KR20190140232A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by chemical formula I or chemical formula II capable of achieving improved luminous efficiency of a device due to excellent hole transport degree and implementing low voltage driving properties of the device without additional p-doping by introducing each moiety having a p-doping function and hole transport properties into one structure.

Description

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

The present invention relates to an organic light emitting compound, and more particularly, an organic light emitting compound that is employed as a hole transporting material of a hole injection layer or a hole transporting layer of an organic light emitting device, and employing the low-voltage driving, light emission efficiency and life characteristics The present invention relates to a significantly improved organic light emitting device.

Recently, the organic light emitting device capable of low-voltage driving by self-emission type has better viewing angle, contrast ratio, etc., does not need backlight, light weight and thinness, is advantageous in terms of power consumption, and color reproduction range compared to the liquid crystal display which is the mainstream of flat panel display devices. It is widely attracting attention as a next generation display device.

An organic light emitting device emits light when electrons and holes are paired and extinguished when electric charge is injected into the organic light emitting layer formed between the electron injection electrode (cathode) and the hole injection electrode (anode). In addition to the device can be formed on the substrate, it is possible to drive at a lower voltage of 10V or less than the plasma display panel or the inorganic light emitting display, has the advantage of relatively low power consumption and excellent color. In addition, since the organic light emitting device can display three colors of green, blue, and red, it has been attracting much attention as a next-generation rich color display device.

The organic light emitting device divides the process for emitting light, that is, charge injection, charge transport, photo-exciter formation, and light generation by using different organic layers. Accordingly, an organic light emitting device having a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like divided between the anode and the cathode and having more layers is used, and the organic light emitting device has the aforementioned characteristics. In order to exert, the material that forms the organic layer in the device must be preceded by a stable and efficient material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an electron blocking material, etc. The development of an efficient organic material layer for an organic light emitting device has not been made sufficiently.

Therefore, in order to realize a more stable organic light emitting device, and to improve the efficiency, long life, and size of the device, further improvement is required in terms of efficiency and lifespan. In this regard, the hole transport layer of the organic light emitting device has recently been improved. For the material, a study is performed to further include a layer containing a p-type material between the electrode and the hole transport layer by doping a p-type material or subdividing the layer in order to improve the mobility of the existing organic material. ought.

In particular, when the organic material is doped, negative conductivity is formed, and even a thick transport layer can lower the voltage drop in the transport layer, and the thin space charge layer formed by increasing the doping level can effectively inject the charge by tunneling. By doping the hole transport layer, it is possible to control the high conductivity of the hole transport layer and the charge density of the charge carriers. Consequently, the conductivity of the organic material layer is improved to improve the characteristics of the device, thereby realizing a low driving voltage and a high efficiency device.

However, there are still problems such as low process efficiency due to the application of additional organic materials and organic layers, and difficulty in implementing low voltage driving due to thickness problems of the organic layers.

Accordingly, the present invention is to solve the above problems, without providing a separate p-doping for the hole transport material, providing a compound of a fused material structure that can be harvested with p-doping and hole transport, and introduced by The present invention is to provide an organic light emitting device capable of stably implementing characteristics such as improved luminous efficiency and long life while driving low voltage at a level equal to or higher than that of a conventional device.

In order to solve the above problems, the present invention is represented by the following [Formula I], and each organic moiety (moiety) having a p-doping function and hole transport characteristics introduced into one structure and [Formula I] Or an organic light emitting device comprising at least one light emitting compound represented by [Formula II] in an organic layer.

[Formula I]

[Formula II]

The structure of [Formula I] or [Formula II] and R ₁ to R ₆ and X ₁ to X ₄ will be described later.

The organic light emitting compound according to the present invention is characterized in that the fusion with one of the p-doping (hole) function and hole transport characteristics, the device introduced this improves the hole transportability without a separate p-doping compared to the conventional device As a result, it is possible to realize improved luminous efficiency and low voltage driving equivalent to that of conventional devices, which can be usefully used for various display devices, and a process having a separate p-type layer or a p-doping process is not required. As a result, device manufacturing process efficiency can be improved.

1 is a representative view showing the structure of an organic light emitting compound according to the present invention.

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

According to the present invention, each moiety having a p-doping function and a hole transport characteristic is introduced into a structure to realize low voltage driving characteristics of the device without additional p-doping, and a hole transport diagram. The present invention relates to an organic light emitting compound represented by the following [Formula I] or [Formula II] capable of achieving an improved luminous efficiency of the device.

[Formula I]

[Formula II]

In [Formula I] or [Formula II],

R ₁ to R ₂ are each independently cyano group (CN), nitro group (NO ₂ ), halogen group, sulfonyl group (SO ₂ R '), sulfoxide group (SO ₃ ), carbonyl group (COR'), carboxyl group ( CO ₂ R '), or an ester group (COO), at least one selected from these is a substituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbohydrates.

R 'may be hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group, halogenated alkyl group, alkenyl group, aryl group, heteroaryl group, alkoxy group, silyl group, preferably May be a hydrogen atom, an alkyl, aryl, heteroaryl radical.

R ₃ to R ₆ are each independently hydrogen, deuterium or a halogen group.

X ₁ to X ₄ is CH, N or CR, at least one of X ₁ to X ₄ is CR, R is hydrogen, deuterium, or any one selected from the following [formula 1] and [formula 2]. .

[Formula 1]

[Formula 2]

In [Formula 1] and [Formula 2],

L ₁ and L ₂ are each a single bond or are selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and n and m are each selected from 1 to 4 In the case where n and m are each 2 or more, a plurality of L ₁ and L ₂ are the same as or different from each other.

Ar ₁ to Ar ₃ are the same as or different from each other, each independently selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, wherein Ar ₁ and Ar ₂ may be bonded to each other or connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be selected from N, S and O. It may be substituted with one or more heteroatoms.

o, p, and q are each an integer of 1 to 3, and when o, p and q are each 2 or more, a plurality of Ar ₁ to Ar ₃ may be the same or different from each other.

In addition, in the 'substituted or unsubstituted', 'substituted' means that L and Ar ₁ to Ar ₃ may each be further substituted with one or more substituents, and the one or more substituents may be a deuterium or cyano group. , Halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, alkenyl group of 2 to 24 carbon atoms, aryl group of 6 to 24 carbon atoms, 2 to 24 carbon atoms It is selected from the group consisting of a heteroaryl group, an alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms and an arylsilyl group having 1 to 24 carbon atoms.

In addition, at least one or more of Ar ₁ to Ar ₂ of [Formula 1] may be [Formula 3] or [Formula 4], and a substituent having the same structure as that of [Formula I] or [Formula II] is hetero It may be a heteroaryl substituent of the amine group.

[Formula 3]

[Structure 4]

In [Formula 3] or [Formula 4],

R ₁ to R ₂ are each independently cyano group (CN), nitro group (NO ₂ ), halogen group, sulfonyl group (SO ₂ R '), sulfoxide group (SO ₃ ), carbonyl group (COR'), carboxyl group ( CO ₂ R '), or an ester group (COO), at least one selected from these is a substituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbohydrates.

The R ′ may be hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group, halogenated alkyl group, alkenyl group, aryl group, heteroaryl group, alkoxy group, silyl group, preferably Preferably a hydrogen atom, an alkyl, aryl, heteroaryl radical.

R ₃ to R ₆ are each independently hydrogen, deuterium or a halogen group.

X ₁ to X ₄ is CH, N or CR, any one of X ₁ to X ₄ is CR, R is connected to [Formula 1].

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

In the present invention, the alkyl group may be linear or branched chain, specific examples are 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 and the like, but are not limited thereto.

In the present invention, the aryl group may be monocyclic or polycyclic, and examples of the monocyclic aryl group include phenyl group, biphenyl group, terphenyl group, stilbene group, and the like, and examples of the polycyclic aryl group include naphthyl group and anthracenyl group. , Phenanthrenyl group, pyrenyl group, peryllenyl group, tetrasenyl group, chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention It is not limited only to these examples.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a hetero atom, and examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group and oxa Diazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl Group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene Group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, etc. There is, but is not limited to these.

In the present invention, the aryl group in the arylthio group, the arylamine group, and the arylsilyl group is the same as the examples of the aryl group described above.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.

Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenyl Amine groups, 9-methyl-anthracenylamine groups, diphenyl amine groups, phenyl naphthyl amine groups, ditolyl amine groups, phenyl tolyl amine groups, carbazole groups, and triphenyl amine groups, but are not limited thereto.

In the present invention, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group and the like. However, the present invention is not limited thereto.

Specific examples of the alkoxy group which is a substituent used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy and the like. At least one hydrogen atom may be substituted with the same substituent as in the case of the aryl group.

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

Specific examples of the alkenyl group used in the present invention represent a linear or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

The organic light emitting compound according to the present invention represented by the above [Formula I] or [Formula II] may be used as an organic material layer of the organic light emitting device due to its structural specificity, and more specifically may be used as a hole transport material in the organic material layer.

Particularly, in the related art, a layer of doping using a p-type dopant or a p-type dopant between the ITO substrate and the hole transport layer is used to control the high conductivity of the hole transport layer formed on the ITO substrate and the charge density of the charge carrier. However, in the present invention, a single hole transport layer made of a compound represented by the above [Formula I] or [Formula II] may be applied without a separate p-type dopant process or insertion.

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

As such, the organic light emitting compound according to the present invention introduces each moiety having a p-doping function and a hole transporting property into one structure, and thus an organic light emitting compound having inherent properties of the substituents introduced therein. As a result, when the organic light emitting compound according to the present invention is applied as a hole transport layer material, it is possible to further improve the low voltage driving characteristics, luminous efficiency and lifetime characteristics of the device.

In addition, the compound of the present invention can be applied to the device according to the general organic light emitting device manufacturing method.

The organic light emitting device according to an embodiment of the present invention may be composed of a structure including a first electrode and a second electrode and an organic material layer disposed therebetween, using the organic light emitting compound according to the invention in the organic material layer of the device Except for the conventional device manufacturing method and materials can be used.

The organic material layer of the organic light emitting device according to the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. However, the present invention is not limited thereto, and may include fewer organic layers.

Accordingly, in the organic light emitting device according to the present invention, the organic material layer may include at least one layer of a hole transport layer, or a layer for simultaneously injecting holes and transporting holes, wherein at least one of the layers is the above [Formula I] or It may include a compound represented by [Formula II].

The organic material layer structure and the like of the preferred organic light emitting device according to the present invention will be described in more detail in the following examples.

In addition, the organic light emitting device according to the present invention using a metal vapor deposition (PVD) method such as sputtering (e-beam evaporation), metal or conductive metal oxides or alloys thereof on the substrate It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material 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 material layer may be formed by using a variety of polymer materials, and by using a process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.

As the cathode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), 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) Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, multilayer such as LiF / Al or LiO ₂ / Al. Structural materials and the like, but are not limited thereto.

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

As a hole transport material, a material capable of transporting holes from an anode or a hole injection layer to be transferred to a light emitting layer is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but the low-voltage driving characteristics, the luminous efficiency, and the lifetime characteristics of the device using the organic light emitting compound according to the present invention. Can be further improved.

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

As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes including Alq ₃ , organic radical compounds, hydroxyflavone-metal complexes, and the like, 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-sided emission type according to the material used.

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

Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate 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: Compound 1 Synthesis

(One) Preparation Example 1  : Synthesis of Intermediate 1-1

4-Bromo-1,2-diaminobenzene (10 g, 0.054 mol, sigma aldrich), 2,3,5,6-tetrafluoro-4-hydroxybenzaldehyde (10.38 g, 0.054 mol, Mascot), p-Toluenesulfonic acid (1.84 g , 0.011 mol, sigma aldrich) and 200 mL of DMF were added and reacted at 80 ° C. for 2 hours. After completion of the reaction, the mixture was extracted using 0.05 M sodium carbonate aqueous solution, and then column purified to obtain 14 g (yield 72.5%) of <Intermediate 1-1>.

(2) Production Example  2: synthesis of intermediate 1-2

Intermediate 1-1 (10 g, 0.035 mol), excess MnO ₂ and 150 mL of methylene chloride were added thereto, and the mixture was stirred under reflux for 24 hours to react. After completion of the reaction, the mixture was extracted and purified by column to obtain 8.7 g (yield 87.5%) of <Intermediate 1-2>.

(3) Production Example  3: Synthesis of Intermediate 1-3

Intermediate 1-2 (10 g, 0.024 mol) , malononitrile (4.80 g, 0.073 mol, sigma aldrich), methylene chloride 300 mL insert was cooled in ice-bath conditions as TiCl ₄ (13.79 g, 0.073 mol, sigma aldrich) was slowly dropped and pyridine (11.50 g, 0.145 mol) was added dropwise very slowly. After 1 hour, the ice bath was removed and the reaction was stirred for 24 hours. After completion of the reaction, the mixture was extracted with an aqueous hydrochloric acid solution and then purified by column to obtain 7.8 g (yield 79%) of <intermediate 1-3>.

(4) Production Example  4: Synthesis of Compound 1

Intermediate 1-3 (7 g, 0.017 mol), 4- (diphenylamino) phenylboronic acid (5.97 g, 0.021 mol, sigma aldrich), potassium carbonate (7.13 g, 0.052 mol, sigma aldrich), Pd (PPh ₃ ) ₄ ( 1 g, 0.0009 mol, sigma aldrich), Tol 150 mL, EtOH, 40 mL, H ₂ O 20 mL was added and reacted under reflux for 12 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 7.3 g (yield 74.3%) of compound 1.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (7.99 / d, 6.5 / d, 5.6 / s) 2H (7.13 / d, 6.81 / m, 6.58 / d) 4H (7.20 / m, 6.63 / d)

LC / MS: m / z = 571 [(M + 1) ⁺ ]

Synthesis Example  2: compound 11 synthesis

(One) Production Example  1: Synthesis of Intermediate 11-1

2-bromo-9,9-dimethyl-9H-fluorene (10 g, 0.037 mol, sigma aldrich), 4-aminobiphenyl (7.43 g, 0.044 mol, sigma aldrich), Sodium tert-butoxide (7.04 g, 0.073 mol, sigma aldrich), 150 ml of Toluene was added to the catalyst Pd (dba) ₂ (1.05 g, 0.0018 mol, sigma aldrich), tri-tert-Bu-phosphine (0.74 g, 0.0037 mol, sigma aldrich) and stirred at 100 ° C. for 5 hours. The reaction was carried out. After completion of the reaction, the mixture was extracted and purified by column to obtain 10.3 g (77.8%) of <Intermediate 11-1>.

(2) Production Example  2: Synthesis of Intermediate 11-2

Intermediate 11-1 (10 g, 0.028 mol), 4-bromophenylboronic acid (6.11 g, 0.030 mol, sigma aldrich), Sodium tert-butoxide (6.65 g, 0.069 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.80 150 mL of Toluene was added to g, 0.0014 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.56 g, 0.0028 mol, sigma aldrich), followed by stirring at 100 ° C. for 4 hours. After the completion of the reaction, the mixture was extracted and purified by column to obtain 10.4 g (yield 78%) of <intermediate 11-2>.

(3) Production Example  3: Synthesis of Compound 11

Intermediate 1-3 (10 g, 0.025 mol), intermediate 11-2 (14.19 g, 0.030 mol), potassium carbonate (10.18 g, 0.074 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (1.42 g, 0.0012 mol, sigma aldrich), Tol 200 mL, EtOH, 40 mL, H ₂ O 20 mL was added and reacted by reflux stirring for 12 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 13.7 g (yield 73%) of compound 11.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (7.99 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.38 / m, 7.28 / m, 6.75 / s, 6.5 / d, 5.6 / s) 2H (7.54 / d, 7.52 / d, 7.51 / m, 7.13 / d, 6.69 / d) 3H (6.58 / d) 6H (1.72 / s)

LC / MS: m / z = 763 [(M + 1) ⁺ ]

Synthesis Example  3: Synthesis of Compound 58

(One) Production Example  1: Synthesis of Intermediate 58-1

4-bromobiphenyl (10 g, 0.043 mol, sigma aldrich), 4-aminophenylboronic acid (6.46 g, 0.047 mol, sigma aldrich), Sodium tert-butoxide (10.31 g, 0.107 mol, sigma aldrich), Pd (dba) ₂ ( 1.23 g, 0.0021 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.87 g, 0.0043 mol, sigma aldrich) add 200 mL of Toluene, 40 mL of EtOH, and 20 mL of H ₂ O and stir at 100 ° C for 4 hours. The reaction was carried out. After completion of the reaction, the mixture was extracted and purified by column to obtain 13.8 g (yield 76.5%) of <Intermediate 58-1>.

(2) Production Example  2: Synthesis of Intermediate 58-2

Intermediate 58-1 (10 g, 0.035 mol), 9-bromophenanthrene (9.66 g, 0.038 mol, sigma aldrich), Sodium tert-butoxide (8.31 g, 0.087 mol, sigma aldrich), Pd (dba) ₂ (0.99 g, 200 mL of Toluene, 40 mL of EtOH, and 20 mL of H ₂ O were added to 0.0017 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.70 g, 0.0035 mol, sigma aldrich), followed by stirring at 100 ° C. for 6 hours. . After completion of the reaction, the mixture was extracted and purified by column to obtain 12.2 g (yield 76.3%) of <intermediate 58-2>.

(3) Production Example  3: Synthesis of Compound 58

Intermediate 1-3 (10 g, 0.025 mol), intermediate 58-2 (13.62 g, 0.030 mol), potassium carbonate (10.18 g, 0.074 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (1.42 g, 0.0012 mol, sigma aldrich), Tol 200 mL, EtOH, 40 mL, H ₂ O 20 mL was added and reacted by reflux stirring for 12 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 13.4 g (yield 73.3%) of compound 58.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (7.99 / d, 7.41 / m, 6.5 / d, 5.6 / s) 2H (7.54 / d, 7.52 / d, 7.51 / m, 7.13 / d, 6.69 / d , 6.58 / d)

LC / MS: m / z = 744 [(M + l) ⁺ ]

Synthesis Example  4: Synthesis of Compound 83

(One) Production Example  1: Synthesis of Intermediate 83-1

3-bromodibenzofuran (20 g, 0.081 mol, Mascot), 4-aminobiphenyl (16.44 g, 0.097 mol, sigma aldrich), Sodium tert-butoxide (15.56 g, 0.16 mol, sigma aldrich), catalyst Pd (dba) ₂ (2.33 300 mL of Toluene was added to g, 0.004 mol, sigma aldrich) and tri-tert-Bu-phosphine (1.64 g, 0.008 mol, sigma aldrich) and reacted by stirring at 100 ° C. for 2 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 19.2 g (yield 70.7%) of <intermediate 83-1>.

(2) Production Example  2: synthesis of intermediate 83-2

3-bromophenylboronic acid (10 g, 0.050 mol, sigma aldrich), intermediate 83-1 (18.37 g, 0.055 mol), Sodium tert-butoxide (11.96 g, 0.125 mol, sigma aldrich), Pd (dba) ₂ (1.43 g , 200 mL of Toluene was added to 0.0025 mol, sigma aldrich) and tri-tert-Bu-phosphine (1.01 g, 0.005 mol, sigma aldrich). After completion of the reaction, the mixture was extracted and purified by column to obtain 16.9 g (yield 74.5%) of <intermediate 83-2>.

(3) Production Example  3: Synthesis of Compound 83

Intermediate 1-3 (10 g, 0.025 mol), intermediate 83-2 (13.42 g, 0.030 mol), potassium carbonate (10.18 g, 0.074 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (1.42 g, 0.0012 mol, sigma aldrich), Tol 200 mL, EtOH, 40 mL, H ₂ O 20 mL was added and reacted by reflux stirring for 12 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 14 g (yield 77.3%) of compound 83.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (7.99 / d, 6.5 / d, 5.6 / s, 7.89 / d, 7.66 / d, 7.64 / d, 7.43 / s, 7.41 / m, 7.38 / m, 7.32 / m, 7.15 / m, 6.53 / d, 6.51 / d, 6.44 / s, 6.33 / d) 2H (7.54 / d, 7.52 / d, 7.51 / m, 6.69 / d)

LC / MS: m / z = 737 [(M + 1) ⁺ ]

Synthesis Example  4: Synthesis of Compound 142

(One) Preparation Example 1  : Synthesis of Intermediate 142-1

3-Bromo-1,2-diaminobenzene (10 g, 0.054 mol, sigma aldrich), 2,3,5,6-tetrafluoro-4-hydroxybenzaldehyde (10.38 g, 0.054 mol, Mascot), p-Toluenesulfonic acid (1.84 g , 0.011 mol, sigma aldrich) and 200 mL of DMF were added and reacted at 80 ° C. for 2 hours. After completion of the reaction, the mixture was extracted using 0.05 M aqueous sodium carbonate solution, and column purified to obtain 14 g (yield 72.5%) of <Intermediate 142-1>.

(2) Production Example  2: Synthesis of Intermediate 142-2

Intermediate 142-1 (10 g, 0.035 mol), excess MnO ₂ and 150 mL of methylene chloride were added thereto, and the mixture was stirred under reflux for 24 hours to react. After completion of the reaction, the mixture was extracted and purified by column to obtain 8.7 g (yield 87.5%) of <intermediate 142-2>.

(3) Production Example  3: Synthesis of Intermediate 142-3

Intermediate 142-2 (10 g, 0.024 mol), malononitrile (4.80 g, 0.073 mol, sigma aldrich), 300 mL of methylene chloride, cooled in an ice-bath and TiCl ₄ (13.79 g, 0.073 mol, sigma aldrich) was slowly dropped and pyridine (11.50 g, 0.145 mol) was added dropwise very slowly. After 1 hour, the ice bath was removed and the reaction was stirred for 24 hours. After completion of the reaction, the mixture was extracted with an aqueous hydrochloric acid solution and then purified by column to obtain 7.8 g (yield 79%) of <intermediate 1-3>.

(4) Production Example  4: Synthesis of Intermediate 142-4

4-Bromobenzotrifluoride (10 g, 0.044 mol, sigma aldrich), 4-aminobiphenyl (8.27 g, 0.049 mol, sigma aldrich), Sodium tert-butoxide (10.68 g, 0.111 mol, sigma aldrich), Pd (dba) ₂ (1.25 200 mL of Toluene was added to g, 0.002 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.90 g, 0.004 mol, sigma aldrich), followed by reaction at 100 ° C. for 4 hours. After the completion of the reaction, the mixture was extracted and purified by column to obtain 10.6 g (yield 76.1%) of <Intermediate 142-4>.

(5) Production Example  5: synthesis of intermediate 142-5

Intermediate 142-4 (10 g, 0.032 mol), 4-bromophenylboronic acid (7.05 g, 0.035 mol, sigma aldrich), Sodium tert-butoxide (7.67 g, 0.080 mol, sigma aldrich), Pd (dba) ₂ (0.92 g , 0.0016 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.65 g, 0.0032 mol, sigma aldrich) were added 200 mL of Toluene and stirred at 100 ° C. for 4 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 10.4 g (yield 75.2%) of <intermediate 142-5>.

(6) Production Example  6: synthesis of compound 142

Intermediate 142-3 (10 g, 0.025 mol), intermediate 142-5 (12.77 g, 0.030 mol), potassium carbonate (10.18 g, 0.074 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (1.42 g, 0.0012 mol, sigma aldrich), Tol 200 mL, EtOH, 40 mL, H ₂ O 20 mL was added and reacted by reflux stirring for 12 hours. After completion of the reaction, the mixture was extracted and purified by column to obtain 13 g (yield 74%) of compound 142.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (7.99 / d, 7.86 / m, 7.41 / m, 6.9 / d) 2H (7.54 / d, 7.52 / d, 7.51 / m, 7.37 / d, 7.13 / d , 6.69 / d, 6.58 / d, 6.56 / d)

LC / MS: m / z = 715 [(M + 1) ⁺ ]

Synthesis Example  5: Synthesis of Compound 228

(One) Production Example  1: Synthesis of Intermediate 228-1

4-bromo-2,3,5,6-tetrafluorobenzonitrile (10 g, 0.039 mol, sigma aldrich), 4-aminobiphenyl (7.33 g, 0.043 mol, sigma aldrich), Sodium tert-butoxide (7.57 g, 0.079 mol, sigma aldrich), 150 ml of Toluene in catalyst Pd (dba) ₂ (1.13 g, 0.002 mol, sigma aldrich), tri-tert-Bu-phosphine (0.80 g, 0.0039 mol, sigma aldrich) and stirred at 100 ° C. for 1 hour. The reaction was carried out. After the completion of the reaction, the mixture was extracted and purified by column to obtain 10 g (yield 74.2%) of <intermediate 228-1>.

(2) Production Example  2: Synthesis of Compound 228

Intermediate 142-3 (10 g, 0.025 mol), intermediate 228-1 (9.25 g, 0.027 mol), Sodium tert-butoxide (4.72 g, 0.049 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.71 g, 0.0012 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.50 g, 0.0025 mol, sigma aldrich) were added 150 mL of Toluene and stirred at 100 ° C. for 1 hour. After completion of the reaction, the mixture was extracted and purified by column to obtain 12 g (yield 73%) of compound 228.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (9.15 / d, 7.99 / d, 4.7 / s, 7.41 / m) 2H (7.54 / d, 7.52 / d, 7.51 / m, 6.69 / d)

LC / MS: m / z = 668 [(M + 1) ⁺ ]

Synthesis Example  6: Synthesis of Compound 257

(One) Production Example  1: Synthesis of Intermediate 257-1

2-bromonaphthalene (10 g, 0.048 mol, sigma aldrich), 4-aminobiphenyl (8.99 g, 0.053 mol, sigma aldrich), Sodium tert-butoxide (9.28 g, 0.097 mol, sigma aldrich), catalyst Pd (dba) ₂ ( 150 mL of Toluene was added to 1.39 g, 0.0024 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.98 g, 0.0048 mol, sigma aldrich), and the mixture was stirred at 100 ° C. for 1 hour. After completion of the reaction, the mixture was extracted and purified by column to obtain 10.8 g (yield 75.7%) of <intermediate 257-1>.

(2) Production Example  2: Synthesis of Compound 257

Intermediate 142-3 (10 g, 0.025 mol), intermediate 257-1 (7.98 g, 0.027 mol), Sodium tert-butoxide (4.72 g, 0.049 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.71 g, 0.0012 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.50 g, 0.0025 mol, sigma aldrich) were added 150 mL of Toluene and stirred at 100 ° C. for 1 hour. After completion of the reaction, the mixture was extracted and purified by column to obtain 11.2 g (yield 73.4%) of compound 257.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (8.55 / d, 8.12 / d, 7.94 / d, 7.63 / d, 7.50 / m, 7.33 / m, 7.29 / m, 7.25 / m) 2H (8.49 / d , 8.07 / d, 7.78 / d, 7.53 / m, 7.37 / d, 7.04 / d, 6.63 / d) 3H (7.41 / m) 6H (7.52 / d, 7.51 / m, 6.69 / d) 8H (7.54 / d )

LC / MS: m / z = 981 [(M + 1) ⁺ ]

Synthesis Example  7: Synthesis of Compound 293

(One) Production Example  1: Synthesis of Intermediate 293-1

4-bromophenylboronic acid (10 g, 0.050 mol, sigma aldrich), 4-aminobiphenyl (9.27 g, 0.055 mol, sigma aldrich), Sodium tert-butoxide (9.57 g, 0.10 mol, sigma aldrich), catalyst Pd (dba) ₂ 150 mL of Toluene was added to (1.43 g, 0.0025 mol, sigma aldrich) and tri-tert-Bu-phosphine (1.01 g, 0.0050 mol, sigma aldrich) and reacted by stirring at 100 ° C. for 1 hour. After completion of the reaction, the mixture was extracted and purified by column to obtain 10.7 g (yield 74.3%) of <Intermediate 293-1>.

(2) Production Example  2: Synthesis of Intermediate 293-2

2-bromooxazole (10 g, 0.068 mol, Mascot.), Intermediate 293-1 (21.5 g, 0.074 mol), Sodium tert-butoxide (12.99 g, 0.135 mol, sigma aldrich), catalyst Pd (dba) ₂ (1.94 g , 15034 Toluene was added to 0.0034 mol, sigma aldrich) and tri-tert-Bu-phosphine (1.37 g, 0.0068 mol, sigma aldrich). After the completion of the reaction, the mixture was extracted and purified by column to obtain 16.6 g (yield 74.8%) of <intermediate 293-2>.

(3) Production Example  3: Synthesis of Compound 293

Intermediate 142-3 (10 g, 0.025 mol), intermediate 293-2 (7.98 g, 0.027 mol), Sodium tert-butoxide (4.72 g, 0.049 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.71 g, 0.0012 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.50 g, 0.0025 mol, sigma aldrich) were added 150 mL of Toluene and stirred at 100 ° C. for 1 hour. After completion of the reaction, the mixture was extracted and purified by column to obtain 11.2 g (yield 73.4%) of compound 293.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (8.68 / d, 7.99 / m, 7.86 / m, 7.69 / d, 7.41 / m, 7.09 / d) 2H (7.52 / d) 4H (7.54 / d, 6.69 / d)

LC / MS: m / z = 638.57 [(M + l) ⁺ ]

Synthesis Example  8: Synthesis of Compound 418

(One) Production Example  1: Synthesis of Intermediate 418-1

2,5-dibromopyridine-3,4-diamine (10 g, 0.038 mol, Mascot.), 2,3,5,6-tetrafluoro-4-hydroxybenzaldehyde (8 g, 0.041 mol, Mascot), p-Toluenesulfonic acid ( 1.29 g, 0.008 mol, sigma aldrich) and 200 mL of DMF were added and stirred at 80 ° C. for 2 hours. After the completion of the reaction, the mixture was extracted with 0.05 M sodium carbonate aqueous solution and column purified to obtain 11.7 g (yield 70.8%) of <intermediate 418-1>.

(2) Production Example  2: synthesis of intermediate 418-2

Intermediate 418-1 (10 g, 0.023 mol), excess MnO ₂ and 150 mL of methylene chloride were added thereto, and the mixture was stirred under reflux for 24 hours to react. After completion of the reaction, the mixture was extracted and purified by column to obtain 8.1 g (yield 81.4%) of <intermediate 418-2>.

(3) Production Example  3: Synthesis of Intermediate 418-3

Intermediate 418-2 (10 g, 0.023 mol), malononitrile (4.50 g, 0.068 mol, sigma aldrich), 300 mL of methylene chloride, cooled in an ice-bath and cooled with TiCl ₄ (12.96 g, 0.068 mol, sigma aldrich) was slowly dropped and pyridine (10.81 g, 0.137 mol) was added dropwise very slowly. After 1 hour, the ice bath was removed and the reaction was stirred for 24 hours. After completion of the reaction, the mixture was extracted with an aqueous hydrochloric acid solution and then purified by column to obtain 8 g (yield 72.1%) of <intermediate 418-3>.

(4) Production Example  4: Synthesis of Intermediate 418-4

4-bromobiphenyl (10 g, 0.043 mol, sigma aldrich), aniline (4.39 g, 0.047 mol, sigma aldrich), Sodium tert-butoxide (8.25 g, 0.086 mol, sigma aldrich), catalyst Pd (dba) ₂ (1.23 g , 0.002 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.87 g, 0.004 mol, sigma aldrich) were added 150 mL of toluene and stirred at 100 ° C. for 1 hour. After completion of the reaction, the mixture was extracted and purified by column to obtain 8 g (yield 76%) of <Intermediate 418-4>.

(5) Production Example  5: Synthesis of Compound 418

4-bromobiphenyl (10 g, 0.021 mol, sigma aldrich), aniline (10.07 g, 0.041 mol, sigma aldrich), Sodium tert-butoxide (3.95 g, 0.041 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.59 g , 150 mL of Toluene was added to 0.001 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.42 g, 0.002 mol, sigma aldrich). After completion of the reaction, the mixture was extracted and purified by column to obtain 12.2 g (yield 72.8%) of compound 418.

H-NMR (200 MHz, CDCl 3): δ ppm, 1H (4.7 / s) 2H (7.41 / m, 6.81 / m) 4H (7.54 / d, 7.52 / d, 7.51 / m, 7.20 / m, 6.69 / d, 6.29 / d)

LC / MS: m / z = 815 [(M + 1) ⁺ ]

Device Example

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, using an ITO glass substrate with an ITO transparent electrode, so that the light emitting area is 2 mm × 2 mm in size. And then washed. The substrate was mounted in a vacuum chamber, and the base pressure was 1 × 10 ⁻⁶ torr. Then, the organic material and the metal were deposited on the ITO with the following structure.

Device Examples 1-6

Using the compound according to the present invention as a hole transport material, a blue light emitting organic light emitting device having a device structure as described below was manufactured, and light emission characteristics including light emission efficiency were measured.

ITO / hole transport layer (100 nm) / electron blocking layer (10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq 30 nm) / LiF (1 nm) / Al (100 nm)

A hole transport layer was formed on the ITO transparent electrode by using Formulas 1, 11, 58, 83, 142, 228, 257, 293, and 418 according to the present invention. The hole blocking layer was formed to a thickness of 10 nm using [EBL1]. In the light emitting layer, [BH1] was used as the host compound, and [BD1] was used as the dopant compound, and the film was formed to have a thickness of about 20 nm. Further, an electron transport layer (doped 50% of the Liq [201] compound) was used. 30 nm and LiF 1 nm and aluminum 100 nm were formed into a film by the vapor deposition method, and the organic light emitting element was produced.

Device Comparative Example 1

The device embodiment according to the present invention is characterized in that the compound according to the present invention is employed in the hole transport layer without a separate doping.

Accordingly, the organic light emitting device of Comparative Example 1 is a device structure of Example 1, except that the compound in which the compound is doped with 5% F4TCNQ in α-NPB instead of the compound of Formula 1 according to the present invention in the hole transport layer The same was prepared.

Experimental Example 1 Luminescence Characteristics of Device Examples 1 to 6

In the organic light emitting device manufactured according to the above embodiment, voltage, current, and luminous efficiency were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and a current density of 10 mA / cm 2 was measured. The voltage to be compared was defined as "driving voltage". The results are shown in the following [Table 1].

Example HTL + p-dopant V cd / A QE (%) CIEx CIEy One Formula 1 4.21 8.12 7.12 0.145 0.152 2 Formula 11 4.22 8.22 7.21 0.144 0.152 3 Formula 33 4.29 8.10 7.11 0.145 0.153 4 Formula 58 4.28 7.98 6.97 0.145 0.152 5 Formula 83 4.25 8.16 7.14 0.144 0.153 6 Formula 107 4.34 8.06 7.05 0.145 0.152 7 Formula 142 4.30 7.94 6.89 0.145 0.154 8 Formula 197 4.34 8.07 7.04 0.145 0.153 9 Formula 228 4.25 8.01 7.00 0.145 0.152 10 Formula 257 4.22 8.14 7.13 0.144 0.153 11 Formula 293 4.36 8.05 7.02 0.145 0.154 12 Formula 324 4.27 8.15 7.14 0.144 0.153 13 Formula 418 4.24 8.27 7.28 0.145 0.153 Comparative Example 1 α-NPB: F4TCNQ 4.7 6.8 5.4 0.147 0.156

Referring to the results shown in [Table 1], first, when the compound according to the present invention is applied to the device hole transport layer, the light emitting efficiency, It can be confirmed that luminescent properties such as quantum efficiency are equivalent or better.

[α-NPB] [EBL1] [BH1]    [BD1]    [201]    [F4TCNQ]

Claims (8)

An organic light emitting compound represented by the following [Formula I] or [Formula II]:
[Formula I]

[Formula II]

In [Formula I] or [Formula II],
R ₁ to R ₂ are each independently cyano group (CN), nitro group (NO ₂ ), halogen group, sulfonyl group (SO ₂ R '), sulfoxide group (SO ₃ ), carbonyl group (COR'), carboxyl group ( CO ₂ R ') or an ester group (COO), at least one selected from these is a substituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms,
R 'is hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, alkenyl group of 2 to 24 carbon atoms, 6 carbon atoms An aryl group having 24 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms and a arylsilyl group having 1 to 24 carbon atoms,
R ₃ to R ₆ are each independently hydrogen, deuterium or a halogen group,
X ₁ to X ₄ is CH, N or CR, at least one of X ₁ to X ₄ is CR, and R is hydrogen, deuterium, or any one selected from the following [formula 1] and [formula 2] ,
[Formula 1]

[Formula 2]

In [Formula 1] and [Formula 2],
L ₁ and L ₂ are each a single bond or are selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and n and m are each selected from 1 to 4 An integer, and when n and m are each 2 or more, a plurality of L ₁ and L ₂ are the same as or different from each other,
Ar ₁ to Ar ₃ are the same as or different from each other, each independently selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
Ar ₁ and Ar ₂ may be bonded to each other or connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, S and May be substituted with any one or more heteroatoms selected from O,
o, p and q are each an integer of 1 to 3, and when o, p and q are each 2 or more, a plurality of Ar ₁ to Ar ₃ may be the same or different from each other. The method of claim 1,
Each of L and Ar ₁ to Ar ₃ may be further substituted with one or more substituents, and the one or more substituents may be deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, 1 to 24 carbon atoms. Alkyl group, C1-C24 halogenated alkyl group, C2-C24 alkenyl group, C6-C24 aryl group, C2-C24 heteroaryl group, C1-C24 alkoxy group, C1-C24 carbon number An organic light emitting compound, characterized in that it is selected from the group consisting of an alkylsilyl group of 1 to 24 and an arylsilyl group of 1 to 24 carbon atoms. The method of claim 1,
At least one or more of Ar ₁ to Ar ₂ of [Formula 1] is an organic light emitting compound, characterized in that [formula 3] or [formula 4]:
[Formula 3]

[Structure 4]

In [Formula 3] or [Formula 4],
R ₁ to R ₂ are each independently cyano group (CN), nitro group (NO ₂ ), halogen group, sulfonyl group (SO ₂ R '), sulfoxide group (SO ₃ ), carbonyl group (COR'), carboxyl group ( CO ₂ R ') or an ester group (COO), at least one selected from these is a substituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms,
R 'is hydrogen, deuterium, cyano group, halogen group, amino group, thiol group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, alkenyl group of 2 to 24 carbon atoms, 6 carbon atoms An aryl group having 24 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms and a arylsilyl group having 1 to 24 carbon atoms,
R ₃ to R ₆ are each independently hydrogen, deuterium or a halogen group,
X ₁ to X ₄ is CH, N or CR, any one of X ₁ to X ₄ is CR, R is connected to [Formula 1]. The method of claim 1,
[Formula I] or [Formula II] is an organic light emitting compound, characterized in that selected from the following [Compound 1] to [Compound 461]:

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic light emitting device comprising the organic light emitting compound of [I] or [II] according to claim 1. The method of claim 5,
The organic material layer may include at least one layer selected from a hole injection layer, a hole transport layer, a layer simultaneously performing hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection functions, and a light emitting layer.
At least one of the layers is an organic light emitting device, characterized in that it comprises an organic light emitting compound represented by the above [Formula I] or [Formula II]. The method of claim 6,
An organic light emitting device comprising an organic light emitting compound represented by the above [Formula I] or [Formula II] in any one selected from the hole transport layer and a layer that simultaneously performs hole injection and hole transport functions. The method of claim 7, wherein
The hole transporting layer, or a layer simultaneously performing a hole injection and a hole transporting function, are each composed of a single layer, and are formed without a p-dopant doping process, and are represented by the above [Formula I] or [Formula II]. An organic light emitting device comprising a light emitting compound.

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