KR20140086880A - Novel organic compound and organic electroluminescent device comprising 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 electroluminescent device comprising the same. The organic compound of the present invention has simple charge transfer properties and has high triplet energy and high glass transition temperatures, and thus can provide low driving voltage, high efficiency, low power consumption and long lifespan for an organic electroluminescent device by being used as a hole injection material or a hole transport material.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel organic compound and an organic light emitting device including the organic compound. [0002]

TECHNICAL FIELD The present invention relates to a novel organic compound, more specifically, a novel organic compound having a high charge transporting property, a high triplet energy and a high glass transition temperature, and an organic light emitting device containing the same.

In recent years, an organic light emitting device capable of being driven by a low voltage in a self-luminous mode has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, It has been attracting attention as a next generation display device because it is advantageous from the viewpoint of power consumption and has a wide color reproduction range.

Generally, an organic light emitting device has a structure including a cathode (electron injection electrode), 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) and an electron injection layer, and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) on the light emitting property 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 recombine in the light emitting layer through the hole transporting layer and the electron transporting layer, respectively, ). The formed luminescent excitons emit light while transitioning to ground states. In order to increase efficiency and stability of a light emitting state, a luminescent material may be doped in a light emitting layer (host).

The luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the emission wavelength. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

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

Various compounds have been known as materials used for hole injection and hole transporting layers of organic light emitting devices. However, organic light emitting devices using known materials have been difficult to put to practical use due to high driving voltage, low efficiency, and short lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high brightness, and long life using a material having excellent hole transporting properties.

In order to solve the above problems, the present invention provides an organic compound having excellent charge transfer characteristics, high triplet energy and a high glass transition temperature (Tg) And an organic electroluminescent device.

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

[Chemical Formula 1]

In this formula,

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 each independently represent hydrogen; heavy hydrogen; Tritium;

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

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

;

Ar ₁ and Ar ₂ are each independently hydrogen; heavy hydrogen; 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 Ar ₁ and Ar ₂ may form a ring.

Also, the present invention provides an organic light emitting device comprising the compound represented by Formula 1 in a hole injection or hole transport layer.

The compound of formula (I) of the present invention has a structure in which indole and furan are ring-closed and an arylamine to facilitate charge transfer characteristics, and simultaneously has high triplet energy and a high glass transition temperature, , White, and the like, and a hole injecting material and / or a hole transporting material that are excellent in hole injection property and hole transporting property suitable for the fluorescent and phosphorescent device of all colors.

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

1 schematically shows a cross section of an OLED according to an embodiment of the present invention.
The sign
10: substrate
11: anode
12: Hole injection layer
13: hole transport layer
14:
15: electron transport layer
16: cathode

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

[Chemical Formula 1]

In this formula,

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 each independently represent hydrogen; heavy hydrogen; Tritium;

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

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

;

Ar ₁ and Ar ₂ are each independently hydrogen; Small and medium water; 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 Ar ₁ and Ar ₂ may form a ring.

The substituent may be a substituent selected from the group consisting of deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₁ to C ₄₀ alkoxy group, a C ₃ to C ₄₀ cycloalkyl group , A C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₃ to C ₄₀ heteroaryl group.

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

In addition, the arylamine 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:

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

X is O, S, Se or Te;

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

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

Ar ₁ to Ar ₇ each independently represent hydrogen; heavy hydrogen; 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 Ar atoms may form ring rings with each other.

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

The compound of the present invention has ring-closing indole for easy charge transfer and ring-closing furan having high triplet energy and is easy to transfer charge property by containing arylamine which is easy to transfer charge, and at the same time, has high triplet energy and high glass transition temperature Lt; / RTI >

The compound of formula (I) according to the present invention can be prepared based on the Suzuki-coupling reaction widely known in the carbon-carbon coupling reaction between an aromatic boron compound and an aromatic halogen compound. For example, the compounds of formulas (2a), (2b), (3a), (3b) and (4a) of the present invention can be prepared as shown in the following Schemes 1 to 5, respectively.

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

[Reaction Scheme 4]

[Reaction Scheme 5]

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

n is an integer from 0 to 2;

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

In addition, the present invention provides an organic light emitting device comprising the compound represented by Formula 1 or a mixture thereof as a hole injecting or hole transporting material.

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

The organic light emitting device includes an organic thin film layer (HIL) such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode May be included.

First, an anode electrode material having a high work function is deposited on the substrate to form an anode. At this time, the substrate can be a substrate used in conventional organic light emitting devices, and it is particularly preferable to use a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. The anode electrode material can be deposited by a conventional anode formation method, and specifically, it can be deposited by a deposition method or a sputtering method.

Next, a compound represented by Formula 1 or a known hole injection layer material may be formed on the anode electrode by a method such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) It is preferable to form it by vacuum evaporation from the viewpoint that a uniform film quality is easily obtained and pin hole is hardly generated. 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 the thermal characteristics of the desired hole injection layer, and the like. Generally, the deposition temperature is 50 to 500 DEG C, A vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness range of 10 Å to 5 탆.

The known hole injection layer material is not particularly limited and may be a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a starburst amine derivative such as TCTA (4,4 ', 4 "-tri (N-carbazolyl ) Triphenylamine), m-MTDATA (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB (4,4' ^{benzene), HI-406 (N 1} , N 1 '- ( biphenyl-4,4'-diyl) bis (N ¹ - (naphthalen-1-yl) -N ^4, N ⁴ - diphenyl benzene -1 , 4-diamine) can be used as a hole injection layer material.

Next, a compound represented by Formula 1 or a known hole transporting layer material may be formed on the hole injection layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, etc. However, , And it is preferable to form it by the vacuum evaporation method in that pin holes are hardly generated. When the hole transporting layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer.

Further, the known hole transporting layer material is not particularly limited, and can be arbitrarily selected from commonly known materials used in the hole transporting layer. Specifically, the hole transport layer material may be a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a carbazole derivative such as N, N'-bis (3-methylphenyl) -N, N'- Phenyl) -4,4'-diamine (TPD), and N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine Derivatives and the like can be used.

Thereafter, the light emitting layer material may be applied on the hole transporting layer by a vapor deposition method or a solution process. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The light emitting layer material may be a known light emitting layer material, and phosphorescent or fluorescent dopant may be used together to form the light emitting layer. At this time, the fluorescent dopant is Idemitsu Co. (Idemitsu Co.), available IDE102 or IDE105, or from BD142 (N ^6, N ^12-bis (3,4-dimethylphenyl) -N ^6, N ¹² - D-mesityl chrysene - can be used to 6,12- diamine), the phosphorescent dopant is a green phosphorescent dopant Ir (ppy) ₃ (tris (2-phenylpyridine) iridium), and the blue phosphorescent dopant F2Irpic (iridium (ⅲ) bis [4,6 -Difluorophenyl) -pyridinate-N, C2 '] picolinate), UDC's red phosphorescent dopant RD61 and the like can be vacuum vacuum deposited (doped).

When the phosphorescent dopant is used together with the phosphorescent dopant, it is preferable to further laminate the hole blocking material (HBL) by vacuum evaporation or spin coating in order to prevent the triplet excitons or holes from diffusing into the electron transport layer . The hole blocking material that can be used at this time is not particularly limited, but any known hole blocking material may be used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open Publication No. 11-329734 (A1) can be exemplified. Typically, Balq (bis Phenanthrolines based compounds such as UDC company BCP (bassocouroin), and the like can be used.

An electron transport layer is formed on the light emitting layer formed as described above. 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 layer material serves to stably transport electrons injected from the electron injection electrode. The material is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq ₃ ), Or ET4 (6,6 '- (3,4-dimemethyl-1,1-dimethyl-1H-silanol-2,5-diyl) di-2,2'-bipyridine). In addition, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transport layer. Examples of the electron injection layer material include LiF, NaCl, CsF, Li ₂ O, BaO Can be used.

The deposition conditions of the electron transporting layer depend on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer.

Thereafter, an electron injection layer material may be formed on the electron transport layer, and the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like, .

Finally, a metal for forming a cathode is formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like, and used as a cathode. As the metal for cathode formation, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof can be used. Specific examples thereof include Li, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic light emitting device of the present invention can have an organic light emitting device having various structures as well as an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode structure, Layer or an intermediate layer of two layers may be further formed.

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

In the present invention, since the thickness of the organic thin film layer can be controlled on a molecular basis, the organic thin film layer containing the compound represented by the formula (1) has uniform surface and excellent shape stability.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.

Synthesis of intermediate 1-3

[Synthesis of 1-1]

To a round bottom flask was added benzofuran-3-ylboronic acid 59.3 g , 4-bromo-2-iodo-1-nitrobenzene 100 g was dissolved in toluene, _{1600 ml K 2 CO 3 (2M} ) 450 ml , and Pd (PPh _{3) 4} 10.5 g And the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 82.5 g (yield: 85%) of Intermediate 1-1.

[Synthesis of 1-2]

The above 1-180 g was dissolved in 400 ml of 1,2-dichlorobenzene, 260 ml of P (OEt) ₃ was added, 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 (yield: 61%) of Intermediate 1-2.

[Synthesis of 1-3]

After dissolving 40 g of the above, 57 g of Iodobenzene, 20.1 g of t-BuONa, 5.1 g of Pd ₂ (dba) _{3 and} 11.3 ml of t-Bu ₃ P in 800 ml of toluene, the mixture was refluxed and stirred. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 13.2 g (yield: 26%) of Intermediate 1-3.

Synthesis of intermediate 2-3

[Synthesis of 2-1]

To a round bottom flask was added benzofuran-3-ylboronic acid 59.3 g , 4-bromo-1-iodo-2-nitrobenzene 100 g was dissolved in toluene, _{1600 ml K 2 CO 3 (2M} ) 450 ml , and Pd (PPh _{3) 4} 10.5 g And the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. 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]

The above 1-170 g was dissolved in 350 ml of 1,2-dichlorobenzene, 220 ml of P (OEt) ₃ was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 35.2 g (yield: 56%) 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, After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 16.6 g (yield 33%) of Intermediate 2-3.

Synthesis of intermediate 3-3

[Synthesis of 3-1]

To a round bottom flask was added benzo [b] thiophen-3- ylboronic acid 65.1 g, 4-bromo-2-iodo-1-nitrobenzene 100 g was dissolved in toluene, _{1600 ml K 2 CO 3 (2M} ) 455 ml , and Pd (PPh ₃ ) _{4 (} 10.5 g) were added thereto, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 87.6 g (yield: 86%) of Intermediate 3-1.

[Synthesis of 3-2]

85 g of the above 3-1 was dissolved in 430 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 then subjected to column purification to obtain 49.1 g (yield: 64%) of Intermediate 3-2.

[Synthesis of 3-3]

49 g of the above 3-2, 69 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 and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 19 g (yield: 31%) of Intermediate 3-3.

Synthesis of intermediate 4-3

[Synthesis of 4-1]

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

[Synthesis of 4-2]

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

[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, After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 17.5 g (yield: 35%) of intermediate 4-3.

Synthesis of Intermediate 5-2

[Synthesis of 5-1]

Reflux, insert the benzofuran-3-ylboronic acid 78.5 g , 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, _{1000 ml K 2 CO 3 (2M} ) 600 ml , and Pd (PPh _{3) 4} 13.9 g round bottom flask Lt; / RTI > After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 78.7 g (yield 82%) of Intermediate 5-1.

[Synthesis of 5-2]

78 g of the above 5-1 was dissolved in 400 ml of 1,2-dichlorobenzene, 260 ml of P (OEt) ₃ was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 36.4 g (yield: 54%) of Intermediate 5-2.

Synthesis of Intermediate 6-2

[Synthesis of 6-1]

To a round bottom flask was added benzo [b] thiophen-3- ylboronic acid 87.7 g, 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, _{1000 ml K 2 CO 3 (2M} ) 600 ml , and Pd (PPh _{3) 4} 13.9 g And the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 82 g (yield: 80%) of Intermediate 6-1.

[Synthesis of 6-2]

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

Synthesis of Compound 1

The N-phenylnaphthalen-1-amine 10 g, 1-bromo-4-iodobenzene 18.0 g, t-BuONa 6.5 g, Pd 2 (dba) 3 1.7 g, (t-Bu) 3 P 2.6 ml round bottom flask, toluene And the mixture was stirred at 50 ° C. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification 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, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 6.8 g (81% yield) of intermediate OP2.

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

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

Synthesis of Compound 2

(naphthalen-1-yl) -N- (4- (4,4,5,5-tetramethyl-1-yl) amine as a starting material, 1,3,2-dioxaborolan-2-yl) phenyl) naphthalen-1-amine.

To a round bottom flask was added 2.0 g of N- (naphthalen-1-yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- naphthalen-1-amine (3.12 g) was dissolved in toluene (40 ml), and 8 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) ₄ were added and stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 2.4 g (yield 70%) of Compound 2.

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

Synthesis of Compound 3

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

To a round bottom flask was added 2.0 g of the intermediate 1-3 2.0 g of N - ([1,1'-biphenyl] -4-yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl) phenyl) naphthalen-1-amine was dissolved in 40 ml of toluene, and 8 ml of K ₂ CO ₃ (2M) and 0.19 g of Pd (PPh ₃ ) ₄ were added and stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and then subjected to column purification to obtain 2.6 g (yield: 73%) of Compound 3.

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

Synthesis of Compound 4

([1,1'-biphenyl] -4-yl) -N- (1,1'-biphenyl-4-yl) amine as starting materials, (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) - [1,1'-biphenyl] -4-amine.

To a round bottom flask was added 2.0 g of the intermediate 1-3 2.0 g of N - ([1,1'-biphenyl] -4-yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl) phenyl) - [ 1,1'-biphenyl] -4-amine 3.4 g was dissolved in toluene _{40 ml K 2 CO 3 (2M} ) 8.2 ml and Pd (PPh _{3) 4} the reflux was placed 0.19 g Lt; / RTI > After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 2.5 g (yield 69%) of Compound 4.

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

Synthesis of Compound 5

N - ([1, 1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluorene- -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) phenyl) -9H -fluoren-2-amine.

To a round-bottomed flask was added 2.0 g of the intermediate 1-3 to a solution of 2.0 g of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl- N- (4- (4,4,5,5-tetramethyl- , 3,2-dioxaborolan-2-yl ) phenyl) -9H-fluoren-2-amine 3.7 g was dissolved in toluene _{40 ml K 2 CO 3 (2M} ) 8.2 ml and Pd (PPh _{3) 4} was placed 0.19 g of And the mixture was refluxed and stirred. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and then subjected to column purification to obtain 2.9 g (yield 73%) of Compound 5.

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

Synthesis of Compound 6

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

To a round-bottomed flask was added 2.0 g of the intermediate 1-3 2-3 g of N - ([1,1'-biphenyl] -4-yl) -9,9-diphenyl-N- (4- (4,4,5,5-tetramethyl- , 3,2-dioxaborolan-2-yl ) phenyl) -9H-fluoren-2-amined 4.5 g was dissolved in toluene _{40 ml K 2 CO 3 (2M} ) 8.2 ml and Pd (PPh _{3) 4} was placed 0.19 g of And the mixture was refluxed and stirred. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 3.0 g (yield 65%) of Compound 6.

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

Synthesis of Compound 7

([1,1'-biphenyl] -4-yl) amine and 1-bromo-3-iodobenzene were prepared in the same manner as OP1 and OP2 of Compound 1, -4-yl) -N- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) phenyl) - [1,1'-biphenyl] Were synthesized.

To a round bottom flask was added 2.0 g of the intermediate 1-3. 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 3.4 g was dissolved in toluene _{40 ml K 2 CO 3 (2M} ) 8.2 ml and Pd (PPh _{3) 4} the reflux was placed 0.19 g Lt; / RTI > After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 2.1 g of Compound 7 (yield: 60%).

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

Synthesis of Compound 8

OP1 and OP2 of Compound 1 were synthesized from the starting materials of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- In the same manner, 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.

To a round-bottomed flask was added 2.0 g of the intermediate 1-3. N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl- N- 3- (4,4,5,5-tetramethyl- , 3,2-dioxaborolan-2-yl ) phenyl) -9H-fluoren-2-amine 3.7 g after the insert the _{K 2 CO 3 (2M) 8} ml , and Pd (PPh _{3) 4} 0.19 g dissolved in 40 ml of toluene And the mixture was refluxed and stirred. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and then subjected to column purification 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

Synthesis of Compound 9

1-3 was synthesized by the same method as Compound 4, except that 3-3 was used.

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

Synthesis of Compound 10

Synthesis was conducted 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

Synthesis of Compound 11

1-3 was synthesized by the same method as Compound 6 except that the compound was reacted with 3-3.

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

Synthesis of Compound 12

1-3 was synthesized by the same method as Compound 7 except that the compound 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

Synthesis of Compound 13

3 was synthesized by the same method as Compound 8 except that 3-3 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

Synthesis of Compound 14

1-3 was changed to 2-3.

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

Synthesis of Compound (15)

Synthesis was conducted in the same manner as in Compound 8, except that 1-3 was reacted at 2-3.

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

Synthesis of Compound 16

Synthesis was conducted in the same manner as in Compound 5 except that 1-3 was reacted with 4-3.

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

Synthesis of Compound 17

Synthesis was conducted in the same manner as in Compound 8 except that 1-3 was reacted with 4-3.

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

Synthesis of compound 18

5-2 in a round bottom flask 2 g, 4-bromo-N , N-diphenylaniline 3.7 g, t-BuONa1.4 g, Pd 2 (dba) 3 0.35 g, (t-Bu) 3 P were dissolved in 0.23 ml toluene 40 ml and stirred under reflux . After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification 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

To a round bottom flask was added 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) were dissolved in 40 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain 3.8 g (yield: 65%) of Compound 19.

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

Synthesis of Compound 20

To a round bottom flask was added 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) 30 ml of toluene for ₃ P 0.15 ml And the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification 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

Synthesis was conducted in the same manner as in Compound 19 except that 5-3 was reacted with 6-2.

m / z 633.22 (100.0%) 634.23 47.9% 635.23 11.6% 635.22 5.16 636.22 634.22 1.9% 636.23 1.9%

Synthesis of Compound 22

Synthesis was conducted in the same manner as in Compound 20 except that 5-3 was reacted with 6-2.

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

Synthesis of Compound 23

Into a round bottom flask, 5-2 3 g of bromobenzene, 2.7 g of t-BuONa, 1.0 g of Pd ₂ (dba) _{3 and} 1.4 ml of (t-Bu) ₃ P were dissolved in 100 ml of toluene and refluxed. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 2.9 g (yield: 71%) of 6-phenyl-6H-benzofuro [2,3- b] indole.

2.9 g of 6-phenyl-6H-benzofuro [2,3-b] indole and 5.5 g of N-Bromosuccinimide were dissolved in 80 ml of MC and then the mixture was 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 then subjected to column purification to obtain 2.9 g (yield 65%) of 2,9-dibromo-6-phenyl-6H-benzofuro [2,3- b] indole.

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

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

Synthesis of Compound 24

Compound 5-2 was synthesized by the same method as Compound 23 except that the compound was reacted with 6-2.

m / z 633.22 (100.0%) 634.23 47.9% 635.23 11.6% 635.22 5.16 636.22 634.22 1.9% 636.23 1.9%

Synthesis of Compound 25

1-2.5 g of 1-bromo-4-iodobenzene, 2.5 g of t-BuONa, 0.6 g of Pd ₂ (dba) _{3 and} 1.5 ml of (t-Bu) ₃ P were dissolved in 100 ml of toluene in a round bottom flask Followed by stirring at 80 ° C. After confirming the reaction by TLC, water was added and the reaction was terminated. 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.

The 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) were dissolved in 100 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. 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

Synthesis of Compound 26

1-2 was synthesized by the same method as Compound 25, except that 3-2 was used.

m / z 633.22 (100.0%) 634.23 47.9% 635.23 11.6% 635.22 5.16 636.22 634.22 1.9% 636.23 1.9%

Manufacture of organic light emitting device

An organic light emitting device was prepared according to the structure shown in FIG. The organic light emitting device includes an anode (hole injecting electrode 11) / a hole injecting layer 12 / a hole transporting layer 13 / a light emitting layer 14 / an electron transporting layer 15 / a cathode (electron injecting electrode 16) Respectively.

The following materials were used for the hole injecting layer 12, the hole transporting layer 13, the light emitting layer 14 and the electron transporting layer 15 in the following examples and comparative examples.

2-TNATA NPB MADN BD01

CBP Ir (ppy) 3 Alq3 TPBi

Example 1

The glass substrate coated with thin film of indium tin oxide (ITO) 1500 Å in thickness was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator) to form a compound 1 600 Å into the hole injecting layer and the hole transporting layer. Next, the light emitting layer was doped with 5% MADN: BD01 to form a 300 Å layer. Next, an Alq3 film was formed to a thickness of 300 angstroms as an electron transporting layer, and LiF 10 angstroms and aluminum (Al) 1000 angstroms were formed, and the device was encapsulated in a glove box to produce an organic light emitting device.

Examples 2 to 17

An organic light emitting device was prepared in the same manner as in Example 1 except that the hole injecting layer and the hole transporting layer were respectively substituted with Compound 2 to 17 instead of Compound 1.

Example 18

The glass substrate coated with thin film of indium tin oxide (ITO) 1500 Å in thickness was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator), 2-TNATA 600 Å as a hole injection layer, and 200 Å as a hole transporting layer. Next, the light emitting layer CBP Ir (ppy) 3 was doped with 7% to form a 300 Å film. Next, TPBi 300 Å was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were formed, and the device was encapsulated in a glove box to produce an organic light emitting device.

Examples 19 to 26

An organic light emitting device was prepared in the same manner as in Example 18, except that compounds 19 to 26 were used instead of compound 18 in the hole transport layer.

Comparative Example 1

A device was fabricated 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

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

Evaluation of performance of organic light emitting device

A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light emitting device of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Tables 1 and 2.

Device configuration @ 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

Device configuration @ 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 Tables 1 and 2, Examples 1 to 26 of the present invention are superior to Comparative Examples 1 and 2 in physical properties in all respects.

Claims (7)

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

In this formula,
X is O, S, Se or Te;
L ₁ to L ₃ each independently represent hydrogen; heavy hydrogen; Tritium;

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

;
Ar ₁ and Ar ₂ are each independently hydrogen; heavy hydrogen; 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 Ar ₁ and Ar ₂ may form a ring. The method according to claim 1,
Wherein the compound of Formula 1 is selected from the group consisting of compounds represented by the following Chemical Formulas 2 to 8:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

X is O, S, Se or Te;
L ₄ to L ₆ each independently represent a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a C ₄ -C ₆₀ heteroaryl group, a C ₆ -C ₃₀ arylene group, a C ₄ -C ₃₀ heteroarylene group or C ₆ -C ₆₀ condensed polycyclic group, and;
n is independently an integer of 0 to 2, provided that at least one of L ₄ to L ₆ is n is 1 or more;
Ar ₁ to Ar ₇ each independently represent hydrogen; heavy hydrogen; 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 Ar atoms may form a ring. The method according to claim 1,
Wherein 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, between two electrodes. 5. The method of claim 4,
Wherein the anode, the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron injecting layer, and the cathode are sequentially stacked. 6. The method of claim 5,
Wherein the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer each have a thickness of 10 to 1,000 nm. 5. The method of claim 4,
Wherein the hole-injecting layer or the hole-transporting layer contains the compound according to claim 1.

Images