WO2016060463A2 - Novel compound and organic light-emitting element comprising same - Google Patents

Abstract

The present invention relates to a novel compound, and in particular, when applied to a fluorescent and phosphorescent organic light-emitting element, the novel compound has superb hole injection and hole transmission characteristics as well as an excellent electron blocking characteristic, can exhibit high triplet energy and Tg, and can impart a low driving voltage, low energy consumption, superb efficiency and a long lifespan.

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, in particular, when applied to the organic light emitting device for fluorescence and phosphorescence excellent hole injection and hole transfer characteristics, at the same time excellent electron blocking characteristics, high triplet energy And a novel compound capable of realizing high Tg and having low driving voltage, low power consumption, high efficiency and long life.

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 can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function. The light emitting material may be classified into a polymer and a low molecule according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. According to the emission color can be divided into blue, green, red light emitting material and yellow and orange light emitting material required to implement a better natural color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.

In particular, many amine derivatives having a carbazole skeleton have been studied in the hole injection and hole transport materials 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 is excellent in the hole injection and hole transfer characteristics when applied to the organic light emitting device, and at the same time excellent in the electron blocking characteristics, high triplet energy and high Tg can be realized, low driving An object of the present invention is to provide a novel compound which can have a voltage, low power consumption, high efficiency and long life, and is particularly suitable for an organic light emitting device for blue and phosphorescence.

The present invention also includes the novel compound, which has excellent hole injection and hole transport characteristics, and at the same time, excellent electron blocking characteristics, and at the same time, can realize high triplet energy and high Tg, and low driving voltage, low power consumption, and high efficiency. And it is an object to provide an organic light emitting device that can have a long life.

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

[Formula 1]

Where

l, m, n, o are each independently an integer selected from 1 to 3, Ar is each independently a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, 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 , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; 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.

The present invention also provides an organic light emitting device including one or more organic material layers containing a compound represented by Chemical Formula 1 between a first electrode, a second electrode, and two electrodes.

The compound of the present invention has excellent hole injection and hole transport characteristics when applied to the organic light emitting device for blue and phosphorescence, at the same time excellent in the electron blocking characteristics, high triplet energy and high Tg, low drive voltage, low consumption It can have power, high efficiency and long life.

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]

Where

l, m, n, o are each independently an integer selected from 1 to 3, Ar is each independently a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, 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 , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; 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.

Specifically, the compound represented by Chemical Formula 1 may be one of the compounds represented by the following Chemical Formulas 1-1 to 1-7.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

N, p, q and r in the formulas are each independently an integer selected from 1 to 3,

Ar ₁ and Ar ₂ are each independently a C _6-50 aryl group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile, or nitro groups; 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 , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , and R ₁₃ are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; 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 ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , Ar ₁ , Ar ₂ may form an adjacent group or a ring with each other.

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

The compound of formula 1 according to the present invention has excellent hole injection and hole transport characteristics when applied to an organic light emitting device, and at the same time excellent in electron blocking characteristics, high triplet energy and high Tg, low driving voltage, low consumption It can have power, high efficiency and long life.

In particular, the compounds represented by Chemical Formulas 1-1 and 1-2 may exhibit more excellent device characteristics in fluorescent and red phosphorescent organic light emitting diodes, and the compounds represented by Chemical Formula 1-7 may be further represented in green phosphorescent organic light emitting diodes It can exhibit excellent device characteristics.

Compounds of the invention can also be prepared via Scheme 1 below:

Scheme 1

In Scheme 1, l, m, n, o, Ar, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ 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. Specifically, it will be included as a hole injection material, a hole transport material, a light emitting auxiliary material, wherein the compound of the present invention may be used alone or in combination with a known organic light emitting compound. More specifically, the organic light emitting device is preferably a fluorescent, red phosphorescent, green phosphorescent organic light emitting device.

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 the method of manufacturing the organic light emitting device is as follows.

The organic light emitting diode includes a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, an emission layer (EML), and an electron transport layer between a first electrode (anode) and a second electrode (cathod). One or more organic material layers, such as (ETL) and an electron injection layer (EIL), may be included.

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 electrode by a method such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB). 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 can be suitably selected 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 μm.

The hole injection layer material may be a compound represented by Formula 1 of the present invention, it may be used with a known material. The known material is not particularly limited, and TCTA (4,4 ′, 4 ″ -tri (N-carbazolyl) triphenyl, which is a phthalocyanine compound or starburst amine derivatives such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 Amine), m-MTDATA (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB (4,4', 4" -tris (3-methylphenylamino) phenoxybenzene) , HI-406 (N1, N1 '-(biphenyl-4,4'-diyl) bis (N1- (naphthalen-1-yl) -N4, N4-diphenylbenzene-1,4-diamine) It can be used as 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, or the like. 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 material may be a compound represented by the formula (1) of the present invention, it may be used with a known material. The known material is not particularly limited, and may be arbitrarily selected and used from conventional known materials used in the hole transport layer. Specifically, the hole transport layer material is carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) Derivatives and the like can be used.

In addition, an auxiliary layer may be further included on the hole transport layer. The auxiliary layer may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, cast, LB, or the like. The auxiliary layer may be a compound represented by the formula (1) of the present invention, in this case, the hole transport layer is preferably used a compound represented by the formula (2).

[Formula 2]

In the above formula,

l, m, n, o are each independently an integer selected from 1 to 3, Ar is each independently a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, 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 , R ₂ , R ₃ , R ₄ , and R ₅ are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; 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.

Specific examples of the compound represented by Formula 2 are as follows:

In such a case, the effect of increasing the efficiency and improving the life may be remarkably improved.

Thereafter, the light emitting layer material may be formed on the hole transport layer or the auxiliary layer by a method such as vacuum deposition, spin coating, cast, LB, or the like. 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 use a known compound as a 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).

In addition, when used with a phosphorescent dopant in the light emitting layer, to prevent the triplet exciton or hole from being diffused into the electron transport layer, the hole suppressing material (HBL) may be further laminated by vacuum deposition or spin coating. 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 described above, wherein the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like.

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, the deposition conditions of the electron transport layer is different depending on the compound used, but can be generally selected in 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 good to form.

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.

The organic light emitting device of the present invention is capable of 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 having a cathode structure, but also an organic light emitting device having various structures, and emits light as necessary. It is also possible to form one or two intermediate layers such as an auxiliary layer.

The thickness of each organic material layer formed according to the present invention as described above can be adjusted according to the required degree, specifically 1 to 1,000 nm, more preferably 5 to 200 nm. Within this range, the effect of high efficiency, long life and high color purity is more excellent.

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 includes the compound represented by Chemical Formula 1, and has excellent hole injection and hole transport characteristics, and at the same time, excellent electron blocking characteristics, high triplet energy and high Tg, and low driving voltage. It has low power consumption, high efficiency and long life.

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

OP synthesis

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

Synthesis of OP1 below is as follows.

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.

The following OP2 to OP19 were synthesized by varying the starting material in the same manner as the OP1.

Synthesis Example of Formula 1

Synthesis of Compound 1

In a round bottom flask, 3.0 g of 1H-indole, 10.54 g of OP1, 3.7 g of t-BuONa, 0.95 g of Pd ₂ (dba) ₃ , and 1.1 ml of (t-Bu) ₃ P were dissolved in 95 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 3.63 g (50% yield) of compound 1.

m / z: 486.21 (100.0%), 487.21 (39.7%), 488.22 (7.5%)

Synthesis of Compound 2

Compound 2 was synthesized using OP2 instead of OP1 in the same manner as compound 1. (Yield 53%)

m / z: 512.23 (100.0%), 513.23 (41.4%), 514.23 (8.7%), 515.24 (1.1%)

Synthesis of Compound 3

Compound 3 was synthesized using OP3 instead of OP1 in the same manner as compound 1. (Yield 48%)

m / z: 552.26 (100.0%), 553.26 (44.7%), 554.26 (9.9%), 555.27 (1.4%)

Synthesis of Compound 4

Compound 4 was synthesized using OP4 instead of OP1 in the same manner as compound 1. (Yield 55%)

m / z: 588.26 (100.0%), 589.26 (48.0%), 590.26 (11.4%), 591.27 (1.7%)

Synthesis of Compound 5

Compound 5 was synthesized using OP5 instead of OP1 in the same manner as compound 1. (Yield 48%)

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

Synthesis of Compound 6

Compound 6 was synthesized using OP6 instead of OP1 in the same manner as compound 1. (Yield 49%)

m / z: 588.26 (100.0%), 589.26 (48.0%), 590.26 (11.4%), 591.27 (1.7%)

Synthesis of Compound 7

Compound 7 was synthesized using OP7 instead of OP1 in the same manner as compound 1. (Yield 48%)

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

Synthesis of Compound 8

Compound 8 was synthesized using the same method as Compound 1 using 3-phenyl-1H-indole instead of 1H-indole and OP4 instead of OP1. (Yield 52%)

m / z: 664.29 (100.0%), 665.29 (54.5%), 666.29 (14.7%), 667.30 (2.5%)

Synthesis of Compound 9

Compound 9 was synthesized in the same manner as in compound 1, using OP5 instead of OP1 as 3-phenyl-1H-indole instead of 1H-indole. (Yield 48%)

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

Synthesis of Compound 10

Compound 10 was synthesized using the same method as Compound 1 using 3-phenyl-1H-indole instead of 1H-indole and OP6 instead of OP1. (50% yield)

m / z: 664.29 (100.0%), 665.29 (54.5%), 666.29 (14.7%), 667.30 (2.5%)

Synthesis of Compound 11

Compound 11 was synthesized using the same method as Compound 1 using 3-phenyl-1H-indole instead of 1H-indole and OP7 instead of OP1. (Yield 49%)

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

Synthesis of Compound 12

Compound 12 was synthesized using the same method as Compound 1 using 3-phenyl-1H-indole instead of 1H-indole and OP8 instead of OP1. (Yield 44%)

m / z: 664.29 (100.0%), 665.29 (54.5%), 666.29 (14.7%), 667.30 (2.5%)

Synthesis of Compound 13

Compound 13 was synthesized in the same manner as in compound 1, using OP9 instead of OP1 as 3-phenyl-1H-indole instead of 1H-indole. (Yield 38%)

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

Synthesis of Compound 14

Compound 14 was synthesized using the same method as Compound 1 using 2-phenyl-1H-indole instead of 1H-indole and OP4 instead of OP1. (Yield 55%)

m / z: 664.29 (100.0%), 665.29 (54.5%), 666.29 (14.7%), 667.30 (2.5%)

Synthesis of Compound 15

Compound 15 was synthesized in the same manner as in compound 1, using OP5 instead of OP1 as 2-phenyl-1H-indole instead of 1H-indole. (Yield 48%)

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

Synthesis of Compound 16

Compound 16 was synthesized in the same manner as in compound 1, using OP6 instead of OP1 as 2-phenyl-1H-indole instead of 1H-indole. (Yield 49%)

m / z: 664.29 (100.0%), 665.29 (54.5%), 666.29 (14.7%), 667.30 (2.5%)

Synthesis of Compound 17

Compound 17 was synthesized in the same manner as in compound 1, using OP7 instead of OP1 with 2-phenyl-1H-indole instead of 1H-indole. (Yield 45%)

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

Synthesis of Compound 18

Compound 18 was synthesized using the same method as Compound 1 using 2-phenyl-1H-indole instead of 1H-indole and OP8 instead of OP1. (Yield 49%)

m / z: 664.29 (100.0%), 665.29 (54.5%), 666.29 (14.7%), 667.30 (2.5%)

Synthesis of Compound 19

Compound 19 was synthesized using the same method as Compound 1 using 2-phenyl-1H-indole instead of 1H-indole and OP9 instead of OP1. (Yield 40%)

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

Synthesis of Compound 20

Compound 20 was synthesized by using OP4 instead of OP1 with 2,3-diphenyl-1H-indole instead of 1H-indole in the same manner as compound 1. (Yield 42%)

m / z: 740.32 (100.0%), 741.32 (61.3%), 742.33 (18.3%), 743.33 (3.6%)

Synthesis of Compound 21

Compound 21 was synthesized in the same manner as in compound 1, using OP5 instead of OP1 as 2,3-diphenyl-1H-indole instead of 1H-indole. (Yield 42%)

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

Synthesis of Compound 22

Compound 22 was synthesized in the same manner as in compound 1, using OP10 instead of OP1 as 3-phenyl-1H-indole instead of 1H-indole. (Yield 44%)

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

Synthesis of Compound 23

Compound 23 was synthesized in the same manner as in compound 1, using OP11 instead of OP1 as 3-phenyl-1H-indole instead of 1H-indole. (Yield 43%)

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

Synthesis of Compound 24

Compound 24 was synthesized using OP13 instead of OP1 in the same manner as in compound 1. (Yield 55%)

m / z: 592.29 (100.0%), 593.29 (48.0%), 594.29 (11.4%), 595.30 (1.7%)

Synthesis of Compound 25

Compound 25 was synthesized using OP14 instead of OP1 in the same manner as Compound 1. (Yield 52%)

m / z: 716.32 (100.0%), 717.32 (59.1%), 718.33 (17.0%), 719.33 (3.2%)

Synthesis of Compound 26

Compound 26 was synthesized using OP15 instead of OP1 in the same manner as in compound 1. (50% yield)

m / z: 592.29 (100.0%), 593.29 (48.0%), 594.29 (11.4%), 595.30 (1.7%)

Synthesis of Compound 27

Compound 27 was synthesized using OP16 instead of OP1 in the same manner as in compound 1. (Yield 51%)

m / z: 716.32 (100.0%), 717.32 (59.1%), 718.33 (17.0%), 719.33 (3.2%)

Synthesis of Compound 28

Compound 28 was synthesized using OP17 instead of OP1 in the same manner as in compound 1. (Yield 45%)

m / z: 592.29 (100.0%), 593.29 (48.0%), 594.29 (11.4%), 595.30 (1.7%)

Synthesis of Compound 29

Compound 29 was synthesized using OP18 instead of OP1 in the same manner as Compound 1. (Yield 47%)

m / z: 716.32 (100.0%), 717.32 (59.1%), 718.33 (17.0%), 719.33 (3.2%)

Synthesis of Compound 30

Compound 30 was synthesized using OP19 instead of OP1 in the same manner as in compound 1. (Yield 47%)

m / z: 714.30 (100.0%), 715.31 (58.8%), 716.31 (17.0%), 717.31 (3.3%)

Synthesis Example of Formula 2

Synthesis of Compound 31

In a round bottom flask, dissolve in 2.2 g of (1-phenyl-1H-indol-2-yl) boronic acid and 70 ml of OP3 4.0 g 1,4-dioxan, 12 ml of K ₂ CO ₃ (2M) and Pd (PPh ₃ ) ₄ 0.3 g was added thereto, followed by stirring under reflux. The reaction was confirmed by TLC and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then recrystallized after column purification to obtain 2.73 g (56% yield) of compound 31.

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

Synthesis of Compound 32

Compound 32 was synthesized using OP5 instead of OP3 in the same manner as compound 31. (Yield 48%)

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

Synthesis of Compound 33

Compound 33 was synthesized using OP12 instead of OP3 in the same manner as compound 31. (Yield 52%)

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

Synthesis of Compound 34

Compound 34 was synthesized in the same manner as compound 31, using OP5 instead of OP1 as (1-phenyl-1H-indol-3-yl) boronic acid instead of (1-phenyl-1H-indol-2-yl) boronic acid. (Yield 55%)

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

Synthesis of Compound 35

Compound 35 was synthesized by using OP7 instead of OP1 as (1-phenyl-1H-indol-3-yl) boronic acid instead of (1-phenyl-1H-indol-2-yl) boronic acid in the same manner as Compound 31. (Yield 55%)

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

Synthesis of Compound 36

Compound 36 was synthesized using OP5 instead of OP1 with (1,2-diphenyl-1H-indol-3-yl) boronic acid instead of (1-phenyl-1H-indol-2-yl) boronic acid in the same manner as compound 35 It was. (Yield 52%)

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

Synthesis of Compound 37

Compound 37 was synthesized by using OP10 instead of OP1 as (1-phenyl-1H-indol-3-yl) boronic acid instead of (1-phenyl-1H-indol-2-yl) boronic acid as Compound 31. (Yield 59%)

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

Synthesis of Compound 38

Compound 38 was synthesized by using OP10 instead of OP1 as (1,2-diphenyl-1H-indol-3-yl) boronic acid instead of (1-phenyl-1H-indol-2-yl) boronic acid in the same manner as Compound 31 It was. (Yield 49%)

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

Fabrication of Organic Light Emitting Diode

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

In FIG. 1, the substrate 10 may be a transparent glass substrate or a flexible plastic substrate when the organic light emitting diode is manufactured.

The hole injection electrode 11 is used as an anode for hole injection of the organic light emitting device. A material having a low work function may be used to inject holes, and may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.

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.

The cathode 16 for electron injection is formed on the electron injection layer 15. Various metals may be used as the cathode. Specific examples include materials such as aluminum, gold, and silver.

Example 1

A glass substrate coated with an indium tin oxide (ITO) 1500 Å thick thin film was washed by distilled water ultrasonically. After the distilled water is washed, 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 using an oxygen plasma. Using an evaporator, a film was deposited with a hole injection layer HT01 600 Å and a compound transport 1 with 250 Å as the hole transport layer. Next, the light emitting layer was doped with BH01: BD01 5% to form 250 Å. Next, ET01: Liq (1: 1) 300 Å was formed into an electron transport layer, followed by LiF 10 Å and aluminum (Al) 1000 막, which were encapsulated in a glove box to produce an organic light emitting device.

Examples 2-25

In the same manner as in Example 1, an organic light emitting diode was manufactured in which the hole transport layer was formed by using compounds 2 to 25, respectively.

Comparative Example 1

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

Comparative Example 2

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

Comparative Example 3

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

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 / cm 2	Cd / A	lm / w	CIEx	CIEy	LT95
Example 1	4.441	10	5.85	4.79	0.141	0.120	22
Example 2	4.352	10	5.85	4.71	0.141	0.117	27
Example 3	4.343	10	5.88	4.76	0.142	0.115	30
Example 4	4.221	10	5.97	4.94	0.139	0.112	32
Example 5	4.212	10	6.00	4.92	0.138	0.113	35
Example 6	4.203	10	6.04	4.94	0.140	0.113	35
Example 7	4.295	10	6.07	4.99	0.140	0.113	37
Example 8	4.157	10	6.70	5.69	0.140	0.111	50
Example 9	4.130	10	6.63	5.64	0.139	0.112	47
Example 10	4.104	10	6.70	5.64	0.141	0.112	49
Example 11	4.100	10	6.59	5.67	0.142	0.112	49
Example 12	4.110	10	6.60	5.69	0.141	0.113	48
Example 13	4.109	10	6.63	5.65	0.142	0.113	50
Example 14	4.241	10	6.11	4.97	0.141	0.114	32
Example 15	4.214	10	6.19	4.80	0.141	0.113	35
Example 16	4.244	10	6.11	4.90	0.141	0.113	32
Example 17	4.253	10	6.13	4.91	0.140	0.114	34
Example 18	4.265	10	6.11	4.87	0.140	0.115	35
Example 19	4.255	10	6.19	4.85	0.140	0.114	32
Example 20	4.245	10	6.11	4.91	0.138	0.115	31
Example 21	4.247	10	6.09	4.79	0.139	0.115	33
Example 22	4.151	10	6.65	5.68	0.140	0.113	47
Example 23	4.109	10	6.69	5.60	0.141	0.112	48
Example 24	4.009	10	6.63	5.59	0.140	0.111	45
Example 25	4.151	10	6.70	5.63	0.140	0.110	47
Comparative Example 1	4.932	10	4.97	3.86	0.143	0.118	10
Comparative Example 2	4.657	10	5.30	4.24	0.141	0.115	19
Comparative Example 3	4.650	10	5.45	4.50	0.142	0.115	18

As shown in Table 1, the Examples evaluated by the hole transport layer of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Examples 1 to 3. In particular, the structure in which the aryl group is substituted at the position of indole 3 as shown in Chemical Formulas 1-1 and 1-2 has better planarity of molecules than simultaneous substitution of indole 2 and indole 2,3, and excellent mobility of molecules in the thin film. It can be seen that the efficiency and device life are significantly improved due to the excellent increase and chemical stability. In addition, when the linking group of Formula 1-6, indole, and arylamine is a phenyl moiety, and when two or more fluorene groups are substituted, the planarity of the fluorene groups improves the arrangement of the thin films, increases mobility, and significantly improves efficiency and lifetime. Able to know.

Example of evaluation of auxiliary layer of organic light emitting device (fluorescence)

Example 26

A glass substrate coated with an indium tin oxide (ITO) 1500 Å thick thin film was washed by distilled water ultrasonically. After the distilled water is washed, 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 using an oxygen plasma. 600 cc of the hole injection layer HT01 and 400 cc of the compound 31 were formed into a first hole transport layer using an evaporator. Next, 150 Å of the compound 8 was formed as an auxiliary layer, and then 250 Å was formed by doping with 5% of BH01: BD01. Next, ET01: Liq (1: 1) 300 Å was formed into an electron transport layer, followed by LiF 10 Å and aluminum (Al) 1000 막, which were encapsulated in a glove box to produce an organic light emitting device.

Example 27

An organic light-emitting device was manufactured in the same manner as in Example 26, using Compound 32 as an auxiliary layer and Compound 8 as an auxiliary layer.

Example 28

In the same manner as in Example 26, an organic light emitting device was manufactured by using the compound 33 as an auxiliary layer and the compound 8 as a hole transport layer.

Example 29

In the same manner as in Example 26, an organic light emitting device was manufactured by using the compound 34 as a hole transport layer and the compound 8 as an auxiliary layer.

Example 30

An organic light-emitting device was manufactured in the same manner as in Example 26, using Compound 35 as an auxiliary layer and Compound 8 as an auxiliary layer.

Example 31

In the same manner as in Example 26, an organic light emitting diode was manufactured by using Compound 36 as an auxiliary layer and Compound 8 as an auxiliary layer.

Example 32

In the same manner as in Example 26, an organic light emitting device was manufactured by using the compound 37 as a hole transport layer and the compound 8 as an auxiliary layer.

Example 33

An organic light-emitting device was manufactured in the same manner as in Example 26, using Compound 38 as an auxiliary layer and Compound 8 as an auxiliary layer.

Comparative Example 4

A device was manufactured in the same manner as in Example 26, except that Compound 24 was used as the NPB as the hole transport layer.

Comparative Example 5

A device was manufactured in the same manner as in Example 26, except that Compound 24 was used as Ref. 3 as the hole transport layer.

Comparative Example 6

A device was manufactured in the same manner as in Example 26, except that Compound 24 was used as Ref. 4 as the hole transport layer.

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 2.

TABLE 2

	Op. V	mA / cm 2	Cd / A	lm / w	CIEx	CIEy	LT95
Example 26	3.841	10	7.09	6.19	0.141	0.112	61
Example 27	3.852	10	7.00	6.11	0.141	0.111	60
Example 28	3.843	10	7.18	6.16	0.142	0.110	63
Example 29	3.821	10	7.05	6.14	0.139	0.112	69
Example 30	3.912	10	7.10	6.12	0.138	0.110	63
Example 31	3.903	10	7.04	6.24	0.140	0.113	61
Example 32	3.895	10	7.17	5.99	0.140	0.112	68
Example 33	3.897	10	7.10	6.09	0.140	0.110	66
Comparative Example 4	4.501	10	5.57	4.30	0.143	0.115	21
Comparative Example 5	4.272	10	5.98	4.90	0.141	0.115	31
Comparative Example 6	4.301	10	6.15	5.11	0.141	0.113	30

As shown in Table 2, the embodiments of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Examples 4 to 6. In particular, when the indole 2-substituted arylamine-substituted compound as the hole transport layer and the indole N-substituted arylamine compound as the auxiliary layer were used together, the driving voltage was significantly lowered, and the efficiency and lifespan were increased. It can have easy homo and fast hole mobility in the hole transport layer in accordance with the 2,3 arylamine substitution of indole, and in the case of indole N substitution, it can form a deep homogeneous easily in the auxiliary layer. It can be seen that greatly improved.

Evaluation example of auxiliary layer of organic light emitting device (phosphorescence)

Example 34

A glass substrate coated with an indium tin oxide (ITO) 1500 Å thick thin film was washed by distilled water ultrasonically. After the distilled water is washed, 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 using an oxygen plasma. Using a evaporator, a film injection layer HT01 600 Å, a hole transport layer to the film 37 to 400 제 was formed into a film. Next, 250 Å of Compound 8 was formed as an auxiliary layer, and then 300 Å was formed by doping with 10% CzT: Ir (ppy) ₃ . Next, ET01: Liq (1: 1) 300 Å was formed into an electron transport layer, followed by LiF 10 Å and aluminum (Al) 1000 막, which were encapsulated in a glove box to produce an organic light emitting device.

Example 35

An organic light-emitting device was manufactured in the same manner as in Example 34, using the auxiliary layer as a compound 26 to form a film.

Example 36

In the same manner as in Example 34, an organic light emitting device was manufactured by using the auxiliary layer as a compound 27.

Example 37

In the same manner as in Example 34, an organic light-emitting device was manufactured by using the auxiliary layer as a compound 28.

Example 38

In the same manner as in Example 34, an organic light-emitting device was manufactured by using the auxiliary layer as a compound 29.

Example 39

An organic light-emitting device was manufactured in the same manner as in Example 34, using the auxiliary layer as a compound 30.

Example 40

In the same manner as in Example 34, an organic light emitting diode was manufactured by using the hole transport layer as an NPB and the auxiliary layer as a compound 30.

Comparative Example 7

A device was fabricated in the same manner as in Example 34, except that Ref. 1 was used as the hole transport layer and NPB.

Comparative Example 8

A device was fabricated in the same manner as in Example 34, except that the hole transport layer was NPB, and the auxiliary layer was Ref.2.

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 3.

TABLE 3

	Op. V	mA / cm 2	Cd / A	lm / w	CIEx	CIEy	LT95
Example 34	4.341	10	51.40	39.19	0.338	0.622	108
Example 35	4.352	10	54.40	40.11	0.336	0.620	113
Example 36	4.343	10	54.29	40.16	0.335	0.621	115
Example 37	4.321	10	55.05	40.14	0.336	0.620	118
Example 38	4.312	10	56.00	41.12	0.338	0.621	127
Example 39	4.303	10	56.04	41.24	0.335	0.621	125
Example 40	4.303	10	45.54	34.24	0.337	0.622	83
Comparative Example 7	4.731	10	38.60	25.30	0.340	0.623	43
Comparative Example 8	4.722	10	39.34	27.90	0.340	0.623	48

As shown in Table 3, the embodiments of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Example 7 and Comparative Example 8. In particular, in the case of the compound in which the linking group between indole N and arylamine is substituted with phenyl moiety and meta, ortho as an auxiliary layer of the phosphor, it may have a wide band gap capable of forming a deep homo with short conjugation length. It can be seen that the triplet energy is easy to block excitons from phosphorescent light emission, thereby improving efficiency and improving lifespan.

The compound of the present invention has excellent hole injection and hole transport characteristics when applied to the organic light emitting device for blue and phosphorescence, at the same time excellent in the electron blocking characteristics, high triplet energy and high Tg, low drive voltage, low consumption It can have power, high efficiency and long life.

Claims (9)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   Where

   l, m, n, o are each independently an integer selected from 1 to 3, Ar is each independently a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, 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 , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; 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.
2. The method of claim 1,

   Compound represented by any one of the following formula 1-1 to 1-7

   [Formula 1-1]

   

   [Formula 1-2]

   

   [Formula 1-3]

   

   [Formula 1-4]

   

   [Formula 1-5]

   

   [Formula 1-6]

   

   [Formula 1-7]

   

   N, p, q and r in the formulas are each independently an integer selected from 1 to 3,

   Ar ₁ and Ar ₂ are each independently a C _6-50 aryl group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile, or nitro groups; 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 , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , and R ₁₃ are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; 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 ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , Ar ₁ , Ar ₂ may form an adjacent group or a ring with each other.
3. The method of claim 1,

   Compound represented by any one of the following formulas:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
4. An organic light emitting device comprising at least one organic layer containing a compound represented by the formula (1) of claim 1 between the first electrode, the second electrode and the two electrodes.
5. The method of claim 4, wherein

   An organic light emitting device in which an organic thin film layer including at least one light emitting layer or a plurality of layers is sandwiched between a first electrode and a second electrode, and at least one layer is disposed between the first electrode and the light emitting layer. An organic light emitting device comprising the compound of claim 1 as an organic layer.
6. The method of claim 5,

   An organic light emitting device in which one layer, which is in contact with the light emitting layer between the first electrode and the light emitting layer, contains the compounds of Formulas 1-1, 1-2, and 1-7 as described in claim 2 as an organic layer.
7. The method of claim 5,

   An organic light emitting device comprising at least one hole transport layer between a first electrode and a light emitting layer, and an auxiliary layer including a compound represented by Formula 1 between the hole transport layer and the light emitting layer.
8. The method of claim 7, wherein

   The hole transport layer is an organic light emitting device comprising a compound represented by the following formula (2).

   [Formula 2]

   

   In the above formula,

   l, m, n, o are each independently an integer selected from 1 to 3, Ar is each independently a C _6-50 aryl group unsubstituted or substituted with deuterium, halogen, amino, nitrile, 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 , R ₂ , R ₃ , R ₄ , and R ₅ are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; 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.
9. The method of claim 8,

   Compound represented by Formula 2 is a compound represented by any one of the following formula:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

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