KR20160080090A - Novel compound and organic electroluminescent device comprising same - Google Patents

Abstract

A novel compound of the present invention can be applied to a light-emitting layer, an electron-injecting layer, an electron-transporting layer, or a hole-inhibiting layer of an organic light-emitting device. The novel compound and the carbazole derivative of the present invention are used together as a host of the organic light-emitting device, thereby properly controlling the exciplex wavelength and maximizing the efficiency and the durability of the organic light-emitting device.

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 comprising the same. In addition, the present invention relates to an organic light emitting device having maximized efficiency and lifetime by appropriately controlling exciplex wavelength by using a compound and a carbazole derivative together as a host.

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 problems, the present invention can be used as a light emitting host, an electron injecting material, an electron transporting material or a hole blocking material in an organic light emitting device, and has a long life, high efficiency, low voltage, And it is an object of the present invention to provide a compound capable of securing thin film stability and maximizing the efficiency and lifetime of an organic light emitting device through formation of exciplex and energy transfer to a dopant.

Another object of the present invention is to provide an organic light emitting device having a long lifetime, high efficiency, low voltage, high Tg, and thin film stability, and capable of maximizing efficiency and lifetime through formation of exciplex and energy transfer to dopant do.

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,

X is each independently N or CR _0, at least two of X are N, wherein R ₀ is hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

Y is O or S,

R ₁ , R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; 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 -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group having _{1 -30} C, _-30 C ₂ alkenyl group, C _{2 -30} alkynyl, C _1-30 a, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the of the C _6-30 aryl An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

m and n are each independently an integer of 0 to 2;

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

The compound of the present invention and the organic light emitting device to which the compound is applied have the following characteristics.

1. By the introduction of triphenylene structure in the compound, it has excellent durability against electron and hole, thus securing the longevity of organic light emitting device.

2. Maintaining high efficiency of organic light-emitting device by keeping triple energy as a green phosphorescent host.

3. It facilitates electron injection and transportation by introducing heteroaryl group in the compound, and ensures low voltage driving and high efficiency of organic light emitting device.

4. Enables high Tg formation by fused ring in compound and improves thin film stability when driving organic light emitting device.

5. When applied to organic light emitting devices, it is possible to facilitate hole injection, electron injection and transport, low voltage driving, and high efficiency using the novel compound (luminescent host 1) and carbazole derivative (luminescent host 2) .

6. The use of the novel compound (luminescent host 1) and the carbazole derivative (luminescent host 2) of the present invention when applied to organic light emitting devices maximizes efficiency through energy transfer to the exciplex and dopant, Enable.

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 compounds of the present invention are represented by the following formula (1).

[Chemical Formula 1]

In this formula,

X is each independently N or CR _0, at least two of X are N, wherein R ₀ is hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

Y is O or S,

R ₁ , R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; 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 -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group having _{1 -30} C, _-30 C ₂ alkenyl group, C _{2 -30} alkynyl, C _1-30 a, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the of the C _6-30 aryl An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

m and n are each independently an integer of 0 to 2, and specifically, m and n are 1.

In the present invention, the compound represented by the formula (1) may be one of the compounds represented by the following formulas (1-1) to (1-6).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

In the above formulas, X and Y are as defined in formula (1).

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

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The compound of formula (1) according to the present invention has excellent electron transfer characteristics, excellent luminous efficiency, high color purity, high efficiency and long life, and exhibits excellent device characteristics when applied to organic light emitting devices. Further, the compound of formula (1) has a LUMO energy level that facilitates electron injection, has excellent electron transporting properties, and can have excellent low voltage, high efficiency, stability and long life due to high Tg when a light emitting layer and an electron transport layer of an organic light emitting device are applied. have.

The compounds of the present invention may also be prepared through the reaction schemes shown in any one of the following Reaction Schemes 1 to 3:

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

Wherein X and Y are as defined 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. At this time, the compound of the present invention can be used singly as a light emitting host, an electron injecting material, an electron transporting material or a hole blocking material, or can be used together with a known compound. More specifically, the compound of the present invention is used as a luminescent host, wherein a luminescent compound (luminescent host 2) represented by the following formula (2) is reacted with a compound represented by the formula (luminescent host 1) It is better to use it together.

(2)

In Formula 2, r ₁ to r ₈ each independently represents hydrogen; heavy hydrogen; Alkyl group of deuterium, halogen group, amino group, nitrile group, C _{1 -30,} which is unsubstituted or substituted with nitro; A C ₂ -C 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 halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} oxy group, a heteroaryl group, a C _6-30 aryl group, or a C _{2 -30} which is unsubstituted or substituted heteroaryl C _{2 -50} of,

Ar is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} alkoxy group, a C _{6 -30} of the An aryl group having _{6 to 30} carbon _atoms or a C _{6 to 50} aryl group optionally substituted with a C _2-30 heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

m is an integer of 1 to 4,

When m is 2 to 4, Ar and r ₁ -r ₈ may be connected to each other.

Specifically, it is preferable that the compound of the formula (2) is any one of the compounds represented by the following formulas (2-1) to (2-7).

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

[Chemical Formula 2-7]

In the above formulas, Ar ₁ , Ar ₂ , Ar ₃ , Ar _{4 , and} Ar ₅ are each independently the same as the definition of Ar in Formula 2,

R ₁ , R ₂ , R ₃ and R ₄ have the same definitions as r ₁ to r _{8 in} the above formula (2)

a and b each independently represent an integer of 0 to 3;

More specifically, the compound of formula (2) is preferably a compound represented by formula (2-3). In this case, the homo structure may be higher by including a structure substituted among the carbazole phenyl moieties contained in the formula, And the driving voltage can be lowered.

When the organic light emitting device of the present invention uses the compound of Formula 2 as a light emitting host, the mixing ratio of Formula 1 and Formula 2 is preferably 9: 1 to 2: 8 by weight. Within the above range, the driving voltage of the organic light emitting device is low and high efficiency and long life can be obtained. However, if the compound represented by the general formula (2) is too much outside the above range, the hole injection and transportation become excessive, .

The specific compounds of formula (2) are as follows.

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And a flex eksi emission wavelength is formed through the first and second light emitting host in the present invention can be formed into 400-650 nm, by the selection of the light emitting host 1 and 2 to form a flex eksi wavelength of 450-500 nm green organic And can be used in a red organic light emitting device by forming an exciplex wavelength of 500-630 nm.

Specifically, it is preferable that the exciplex wavelength formed by the combination of the light emitting host is formed at a shorter wavelength than the light emission wavelength of the dopant as a guest of the light emitting layer. This is because energy transfer occurs efficiently in the process of phosphorescence doped phosphorescent doped phosphorescent phosphorescent phosphorescent phosphorescent phosphorescent doped phosphorescent phosphorescent phosphorescent phosphorescent phosphorescent phosphorescent phosphorescent dopant phosphorescent dopant phosphorescent dopant phosphorescent phosphorescent phosphorescent phosphorescent phosphorescent dopant

In addition, the organic light emitting device of the present invention can produce an organic light emitting device using a known method for manufacturing an organic light emitting device, except that the organic light emitting device includes one or more organic layers including a compound represented by Formula 1. [ A method of manufacturing an 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, a Langmuir-Blodgett (LB) method, or the like. As the hole injection layer material, a known hole injection layer material may be used. For example, 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 " M-MTDAPA (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine) 3-methyl-phenyl-amino) phenoxy ^{benzene), HI-406 (N 1} , N 1 '- ( biphenyl-4,4'-diyl) bis (N ¹ - (naphthalen-1-yl) -N ^4, N ⁴ -Diphenylbenzene-1,4-diamine) or the like 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 a vacuum deposition method, a spin coating method, a casting method, or an LB method.

The hole transport layer material may be a known hole transport layer material. Specifically, known hole transporting layer materials include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'- Having an aromatic condensed ring such as 1-biphenyl-4,4'-diamine (TPD) and N, N'-di (naphthalen- 1 -yl) -N, N'- Conventional amine 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 evaporation method, a spin coating method, a casting method, an LB method, or the like. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer.

The light emitting layer material may be a known host or a dopant. The compound represented by the general formula (1) of the present invention is preferably used as a host. More specifically, the compound represented by general formula (1) (Luminescent host 2) represented by formula (1) and compound (luminescent host 2) represented by formula (2) are simultaneously used at the same time. More specifically, It is good to use. As the luminescent host, an exciplex wavelength formed by a combination of the compound represented by Formula 1 (luminescent host 1) of the present invention and the compound represented by Formula 2 (luminescent host 2) is formed at a shorter wavelength than the luminescent wavelength of the dopant of the luminescent layer It is recommended to use a dopant material so that it can be used.

Examples of usable fluorescent dopants include IDE102 or IDE105 available from Idemitsu, or BD142 (N ⁶ , N ¹² -bis (3,4-dimethylphenyl) -N ⁶ , N ¹² -dimethylylclycine- 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).

Further, a light emission-assisting layer may be further included between the hole transporting layer and the light emitting layer, and known materials may be used as the light emitting assisting layer material.

Further, a hole blocking material (HBL) may be further laminated by a vacuum deposition method or a spin coating method to prevent the triplet excitons or holes from diffusing into the electron transporting layer in the light emitting layer. The hole blocking material which can be used at this time may be selected from any known materials used as the compound represented by the formula (1) or the hole blocking material, alone or in combination. Known materials include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and hole blocking materials described in Japanese Patent Application Laid-Open No. 11-329734 (A1). Representative examples include Balq (8-hydroxy-2-methylquinolinonato) -aluminum biphenoxide), phenanthrolines (for example, UDC company BCP (Bassocouplin)) and the like can be used.

The electron transport layer may be formed by vacuum evaporation, spin coating, casting, or the like on the light emitting layer formed as described above.

Examples of well-known materials 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) can be used.

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. As the electron injection layer material, a compound represented by Formula 1 or LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used.

Finally, a metal for forming a cathode is formed on the electron transporting layer or the electron injecting layer by a vacuum deposition 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 depending on the required degree, specifically 10 to 1,000 nm, more specifically 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.

INDUSTRIAL APPLICABILITY The organic light emitting device of the present invention is excellent in durability against electrons and holes and can ensure long lifetime, low voltage driving and high efficiency of an organic light emitting device, and is excellent in thin film stability. The novel compound (light emitting host 1) It is possible to facilitate injection and transport of electrons, enable low voltage driving and high efficiency, maximize efficiency through formation of exciplex and energy transfer to dopant, and enable high efficiency and long life by using sol derivative (light emitting host 2) .

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

[ Formula 1 ] Synthesis of

Intermediate I1 Synthesis of

[Synthesis of I1-1]

The triphenylen-2-ylboronic acid 8.4g, 2,8-dibromodibenzo [b, d] furan 10.0g in 280ml round bottom flask and dissolved in toluene into a K ₂ CO ₃ (2M) 46ml and Pd (PPh _{3) 4} 1.1g Followed by reflux stirring. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 8.1 g (yield: 56%) of Intermediate I1-1.

[Synthesis of I1]

8.1 g of Intermediate I1-1, 5.6 g of bis (pinacolato) diboron, 0.06 g of Pd (dppf) Cl ₂ and 5.04 g of KOAc were dissolved in 200 ml of 1,4-dioxane and then stirred under reflux. The reaction was confirmed by TLC, and the organic layer was subjected to MC extraction and column purification to obtain 7.0 g (yield 79%) of Intermediate I1.

Intermediate I2 Synthesis of

Intermediate I2 was synthesized by using 4,6-dibromodibenzo [b, d] furan instead of 2,8-dibromodibenzo [b, d] furan in the same manner as in the synthesis of Intermediates I1-1 and I1 (yield 50%

Intermediate I3 Synthesis of

[Synthesis of I3-1]

To a round bottom flask was added 2-bromotriphenylene 15.0g, dibenzo [b , d] furan-4-ylboronic acid 10.5g was dissolved in toluene _{380ml K 2 CO 3 (2M)} 75ml and Pd (PPh ₃₎ was placed under reflux for ₄ 1.7g Lt; / RTI > After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 15.2 g (yield: 66%) of Intermediate I3-1.

[Synthesis of I3-2]

15.0 g of Intermediate I3-1 was dissolved in 150 ml of DMF, and then 7.5 g of N-Bromosuccinimide dissolved in 70 ml of DMF was slowly added dropwise, followed by stirring for 16 hours. The reaction was confirmed by TLC and precipitation with distilled water and recrystallization to obtain 13.5 g (yield 75%) of intermediate I3-2.

[Synthesis of I3]

13.5 g of Intermediate I1-1, 9.4 g of bis (pinacolato) diboron, 0.1 g of Pd (dppf) Cl ₂ and 8.4 g of KOAc were dissolved in 350 ml of 1,4-dioxane and then stirred under reflux. The reaction was confirmed by TLC, and the organic layer was subjected to MC extraction and column purification to obtain 10.8 g (yield 73%) of Intermediate I3.

Intermediate I4 Synthesis of

Intermediate I4 was synthesized by using 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-bromotriphenylene in the same manner as in the synthesis of Intermediates I3-1 to I3 (yield 47%).

Intermediate I5 Synthesis of

Intermediate I5 was synthesized by using 2,8-dibromodibenzo [b, d] thiophene instead of 2,8-dibromodibenzo [b, d] furan in the same manner as in the synthesis of Intermediates I1-1 and I1 (yield 53%

Intermediate I6 Synthesis of

Intermediate I6 was synthesized using 4,6-dibromodibenzo [b, d] thiophene instead of 2,8-dibromodibenzo [b, d] furan in the same manner as in the synthesis of Intermediates I1-1 and I1 (yield 48%).

Intermediate I7 Synthesis of

Intermediate I7 was synthesized using dibenzo [b, d] thiophen-4-ylboronic acid instead of dibenzo [b, d] furan-4-ylboronic acid in the same manner as in the synthesis of Intermediates I3-1 to I3. )

Intermediate I8 Synthesis of

4-ylboronic acid instead of 2-bromotriphenylene and dibenzo [b, d] furan-4-ylboronic acid in the same manner as in the synthesis of Intermediates I3-1 to I3, , d] thiophen-4-ylboronic acid. Intermediate I8 was synthesized (yield: 45%).

Synthesis of [Formula 1]

Compound 1-1

To a round bottom flask was added the intermediate I1 5.0g, 2-chloro-4,6 -diphenyl-1,3,5-triazine 2.8g was dissolved in toluene _{120ml K 2 CO 3 (2M)} 15ml and Pd (PPh _{3) 4} 0.33 g, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 4.0 g (yield 67%) of Compound 1-1.

m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%

Compound 1-2

Compound 1-2 was synthesized by the same method as Compound 1-1 using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. %)

m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23

Compound 1-3

Compound 1-3 was synthesized by the same method as Compound 1-1 using 2-chloro-4,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. (Yield 65 %)

m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23

Compound 1-4

Compound 1-4 was synthesized using Intermediate I2 instead of Intermediate I1 in the same manner as Compound 1-1 (Yield: 59%).

m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%

Synthesis of Compound 1-5

Intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used instead of Intermediate I2 and 4-chloro-2,6-diphenylpyrimidine in the same manner as Compound 1-1, (Yield: 63%).

m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23

Synthesis of Compound 1-6

Intermediate I1 and 2-chloro-4,6-diphenylpyrimidine were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as Compound 1-1, (Yield: 60%).

m / z: 624.22 (100.0%), 625.22 (50.5%), 626.23 (12.3%), 627.23

Compound 1-7

Compound 1-7 was synthesized using Intermediate I3 instead of Intermediate I1 in the same manner as Compound 1-1 above (yield: 64%).

m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%

Compound 1-8

Compound 1-8 was synthesized by using Intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine instead of Intermediate I1 and 2-bromotriphenylene in the same manner as Compound 1-1 above (Yield: 60 %)

m / z: 625.22 (100.0%), 626.22 (49.0%), 627.22 (12.3%), 628.23 (1.8%

Compound 1-9

Compound 1-9 was synthesized by using the intermediate I5 instead of Intermediate I1 in the same manner as the compound 1-1 (yield 60%).

m / z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20

Compound 1-10

Compound 1-10 was synthesized using intermediate I5 and 4-chloro-2,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5- (Yield: 65%).

m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%

Compound 1-11

Compound 1-11 was synthesized using intermediate I5 and 2-chloro-4,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5- (Yield: 62%).

m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%

Compound 1-12

Compound 1-12 was synthesized by using Intermediate I6 instead of Intermediate I1 in the same manner as Compound 1-1 above (Yield: 65%).

m / z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20

Compound 1-13

Intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used instead of Intermediate I6 and 4-chloro-2,6-diphenylpyrimidine in the same manner as Compound 1-1, (Yield: 60%).

m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%

Compound 1-14

Compound 1-14 was synthesized using intermediate I6 and 2-chloro-4,6-diphenylpyrimidine instead of intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5- (Yield: 62%).

m / z: 640.20 (100.0%), 641.20 (50.9%), 642.20 (12.9%), 642.19 (4.5%), 643.20 (2.5%

Compound 1-15

Compound 1-15 was synthesized by using Intermediate I7 instead of Intermediate I1 in the same manner as Compound 1-1 above (Yield: 65%).

2,4-diphenyl-6- (6- (triphenylen-2-yl) dibenzo [b, d] thiophen-2-yl) -1,3,5-triazine

Compound 1-16

Compound 1-16 was synthesized using Intermediate I1 and 2-chloro-4,6-diphenyl-1,3,5-triazine in place of Intermediate I1 and 2-bromotriphenylene in the same manner as Compound 1-1. %)

m / z: 641.19 (100.0%), 642.20 (49.0%), 643.20 (12.1%), 643.19 (5.1%), 644.19 (2.3%), 644.20

Synthesis of Formula 2

Compound 2-1

To a round bottom flask was added 3-phenyl-9H-carbazole 5.0g , 3,3'-dibromo-1,1'-biphenyl 3.21g, t-BuONa 2.96g, Pd 2 (dba) 3 0.75g, (t-Bu) ₃ P was dissolved in 100 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 8.64 g (yield: 66%) of Compound 2-1.

m / z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27

Compound 2-2

To a round bottom flask was added 8.0 g of (9- (9H-carbazol-9-yl) -3-bromo-9H- phenyl) boronic acid were dissolved in 200 ml of toluene, and 25 ml of K ₂ CO ₃ (2M) and 0.6 g of Pd (PPh ₃ ) ₄ were added, followed by reflux stirring. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 7.62 g (yield 71%) of Compound 2-2.

m / z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27

Compound 2-3

To a round bottom flask 9H, 9'H-3,3'-bicarbazole 10.0g , 3-bromo-1,1'-biphenyl 14.1g, t-BuONa 4.4g, Pd 2 (dba) 3 1.1g, (t- Bu) ₃ P (2.5 ml) were dissolved in 200 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 14.2 g (yield: 73%) of Compound 2-3.

m / z: 636.26 (100.0%), 637.26 (52.3%), 638.26 (13.6%), 639.27

Compound 2-4

5.0 g of 9'H-3,3'-bicarbazole, 4.0 g of 3-bromo-1,1'-biphenyl, 1.8 g of t-BuONa and 0.5 g of Pd ₂ (dba) ₃ were added to a round bottom flask. , 0.5 ml of (t-Bu) ₃ P was dissolved in 70 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 5.33 g (yield 67%) of Compound 2-4.

m / z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%

Compound 2-5

To a round bottom flask was added 9 - ([1,1'-biphenyl] -3-yl) -3,6-dibromo-9H-carbazole 5.0g, 9H-carbazole 3.7g, t-BuONa 1.5g, Pd 2 (dba) ₃ and 0.9 ml of (t-Bu) ₃ P were dissolved in 70 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 4.22 g (yield: 62%) of Compound 2-5.

m / z: 649.25 (100.0%), 650.26 (52.3%), 651.26 (13.4%), 652.26 (2.4%

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 is composed of an anode (hole injecting electrode 11) / hole injecting layer 12 / hole transporting layer 13 / light emitting layer 14 / electron transporting layer 15 / 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 of the examples and comparative examples.

Host 1 / host 2 (1: 1) was deposited on a glass substrate to examine the combination of host 1 and host 2 for efficient energy transfer to the phosphorescent dopant formed by the exciplex prior to the fabrication of the organic light emitting device The exciplex wavelength was measured and the results are shown in Table 1 below.

Host 1 Host 2 Host 1: Host 2 compound T1 (eV) compound T1 (eV) Exciplex (nm) Combination example 1 1-1 2.54 2-1 2.87 460 Combination example 2 1-1 2.54 2-2 2.81 467 Combination example 3 1-1 2.54 2-3 2.76 483 Combination example 4 1-1 2.54 2-4 2.76 491 Combination example 5 1-1 2.54 2-5 2.84 468 Combination example 6 1-2 2.57 2-3 2.76 473 Combination example 7 1-3 2.57 2-3 2.76 472 Combination example 8 1-4 2.55 2-3 2.76 480 Combination example 9 1-5 2.57 2-3 2.76 472 Combination example 10 1-6 2.57 2-3 2.76 470 Combination example 11 1-7 2.55 2-3 2.76 481 Combination example 12 1-8 2.52 2-3 2.76 489 Combination example 13 1-9 2.54 2-3 2.76 482 Combination example 14 1-10 2.56 2-3 2.76 473 Combination example 15 1-11 2.56 2-3 2.76 473 Combination example 16 1-12 2.56 2-3 2.76 480 Combination example 17 1-13 2.58 2-3 2.76 470 Combination example 18 1-14 2.57 2-3 2.76 470 Combination example 19 1-15 2.59 2-3 2.76 481 Combination example 20 1-16 2.52 2-3 2.76 488 Combination Comparative Example 1 CBP 2.64 2-3 2.76 X Combination Comparative Example 2 Ref.1 2.53 2-3 2.76 X Combination Comparative Example 3 Ref.2 2.54 2-3 2.76 X Combination Comparative Example 4 Ref.3 2.43 2-3 2.76 512

As shown in Table 1, wavelengths of exciplexes were not observed in combination comparison examples 1 to 3, and wavelengths were observed at 510 nm or more in combination comparison example 4. It can be seen that energy transfer occurs inefficiently considering the absorption wavelength (the rightmost 450nm-500nm region) of the phosphorescent dopant in the green region.

Manufacture of organic light emitting device

Example  One

A thin glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å 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 HI01 of 600 ANGSTROM and a hole transport layer of NPB 250 ANGSTROM. Next, the light emitting layer was doped with 10% of Compound 1-1 / Ir (ppy) ₃ to form a 300 Å layer. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transporting layer, and then 10 Å of LiF and 1000 Å of aluminum (Al) were formed and encapsulated in a glove box to prepare a green organic light emitting device.

Example  2

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

Example  3

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1-4 was used instead of Compound 1-1 as the light emitting layer host.

Example  4

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1-8 was used instead of Compound 1-1 as the light emitting layer host.

Example  5

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1-11 was used instead of Compound 1-1 as the light emitting layer host.

Example  6

A thin glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å 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 HI01 of 600 ANGSTROM and a hole transport layer of NPB 250 ANGSTROM. Next, the light emitting layer was doped with a compound 1-1: a compound 2-3 (6: 4w%) mixture / Ir (ppy) ₃ 10% to form a 300 Å layer. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transporting layer, and then 10 Å of LiF and 1000 Å of aluminum (Al) were formed and encapsulated in a glove box to prepare a green organic light emitting device.

Example  7 to Example  21

Green organic light emitting devices (OLEDs) formed by using the mixture of Compound 1-2 to 1-16: Compound 2-3 (6: 4w%) instead of Compound 1-1: Compound 2-3 as a light emitting layer host in the same manner as in Example 6 Respectively.

Comparative Example  One

A green organic light emitting device was fabricated in the same manner as in Example 1, except that CBP was used 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 Ref.1 was used 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 Ref.2 was used as the light emitting layer host.

Comparative Example  4

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Ref.3 was used 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 device of 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 2.

Op. V QE (%) Cd / A lm / w CIEx CIEy life span@
10000nit Example 1 4.31 17.31 44.68 35.31 0.301 0.621 55 Example 2 4.50 17.19 43.21 35.03 0.301 0.619 52 Example 3 4.31 17.30 44.88 35.22 0.300 0.620 50 Example 4 4.32 17.33 44.81 35.51 0.300 0.622 55 Example 5 4.30 17.35 44.21 35.99 0.299 0.620 54 Example 6 3.98 18.20 54.02 43.24 0.300 0.619 83 Example 7 4.05 18.11 53.01 41.12 0.300 0.618 72 Example 8 4.00 18.25 53.65 40.01 0.302 0.619 72 Example 9 3.98 18.10 54.18 43.12 0.300 0.620 80 Example 10 4.02 18.12 53.25 43.91 0.300 0.623 75 Example 11 4.03 18.06 53.11 40.00 0.301 0.622 81 Example 12 4.00 18.09 53.92 43.91 0.301 0.620 74 Example 13 4.03 18.15 53.01 40.22 0.299 0.620 73 Example 14 3.97 18.21 53.95 43.01 0.301 0.622 78 Example 15 4.02 18.23 53.28 41.00 0.300 0.620 71 Example 16 4.00 18.00 53.25 42.78 0.300 0.622 74 Example 17 3.97 18.07 53.91 43.54 0.299 0.620 82 Example 18 4.00 18.09 53.00 40.11 0.302 0.619 76 Example 19 4.04 18.07 53.01 40.01 0.303 0.615 76 Example 20 4.00 18.04 53.65 43.72 0.301 0.620 79 Example 21 4.00 18.00 53.47 42.00 0.300 0.618 74 Comparative Example 1 5.02 6.43 13.12 7.72 0.301 0.623 - Comparative Example 2 5.01 11.51 30.01 24.83 0.301 0.621 33 Comparative Example 3 5.00 11.10 32.01 25.95 0.302 0.625 30 Comparative Example 4 4.64 12.70 37.40 30.40 0.310 0.611 39

As shown in Table 2, it can be seen that the embodiments of the present invention have a lower driving voltage, higher efficiency, and longer life than those of Comparative Examples 1 to 4, and have excellent physical properties in all respects. Examples of the present invention have dibenzothiophene and dibenzothiophene as coupling groups in triphenylene and heteroaromatic as compared with Comparative Examples 2 to 4, facilitating injection and transport of electrons, And the lifetime is increased. It can be confirmed that the use of the host 2 compound, which is easy to inject and transport holes, brings the driving voltage to a further lowered level and has a long life with good durability even at a high current density. This makes it possible to lower the driving voltage by effectively using the host 2 compound which is easy to inject and transport holes in the host 1 compound which is easy to inject and transport electrons, effectively clog the excitons in the light emitting layer, increase the efficiency, inhibit the roll- off phenomenon at high current density, It has good durability and long life.

Example  22

A green organic luminescent device was fabricated in the same manner as in Example 6 by using Compound 1-1: Compound 2-3 (7: 3w%) as a light emitting layer host.

Example  23

A green organic light emitting device was produced in the same manner as in Example 6, except that Compound 1-1: Compound 2-3 (8: 2w%) was used as a light emitting layer host.

Example  24

A green organic light-emitting device was fabricated in the same manner as in Example 6 by using Compound 1-1: Compound 2-3 (4: 6w%) as a light-emitting layer host.

Example  25

A green organic light-emitting device was fabricated in the same manner as in Example 6 by using Compound 1-1: Compound 2-3 (2: 8w%) as a light-emitting layer host.

Reference example  One

A green organic light-emitting device was fabricated in the same manner as in Example 6 by using Compound 1-1: Compound 2-3 (1: 9w%) as a light-emitting layer host.

For Examples 22 to 25 and Reference Example 1, electrons and holes were injected by applying a voltage to a Kiethley 2400 source measurement unit, and a Konica Minolta spectrophotometer (CS-2000) , The performance of the organic light emitting devices of Examples and Comparative Examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under atmospheric pressure conditions and the results are shown in Table 3 .

Op. V QE (%) Cd / A lm / w CIEx CIEy life span@
10000nit Example 6 3.98 18.20 54.02 43.24 0.300 0.619 83 Example 22 4.00 18.45 55.65 44.00 0.302 0.620 90 Example 23 4.03 18.40 55.18 43.72 0.300 0.619 86 Example 24 3.96 18.01 53.01 42.12 0.300 0.619 80 Example 25 3.93 16.10 43.18 35.12 0.300 0.622 60 Reference Example 1 3.90 12.10 33.18 25.12 0.300 0.624 42

In Table 3, device characteristics according to the combination ratios of Chemical Formula 1 and Chemical Formula 2 were confirmed. As a result, the efficiency and lifetime decreased when the ratios of the compounds of the formulas (1) and (2) were 1: 9, which is a result of excessive injection and transport of holes due to the formula (2) Specifically, the favorable characteristics of the combination of the light emitting host can be confirmed at the ratio of the formula (1) and the formula (2) from 9: 1 to 2: 8.

Claims (14)

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

In this formula,
X is each independently N or CR _0, at least two of X are N, wherein R ₀ is hydrogen; heavy hydrogen; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,
Y is O or S,
R ₁ , R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Alkyl group of deuterium, halogen group, amino group, nitrile group, C _{1 -30,} which is unsubstituted or substituted with nitro; A C ₂ -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of the alkyl group having _{1 -30} C, _-30 C ₂ alkenyl group, C _{2 -30} alkynyl, C _1-30 a, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the of the C _6-30 aryl An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,
m and n are each independently an integer of 0 to 2; The method according to claim 1,
(1) is a compound represented by any one of the following formulas (1-1) to (1-6):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

In the above formulas, X and Y are as defined in formula (1). The method according to claim 1,
Wherein the formula 1 is represented by any one of the following formulas:

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An organic light emitting device comprising at least one organic compound layer containing an anode, a cathode and a compound represented by the general formula (1) according to claim 1 between two electrodes. 5. The method of claim 4,
Wherein the organic material layer is a light emitting layer, an electron injection layer, an electron transporting layer, or a hole blocking layer. 6. The method of claim 5,
Wherein the light emitting layer comprises a compound represented by Formula 1 as a light emitting host. 6. The method of claim 5,
Wherein the light emitting layer comprises the compound represented by Formula 1 (light emitting host 1) and the compound represented by Formula 2 (light emitting host 2)
(2)

In Formula 2, r ₁ to r ₈ each independently represents hydrogen; heavy hydrogen; Alkyl group of deuterium, halogen group, amino group, nitrile group, C _{1 -30,} which is unsubstituted or substituted with nitro; A C ₂ -C 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 halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; Heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the, aryloxy of C _{6 -30} A C _{6 -30} aryl group, or a C _{6 -50} aryl group unsubstituted or substituted with a C _{2 -30} heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} oxy group, a heteroaryl group, a C _6-30 aryl group, or a C _{2 -30} which is unsubstituted or substituted heteroaryl C _{2 -50} of,
Ar is a deuterium, a halogen, an amino group, a nitrile group, a nitro group, a C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} alkoxy group, a C _{6 -30} of the An aryl group having _{6 to 30} carbon _atoms or a C _{6 to 50} aryl group optionally substituted with a C _2-30 heteroaryl group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,
m is an integer of 1 to 4,
When m is 2 to 4, Ar and r1 to r8 may be connected to each other. 8. The method of claim 7,
Wherein the compound represented by Formula 2 is any one of compounds represented by the following Formulas 2-1 to 2-7:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

[Chemical Formula 2-7]

In the above formulas, Ar ₁ , Ar ₂ , Ar ₃ , Ar _{4 , and} Ar ₅ are each independently the same as the definition of Ar in Formula 2,
R ₁ , R ₂ , R ₃ and R ₄ have the same definitions as r ₁ to r _{8 in} the above formula (2)
a and b each independently represent an integer of 0 to 3; 9. The method of claim 8,
Wherein the compound represented by Formula 2 is represented by Formula 2-3.
[Formula 2-3]

In the above formula, Ar ₁ , Ar ₂ and Ar ₃ are each independently the same as defined for Ar in the above formula (2)
R ₁ and R ₂ are as defined for r ₁ to r _{8 in} the above formula (2)
a is an integer of 0 to 3; 8. The method of claim 7,
Wherein the compound represented by Formula 2 is any one of the following Formulas:

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8. The method of claim 7,
And an exciplex emission wavelength formed through the light emitting hosts 1 and 2 is 400-650 nm. 8. The method of claim 7,
And an exciplex light emission wavelength formed through the green light emitting hosts 1 and 2 is 450 to 500 nm. 8. The method of claim 7,
Wherein the mixing ratio of the compound of Formula 1 and Formula 2 is 9: 1 to 2: 8 by weight. 8. The method of claim 7,
Wherein an exciplex emission wavelength formed through the light emitting hosts 1 and 2 is formed at a shorter wavelength than a light emission wavelength of a dopant that is a guest of the light emitting layer.

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