WO2015174792A1 - Novel compound and organic light-emitting element comprising same - Google Patents

Abstract

The novel compound according to the present invention has an HOMO energy level that facilitates hole injection, has a high LUMO energy level that enables the blocking of electrons, has excellent hole transportation properties, and, when applied to the hole injection layer, hole transportation layer or hole transportation auxiliary layer of an organic light-emitting element, can impart stability and extended lifespan due to having excellent low voltage, high efficiency and high Tg.

Description

Novel compound and organic light emitting device comprising the same

The present invention relates to a novel compound and an organic light emitting device comprising the same, and more particularly to a compound useful as a hole injection, a hole transport material, or a hole transport auxiliary material.

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.

The material used as the organic material layer in the organic light emitting device may be largely classified into light emitting materials, hole injection materials, hole transport materials, hole transport auxiliary materials, electron transport materials, electron injection materials and the like according to functions.

Until now, a lot of amine derivatives having a carbazole skeleton have been studied for the hole injection hole transport material used in the organic light emitting device, but there are many difficulties in practical use due to the higher driving voltage, lower efficiency, and shorter lifetime. Therefore, efforts have been made to develop organic light emitting diodes having low voltage driving, high brightness and long life using materials having excellent characteristics.

In order to solve the above problems, the present invention has a HOMO energy level easy hole injection, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, hole injection layer of the organic light emitting device, It is an object of the present invention to provide a novel compound capable of having excellent low voltage, high efficiency, high Tg stability and long life when applied to a hole transport layer or a hole transport auxiliary layer.

It is another object of the present invention to provide an organic light emitting device including the compound, which has improved hole injection and hole transport characteristics, and at the same time has electron blocking characteristics, and has excellent low voltage, high efficiency, stability due to high Tg, and long life. .

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

[Formula 1]

In Chemical Formula 1,

Ar each independently represents a C _6-50 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C _2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group,

R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; C _1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C _2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C _1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C _6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C _6-50 aryl group which is _optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C _2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group, R ₁ and R ₂ may form a ring with each other,

o is an integer from 0 to 3,

p and q are each independently an integer of 1-4.

In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1).

The compound of the present invention has a HOMO energy level that is easy to inject holes, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, hole injection layer, hole transport layer or hole transport auxiliary layer of the organic light emitting device It can have stability and long life due to excellent low voltage, high efficiency and high Tg.

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

Sign of drawing

10: substrate

11: anode

12: hole injection layer

13: hole transport layer

14: light emitting layer

15: electron transport layer

16: cathode

The compound of the present invention is characterized by represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

Ar each independently represents a C _6-50 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C _2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group,

R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; C _1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C _2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C _1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C _6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C _6-50 aryl group which is _optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C _2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group, R ₁ and R ₂ may form a ring with each other,

o is an integer from 0 to 3,

p and q are each independently an integer of 1-4.

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

Compound of Formula 1 according to the present invention has a HOMO energy level easy hole injection, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, hole injection layer, hole transport layer, Alternatively, when applied to the hole transport auxiliary layer, it can have stability and long life due to excellent low voltage, high efficiency, and high Tg.

In addition, the compound of the present invention can be prepared through the following process.

Scheme 1

In the above scheme, the target compound is a compound represented by Formula 1, and Ar, R ₁ , R ₂ , o, p, q are as defined in Formula 1.

The present invention also provides an organic light emitting device comprising the compound represented by Chemical Formula 1 in an organic material layer. In this case, the compound of the present invention is preferably used alone as a hole injection material, a hole transport material, or a hole transport auxiliary material, or may be used together with a known hole injection, hole transport material, or hole transport auxiliary material.

In addition, the organic light emitting device of the present invention includes one or more organic material layers including the compound represented by Chemical Formula 1, and as an example, a method of manufacturing the organic light emitting device will be described below.

The organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between an anode and a cathode. It may contain one or more. In addition, it may further include a hole transport auxiliary layer between the hole transport layer and the light emitting layer.

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.

Subsequently, the hole injection layer material may be formed on the anode by vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), etc., but it is easy to obtain a uniform film quality and also pinholes. It is preferable to form by the vacuum evaporation method in that it is hard to generate | occur | produce. 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 generally, a deposition temperature of 50-500 ° 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.

As the hole injection layer material, the compound represented by Formula 1 of the present invention may be used alone or a known hole injection layer material may be used. For example, a phthalocyanine compound or starburst such as copper phthalocyanine disclosed in US Pat. No. 4,356,429. TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine) and m-MTDATA (4,4', 4" -tris (3-methylphenylamino) triphenylamine) , m-MTDAPB (4,4 ', 4 "-tris (3-methylphenylamino) phenoxybenzene), 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 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 and is difficult to generate pin holes. It is preferable to form by a vapor deposition method. 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 hole transport layer material may be a compound represented by the formula (1) of the present invention may be used alone or a mixture of known hole transport layer materials. Specifically, the known hole transport layer material includes carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1, Having an aromatic condensed ring such as 1-biphenyl] -4,4'-diamine (TPD) and N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) Conventional amine derivatives and the like can be used.

Thereafter, the light emitting layer material may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, casting, LB, etc., but the vacuum deposition method is easy to obtain a uniform film quality and hard to generate pin holes. It is preferable to form by. 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 condition range as the formation of the hole injection layer. In addition, the light emitting layer material may be used as a known host or dopant. For example, a fluorescent dopant may be IDE102 or IDE105 available from Idemitsu, or BD142 (N ⁶ , N ¹² -bis (3,4-dimethylphenyl) -N ⁶ , N ¹² -dimethycrylicene- 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), a red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but the dopant is preferably doped at 0.01 to 15 parts by weight based on 100 parts by weight of the host.

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 layer material functions to stably transport electrons injected from the electron injection electrode, and the type thereof is not particularly limited, and examples thereof include 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 or IZO may be used to obtain the front light emitting device.

In addition, the organic light emitting device of the present invention may further include a hole transport auxiliary layer between the hole transport layer and the light emitting layer. The hole transport auxiliary layer may be formed through a known method as described in Korean Unexamined Patent Publication No. 10-2010-0015029, and preferably, using the compound 1 of the present invention as a hole transport auxiliary material, a hole transport auxiliary layer Can be formed.

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. Preferably, the organic light emitting device of the present invention further includes a hole transport auxiliary layer.

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

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

The organic light emitting device of the present invention has improved hole injection and hole transport characteristics, and at the same time has electron blocking characteristics, and excellent device characteristics such as excellent low voltage, high efficiency, stability due to high Tg, and long life.

Hereinafter, preferred examples are provided to help understanding of the present invention. However, the following examples are merely provided to more easily understand the present invention, and the contents of the present invention are not limited by the examples.

Synthesis of Intermediate 1-1

25 g of (4-bromophenyl) hydrazine hydrochloride was dissolved in 700 ml of acetic acid under nitrogen stream, and 25 g of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one was added thereto for 1 hour at room temperature. After stirring, the mixture was stirred at reflux for 12 hours. After cooling to room temperature, acetic acid was concentrated and the resulting solid was filtered and recrystallized with MC and hexane to give 31.53 g (52% yield) of intermediate 1-1.

Synthesis of Intermediate 1-2

25 g of (3-bromophenyl) hydrazine hydrochloride was dissolved in 700 ml of acetic acid under nitrogen stream, and 25 g of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one was added thereto for 1 hour at room temperature. After stirring, the mixture was stirred at reflux for 12 hours. After cooling to room temperature, acetic acid was concentrated and the resulting solid was filtered and recrystallized with MC and hexane to obtain 29.71 g of Intermediate 1-1 (yield 49%).

Preparation of OP for synthesis of the desired compound was carried out via the above steps.

As an example, the synthesis method of OP1 is shown below.

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%).

The following OP1 to OP9 intermediates were synthesized in the same manner as OP1.

Synthesis of Compound 1

In a round bottom flask, Intermediate 1-1 2.0 g, di ([1,1'-biphenyl] -4-yl) amine 2.0 g, t-BuONa 0.74 g, Pd ₂ (dba) ₃ 0.20 g, (t-Bu) ₃ ml of 0.25 ml was dissolved in 30 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 1.90 g (yield 59%) of compound 1.

m / z: 628.29 (100.0%), 629.29 (51.2%), 630.29 (13.0%), 631.30 (2.1%)

Synthesis of Compound 2

Reaction of di ([1,1'-biphenyl] -4-yl) amine with N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine Except that Compound 2 was synthesized in the same manner as Compound 1. (63% yield)

m / z: 668.32 (100.0%), 669.32 (54.8%), 670.33 (14.6%), 671.33 (2.5%)

Synthesis of Compound 3

In a round bottom flask, intermediate 1-1 2.0 g, OP1 2.60 g, and 1,4-dioxan were dissolved in 30 ml, 7.7 ml of K ₂ CO ₃ (2M) and 0.18 g of Pd (PPh ₃ ) ₄ were added thereto, and 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 MC, filtered under reduced pressure and purified by column to obtain 1.83 g (yield 59%) of compound 3.

m / z: 602.27 (100.0%), 603.28 (49.1%), 604.28 (11.8%), 605.28 (1.9%)

Synthesis of Compound 4

Compound 4 was synthesized in the same manner as Compound 3, except that OP1 was reacted with OP2. (Yield 60%)

m / z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)

Synthesis of Compound 5

Compound 5 was synthesized in the same manner as in compound 3, except that OP1 was reacted with OP3. (Yield 65%)

m / z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)

Synthesis of Compound 6

Compound 6 was synthesized in the same manner as in compound 3, except that OP1 was reacted with OP6. (Yield 58%)

m / z: 780.35 (100.0%), 781.35 (64.6%), 782.36 (20.3%), 783.36 (4.2%)

Synthesis of Compound 7

Compound 7 was synthesized in the same manner as in compound 3, except that OP1 was reacted with OP7. (Yield 58%)

m / z: 820.38 (100.0%), 821.39 (67.6%), 822.39 (22.5%), 823.39 (5.1%)

Synthesis of Compound 8

Compound 8 was synthesized in the same manner as in compound 3, except that OP1 was reacted with OP8. (Yield 52%)

m / z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)

Synthesis of Compound 9

Compound 9 was synthesized in the same manner as in compound 3, except that OP1 was reacted with OP9. (50% yield)

m / z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)

Synthesis of Compound 10

In a round bottom flask, Intermediate 1-2 2.0 g, di ([1,1'-biphenyl] -4-yl) amine 2.0 g, t-BuONa 0.74 g, Pd ₂ (dba) ₃ 0.20 g, (t-Bu) ₃ ml of 0.25 ml was dissolved in 30 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 1.78 g (yield 55%) of compound 10.

Synthesis of Compound 11

Reaction of di ([1,1'-biphenyl] -4-yl) amine with N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine Except for the synthesis of compound 11 in the same manner as in compound 10. (Yield 55%)

m / z: 668.32 (100.0%), 669.32 (54.8%), 670.33 (14.6%), 671.33 (2.5%)

Synthesis of Compound 12

The round bottom flask was dissolved in 2.0 g of intermediate 1-2, 3.08 g of OP2, and 30 ml of 1,4-dioxan, and 7.7 ml of K ₂ CO ₃ (2M) and 0.18 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 MC, filtered under reduced pressure and purified by column to obtain 2.0 g (yield 55%) of compound 12.

m / z: 704.32 (100.0%), 705.32 (58.1%), 706.33 (16.4%), 707.33 (3.0%)

Synthesis of Compound 13

Compound 13 was synthesized in the same manner as Compound 12, except that OP2 was reacted with OP3. (Yield 52%)

m / z: 744.35 (100.0%), 745.35 (61.3%), 746.36 (18.3%), 747.36 (3.6%)

Synthesis of Compound 14

Compound 14 was synthesized in the same manner as Compound 12, except that OP2 was reacted with OP6. (50% yield)

m / z: 780.35 (100.0%), 781.35 (64.6%), 782.36 (20.3%), 783.36 (4.2%)

Synthesis of Compound 15

Compound 15 was synthesized in the same manner as Compound 12, except that OP2 was reacted with OP7. (Yield 53%)

m / z: 820.38 (100.0%), 821.39 (67.6%), 822.39 (22.5%), 823.39 (5.1%)

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 stacked in the order of the hole injection electrode 11 / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transfer layer 15 / electron injection electrode 16 from below.

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

Fabrication of Organic Light Emitting Diode

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 1 250 Hz was formed into a hole injection layer HT01 600 Hz and a hole transport layer using the evaporator. Next, the light emitting layer was doped with 5% of BH01: BD01 to form 300 Å. Next, ET01: Liq (1: 1) 300 Å was formed into an electron transport layer, and then Liq 10 Å and aluminum (Al) 1000 막 were formed and the device was encapsulated in a glove box to produce an organic light emitting device.

Examples 2-15

In the same manner as in Example 1, an organic light emitting diode was manufactured in which the hole injection layer and the hole transport layer were formed using the compounds 2 to 15, respectively.

Comparative Example 1

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

Comparative Example 2

A device was manufactured in the same manner as in Example 1, except that the hole transport layer of Ref. 1 was used.

Comparative Example 3

A device was manufactured in the same manner as in Example 1, except that the hole transport layer of Ref. 2 was used.

Comparative Example 4

A device was manufactured in the same manner as in Example 1, except that the hole transport layer of Ref. 3 was used.

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 Table 1.

Table 1 Op. V mA / cm2 Cd / A lm / w CIEx CIEy LT95 (hr) Example 1 4.10 10 6.09 5.02 0.141 0.112 34 Example 2 4.05 10 6.05 5.00 0.141 0.112 35 Example 3 4.04 10 6.25 5.25 0.142 0.111 38 Example 4 4.00 10 6.22 5.30 0.139 0.111 39 Example 5 3.89 10 6.83 5.95 0.138 0.110 47 Example 6 4.00 10 6.30 5.40 0.140 0.111 38 Example 7 3.92 10 6.80 5.90 0.140 0.110 45 Example 8 4.01 10 6.30 5.27 0.140 0.110 42 Example 9 4.02 10 6.33 5.40 0.138 0.112 41 Example 10 4.00 10 6.29 5.29 0.141 0.111 42 Example 11 4.00 10 6.35 5.35 0.142 0.111 40 Example 12 4.01 10 6.40 5.35 0.141 0.111 45 Example 13 3.88 10 6.88 5.90 0.140 0.111 48 Example 14 4.04 10 6.31 5.42 0.140 0.110 44 Example 15 3.90 10 6.82 5.85 0.140 0.110 50 Comparative Example 1 5.03 10 5.35 4.24 0.143 0.120 13 Comparative Example 2 5.12 10 5.18 4.11 0.145 0.121 7 Comparative Example 3 4.41 10 5.68 4.70 0.141 0.113 25 Comparative Example 4 4.50 10 5.59 4.62 0.142 0.114 21

As shown in Table 1, Examples 1 to 15 of the present invention was confirmed to have excellent physical properties in all aspects compared to Comparative Examples 1 to 4. The compound represented by Formula 1 of the present invention has a high LUMO to effectively block electrons in the light emitting layer, and the hole injection from the hole injection layer forms a smooth HOMO, and also has a great effect on efficiency and lifespan due to excellent hole mobility. It seems to have given.

The compound of the present invention has a HOMO energy level that is easy to inject holes, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, hole injection layer, hole transport layer or hole transport auxiliary layer of the organic light emitting device It can have stability and long life due to excellent low voltage, high efficiency and high Tg.

Claims (5)

Compound represented by the following formula (1): [Formula 1]

In Chemical Formula 1, Ar each independently represents a C _6-50 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C _2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group, R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; C _1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C _2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C _1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C _6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C _6-50 aryl group which is _optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C _2-50 heteroaryl group unsubstituted or substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group, R ₁ and R ₂ may form a ring with each other, o is an integer from 0 to 3, p and q are each independently an integer of 1-4. The method of claim 1, Compounds characterized in that represented by any one of the following formula:

The preparation method of Chemical Formula 1 represented by Scheme 1 below: Scheme 1

In the above scheme, the target compound is a compound represented by Formula 1, and Ar, R ₁ , R ₂ , o, p, q are as defined in Formula 1. An organic light emitting device comprising an anode, a cathode and at least one organic layer containing the compound of claim 1 between two electrodes. The method of claim 4, wherein The organic light emitting device, characterized in that the organic material layer is a hole injection layer, a hole transport layer or a hole transport auxiliary layer.

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