WO2014104797A1 - Novel organic compound and organic light emitting device containing same - Google Patents

Abstract

The present invention relates to a novel organic compound, and more specifically, to: a novel organic compound having a ring closing structure of indole and furan and an arylamine group; and an organic light emitting device containing the same. The organic compound of the present invention has a simple charge transfer property and has high triplet energy and high glass transition temperature, and thus can provide low driving voltage, high efficiency, low power consumption and long lifespan to an organic light emitting device by being used as a hole injection or a hole transport material.

Description

Novel organic compound and organic light emitting device comprising the same

The present invention relates to a novel organic compound, and more particularly to a novel organic compound having easy charge transfer characteristics and at the same time having a high triplet energy and a high glass transition temperature, and an organic light emitting device comprising the same.

Recently, an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices. In terms of power consumption and wide color reproduction range, it is attracting attention as a next-generation display device.

In general, the organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and an organic layer between the two electrodes. In this case, the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML). , an electron injection layer, and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to the light emission characteristics of the light emitting layer.

When an electric field is applied to the organic light emitting device having such a structure, holes are injected from the anode, electrons are injected from the cathode, and holes and electrons are recombined in the light emitting layer through the hole transport layer and the electron transport layer, respectively, thereby excitons ). The formed light exciton emits light as it transitions to ground states. In order to increase the efficiency and stability of the light emitting state, the light emitting material may be doped into the light emitting layer (host).

The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors according to light emission wavelengths. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.

The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.

Various compounds are known as materials used for the hole injection and hole transport layer of the organic light emitting device, but the organic light emitting device using a known material has a lot of difficulties in practical use due to the high driving voltage, low efficiency and short life. Therefore, efforts have been made to develop organic light emitting diodes having low voltage driving, high brightness and long life using materials having excellent hole transport characteristics.

In order to solve the above problems, the present invention has excellent charge transfer characteristics, and at the same time an organic compound having a high triplet energy and a high glass transition temperature (Tg) and low drive voltage, high efficiency, low power consumption and long life, including the same It is an object to provide an organic light emitting device having a.

In order to achieve the above object, the present invention provides an organic compound represented by the following Chemical Formula 1:

[Formula 1]

Where

X is O, S, Se or Te;

; 또는 치환 또는 비치환된 C₆-C₆₀ 아릴기, C₄-C₆₀ 헤테로아릴기, C₆-C₃₀ 아릴렌기, C₄-C₃₀ 헤테로아릴렌기 또는 C₆-C₆₀ 축합 다환기이고;L ₁ to L ₃ are each independently hydrogen; heavy hydrogen; Tritium;

; Or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, C ₆ -C ₃₀ arylene group, C ₄ -C ₃₀ heteroarylene group or C ₆ -C ₆₀ condensed polycyclic group;

을 포함하며;n are each independently an integer of 0 to 2, wherein at least one of L ₁ to L ₃ is n is 1 or more

It includes;

Ar ₁ and Ar ₂ are each independently hydrogen; heavy hydrogen; Tritium or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group or C ₆ -C ₆₀ condensed polycyclic group, Ar ₁ and Ar ₂ may form a ring.

In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1) in the hole injection or hole transport layer.

The compound of Formula 1 of the present invention includes a structure in which indole and furan are ring closed and an arylamine, which facilitate charge transfer characteristics, and at the same time have a high triplet energy and a high glass transition temperature. It can be usefully used as a hole injection material and / or a hole transport material having excellent hole injection characteristics and hole transfer characteristics suitable for fluorescence and phosphorescent devices of all colors such as white and white.

In addition, when the compound of Formula 1 is used in the hole injection or hole transport layer, an organic light emitting device having low driving voltage, high efficiency, low power consumption, and long life may be manufactured.

1 schematically illustrates a cross section of an OLED according to an embodiment of the invention.

The compound of the present invention represented by the following formula (1) is characterized in that the indole and furan have a ring-closed structure and an arylamine group:

[Formula 1]

Where

X is O, S, Se or Te;

; 또는 치환또는 비치환된 C₆-C₆₀ 아릴기, C₄-C₆₀ 헤테로아릴기, C₆-C₃₀ 아릴렌기, C₄-C₃₀ 헤테로아릴렌기 또는 C₆-C₆₀ 축합 다환기이고;L ₁ to L ₃ are each independently hydrogen; heavy hydrogen; Tritium;

; Or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, C ₆ -C ₃₀ arylene group, C ₄ -C ₃₀ heteroarylene group or C ₆ -C ₆₀ condensed polycyclic group;

을 포함하며;n are each independently an integer of 0 to 2, wherein at least one of L ₁ to L ₃ is n is 1 or more

It includes;

Ar ₁ and Ar ₂ are each independently hydrogen; Small and medium numbers; Tritium or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group or C ₆ -C ₆₀ condensed polycyclic group, Ar ₁ and Ar ₂ may form a ring.

Further, the substituent is a deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group One or more groups selected from the group consisting of C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₃ to C ₄₀ heteroaryl group may be substituted.

In the compound of the present invention, since the furan has a high triplet energy, when applied to the organic light emitting device, it serves to provide a low driving voltage, high efficiency and low power consumption, indole facilitates charge transfer. Therefore, when the furan and indole are ring-closed, a high glass transition temperature can be obtained, and thus, when applied to an organic light emitting device, thermal stability and long life can be obtained.

In addition, the arylamine moiety (moiety) serves to facilitate charge transfer.

In the present invention, the compound of Formula 1 may be selected from the group consisting of compounds represented by the following Formulas 2 to 8, but is not limited thereto:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

X is O, S, Se or Te;

L ₄ to L ₆ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, C ₆ -C ₃₀ arylene group, C ₄ -C ₃₀ heteroarylene group or C _6- C ₆₀ condensed polycyclic group;

n are each independently an integer of 0 to 2, wherein at least one of L ₄ to L ₆ is n is 1 or more;

Ar ₁ to Ar ₇ are each independently hydrogen; heavy hydrogen; It is a tritium or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a C ₄ -C ₆₀ heteroaryl group, or a C ₆ -C ₆₀ condensed polycyclic group, and adjacent Ars may form a ring with each other.

In the present invention, preferred examples of the compound represented by Formula 1 are as follows:

The compound of the present invention has an indole which is easy to transfer charges and a furan having a high triplet energy ring-closing, and an arylamine which is easy to transfer charges, thereby facilitating charge transfer characteristics, and at the same time high triplet energy and high glass transition temperature. It can have

The compound of Formula 1 according to the present invention may be prepared based on the Suzuki-coupling reaction of the aromatic boron compound and the aromatic halogen compound in the carbon-carbon coupling reaction. For example, the compounds of formulas 2a, 2b, 3a, 3b and 4a of the present invention can be prepared as shown in Schemes 1-5, respectively.

Scheme 1

Scheme 2

Scheme 3

Scheme 4

Scheme 5

L ₆ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, C ₆ -C ₃₀ arylene group, C ₄ -C ₃₀ heteroarylene group or C ₆ -C ₆₀ condensed polycyclic group ego;

n is an integer from 0 to 2;

Ar ₁ to Ar ₇ are each independently hydrogen; Or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, or C ₆ -C ₆₀ condensed polycyclic group.

In addition, the present invention provides an organic light emitting device comprising a compound represented by the formula (1) or a mixture thereof as a hole injection or hole transport material.

In addition, the organic light emitting device of the present invention includes one or more organic thin film layers including the compound represented by Chemical Formula 1, and the method of manufacturing the organic light emitting device is as follows. Preferably, at least one organic thin film layer including the compound represented by Formula 1 is a hole injection layer or a hole transport layer.

The organic light emitting device is an organic thin film layer, such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between the anode (anode) and the cathode (cathode) It may include one or more.

First, an anode is formed by depositing a material for an anode electrode having a high work function on the substrate. In this case, the substrate may be a substrate used in a conventional organic light emitting device, it is particularly preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof. In addition, as the anode electrode material, transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like may be used. The anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.

Then, the compound represented by the formula (1) or a known hole injection layer material on the anode electrode can be formed by a method such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, It is preferable to form by the vacuum evaporation method from the point of obtaining a uniform film | membrane quality, and hard to produce a pinhole. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and the deposition temperature of 50 to 500 ° C., It is preferable to select appropriately from a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 kPa / sec, and a layer thickness of 10 kPa to 5 mu m.

The well-known hole injection layer material is not particularly limited, and TCTA (4,4 ′, 4 ″ -tri (N-carbazolyl), which is a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Pat. No. 4,356,429. ) Triphenylamine), m-MTDATA (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB (4,4', 4" -tris (3-methylphenylamino) phenoxy Cybenzene), HI-406 (N ¹ , N ¹ '-(biphenyl-4,4'-diyl) bis (N 1-(naphthalen- ¹ -yl) -N ⁴ , N ⁴ -diphenylbenzene-1 , 4-diamine) and the like can be used as the hole injection layer material.

Next, the compound represented by Chemical Formula 1 or a known hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, etc., but it is easy to obtain a uniform film quality. It is preferable to form by the vacuum evaporation method in that pinholes are unlikely to generate | occur | produce. In the case of forming the hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in the same condition range as the formation of the hole injection layer.

In addition, the well-known hole transport layer material is not particularly limited, and may be arbitrarily selected and used from the conventional well-known materials used in the hole transport layer. Specifically, the hole transport layer material is carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) Derivatives and the like can be used.

Thereafter, the light emitting layer material may be coated on the hole transport layer by a deposition method or a solution process. In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same conditions as the formation of the hole injection layer. In addition, as the light emitting layer material, a known light emitting layer material may be used, and a light emitting layer may be formed by using a phosphorescent or fluorescent dopant together. In this case, the fluorescent dopant may be IDE102 or IDE105, or BD142 (N ⁶ , N ¹² -bis (3,4-dimethylphenyl) -N ⁶ , N ¹² -dimethycrylicene- which can be purchased from Idemitsu Co., Ltd.). 6,12-diamine) can be used as green phosphorescent dopant Ir (ppy) ₃ (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6] -Difluorophenyl) -pyridinato-N, C2 '] picolinate), red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).

In addition, when using the phosphorescent dopant in the light emitting layer, it is preferable to further laminate the hole suppression material (HBL) by vacuum deposition or spin coating to prevent the triplet excitons or holes from diffusing into the electron transport layer. . The hole-suppressing material that can be used at this time is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1) can be cited. Oxy-2-methylquinolinolato) -aluminum biphenoxide), a phenanthrolines-based compound (e.g., BCP (vasocuproin) from UDC) can be used.

An electron transport layer is formed on the light emitting layer formed as above, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.

The electron transport material as a function to transport a steady stream of electrons injected from the electron injecting electrode that kind is not particularly limited, for example, quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq ₃ ), Or ET4 (6,6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine). In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer material may be LiF, NaCl, CsF, Li ₂ O, BaO, or the like. The substance of can be used.

In addition, although the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.

Subsequently, an electron injection layer material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is preferable to form by.

Finally, a cathode forming metal is formed on the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode. The cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this. In addition, a transmissive cathode using ITO and IZO may be used to obtain a top emitting element.

The organic light emitting device of the present invention is not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device of the cathode structure, but also the structure of an organic light emitting device of various structures, 1 It is also possible to form a layer or two intermediate layers.

The thickness of each organic thin film layer formed according to the present invention as described above can be adjusted according to the required degree, preferably 10 to 1,000 nm, more preferably 20 to 150 nm.

In addition, in the present invention, the organic thin film layer including the compound represented by Chemical Formula 1 has an advantage that the surface is uniform and excellent in shape stability because the thickness of the organic thin film layer can be adjusted in molecular units.

Hereinafter, preferred examples are provided to help understanding of the present invention, but the following examples are merely to illustrate the present invention, and the scope of the present invention is not limited to the following examples.

Synthesis of Intermediate 1-3

[Synthesis of 1-1]

In a round bottom flask, 59.3 g of benzofuran-3-ylboronic acid and 100 g of 4-bromo-2-iodo-1-nitrobenzene were dissolved in 1600 ml of toluene, 450 ml of K ₂ CO ₃ (2M) and 10.5 g of Pd (PPh ₃ ) ₄ After stirring, the mixture was stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 82.5 g (yield 85%) of intermediate 1-1.

[Synthesis of 1-2]

After dissolving 80 g of 1-1 in 400 ml of 1,2-dichlorobenzene, 260 ml of P (OEt) ₃ was added thereto, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 43.9 g (61%) of intermediate 1-2.

[Synthesis of 1-3]

The above 1-2 40 g, Iodobenzene 57 g, t-BuONa 20.1 g, Pd ₂ (dba) ₃ 5.1 g, (t-Bu) ₃ P 11.3 ml was dissolved in 800 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 13.2 g (26% yield) of Intermediate 1-3.

Synthesis of Intermediate 2-3

[Synthesis of 2-1]

In a round bottom flask, 59.3 g of benzofuran-3-ylboronic acid and 100 g of 4-bromo-1-iodo-2-nitrobenzene were dissolved in 1600 ml of toluene, 450 ml of K ₂ CO ₃ (2M) and 10.5 g of Pd (PPh ₃ ) ₄ After stirring, the mixture was stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 73.7 g (yield 76%) of intermediate 2-1.

[Synthesis of 2-2]

After dissolving 70 g of 1-1 in 350 ml of 1,2-dichlorobenzene, 220 ml of P (OEt) ₃ was added thereto, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 35.2 g (56% yield) of Intermediate 2-2.

[Synthesis of 2-3]

35 g of 2-2, 49 g of Iodobenzene, 17.6 g of t-BuONa, 4.5 g of Pd ₂ (dba) ₃ , and 10 ml of (t-Bu) ₃ P were dissolved in 700 ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 16.6 g of Intermediate 2-3 (yield 33%).

Synthesis of Intermediate 3-3

[Synthesis of 3-1]

In a round bottom flask, 65.1 g of benzo [b] thiophen-3-ylboronic acid and 100 g of 4-bromo-2-iodo-1-nitrobenzene were dissolved in 1600 ml of toluene, 455 ml of K ₂ CO ₃ (2M) and Pd (PPh _{3). 4} ) 10.5 g was added thereto, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 87.6 g (yield 86%) of intermediate 3-1.

[Synthesis of 3-2]

After dissolving 85 g of 3-1 in 430 ml of 1,2-dichlorobenzene, 260 ml of P (OEt) ₃ was added and stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 49.1 g (64% yield) of Intermediate 3-2.

[Synthesis of 3-3]

49 g of 3-2, 66 g of Iodobenzene, 23.3 g of t-BuONa, 5.9 g of Pd ₂ (dba) ₃ , and 13.1 ml of (t-Bu) ₃ P were dissolved in 980 ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 19 g of intermediate 3-3 (yield 31%).

Synthesis of Intermediate 4-3

4-1 Synthesis

In a round bottom flask, 65.1 g of benzo [b] thiophen-3-ylboronic acid and 100 g of 4-bromo-1-iodo-2-nitrobenzene were dissolved in 1600 ml of toluene, 455 ml of K ₂ CO ₃ (2M) and Pd (PPh _{3). 4} ) 10.5 g was added thereto, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 84.5 g (83% yield) of Intermediate 4-1.

[Synthesis of 4-2]

After dissolving 84 g of 4-1 in 420 ml of 1,2-dichlorobenzene, 250 ml of P (OEt) ₃ was added thereto, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 41.7 g of Intermediate 4-2 (yield 55%).

[Synthesis of 4-3]

40 g of 4-2, 54 g of Iodobenzene, 19 g of t-BuONa, 4.8 g of Pd ₂ (dba) ₃ , and 10.7 ml of (t-Bu) ₃ P were dissolved in 800 ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 17.5 g (yield 35%) of intermediate 4-3.

Synthesis of Intermediate 5-2

[Synthesis of 5-1]

Dissolve 78.5 g of benzofuran-3-ylboronic acid and 100 g of 1-iodo-2-nitrobenzene in 1000 ml of toluene in a round bottom flask, add 600 ml of K ₂ CO ₃ (2M) and 13.9 g of Pd (PPh ₃ ) ₄ , and reflux. Stirred. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 78.7 g (yield 82%) of intermediate 5-1.

[Synthesis of 5-2]

78 g of the 5-1 was dissolved in 400 ml of 1,2-dichlorobenzene and 260 ml of P (OEt) ₃ was added thereto, followed by stirring under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 36.4 g of Intermediate 5-2 (yield 54%).

Synthesis of Intermediate 6-2

[Synthesis of 6-1]

In a round bottom flask, 87.7 g of benzo [b] thiophen-3-ylboronic acid and 100 g of 1-iodo-2-nitrobenzene are dissolved in 1000 ml of toluene, 600 ml of K ₂ CO ₃ (2M) and 13.9 g of Pd (PPh ₃ ) ₄ After the addition was stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 82 g of intermediate 6-1 (yield 80%).

[Synthesis of 6-2]

80 g of the 6-1 was dissolved in 400 ml of 1,2-dichlorobenzene, and 310 ml of P (OEt) ₃ was added thereto, followed by stirring under reflux. The organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 39.8 g of Intermediate 6-2 (yield 57%).

Synthesis of Compound 1

Toluene was added 10 g of N-phenylnaphthalen-1-amine, 18.0 g of 1-bromo-4-iodobenzene, 6.5 g of t-BuONa, 1.7 g of Pd ₂ (dba) _{3 and} 2.6 ml of (t-Bu) ₃ P in a round bottom flask. After dissolving in 100 ml and stirred at 50 ℃. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 7.6 g (yield 45%) of intermediate OP1.

6.62 g of OP1 7.5 g bis (pinacolato) diboron, 0.07 g of Pd (dppf) Cl ₂ , and 5.9 g of KOAc were dissolved in 80 ml of toluene, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 6.8 g of intermediate OP2 (yield 81%).

2.0 g of the intermediate 1-3 and 2.8 g of OP2 were dissolved in 40 ml of toluene in a round bottom flask, 8 ml of K ₂ CO ₃ (2M) and 0.2 g of Pd (PPh ₃ ) ₄ were added thereto, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain compound 1 2.3 g (72% yield).

m / z: 576.22 (100.0%), 577.22 (46.2%), 578.23 (10.2%), 579.23 (1.6%)

Synthesis of Compound 2

Using di (naphthalen-1-yl) amine as starting material, N- (naphthalen-1-yl) -N- (4- (4,4,5,5-tetramethyl-) in the same manner as OP1 and OP2 of compound 1 1,3,2-dioxaborolan-2-yl) phenyl) naphthalen-1-amine was synthesized.

Intermediate 1-3 2.0 g N- (naphthalen-1-yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) in a round bottom flask 3.12 g of naphthalen-1-amine was dissolved in 40 ml of toluene, 8 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) ₄ were added thereto, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain compound 2 2.4 g (yield 70%).

m / z: 626.24 (100.0%), 627.24 (50.1%), 628.24 (12.7%), 629.25 (2.0%)

Synthesis of Compound 3

N-([1,1'-biphenyl] -4-yl) naphthalen-1-amine as a starting material and N-([1,1'-biphenyl] -4- in the same manner as in OP1 and OP2 of compound 1 yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) naphthalen-1-amine was synthesized.

Intermediate 1-3 2.0 g N-([1,1'-biphenyl] -4-yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan in a round bottom flask 3.3 g of -2-yl) phenyl) naphthalen-1-amine was dissolved in 40 ml of toluene, 8 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) ₄ were added thereto, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain compound 3 2.6 g (yield 73%).

m / z: 652.25 (100.0%), 653.25 (52.7%), 654.26 (13.6%), 655.26 (2.4%)

Synthesis of Compound 4

Using di ([1,1'-biphenyl] -4-yl) amine as starting material, N-([1,1'-biphenyl] -4-yl) -N- in the same manner as OP1 and OP2 of compound 1 (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,1'-biphenyl] -4-amine was synthesized.

Intermediate 1-3 2.0 g N-([1,1'-biphenyl] -4-yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan in a round bottom flask Dissolve 3.4 g of -2-yl) phenyl)-[1,1'-biphenyl] -4-amine in 40 ml of toluene, add 8.2 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) ₄ , and reflux. Stirred. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain compound 4 2.5 g (69% yield).

m / z: 678.27 (100.0%), 679.27 (54.5%), 680.27 (15.0%), 681.28 (2.5%)

Synthesis of Compound 5

N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine as a starting material and N-([1 , 1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H -fluoren-2-amine was synthesized.

Intermediate 1-3 2.0 g N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1) in a round bottom flask Dissolve 3.7 g of, 3,2-dioxaborolan-2-yl) phenyl) -9H-fluoren-2-amine in 40 ml of toluene, add 8.2 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) _4. It was stirred at reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain compound 5 (2.9 g, yield 73%).

m / z: 718.30 (100.0%), 719.30 (58.5%), 720.31 (16.4%), 721.31 (3.2%)

Synthesis of Compound 6

N-([1,1'-biphenyl] -4-yl) -9,9-diphenyl-9H-fluoren-2-amine as a starting material and N-([1 , 1'-biphenyl] -4-yl) -9,9-diphenyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H -fluoren-2-amined was synthesized.

Intermediate 1-3 2.0 g N-([1,1'-biphenyl] -4-yl) -9,9-diphenyl-N- (4- (4,4,5,5-tetramethyl-1) in a round bottom flask 4.5 g of, 3,2-dioxaborolan-2-yl) phenyl) -9H-fluoren-2-amined was dissolved in 40 ml of toluene, 8.2 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) _4. It was stirred at reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain compound 6 3.0 g (yield 65%).

m / z: 842.33 (100.0%), 843.33 (68.9%), 844.34 (23.2%), 845.34 (5.3%)

Synthesis of Compound 7

Using di ([1,1'-biphenyl] -4-yl) amine and 1-bromo-3-iodobenzene as starting materials, N-([1,1'-biphenyl] -4-yl) -N- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,1'-biphenyl] -4-amine Synthesized.

Intermediate 1-3 2.0 g N-([1,1'-biphenyl] -4-yl) -N- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan in a round bottom flask Dissolve 3.4 g of -2-yl) phenyl)-[1,1'-biphenyl] -4-amine in 40 ml of toluene, add 8.2 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) ₄ , and reflux. Stirred. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 2.1 g (yield 60%) of compound 7.

m / z: 678.27 (100.0%), 679.27 (54.5%), 680.27 (15.0%), 681.28 (2.5%)

Synthesis of Compound 8

N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine and 1-bromo-3-iodobenzene as starting materials, and OP1, OP2 and In the same way, N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) phenyl) -9H-fluoren-2-amine was synthesized.

Intermediate 1-3 2.0 g N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (3- (4,4,5,5-tetramethyl-1) in a round bottom flask Dissolve 3.7 g of 3,2-dioxaborolan-2-yl) phenyl) -9H-fluoren-2-amine in 40 ml of toluene, add 8 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) _4. It was stirred at reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 2.4 g (yield 62%) of compound 8.

m / z: 718.30 (100.0%), 719.30 (58.5%), 720.31 (16.4%), 721.31 (3.2%)

Synthesis of Compound 9

Synthesis was carried out in the same manner as in Compound 4, except that 1-3 was reacted with 3-3.

m / z: 694.24 (100.0%), 695.25 (54.5%), 696.25 (15.0%), 696.24 (4.9%), 697.25 (2.7%), 697.24 (2.5%), 695.24 (1.5%)

Synthesis of Compound 10

Synthesis was carried out in the same manner as in Compound 5, except that 1-3 was reacted with 3-3.

m / z: 734.28 (100.0%), 735.28 (57.8%), 736.28 (17.0%), 736.27 (4.5%), 737.29 (3.0%), 737.27 (2.6%), 735.27 (1.5%)

Synthesis of Compound 11

Except for reacting 1-3 with 3-3, it was synthesized in the same manner as in compound 6.

m / z: 858.31 (100.0%), 859.31 (69.4%), 860.31 (23.9%), 861.32 (5.1%), 860.30 (4.5%), 861.31 (3.5%), 862.31 (1.1%)

Synthesis of Compound 12

Except for reacting 1-3 with 3-3, it was synthesized in the same manner as in compound 7.

m / z: 694.24 (100.0%), 695.25 (54.5%), 696.25 (15.0%), 696.24 (4.9%), 697.25 (2.7%), 697.24 (2.5%), 695.24 (1.5%)

Synthesis of Compound 13

Synthesis was carried out in the same manner as in Compound 8, except that 1-3 was reacted with 3-3.

m / z: 734.28 (100.0%), 735.28 (57.8%), 736.28 (17.0%), 736.27 (4.5%), 737.29 (3.0%), 737.27 (2.6%), 735.27 (1.5%)

Synthesis of Compound 14

Except for reacting 1-3 with 2-3, it was synthesized in the same manner as in compound 5.

m / z: 718.30 (100.0%), 719.30 (58.5%), 720.31 (16.4%), 721.31 (3.2%)

Synthesis of Compound 15

Synthesis was carried out in the same manner as in Compound 8, except that 1-3 was reacted with 2-3.

m / z: 718.30 (100.0%), 719.30 (58.5%), 720.31 (16.4%), 721.31 (3.2%)

Synthesis of Compound 16

Except for reacting 1-3 with 4-3, it was synthesized in the same manner as in compound 5.

m / z: 734.28 (100.0%), 735.28 (57.8%), 736.28 (17.0%), 736.27 (4.5%), 737.29 (3.0%), 737.27 (2.6%), 735.27 (1.5%)

Synthesis of Compound 17

Except for reacting 1-3 with 4-3, it was synthesized in the same manner as in compound 8.

m / z: 734.28 (100.0%), 735.28 (57.8%), 736.28 (17.0%), 736.27 (4.5%), 737.29 (3.0%), 737.27 (2.6%), 735.27 (1.5%)

Synthesis of Compound 18

5-2 with round bottom flask 2 g, 4-bromo-N, N-diphenylaniline 3.7 g, t-BuONa 1.4 g, 0.35 g of Pd ₂ (dba) ₃ , 0.23 ml of (t-Bu) ₃ P were dissolved in 40 ml of toluene and stirred under reflux. . The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 2.47 g (yield 63%) of compound 18.

m / z: 450.17 (100.0%), 451.18 (34.9%), 452.18 (6.1%)

Synthesis of Compound 19

5-2 2 g, 5-bromo-N1, N1, N3, N3-tetraphenylbenzene-1,3-diamine 5.7 g, t-BuONa 1.4 g, Pd ₂ (dba) ₃ 0.35 g, (t- Bu) ₃ P 0.23 ml was dissolved in 40 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain compound 19 (3.8 g, yield 65%).

m / z: 617.25 (100.0%), 618.25 (48.0%), 619.25 (11.8%), 620.26 (1.7%), 618.24 (1.1%)

Synthesis of Compound 20

In a round bottom flask, 5-2 1.5 g, 4-bromo-N, N-diphenylaniline 1.46 g, t-BuONa 1.0 g, Pd ₂ (dba) ₃ 0.3 g, (t-Bu) ₃ P 0.15 ml to 30 ml of toluene It was dissolved in and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 2.61 g (yield 55%) of compound 20.

m / z: 657.24 (100.0%), 658.24 (50.9%), 659.25 (12.7%), 660.25 (2.3%)

Synthesis of Compound 21

5-3 was synthesized in the same manner as in Compound 19, except that 6-2 was reacted.

m / z: 633.22 (100.0%), 634.23 (47.9%), 635.23 (11.6%), 635.22 (5.1%), 636.22 (2.2%), 634.22 (1.9%), 636.23 (1.9%)

Synthesis of Compound 22

5-3 was synthesized in the same manner as in Compound 20, except that 6-2 was reacted.

m / z: 689.20 (100.0%), 690.20 (51.7%), 691.20 (13.5%), 691.19 (9.1%), 692.20 (4.9%), 692.21 (2.0%), 693.20 (1.1%), 690.19 (1.1% )

Synthesis of Compound 23

In a round bottom flask, 5-2 3 g, bromobenzene 2.7 g, t-BuONa 2.1 g, Pd ₂ (dba) ₃ 1.0 g, and (t-Bu) ₃ P 1.4 ml were dissolved in 100 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 2.9 g (71%) of 6-phenyl-6H-benzofuro [2,3-b] indole.

6-phenyl-6H-benzofuro [2,3-b] indole 2.9 g and N-Bromosuccinimide 5.5 g in a round bottom flask were dissolved in 80 ml of MC and stirred at room temperature for 6 hours. The reaction was confirmed by TLC and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column to obtain 2.9 g (yield 65%) of 2,9-dibromo-6-phenyl-6H-benzofuro [2,3-b] indole.

2.9 g of 2,9-dibromo-6-phenyl-6H-benzofuro [2,3-b] indole, 2.4 g of diphenylamine, 0.9 g of t-BuONa, 0.5 g of Pd ₂ (dba) ₃ , (t-Bu) ₃ 1.1 ml of P was dissolved in 100 ml of toluene and stirred at reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA and filtered under reduced pressure to obtain compound 23 (2.8 g, yield 70%).

m / z: 617.25 (100.0%), 618.25 (48.0%), 619.25 (11.8%), 620.26 (1.7%), 618.24 (1.1%)

Synthesis of Compound 24

5-2 was synthesized in the same manner as in Compound 23, except that 6-2 was reacted.

m / z: 633.22 (100.0%), 634.23 (47.9%), 635.23 (11.6%), 635.22 (5.1%), 636.22 (2.2%), 634.22 (1.9%), 636.23 (1.9%)

Synthesis of Compound 25

In a round bottom flask, 1-2 5.0 g, 1-bromo-4-iodobenzene 9.89 g, t-BuONa 2.5 g, Pd ₂ (dba) ₃ 0.6 g and (t-Bu) ₃ P 1.5 ml were dissolved in 100 ml of toluene. After stirring at 80 ℃. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA, filtered under reduced pressure, and purified by column to obtain 2.8 g (yield 37%) of 9-bromo-6- (4-bromophenyl) -6H-benzofuro [2,3-b] indole.

9-bromo-6- (4-bromophenyl) -6H-benzofuro [2,3-b] indole 2.8 g, diphenylamine 3.6 g, t-BuONa 1.5 g, Pd ₂ (dba) ₃ 0.7 g, (t-Bu ) ₃ P 2.0 ml was dissolved in 100 ml of toluene and stirred under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with EA and filtered under reduced pressure to obtain 3.7 g (yield 62%) of compound 25.

m / z: 617.25 (100.0%), 618.25 (48.0%), 619.25 (11.8%), 620.26 (1.7%), 618.24 (1.1%)

Synthesis of Compound 26

Except for reacting 1-2 with 3-2, it was synthesized in the same manner as in compound 25.

m / z: 633.22 (100.0%), 634.23 (47.9%), 635.23 (11.6%), 635.22 (5.1%), 636.22 (2.2%), 634.22 (1.9%), 636.23 (1.9%)

Fabrication of Organic Light Emitting Diode

An organic light emitting device was manufactured according to the structure of FIG. 1. The organic light emitting element is formed from the bottom of the anode (hole injection electrode 11) / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transfer layer 15 / cathode (electron injection electrode 16) It is laminated in order.

The following materials were used for the hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of the following Examples and Comparative Examples.

Example 1

A glass substrate coated with an indium tin oxide (ITO) 1500 Å thick thin film was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes by using an oxygen plasma. Compound 1 600 kPa was formed into a hole injection layer and a hole transport layer by using an evaporator. Next, the light emitting layer was doped with MADN: BD01 5% to form 300 Å. Next, Alq3 300 300 was formed into an electron transport layer, followed by LiF 10 Å and aluminum (Al) 1000 Å, which were encapsulated in a glove box to produce an organic light emitting device.

Examples 2 to 17

An organic light emitting diode was manufactured according to the same method as Example 1, but the organic light emitting diode was manufactured using the compounds 2 to 17 instead of the compound 1 as the hole injection layer and the hole transport layer.

Example 18

A glass substrate coated with an indium tin oxide (ITO) 1500 Å thick thin film was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and then the substrate is cleaned for 5 minutes by using an oxygen plasma. Using a evaporator, 200 을 of 2-TNATA 600 으로 was used as the hole injection layer and the synthesized compound 18 was used as the hole transport layer. Next, the film was doped with 7% of the light emitting layer CBP Ir (ppy) 3 to form 300 Å. Next, TPBi 300 B was formed into an electron transport layer, followed by LiF 10 Å and aluminum (Al) 1000 Å, which were encapsulated in a glove box to produce an organic light emitting device.

Examples 19-26

An organic light emitting diode was manufactured according to the same method as Example 18, but the organic light emitting diode was manufactured using the compounds 19 to 26 instead of the compound 18 as the hole transport layer.

Comparative Example 1

A device was manufactured in the same manner as in Example 1, except that the hole injection layer and the hole transport layer were used as NPB.

Comparative Example 2

A device was fabricated in the same manner as in Example 18, except that the hole transport layer of Example 18 was used as the NPB.

Performance Evaluation of Organic Light Emitting Diode

Inject electrons and holes by applying voltage to a Keithley 2400 source measurement unit and measure the luminance when light is emitted using the Konica Minolta Spectroradiometer (CS-2000) Thus, the performance of the organic light emitting diodes of Examples and Comparative Examples was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Tables 1 and 2.

Table 1 Device composition @ 10mA / cm2 Cd / A CIE xy Half-life Example 1 ITO / HI01 / Compound 1 / MADN: BD01 / Alq3 / LiF / Al 6.12 0.142, 0.137 350 Example 2 ITO / HI01 / Compound 2 / MADN: BD01 / Alq3 / LiF / Al 6.31 0.144, 0.136 380 Example 3 ITO / HI01 / Compound 3 / MADN: BD01 / Alq3 / LiF / Al 6.62 0.142, 0.139 390 Example 4 ITO / HI01 / Compound 4 / MADN: BD01 / Alq3 / LiF / Al 6.71 0.142, 0.137 420 Example 5 ITO / HI01 / Compound 5 / MADN: BD01 / Alq3 / LiF / Al 6.85 0.143, 0.137 450 Example 6 ITO / HI01 / Compound 6 / MADN: BD01 / Alq3 / LiF / Al 6.22 0.141, 0.136 430 Example 7 ITO / HI01 / Compound 7 / MADN: BD01 / Alq3 / LiF / Al 6.15 0.142, 0.138 380 Example 8 ITO / HI01 / Compound 8 / MADN: BD01 / Alq3 / LiF / Al 6.65 0.143, 0.139 400 Example 9 ITO / HI01 / Compound 9 / MADN: BD01 / Alq3 / LiF / Al 6.19 0.142, 0.137 360 Example 10 ITO / HI01 / Compound 10 / MADN: BD01 / Alq3 / LiF / Al 6.16 0.143, 0.138 370 Example 11 ITO / HI01 / Compound 11 / MADN: BD01 / Alq3 / LiF / Al 6.29 0.141, 0.138 380 Example 12 ITO / HI01 / Compound 12 / MADN: BD01 / Alq3 / LiF / Al 6.33 0.142, 0.139 380 Example 13 ITO / HI01 / Compound 13 / MADN: BD01 / Alq3 / LiF / Al 6.07 0.142, 0.140 400 Example 14 ITO / HI01 / Compound 14 / MADN: BD01 / Alq3 / LiF / Al 6.69 0.143, 0.140 410 Example 15 ITO / HI01 / Compound 15 / MADN: BD01 / Alq3 / LiF / Al 6.71 0.142, 0.138 410 Example 16 ITO / HI01 / Compound 16 / MADN: BD01 / Alq3 / LiF / Al 6.63 0.143, 0.139 370 Example 17 ITO / HI01 / Compound 17 / MADN: BD01 / Alq3 / LiF / Al 6.55 0.144, 0.137 350 Comparative Example 1 ITO / HI01 / NPB / MADN: BD01 / Alq3 / LiF / Al 3.75 0.14, 0.13 120

TABLE 2 Device composition @ 1000nit LE (cd / A) EQE (%) PE (lm / w) Example 18 ITO / 2-TNATA / Compound 18 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 43 16.9 15.7 Example 19 ITO / 2-TNATA / Compound 19 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 50 17.7 18.1 Example 20 ITO / 2-TNATA / Compound 20 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 47 18.1 17.5 Example 21 ITO / 2-TNATA / Compound 21 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 47 17.5 17.7 Example 22 ITO / 2-TNATA / Compound 22 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 49 17.6 18.3 Example 23 ITO / 2-TNATA / Compound 23 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 49 18.2 17.6 Example 24 ITO / 2-TNATA / Compound 24 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 47 17.9 18.0 Example 25 ITO / 2-TNATA / Compound 25 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 48 18.0 18.2 Example 26 ITO / 2-TNATA / Compound 26 / CBP: Ir (ppy) 3 / TPBi / LiF / Al 47 17.8 17.8 Comparative Example 2 ITO / 2-TNATA / NPB / CBP: Ir (ppy) 3 / TPBi / LiF / Al 38 16.6 15.2

As shown in Table 1 and Table 2, Examples 1 to 26 of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Example 1 and Comparative Example 2.

The compound of Formula 1 of the present invention includes a structure in which indole and furan are ring closed and an arylamine, which facilitate charge transfer characteristics, and at the same time have a high triplet energy and a high glass transition temperature. It can be usefully used as a hole injection material and / or a hole transport material having excellent hole injection characteristics and hole transfer characteristics suitable for fluorescence and phosphorescent devices of all colors such as white and white.

In addition, when the compound of Formula 1 is used in the hole injection or hole transport layer, an organic light emitting device having low driving voltage, high efficiency, low power consumption, and long life may be manufactured.

Claims (7)

An organic compound represented by the following formula (1): [Formula 1]

Where X is O, S, Se or Te; L ₁ to L ₃ are each independently hydrogen; heavy hydrogen; Tritium;

; Or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, C ₆ -C ₃₀ arylene group, C ₄ -C ₃₀ heteroarylene group or C ₆ -C ₆₀ condensed polycyclic group; n are each independently an integer of 0 to 2, wherein at least one of L ₁ to L ₃ is n is 1 or more

It includes; Ar ₁ and Ar ₂ are each independently hydrogen; heavy hydrogen; Tritium or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group or C ₆ -C ₆₀ condensed polycyclic group, Ar ₁ and Ar ₂ may form a ring. The method of claim 1, An organic compound, characterized in that the compound of Formula 1 is selected from the group consisting of compounds represented by the following formulas 2 to 8: [Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

X is O, S, Se or Te; L ₄ to L ₆ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, C ₆ -C ₃₀ arylene group, C ₄ -C ₃₀ heteroarylene group or C _6- C ₆₀ condensed polycyclic group; n are each independently an integer of 0 to 2, wherein at least one of L ₄ to L ₆ is n is 1 or more; Ar ₁ to Ar ₇ are each independently hydrogen; heavy hydrogen; Tritium or a substituted or unsubstituted C ₆ -C ₆₀ aryl group, C ₄ -C ₆₀ heteroaryl group, or C ₆ -C ₆₀ condensed polycyclic group, and adjacent Ar may form a ring. The method of claim 1, An organic compound, characterized in that the compound of Formula 1 is selected from the group consisting of

An organic light emitting device comprising an anode, a cathode and a compound of claim 1 or a mixture of two or more. The method of claim 4, wherein An organic light emitting device comprising: a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked. The method of claim 5, And the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer each have a thickness of 10 to 1,000 nm. The method of claim 4, wherein An organic light emitting device, characterized in that the hole injection layer or the hole transport layer contains the compound of claim 1.

Images