KR20150124924A - Novel compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to a novel compound and, particularly, to a novel compound having excellent hole and electron transport properties, capable of simultaneously implementing high triplet energy and high Tg, and capable of allowing the organic light emitting device to have low driving voltage, low power consumption, high efficiency and long lifetime when applied to the organic light emitting device; and an organic light emitting device comprising the same.

Description

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

The present invention relates to a novel compound and an organic light emitting device including the same. More particularly, the present invention relates to an organic light emitting device having excellent hole and electron transfer characteristics, high triplet energy and high Tg, Low power consumption, high efficiency and long life.

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 in terms of power consumption and has a wide color reproduction range.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excitation state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism, Can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color depending on the emission color. 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 in such 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 luminance, and long life using a material having excellent characteristics.

In order to solve the above-mentioned problems, the present invention provides an organic electroluminescent device having excellent hole and electron transfer characteristics, high triplet energy and high Tg, And to provide a novel compound which is capable of producing a compound having an amino acid sequence represented by SEQ ID NO:

The present invention also provides an organic electroluminescent device capable of realizing high triplet energy and high Tg and having high hole and electron transfer characteristics, including the novel compound, at the same time, has low driving voltage, low power consumption, high efficiency and long life And an object thereof is to provide a device.

In order to accomplish the above object, the present invention provides a compound represented by the following formula 1:

[Chemical Formula 1]

In this formula,

* Are combined with 1 and 2 respectively,

X is O, S, Se, Te, or NAr, wherein Ar is a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro; Or a deuterium, a halogen, an amino group, a nitrile group, a heteroaryl group of C _{2 -50} which is unsubstituted or substituted with a nitro group,

A is each independently N or CR, wherein each R is independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C _2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C _6-30 aryloxy group _optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C _6-50 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C _2-50 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, an amino group, a nitrile group, a nitro group,

R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C _2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C _6-30 aryloxy group _optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C _6-50 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C _2-50 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a nitrile group and a nitro group, and R ₁ and R ₂ in the dotted line may be connected to each other.

Also, the present invention provides an organic light emitting device including the compound represented by Formula 1.

The compound of the present invention can exhibit excellent hole and electron transfer characteristics, high triplet energy and high Tg when applied to an organic light emitting device, and can have low driving voltage, low power consumption, high efficiency and long life.

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 is characterized by being represented by the following general formula (1).

[Chemical Formula 1]

In this formula,

* Are combined with 1 and 2 respectively,

X is O, S, Se, Te, or NAr, wherein Ar is a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro; Or a C _2-50 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, amino, nitrile, nitro,

A is each independently N or CR, wherein each R is independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C _2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C _6-30 aryloxy group _optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C _6-50 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C _2-50 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, an amino group, a nitrile group, a nitro group,

R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C _2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C _6-30 aryloxy group _optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C _6-50 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C _2-50 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a nitrile group and a nitro group, and R ₁ and R ₂ in the dotted line may be connected to each other.

In the present invention, the compound represented by the formula (1) may be represented by the following formula (2) or (3).

(2)

(3)

Was in the general formula (2) or X 3, A, R ₁ and R ₂ are the same as defined in Formula 1, the broken line R ₁ and R ₂ may be connected to each other.

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

The compound of formula (1) according to the present invention has excellent hole and electron transfer characteristics, can realize high triplet energy and high Tg, has low driving voltage, low power consumption, high efficiency and long life, And excellent device characteristics can be exhibited.

The compounds of the present invention may also be prepared through the reaction schemes represented by the following Reaction Schemes 1 or 2:

[Reaction Scheme 1]

[Reaction Scheme 2]

In the above schemes, X and A are the same as defined in Formula (1), and R is the same as R ₁ and R ₂ in Formula (1).

Also, the present invention provides an organic light emitting device comprising a compound represented by Formula 1 in an organic material layer. Preferably a light emitting material, At this time, the compound of the present invention may be used alone or in combination with a known organic light emitting compound.

In addition, the organic light emitting device of the present invention includes one or more organic layers including the compound represented by Formula 1, and the method of manufacturing the organic light emitting device will now be described.

The organic light emitting device includes an organic layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode One or more can 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 hole injection layer material may be formed on the anode electrode by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB (Langmuir-Blodgett) method, but it is easy to obtain a uniform film quality, It is preferable to form it by a vacuum evaporation method. 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 like. In general, the deposition temperature is 50-500 [ 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 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 star burst type amine derivative TCTA (4,4 ', 4 "-tri (N-carbazolyl) tri (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB ^{), HI-406 (N 1} , N 1 '- ( biphenyl-4,4'-diyl) bis (N ¹ - (naphthalen-1-yl) -N ^4, N ⁴ - benzene-1,4-diphenyl -Diamine) can be used as a hole injection layer material.

Next, a hole transporting layer material may be formed on the hole injecting layer by a method such as vacuum deposition, spin coating, casting, LB, etc. However, It is preferably formed by a vapor deposition method. 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.

In addition, the hole transport layer material is not particularly limited, and may be selected from any conventionally known materials used in the hole transport 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 formed on the hole transporting layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, etc. However, from the viewpoint of obtaining a uniform film quality and difficulty in producing pin holes, As shown in Fig. 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 use the compound represented by the formula (1) of the present invention as a host or a dopant.

When the compound represented by Formula 1 is used as a light emitting host, a phosphorescent or fluorescent dopant may be used together to form a light emitting layer. At this time, the fluorescent dopant to the possible purchase from Idemitsu Co. (Idemitsu Corporation) IDE102 or IDE105, or BD142 (N ^6, N ^12-bis (3,4-dimethylphenyl) -N ^6, N ¹² - D-mesityl chrysene - as may be used to 6,12- diamine), the phosphorescent dopant is a green phosphorescent dopant Ir (ppy) ₃ (tris (2-phenylpyridine) iridium), a blue phosphorescent dopant F2Irpic (iridium (ⅲ) bis [4,6- Pyridino-N, C2 '] picolinate), UDC's red phosphorescent dopant RD61, and the like can be vacuum vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but is preferably doped with 0.01 to 15 parts by weight of the dopant relative to 100 parts by weight of the host. If the content of the dopant is less than 0.01 part by weight, the amount of the dopant is not sufficient and color development is not properly performed. If the amount is more than 15 parts by weight, the efficiency is drastically reduced due to the concentration quenching phenomenon.

When the phosphorescent dopant is used together with the phosphorescent dopant, it is preferable to further laminate the hole blocking material (HBL) by a vacuum evaporation method or a spin coating method in order to prevent the triplet exciton or hole from diffusing into the electron transporting 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 material layer formed according to the present invention can be controlled according to the required degree, preferably 10 to 1,000 nm, and more preferably 20 to 150 nm.

In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.

The organic electroluminescent device of the present invention includes the compound represented by the formula (1), and can exhibit high hole and electron transfer characteristics, high triplet energy and high Tg, low driving voltage, low power consumption, high efficiency and long life I have.

Hereinafter, the structure of a compound according to the present invention will be described, and an organic electroluminescent device using the same will be described.

Synthesis of intermediate A1

[Synthesis of A1-1]

10.0 g of benzofuran-3-ylboronic acid and 15.0 g of 1-bromo-2-nitrobenzene were dissolved in 200 ml of 1,4-dioxane, and 92 ml of K ₂ CO ₃ (2M) and 2.15 g of Pd (PPh ₃ ) ₄ were added to a round bottom flask 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 12.3 g (83% yield) of intermediate A1-1.

[Synthesis of A1-2]

12.2 g of the above intermediate A1-1 was dissolved in 130 ml of 1,2-dichlorobenzene, and then 54 g of PPh ₃ was added and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 6.56 g (yield: 62%) of Intermediate A1-2.

[Synthesis of A1-3]

After dissolving 6.5 g of the intermediate A1-2, 11.7 g of methyl 4-bromo-2-iodobenzoate, 4.5 g of t-BuONa, 1.2 g of Pd ₂ (dba) _{3 and} 1.5 ml of (t-Bu) ₃ P in 150 ml of toluene And the mixture was refluxed and stirred. After the completion of the reaction was confirmed by TLC, the organic layer was extracted with MC, filtered under reduced pressure and purified by column to obtain 8.83 g (yield 67%) of Intermediate A1-3.

[Synthesis of A1-4]

8.8 g of the intermediate A1-3 was dissolved in 150 ml of THF, and then the temperature was lowered to 0 占 폚. 21 ml of CH ₃ MgBr was added slowly, and the mixture was stirred at room temperature for 2 hours and then refluxed. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 5.7 g (yield 65%) of Intermediate A1-4.

[Synthesis of A1-5]

60 ml of acetic acid and 0.5 ml of hydrochloric acid were added to 5.7 g of the intermediate A1-4, and the mixture was refluxed for 15 hours and then cooled to room temperature. The precipitated solid was filtered and then the column was refined to obtain 20.3 g (yield: 65%) of Intermediate A1-5.

m / z: 401.04 (100.0%), 403.04 (97.4%), 402.04 (25.2%), 404.04 (24.6%), 403.05 (3.2%

[Synthesis of A1]

3.9 g of Intermediate A1-5, 3.0 g of bis (pinacolato) diboron, 0.03 g of Pd (dppf) Cl ₂ and 2.73 g of KOAc were dissolved in 60 ml of toluene, and the mixture was refluxed for 12 hours. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 3.17 g (yield 76%) of Intermediate A1-4.

m / z: 449.22 (100.0%), 450.22 (29.6%), 448.22 (23.0%), 451.22 (5.1%), 450.23

Synthesis of intermediate A2

Intermediate A2 was synthesized in the same manner as Intermediate A1 except that methyl 5-bromo-2-iodobenzoate was used instead of methyl 4-bromo-2-iodobenzoate.

m / z: 449.22 (100.0%), 450.22 (29.6%), 448.22 (23.0%), 451.22 (5.1%), 450.23

Synthesis of intermediate A3

Intermediate A3 was synthesized by the same procedure as Intermediate A1, except that methyl 2-iodobenzoate was used instead of methyl 4-bromo-2-iodobenzoate as 2,4-dibromo-1-nitrobenzene instead of 1-bromo-2-nitrobenzene.

m / z: 449.22 (100.0%), 450.22 (29.6%), 448.22 (23.0%), 451.22 (5.1%), 450.23

The following intermediate B1 to intermediate D3 were synthesized in the same manner as A1, A2 and A3.

Synthesis of Compound 1

2.0 g of intermediate A1 and 1.43 g of 2-chloro-4,6-diphenyl-1,3,5-triazine were dissolved in 30 ml of 1,4-dioxane, and 6.6 ml of K ₂ CO ₃ (2M) PPh ₃ ) _{4 (} 0.15 g) were added, 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 1.43 g (yield: 58%) of Compound 1.

m / z: 554.21 (100.0%), 555.21 (42.6%), 556.22 (8.4%), 557.22

Synthesis of Compound 2

Compound 2 was synthesized in the same manner as Compound 1, except that 4-chloro-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

m / z: 553.22 (100.0%), 554.22 (42.5%), 555.22 (9.4%), 556.23 (1.2%

Synthesis of Compound 3

Compound 3 was synthesized in the same manner as Compound 1, except that 2-chloro-4,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

m / z: 553.22 (100.0%), 554.22 (42.5%), 555.22 (9.4%), 556.23 (1.2%

Synthesis of Compound 4

Compound 4 was synthesized in the same manner as Compound 1, except that 4-chloro-2,6-diphenylpyridine was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine.

m / z: 552.22 (100.0%), 553.22 (44.0%), 554.23 (9.3%), 555.23

Synthesis of Compound 5

Compound 5 was synthesized in the same manner as Compound 1 except that Intermediate Al was reacted with Intermediate A2.

m / z: 554.21 (100.0%), 555.21 (42.6%), 556.22 (8.4%), 557.22

Synthesis of Compound 6

Compound 6 was synthesized in the same manner as Compound 1 except that Intermediate Al was reacted with Intermediate A3.

m / z: 554.21 (100.0%), 555.21 (42.6%), 556.22 (8.4%), 557.22

Synthesis of Compound 7

Compound 7 was synthesized in the same manner as Compound 1 except that Intermediate Al was reacted with Intermediate B1.

m / z: 570.19 (100.0%), 571.19 (42.2%), 572.19 (9.2%), 572.18 (4.5%), 573.19 (2.1%), 571.18

Synthesis of Compound 8

Compound 8 was synthesized in the same manner as Compound 1 except that Intermediate Al was reacted with Intermediate B3.

m / z: 570.19 (100.0%), 571.19 (42.2%), 572.19 (9.2%), 572.18 (4.5%), 573.19 (2.1%), 571.18

Synthesis of Compound 9

Compound 9 was synthesized in the same manner as Compound 1 except that Intermediate Al was reacted with Intermediate C1.

m / z: 554.21 (100.0%), 555.21 (42.6%), 556.22 (8.4%), 557.22

Compound 10  synthesis

Compound 10 was synthesized in the same manner as Compound 1 except that Intermediate Al was reacted with Intermediate C3.

m / z: 554.21 (100.0%), 555.21 (42.6%), 556.22 (8.4%), 557.22

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 Examples and Comparative Examples.

Manufacture of organic light emitting device

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 washed 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 hole injection layer HT01 600 Å and a hole transport layer NPB 250 Å. Next, the light emitting layer was doped with 10% Ir (ppy) ₃ as a compound 1 to form a 250 Å layer. Next, an ET01: Liq (1: 1) 300 Å film 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 a green organic light emitting device .

Examples 2 to 10

A green organic light emitting device was fabricated in the same manner as in Example 1 by using Compound 2 to 10 as the light emitting layer host respectively.

Comparative Example 1

A green organic light emitting device was fabricated in the same manner as in Example 1 except that CBP was used instead of Compound 1 as the light emitting layer host.

Comparative Example 2

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1 was used instead of Compound 1 as the light emitting layer host.

Comparative Example 3

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 2 was used instead of Compound 1 as the light emitting layer host.

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 devices 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 Table 1.

Op. V QE (%) Cd / A lm / w CIEx CIEy life span@
5000nit Example 1 5.88 17.33 45.98 19.81 0.301 0.621 95 Example 2 5.94 17.10 47.13 21.03 0.299 0.619 90 Example 3 6.00 16.98 50.20 20.04 0.298 0.620 87 Example 4 6.10 17.54 47.22 19.98 0.300 0.623 80 Example 5 6.00 16.85 48.39 21.23 0.298 0.614 92 Example 6 5.99 17.26 46.83 18.72 0.298 0.609 90 Example 7 5.95 17.01 49.17 22.46 0.297 0.618 72 Example 8 5.92 17.07 45.55 21.98 0.302 0.609 73 Example 9 5.97 16.93 43.62 20.76 0.300 0.620 85 Example 10 5.95 17.36 47.45 18.99 0.299 0.622 85 Comparative Example 1 7.02 12.43 22.12 10.72 0.301 0.623 25 Comparative Example 2 6.52 14.56 35.98 15.60 0.300 0.613 42 Comparative Example 3 7.74 6.12 8.31 7.76 0.667 0.333 -

As shown in Table 1, Example 1-10 of the present invention shows excellent physical properties in all aspects when used as a light emitting layer host of a green organic light emitting device as compared with Comparative Example 1-3.

Claims (6)

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

In this formula,
* Are combined with 1 and 2 respectively,
X is O, S, Se, Te, or NAr, wherein Ar is a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro; Or a C _2-50 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, amino, nitrile, nitro,
A is each independently N or CR, wherein each R is independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C _2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C _6-30 aryloxy group _optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C _6-50 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C _2-50 heteroaryl group which is unsubstituted or substituted by deuterium, halogen, an amino group, a nitrile group, a nitro group,
R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C _2-30 alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _2-30 alkynyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C _1-30 alkoxy group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group, a nitro group; A C _6-30 aryloxy group _optionally substituted by deuterium, halogen, an amino group, a nitrile group, or a nitro group; A C _6-50 aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a C _2-50 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of a hydrogen atom, a halogen atom, an amino group, a nitrile group and a nitro group, and R ₁ and R ₂ in the dotted line may be connected to each other. The method according to claim 1,
A compound represented by one of the following formulas (2) or (3):
(2)

(3)

In Formula 2 or 3, X, A, R ₁ and R ₂ are as defined in Formula (1). The method according to claim 1,
A compound represented by any one of the following formulas:

A process for producing a compound represented by the following formula (1) or (2):
[Reaction Scheme 1]

[Reaction Scheme 2]

In the above schemes, X and A are the same as defined in Formula (1), and R is the same as R ₁ and R ₂ in Formula (1). An organic light emitting device comprising at least one layer of an organic material containing an anode, a cathode, and a compound according to claim 1 between two electrodes. 6. The method of claim 5,
Wherein the organic material layer contains the compound of claim 1 as a light emitting host or a dopant.

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