁺ ]

synthesis example 10: synthesis of compound 172

(One) manufacturing example 1: Synthesis of Compound 172

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-Bu ₃ P (0.6 g, 3.04 mmol) into 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 15.2 g (yield: 71.2%) of <Compound 172> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z = 562 [(M) ⁺ ]

synthesis example 11: synthesis of compound 212

(One) manufacturing example 1: synthesis of intermediate 212-1

2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), 2-Cyanophenylboronic acid (7.3 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 7.9 g (yield 72.4%) of <Intermediate 212-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: synthesis of compound 212

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-Bu ₃ P (0.6 g, 3.04 mmol) were added to 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 14.1 g (yield 63.2%) of <Compound 212> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=588 [(M) ⁺ ]

synthesis example 12: synthesis of compound 233

(One) manufacturing example 1: synthesis of intermediate 233-1

2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), 3,5-Dicyanophenylboronic acid (8.5 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g , 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 8.5 g (yield 71.1%) of <Intermediate 233-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of Compound 233

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-Bu ₃ P (0.6 g, 2.8 mmol) were added with 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 14.8 g (yield 69.6%) of <Compound 233> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=613 [(M) ⁺ ]

synthesis example 13: synthesis of compound 242

(One) manufacturing example 1: Synthesis of Compound 242

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-Bu ₃ P (0.6 g, 2.8 mmol) were added with 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 15.0 g (yield: 66.2%) of <Compound 242> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=653 [(M) ⁺ ]

synthesis example 14: synthesis of compound 248

(One) manufacturing example 1: synthesis of intermediate 248-1

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-Bu ₃ P (0.4 g, 2.0 mmol) were added with 150 mL of Toluene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 8.8 g (yield 71.9%) of <Intermediate 248-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of Compound 248

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), t-Bu ₃ 150 mL of Xylene was added to P (0.6 g, 2.8 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 15.3 g (yield: 60.0%) of <Compound 248> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=735 [(M) ⁺ ]

synthesis example 15: synthesis of compound 254

(One) manufacturing example 1: synthesis of intermediate 254-1

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 Toluene (150 mL) was added to (dba) ₂ (0.6 g, 1.0 mmol) and t-Bu ₃ P (0.4 g, 2.0 mmol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, 9.6 g (yield: 72.5%) of <Intermediate 254-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of compound 254

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), t-Bu ₃ 150 mL of Xylene was added to P (0.6 g, 2.8 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 16.2 g (yield: 60.3%) of <Compound 254> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=775 [(M) ⁺ ]

synthesis example 16: synthesis of compound 258

(One) manufacturing example 1: synthesis of intermediate 258-1

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), Phenyl-d5-boronic acid (11.3 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), Pd(PPh ₃ ) ₄ ( 0.9 g, 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 7.6 g of <Intermediate 258-1> (yield: 74.8%).

(2) manufacturing example 2: synthesis of intermediate 258-2

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), t-Bu ₃ P (0.6 g, 2.88 mmol) was reacted by adding 150 mL of Xylene and stirring at 70 °C for 4 hours. After completion of the reaction, 9.7 g (yield 63.2%) of <Intermediate 258-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of Compound 258

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), t-Bu ₃ 150 mL of Xylene was added to P (0.6 g, 2.8 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 15.9 g (yield 68.1%) of <Compound 258> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z = 673 [(M) ⁺ ]

synthesis example 17: synthesis of compound 262

(One) manufacturing example 1: synthesis of intermediate 262-1

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-Bu ₃ P (0.4 g, 2.0 mmol) into 150 mL of Toluene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 9.3 g (yield 76.2%) of <Intermediate 262-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of compound 262

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), t-Bu ₃ 150 mL of Xylene was added to P (0.6 g, 2.8 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 16.4 g (yield: 64.0%) of <Compound 262> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=739 [(M) ⁺ ]

synthesis example 18: synthesis of compound 263

(One) manufacturing example 1: Synthesis of compound 263

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-Bu ₃ P (0.6 g, 2.8 mmol) were added with 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 14.3 g (yield 68.6%) of <Compound 263> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=604 [(M) ⁺ ]

synthesis example 19: synthesis of compound 281

(One) manufacturing example 1: synthesis of intermediate 281-1

Intermediate 233-1 (10.0 g, 0.035 mol), Bis(pinacolato)diboron (23.8 g, 0.042 mol), CH ₃ COOK (6.8 g, 0.070 mol), Pd(dppf)Cl ₂ (0.8 g, 1.05 mmol), 200 mL of Dioxane was added to X-phos (0.6 g, 1.26 mmol), followed by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 8.4 g of <Intermediate 281-1> (yield: 63.8%).

(2) manufacturing example 2: synthesis of intermediate 281-2

1-Bromo-4-chlorobenzene (10.0 g, 0.052 mol), intermediate 281-1 (23.8 g, 0.062 mol), K ₂ CO ₃ (21.7 g, 0.156 mol), Pd(PPh ₃ ) ₄ (1.2 g, 1.04 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 14.3 g of <Intermediate 281-2> (yield: 75.0%).

(3) manufacturing example 3: synthesis of intermediate 281-3

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), t-Bu ₃ 150 mL of Toluene was added to P (0.6 g, 3.04 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 11.1 g (yield 68.3%) of <Intermediate 281-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) manufacturing example 4: Synthesis of Compound 281

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), t-Bu ₃ 150 mL of Xylene was added to P (0.4 g, 2.16 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, 12.8 g (yield: 61.8%) of <Compound 281> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=755 [(M) ⁺ ]

synthesis example 20: synthesis of compound 285

(One) manufacturing example 1: synthesis of intermediate 285-1

2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), intermediate 281-1 (18.9 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 12.7 g (yield: 73.9%) of <Intermediate 285-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of Compound 285

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-Bu ₃ P (0.4 g, 1.92 mmol) were added with 150 mL of Xylene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 12.3 g (yield: 65.4%) of <Compound 285> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=779 [(M) ⁺ ]

device Example ( HTL )

In an embodiment according to the present invention, the ITO transparent electrode is patterned on a glass substrate of 25 mm × 25 mm × 0.7 mm so that the light emitting area is 2 mm × 2 mm in size by using an ITO glass substrate to which the ITO transparent electrode is attached. After that, it was washed. After the substrate was mounted in a vacuum chamber and the base pressure was 1 × 10 ^-6 torr, an organic material and a metal were deposited on the ITO in the following structure.

device Example 1 to 72

After employing the compound implemented according to the present invention as a hole transport layer and manufacturing an organic light emitting device having the following device structure, emission and driving characteristics of the compound implemented according to the present invention were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (100 nm) / electron blocking layer (EB1, 10 nm) / light emitting layer (20 nm) / electron transport layer (ET1:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

[HAT-CN] was formed on top of the ITO transparent electrode to form a hole injection layer with a thickness of 5 nm, and then the compound according to the present invention described in [Table 1] was formed to a thickness of 100 nm to form a hole transport layer. Thereafter, [EB1] was formed to a thickness of 10 nm to form an electron blocking layer, and an emission layer was formed by co-evaporation to a thickness of 20 nm using [BH1] as a host compound and [BD1] as a dopant compound. Thereafter, an electron transport layer (the [ET1] compound Liq 50% doped) was deposited to a thickness of 30 nm, and then LiF was deposited to a thickness of 1 nm to form an electron injection layer. Thereafter, an Al film was formed to a thickness of 100 nm to fabricate an organic light emitting device.

device comparative example One

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

device comparative example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as the device structure of Example 2, except that the following [HT1] was used instead of the compound according to the present invention in the hole transport layer.

Experimental example 1: element Example Luminescence characteristics of 1 to 72

The organic light emitting device manufactured according to the above Examples and Comparative Examples was measured for driving voltage, current efficiency and color coordinates using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), based on 1,000 nit The result values are shown in [Table 1] below.

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

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

[HAT_CN] [α-NPB] [BH1] [BD1] [ET1]

[EB1] [HT1]

Claims (6)

A compound represented by the following [Formula I]:
[Formula I]

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

[Structural Formula 2]

L is a single bond, or any one 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 when m is 2 or more, a plurality of L's are the same as or different from each other;
Ar ₁ and Ar ₂ are each independently any one 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;
R ₁ to R ₃ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted Any one selected from a cyclic amine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted silyl group,
o is an integer from 0 to 4, p and q are integers from 0 to 6, and when o, p and q are 2 or more, a plurality of R ₁ to R ₃ are the same as or different from each other,
CN is a cyano group, and n is 1 or 2. According to claim 1,
In the definition of L, Ar ₁ , Ar ₂ and R ₁ to R ₃ , 'substituted or unsubstituted' means that L, Ar ₁ , Ar ₂ and R ₁ to R ₃ are deuterium, a halogen group, or cyanide, respectively. No group, nitro group, hydroxyl group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, amine group, aryl group, heteroaryl group, alkyl A compound characterized in that it is substituted with one or two or more substituents selected from the group consisting of a silyl group and an arylsilyl group, or is substituted with a substituent in which two or more substituents among the substituents are connected, or does not have any substituents. According to claim 1,
[Formula I] is a compound characterized in that any one selected from the following [Compound 1] to [Compound 308]:

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,
At least one layer of the organic layer is an organic light emitting device comprising a compound represented by [Chemical Formula I] according to claim 1. According to claim 4,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection functions, an electron blocking layer, a hole blocking layer, and a light emitting layer. Including one or more floors,
An organic light emitting device, wherein at least one of the layers includes the compound represented by [Chemical Formula I]. According to claim 5,
An organic light emitting device comprising the compound represented by [Chemical Formula I] in any one of the hole transport layer, the hole injection layer, and the hole transport and hole injection layers.