KR102013982B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same, the compound according to the present invention can be used in the organic material layer of the organic electroluminescent device can improve the luminous efficiency, driving voltage, lifespan, etc. of the organic electroluminescent device. have.

Description

Organic compound and organic electroluminescent device including the same TECHNICAL FIELD

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, a novel compound having excellent carrier transporting ability, luminescent ability, and the like, and the compound as a material of an organic material layer, for example, luminous efficiency, driving voltage, and lifetime. It relates to an organic electroluminescent device having improved characteristics such as.

From the observation of organic thin-film emission by Bernanose in the 1950s, the study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') was followed by blue electroluminescence using anthracene single crystal in 1965. In 1987, Tang proposed an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Thereafter, in order to improve the efficiency and lifespan of the organic EL device, it has been developed in the form of introducing a characteristic organic material layer in the device, and also led to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting material may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, it can be divided into yellow and orange light emitting materials required to achieve a better natural color. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically improve luminous efficiency up to four times compared to fluorescence, attention is being paid not only to phosphorescent dopants but also to phosphorescent host materials.

Hole injection layer, hole transport layer to date. As the material used for the hole blocking layer and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. Particularly, phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ , which are blue and green. It is used as a red dopant material. To date, CBP has shown excellent properties as a phosphorescent host material.

However, since the conventional light emitting materials have a low glass transition temperature and very poor thermal stability, the light emitting materials are not satisfactory in terms of lifespan of the organic EL device, and there is a need for improvement in terms of light emission characteristics. Therefore, there is a demand for development of a light emitting material having excellent performance.

Japanese Patent Laid-Open No. 2001-160489

The present invention is excellent in heat resistance, carrier transporting ability, light emitting ability, etc., a novel compound that can be used as an organic material layer material of the organic electroluminescent device, specifically, a light emitting layer material, a life improvement layer material, a light emission auxiliary layer material, or an electron transporting layer material, etc. The purpose is to provide.

Another object of the present invention is to provide an organic electroluminescent device including the novel compound having a low driving voltage, a high luminous efficiency, and an improved lifetime.

The present invention provides a compound represented by Formula 1:

In Chemical Formula 1,

X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ), and Si (Ar ₄ ) (Ar ₅ ) Wherein at least one of X ₁ and X ₂ is N (Ar ₁ );

Y ₁ to Y ₁₂ are the same as or different from each other, and each independently N or C (R ₁ ), wherein when R ₁ is a plurality, they are the same or different;

Ar ₁ to Ar ₅ are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ May be selected from the group consisting of arylamine groups, or may combine with adjacent groups to form a condensed ring,

R ₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ May be selected from the group consisting of arylamine groups, or may combine with adjacent groups to form a condensed ring,

An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group of Ar ₁ to Ar ₅ and R ₁ , an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C ₆ ~ C ₆₀ aryl group, nuclear atom 5 ~ 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group , C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide groups and C ₆ ~ substituted by one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted, wherein the substituents are adjacent tile When combined may form a condensed ring, but the plurality of the above substituents, they may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device characterized in that it comprises a.

Here, according to an example of the present invention, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, wherein at least one organic material layer including the compound represented by Formula 1 Is a light emitting layer or an electron transporting layer.

In addition, according to another example of the present invention, the one or more organic material layers may include a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer. At this time, at least one organic material layer including the compound represented by Formula 1 is a light emission auxiliary layer.

In addition, according to another example of the present invention, the one or more organic material layers may include a hole injection layer, a hole transport layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer. At this time, at least one organic material layer including the compound represented by Formula 1 is a life improvement layer.

Since the compound represented by Formula 1 according to the present invention is excellent in heat resistance, carrier transporting ability, light emitting ability, and the like, it may be used as an organic material layer material of an organic EL device.

In addition, the organic electroluminescent device including the compound according to the present invention can greatly improve aspects such as light emission performance, driving voltage, lifespan, efficiency, etc., and thus can be effectively applied to a full color display panel.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.

1. New Compound

The novel organic compounds according to the present invention are dibenzoazine (5H-dibenzo [b, f] azepine), dibenzooxepine (dibenzo [b, f] oxepine), dibenzothiepine (dibenzo [b, f] thiepine), 5H-dibenzo [b, f] silepine, or 5-membered heteroaromatic ring moiety, indene moiety, in which benzene is condensed to dibenzocycloheptene (5H-dibenzo [a, d] cycloheptene) A tee (indene moiety), or indole moiety (indole moiety) is condensed to form a basic skeleton, characterized in that represented by the formula (1). Since the compound represented by Chemical Formula 1 has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], the glass transition temperature is high, and thus the thermal stability is excellent. In addition, the carrier transporting ability, the light emitting ability and the like are excellent. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.

In general, in the phosphorescent layer of an organic electroluminescent device, the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved. The compound of Formula 1 has a triplet energy of 2.3 eV or more. In addition, the compound represented by the formula (1) can be adjusted higher than the dopant by introducing a specific substituent on the basic skeleton condensed with a broad singlet energy level and indole derivative having a high triplet energy level Can be used as host material.

In addition, since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer. Therefore, when the organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, the exciton is prevented from being diffused by the compound, and thus the first exciton is diffused. Unlike conventional organic electroluminescent devices that do not include a barrier layer, the number of excitons that substantially contribute to light emission in the light emitting layer may be increased, thereby improving the luminous efficiency of the device. In addition, even when an organic material layer (hereinafter, referred to as a "life improvement layer") is formed between the light emitting layer and the electron transport layer by using the compound of Formula 1, the diffusion of excitons by the compound of Formula 1 prevents the organic electric field Durability and stability of the light emitting device can be improved, thereby effectively increasing the half life of the device. As such, the compound represented by Chemical Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material other than the host of the light emitting layer.

In addition, the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport. For example, when the compound has a high electron-absorbing electron withdrawing group (EWG) such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, the entire molecule is Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron. As such, the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used. On the other hand, when the compound of Formula 1 is combined with an electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., the hole injection and transport is smooth. In addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.

As described above, the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics. . Accordingly, the compound of formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / injection layer Material, light emitting auxiliary layer material, life improving layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, and life improving layer material.

In addition, the compound of Formula 1 has a variety of substituents, particularly aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby conventional light emission It may have a higher thermal stability than the material (eg CBP). In addition, the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.

In the compound represented by Formula 1 according to the present invention, X ₁ and X ₂ are the same as or different from each other, and each independently O, S, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ), and Si ( Ar ₄ ) (Ar ₅ ), and are preferably each independently selected from the group consisting of O, S and N (Ar ₁ ). At least one of X ₁ and X ₂ is N (Ar ₁ ).

The compound represented by Formula 1 may be embodied by any one of the following Formulas 2 to 10.

In Chemical Formulas 2 to 10,

Ar ₁ to Ar ₅ and Y ₁ to Y ₁₂ are the same as defined in Chemical Formula 1.

In Formulas 1 to 10, Ar ₁ to Ar ₅ are the same as or different from each other, and each independently a C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atom of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide Groups and C ₆ -C ₆₀ arylamine groups, or can be combined with adjacent groups to form a condensed ring.

Preferably Ar ₁ may be selected from the group consisting of C ₆ ~ C ₆₀ aryl group, and a heteroaryl group of 5 to 60 nuclear atoms.

Preferably Ar ₂ to Ar ₅ is the same as or different from each other, each independently may be selected from the group consisting of an alkyl group of C ₁ ~ C ₄₀ , and an aryl group of C ₆ ~ C ₆₀ , More preferably Ar _{2 To} Ar ₅ Are the same as or different from each other, and may each independently be a methyl group or a phenyl group.

Y ₁ to Y ₁₂ are the same as or different from each other, and each independently N or C (R ₁ ), preferably Y ₁ to Y ₁₂ are all C (R ₁ ) or one of Y ₁ to Y ₁₂ . May be N and the remainder may be C (R ₁ ). At this time, when there are a plurality of R ₁ , they are the same or different.

R ₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ May be selected from the group consisting of arylamine groups, or may be combined with adjacent groups to form a condensed ring.

An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group of Ar ₁ to Ar ₅ and R ₁ , an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently a heavy hydrogen (D), a halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the Heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₅ ~ C ₆₀ heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Aryl silyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl substituted with at least one selected the group consisting of amine group for more substituents or may be unsubstituted, wherein the substituent group adjacent Combine to form a condensed ring. However, when the substituents are plural, they may be the same or different from each other.

In addition, Ar ₁ to Ar ₅ and R ₁ are the same as or different from each other, each independently may be selected from the group consisting of hydrogen (except Ar ₁ to Ar ₅ ) or the following substituents S1 to S204, but is not limited thereto. It is not.

In addition, in Formulas 1 to 10, Ar ₁ and R ₁ are the same as or different from each other, each independently represent a substituent represented by the following formula (11), or a C ₆ ~ C ₆₀ aryl group (for example, phenyl group, biphenyl group, Terphenyl group, fluorene group, etc.),

At this time, the Ar ₁ and R ₁ aryl group is deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C ₆ of the Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ ~ C ₄₀ , aryloxy group of C ₆ ~ C ₆₀ , alkylsilyl group of C ₁ ~ C ₄₀ , C ₆ An arylsilyl group of ˜C ₆₀ , an alkyl boron group of C ₁ ˜C _40, an aryl boron group of C ₆ ˜C ₆₀ , an arylphosphine group of C ₆ ˜C ₆₀ , an arylphosphine oxide group of C ₆ ˜C ₆₀ , and It may be unsubstituted or substituted with one or more substituents selected from the group consisting of C ₆ to C ₆₀ arylamine groups, wherein the substituents may be bonded to adjacent groups to form a condensed ring. It may be the same or different from each other.

In Chemical Formula 11,

L is a single bond or is selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, or may be a phenylene group or a biphenylene group;

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), provided that at least one of Z ₁ to Z ₅ is N, wherein when C (R ₁₁ ) is plural, they are each other; Same or different;

R ₁₁ is hydrogen, deuterium (D), halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5-40 heteroaryl group, C ₆ -C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or to groups bonded adjacent to form a condensed ring Can;

In this case, the alkyl group of said R _11, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group, and aryl The silyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C substituted with one or more substituents selected from the group consisting of arylsilyl ₄₀ or may be unsubstituted, wherein when the substituent of the plurality, It may be the same or different from each other.

Examples of the substituent represented by Formula 11 include a substituent represented by any one of the following Formulas A-1 to A-15, but are not limited thereto.

In Chemical Formulas A-1 to A-15,

L and R ₁₁ are each as defined in Formula 11,

When R ₁₂ is plural, they are the same as or different from each other,

R ₁₂ is hydrogen, deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or to groups bonded adjacent to form a condensed ring Can,

n is an integer from 1 to 4,

In this case, the alkyl group of said R _12, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group, and aryl The silyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C substituted with one or more substituents selected from the group consisting of arylsilyl ₄₀ or may be unsubstituted, wherein when the substituent of the plurality, It may be the same or different from each other.

The compound represented by Formula 1 according to the present invention may be embodied by any one of the following Formulas 12 to 20, but is not limited thereto.

In Chemical Formulas 12 to 20,

Ar ₁ to Ar ₅ are as defined in Formula 1, respectively,

When there are a plurality of Ar ₁ , they are the same as or different from each other.

Examples of the compound represented by Formula 1 according to the present invention include Compounds A-1 to A-23, Compounds B-1 to B-23, Compounds C-1 to C-23, Compounds D-1 to D-23, Compound E-1 to E-23, compound F-1 to F-23, compound G-1 to G-23, compound H-1 to H-23, compound I-1 to I-23, compound J-1 to J-10, compound K-1 to K-10, compound L-1 to L-3, compound M-1 to M-3, compound N-1 to N-3, compound O-1 to O-3, compound P-1 to P-16, compounds Q-1 to Q41, and the like, but are not limited thereto.

As used herein, "unsubstituted alkyl" refers to a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, non-limiting examples of which are methyl, ethyl, propyl, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

As used herein, "unsubstituted cycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms. Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.

As used herein, "unsubstituted heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and at least one carbon in the ring , Preferably 1 to 3 carbons are substituted with a hetero atom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine and the like.

As used herein, "unsubstituted aryl" means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms, alone or in combination of two or more rings. In this case, the two or more rings may be attached in a simple or condensed form with each other. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.

As used herein, "unsubstituted heteroaryl" is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably Preferably 1 to 3 carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). In this case, the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

As used herein, "unsubstituted alkyloxy" refers to a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and is linear, branched or cyclic. ) May include a structure. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

As used herein, "unsubstituted aryloxy" refers to a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

As used herein, "unsubstituted alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms, and " Unsubstituted alkyl boron group "means a boron group substituted with alkyl having 1 to 40 carbon atoms," unsubstituted aryl boron group "means a boron group substituted with aryl having 6 to 60 carbon atoms," unsubstituted aryl Phosphine group "means a phosphine group substituted with an aryl having 1 to 60 carbon atoms," unsubstituted arylamine "means an amine substituted with an aryl having 6 to 60 carbon atoms.

As used herein, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

2. Organic electroluminescent device

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound represented by Formula 1 may be used alone or in combination of two or more.

According to an embodiment of the present invention, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, wherein at least one organic material layer may include a compound represented by Formula 1 Can be. Preferably, the organic material layer including the compound of Formula 1 may be a light emitting layer or an electron transport layer. Optionally, a hole blocking layer may be interposed between the light emitting layer and the electron transport layer.

For example, when the emission layer of the organic EL device includes a host material, the compound represented by Chemical Formula 1 may be included as the host material. As such, when the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a green or red phosphorescent host, the binding force between holes and electrons in the light emitting layer is increased, so that the efficiency of the organic electroluminescent device is increased. (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.

According to another example of the present invention, the at least one organic material layer may include a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer, preferably light emitting auxiliary The layer may comprise a compound of Formula 1 above. Optionally, a hole blocking layer may be interposed between the light emitting layer and the electron transport layer.

In addition, according to another example of the present invention, the one or more organic material layers may include a hole injection layer, a hole transport layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer, preferably The life improvement layer may include the compound of Formula 1. When the compound of Formula 1 is used as a life improving layer material, since the compound has a triplet energy higher than that of the conventional BCP, the life of the organic EL device can be improved.

The structure of the organic EL device according to the present invention described above is not particularly limited, and for example, an anode, one or more layers of organic material and a cathode are sequentially stacked on a substrate, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer. It may be a structure.

Specifically, the organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked on a substrate. Optionally, a light emission auxiliary layer may be interposed between the hole transport layer and the light emitting layer. In addition, a life improvement layer may be interposed between the light emitting layer and the electron transport layer. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer electron injection layer, the light emission auxiliary layer, and the life improvement layer may include a compound represented by the formula (1), preferably a phosphorescent light emitting layer, electrons At least one of the transport layer, the life improvement layer, and the emission auxiliary layer may include the compound represented by Chemical Formula 1.

The organic electroluminescent device of the present invention is formed so that at least one or more of the organic material layers (eg, at least one of the light emitting layer, the electron hydrogen layer, the light emission auxiliary layer, and the life improvement layer) includes the compound represented by Chemical Formula 1 above. May be prepared by forming other organic material layers and electrodes using materials and methods known in the art.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

Preparation Example 1 Synthesis of Compound IAz-1

<Step 1> Synthesis of 1- (5H-dibenzo [b, f] azepin-5-yl) ethanone

5H-dibenzo [b, f] azepine (100.0 g, 517.5 mmol), acetyl chloride (44.3 ml, 621.0 mmol) and toluene (1000 ml) were mixed under nitrogen stream and stirred at 80 ° C. for 2 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, concentrated and recrystallized with ethanol to give 1- (5H-dibenzo [b, f] azepin-5-yl) ethanone (113.2 g, yield 93%).

¹ H-NMR: δ 1.86 (s, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.26-7.45 (m, 8H)

<Step 2> Synthesis of 1- (1aH-dibenzo [b, f] oxireno [2,3-d] azepin-6 (10bH) -yl) ethanone

1 obtained in <Step 1> Preparation of Example 1 in a nitrogen atmosphere (5H-dibenzo [b, f ] azepin-5-yl) ethanone (113.2 g, 481.3 mmol), meta- chloroperoxybenzoic acid (99.7 g, 577.5 mmol) , silica (226.5 g), NaOCl (226.5 g), and acetonitrile (1100 ml) were mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated, the organic layer was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to obtain 1- (1aH-dibenzo [b, f] oxireno [2,3-d] azepin-6 (10bH) -yl) ethanone (87.1 g, yield 72%). .

¹ H-NMR: δ 1.95 (s, 3H), 4.28 (s, 2H), 7.26-7.53 (m, 8H)

Step 3 Synthesis of 5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one

1- (1aH-dibenzo [b, f] oxireno [2,3-d] azepin-6 (10bH) -yl) ethanone (87.1 g, 346.5 mmol) obtained in <Step 2> of Preparation Example 1 under a nitrogen stream; lithium iodide (55.7 g, 415.8 mmol) and chloroform (870 ml) were mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction, the organic layer was extracted with ethyl acetate, followed by water removal with MgSO ₄ , and recrystallization from ethanol to 5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one (70.5 g, yield 81 %) Was obtained.

¹ H-NMR: δ 2.10 (s, 3H), 3.85 (d, 1H), 4.33 (d, 1H), 7.30-7.40 (m, 5H), 7.51-7.59 (m, 2H), 8.10 (d, 1H )

Step 4 Synthesis of 5H-dibenzo [b, f] azepin-10 (11H) -one

5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one (70.5 g, 280.7 mmol) obtained in <Step 3> of Preparation Example 1 under nitrogen stream, potassium hydroxide (17.3 g, 308.7 mmol) And ethylene glycol (700 ml) were mixed and stirred at 200 ° C. for 6 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, and then water was removed with MgSO ₄ , purified by column chromatography (Hexane: EA = 6: 1 (v / v)), and purified by 5H-dibenzo [b, f] azepin-. 10 (11H) -one (52.9 g, yield 90%) was obtained.

¹ H-NMR: δ 3.80 (d, 1H), 4.25 (d, 1H), 7.20-7.35 (m, 5H), 7.45-7.51 (m, 2H), 7.61 (b, 1H), 8.07 (d, 1H )

Step 5 Synthesis of Compound IAz-1

5H-dibenzo [b, f] azepin-10 (11H) -one (52.9 g, 252.6 mmol) and N, N- diphenylhydrazine (51.2 g, 277.9 mmol) obtained in <Step 4> of Preparation Example 1 under nitrogen stream; And acetic acid (500 ml) was added, and stirred at 120 ℃ for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain a compound IAz-1 (66.1 g, yield 73%).

¹ H-NMR of IAz-1: δ 6.68-6.70 (m, 2H), 6.91-6.99 (m, 2H), 7.09 (t, 1H), 7.19-7.25 (m, 7H), 7.34-7.39 (m, 3H), 7.60 (b, 1H), 7.88 (d, 1H), 8.02 (d, 1H)

Preparation Example 2 Synthesis of Compound IAz-2

<Step 1> Synthesis of 5-phenyl-5H-dibenzo [b, f] azepine

5H-dibenzo [b, f] azepine (100 g, 517.5 mmol), iodobenzene (126.7 g, 621.0 mmol), Cu (16.4 g, 258.7 mmol), K ₂ CO ₃ (143.0 g, 1,035.0 mmol) under a nitrogen stream and nitrobenzene (1000 ml) was mixed and stirred at 210 ° C. for 12 h.

After completion of the reaction, the organic layer was extracted with ethyl acetate, concentrated and recrystallized with ethanol to give 5-phenyl-5H-dibenzo [b, f] azepine (100.4 g, 72% yield).

¹ H-NMR: δ 6.63-6.81 (m, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.20 (d, 2H), 7.26-7.45 (m, 8H)

<Step 2> Synthesis of 6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine

Of Preparation Example 2 in a nitrogen stream obtained in <Step 1> 5-phenyl-5H- dibenzo [b, f] azepine (100.4 g, 372.6 mmol), meta- chloroperoxybenzoic acid (77.2 g, 447.1 mmol), silica (200.7 g ), NaOCl (200.7 g) and acetonitrile (1000 ml) were mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated, the organic layer was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to obtain 6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine (84.0 g, 79% yield).

¹ H-NMR: δ 4.31 (s, 2H), 6.63-6.81 (m, 3H), 7.24-7.53 (m, 10H)

<Step 3> Synthesis of 5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) -one

6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine (84.0 g, 294.3 mmol) obtained in <Step 2> of Preparation Example 2 under nitrogen stream, lithium iodide (47.3 g, 353.2 mmol) and chloroform (840 ml) were mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction, the organic layer was extracted with ethyl acetate, and then water was removed with MgSO ₄ and recrystallized from ethanol to 5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) -one (68.0 g, yield). 81%).

¹ H-NMR: δ 3.42 (d, 1H), 4.21 (d, 1H), 6.62-6.74 (m, 3H), 7.25-7.40 (m, 7H), 7.51-7.59 (m, 2H), 8.10 (d , 1H)

Step 4 Synthesis of Compound IAz-2

5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) -one (68.0 g, 238.4 mmol) and phenylhydrazine obtained in <Step 3> of Preparation Example 2 under nitrogen stream (28.4 g, 262.3 mmol), and acetic acid (700 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain a compound IAz-2 (60.7 g, 71% yield).

¹ H-NMR of IAz-2: δ 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 7.08-7.20 (m, 6H), 7.44-7.56 (m, 3H), 8.83 (d, 1H), 11.36 (b, 1H)

Preparation Example 3 Synthesis of Compound IAz-3

<Step 1> Synthesis of 5- (1-bromo-3,5-diphenylbenzene) -5H-dibenzo [b, f] azepine

5H-dibenzo [b, f] azepine (100 g, 517.5 mmol), 1-bromo-3,5-diphenylbenzene (192.0 g, 621.0 mmol), Cu (16.4 g, 258.7 mmol), K ₂ CO ₃ under nitrogen stream (143.0 g, 1,035.0 mmol) and nitrobenzene (1000 ml) were mixed and stirred at 210 ° C for 12 h.

After completion of the reaction, the organic layer was extracted with ethyl acetate, concentrated, and recrystallized with ethanol to give 5- (1-bromo-3,5-diphenylbenzene) -5H-dibenzo [b, f] azepine (146.2 g, 67% yield). Got.

¹ H-NMR: δ 6.63 (d, 2H), 6.81-6.85 (m, 4H), 6.99-7.06 (m, 5H), 7.25 (d, 2H), 7.41-7.52 (m, 10H)

<Step 2> Synthesis of 6- (1-bromo-3,5-diphenylbenzene) -6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine

<Step 1> 5- (1-bromo- 3,5-diphenylbenzene) -5H-dibenzo [b, f] azepine (146.2 g, 346.7 mmol) obtained in Preparation Example 3 was conducted in a nitrogen atmosphere, meta- chloroperoxybenzoic acid (71.8 g, 416.1 mmol), silica (292.3 g), NaOCl (292.3 g), and acetonitrile (1500 ml) were mixed and stirred at 80 ° C. for 2 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to give 6- (1-bromo-3,5-diphenylbenzene) -6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine (113.8 g, yield 75%) was obtained.

¹ H-NMR: δ 4.20 (s, 2H), 6.56 (d, 2H), 6.74 (t, 2H), 6.85 (s, 2H), 7.06-7.13 (m, 5H), 7.41-7.52 (m, 10H )

<Step 3> Synthesis of 5- (1-bromo-3,5-diphenylbenzene) -5H-dibenzo [b, f] azepin-10 (11H) -one

6- (1-bromo-3,5-diphenylbenzene) -6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine obtained in <Step 2> of Preparation Example 3 under nitrogen stream (113.8 g, 260.0 mmol), lithium iodide (41.8 g, 312.0 mmol) and chloroform (1100 ml) were mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction, the organic layer was extracted with ethyl acetate and then water was removed with MgSO ₄ , and recrystallized from ethanol to give 5- (1-bromo-3,5-diphenylbenzene) -5H-dibenzo [b, f] azepin-10 ( 11H) -one (89.9 g, yield 79%) was obtained.

¹ H-NMR: δ 3.41 (d, 1H), 4.20 (d, 1H), 6.51 (d, 1H), 6.69-6.74 (m, 2H), 6.85 (s, 2H), 6.92-7.06 (m, 4H ), 7.39-7.54 (m, 12H)

Step 4 Synthesis of Compound IAz-3

5- (1-bromo-3,5-diphenylbenzene) -5H-dibenzo [b, f] azepin-10 (11H) -one (89.9 g, 205.4 mmol) obtained in <Step 3> of Preparation Example 3 under nitrogen stream And phenylhydrazine (24.4 g, 226.0 mmol), and acetic acid (900 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain a compound IAz-3 (69.2 g, 66% yield).

¹ H-NMR of IAz-3: δ 6.69-6.70 (m, 2H), 6.85-6.87 (m, 4H), 7.08-7.16 (m, 5H), 7.41-7.54 (m, 13H), 8.83 (d, 1H), 11.36 (b, 1H)

Preparation Example 4 Synthesis of Compound IAz-4

Step 1 Synthesis of 5-acetyl-10,11- (1H-indolo) -5H-dibenzo [b, f] azepin

5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one (70.5 g, 280.7 mmol) and phenylhydrazine obtained in <Step 3> of Preparation Example 1 under nitrogen stream (33.4 g, 308.7 mmol) and acetic acid (700 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, followed by water removal with MgSO ₄ , and recrystallization from ethanol to 5-acetyl-10,11- (1H-indolo) -5H-dibenzo [b, f] azepin (59.2 g, yield 65%).

¹ H-NMR: δ 2.04 (s, 3H), 7.08-7.10 (m, 2H), 7.25-7.27 (m, 2H), 7.39-7.44 (m, 3H), 7.56 (d, 1H), 7.77-7.87 (m, 3H), 9.06 (d, 1H), 11.36 (b, 1H)

<Step 2> Synthesis of 5-acetyl-10,11- [1- (1-bromo-3,5-diphenylbenzene) -1H-indolo] -5H-dibenzo [b, f] azepin

5-acetyl-10,11- (1H-indolo) -5H-dibenzo [b, f] azepin (59.2 g, 182.4 mmol), 1-bromo-3, obtained in <Step 1> of Preparation Example 4 under nitrogen stream 5-diphenylbenzene (67.7 g, 218.9 mmol), Cu (5.8 g, 91.2 mmol), K ₂ CO ₃ (50.4 g, 364.9 mmol) and nitrobenzene (600 ml) were mixed and stirred at 210 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, and then water was removed with MgSO ₄ and recrystallized from ethanol to 5-acetyl-10,11- [1- (1-bromo-3,5-diphenylbenzene) -1H- indolo] -5H-dibenzo [b, f] azepin (67.6 g, yield 67%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.25-7.26 (m, 2H), 7.39-7.52 (m, 14H), 7.71-7.77 (m, 2H), 7.87-7.88 (m, 3H), 8.05 -8.06 (m, 2H), 8.17 (d, 1H), 9.06 (d, 1H)

Step 3 Synthesis of Compound IAz-4

5-acetyl-10,11- [1- (1-bromo-3,5-diphenylbenzene) -1H-indolo] -5H-dibenzo [b, f] azepin obtained in <Step 2> of Preparation Example 4 under nitrogen stream (67.6 g, 122.2 mmol), potassium hydroxide (7.5 g, 134.4 mmol) and ethylene glycol (700 ml) were mixed and stirred at 200 ° C. for 6 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, and then water was removed using MgSO ₄ , and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to give a compound IAz-4 (53.1 g, yield 85 %) Was obtained.

¹ H-NMR of IAz-4: δ 6.68-6.69 (m, 2H), 6.87-6.88 (m, 2H), 7.16-7.17 (m, 2H), 7.42-7.54 (m, 13H), 7.60 (b, 1H), 7.71 (d, 1H), 7.88 (s, 1H), 8.05-8.06 (m, 2H), 8.17 (d, 1H), 8.83 (d, 1H)

Preparation Example 5 Synthesis of Compound IAz-5

Step 1 Synthesis of 5-acetyl-10,11- (7-phenyl-1H-indolo) -5H-dibenzo [b, f] azepin

5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one (70.5 g, 280.7 mmol) and biphenyl-2-ylhydrazine obtained in <Step 3> of Preparation Example 1 under nitrogen stream (56.9 g, 308.7 mmol), and acetic acid (700 ml) were mixed and then stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, then water was removed with MgSO ₄ , and recrystallized from ethanol to 5-acetyl-10,11- (7-phenyl-1H-indolo) -5H-dibenzo [b, f] Azepin (66.3 g, yield 59%) was obtained.

¹ H-NMR: δ 2.03 (s, 3H), 7.14-7.25 (m, 5H), 7.39-7.52 (m, 6H), 7.77-7.87 (m, 4H), 9.06 (d, 1H), 11.36 (b , 1H)

<Step 2> Synthesis of 5-acetyl-10,11- (1,7-diphenyl-1H-indolo) -5H-dibenzo [b, f] azepin

5-acetyl-10,11- (7-phenyl-1H-indolo) -5H-dibenzo [b, f] azepin (66.3 g, 165.6 mmol) and iodobenzene obtained in <Step 1> of Preparation Example 4 under nitrogen stream 40.5 g, 198.7 mmol), Cu (5.3 g, 82.8 mmol), K ₂ CO ₃ (45.8 g, 331.2 mmol) and nitrobenzene (650 ml) were mixed and stirred at 210 ° C for 12 h.

After completion of the reaction, the organic layer was extracted with ethyl acetate and then water was removed with MgSO ₄ , and recrystallized from ethanol to 5-acetyl-10,11- (1,7-diphenyl-1H-indolo) -5H-dibenzo [b, f] azepin (56.0 g, 71% yield) was obtained.

¹ H-NMR: δ 2.03 (s, 3H), 7.19-7.25 (m, 4H), 7.39-7.58 (m, 11H), 7.77 (d, 1H), 7.87-7.88 (m, 2H), 8.13 (d , 1H), 8.39 (d, 1H), 9.06 (d, 1H)

Step 3 Synthesis of Compound IAz-5

5-acetyl-10,11- (1,7-diphenyl-1H-indolo) -5H-dibenzo [b, f] azepin (56.0 g, 117.6 mmol) obtained in <Step 2> of Preparation Example 4 under nitrogen stream, Potassium hydroxide (7.3 g, 129.3 mmol) and ethylene glycol (550 ml) were mixed and stirred at 200 ° C. for 6 hours.

After completion of the reaction, the organic layer was extracted with ethyl acetate, and then water was removed with MgSO ₄ , and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give a compound IAz-5 (45.0 g, yield 88). %) Was obtained.

¹ H-NMR of IAz-5: δ 6.69-6.70 (m, 2H), 6.86-6.87 (m, 2H), 7.16-7.19 (m, 4H), 7.41-7.58 (m, 10H), 7.60 (b, 1H), 8.13 (d, 1H), 8.39 (d, 1H), 8.83 (d, 1H)

Preparation Example 6 Synthesis of Compound IAz-6

<Step 1> Synthesis of 1a, 10b-dihydrodibenzo [b, f] oxireno [2,3-d] oxepine

In a nitrogen atmosphere dibenzo [b, f] oxepine ( 100.0 g, 514.9 mmol), meta- chloroperoxybenzoic acid (106.6 g, 617.8 mmol), silica (200.0 g), NaOCl (200.0 g), and acetonitrile (1000 ml) were mixed and stirred at 80 ° C. for 2 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to obtain 1a, 10b-dihydrodibenzo [b, f] oxireno [2,3-d] oxepine (87.7 g, yield 81%).

¹ H-NMR: δ 4.30 (s, 2H), 7.10 (d, 2H), 7.26-7.34 (m, 6H)

<Step 2> Synthesis of dibenzo [b, f] oxepin-10 (11H) -one

1a, 10b-dihydrodibenzo [b, f] oxireno [2,3-d] oxepine (87.7 g, 417.0 mmol) obtained in <Step 1> of Preparation Example 6 under nitrogen stream, lithium iodide (67.0 g, 500.4 mmol) and Chloroform (900 ml) was mixed and stirred at 60 ° C for 1 hour.

After completion of the reaction, the organic layer was extracted with ethyl acetate, water was removed with MgSO ₄ and recrystallized from ethanol to obtain dibenzo [b, f] oxepin-10 (11H) -one (69.3 g, yield 79%).

¹ H-NMR: δ 3.51 (d, 1H), 4.42 (d, 1H), 7.05 (t, 1H), 7.19-7.28 (m, 4H), 7.43-7.44 (m, 2H), 7.60 (t, 1H )

Step 3 Synthesis of Compound IAz-6

Dibenzo [b, f] oxepin-10 (11H) -one (69.3 g, 329.5 mmol) and phenylhydrazine obtained in <Step 2> of Preparation Example 6 under nitrogen stream (39.2 g, 362.4 mmol), and acetic acid (700 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain a compound IAz-6 (60.7 g, 65% yield).

¹ H-NMR of IAz-6: δ 7.08-7.09 (m, 2H), 7.20-7.23 (m, 4H), 7.37-7.44 (m, 3H), 7.56 (d, 1H), 7.75 (d, 1H) , 8.39 (d, 1 H), 11.36 (b, 1 H)

Preparation Example 7 Synthesis of Compound IAz-7

Dibenzo [b, f] oxepin-10 (11H) -one (69.3 g, 329.5 mmol) and biphenyl-2-ylhydrazine obtained in <Step 2> of Preparation Example 6 under a nitrogen stream. (66.8 g, 362.4 mmol), and acetic acid (700 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain a compound IAz-7 (55.1 g, 59% yield).

¹ H-NMR of IAz-7: δ 7.14-7.23 (m, 7H), 7.37-7.52 (m, 6H), 7.75-7.78 (m, 2H), 8.39 (d, 1H), 11.36 (b, 1H)

Preparation Example 8 Synthesis of Compound IAz-8

<Step 1> Synthesis of 1a, 10b-dihydrodibenzo [b, f] oxireno [2,3-d] thiepine

In a nitrogen atmosphere dibenzo [b, f] thiepine ( 100.0 g, 475.5 mmol), meta- chloroperoxybenzoic acid (98.5 g, 570.6 mmol), silica (200.0 g), NaOCl (200.0 g), and acetonitrile (1000 ml) were mixed and stirred at 80 ° C. for 2 hours.

After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent from the obtained organic layer, it was recrystallized with ethanol to give 1a, 10b-dihydrodibenzo [b, f] oxireno [2, 3-d] thiepine (80.7 g, yield 75%).

¹ H-NMR: δ 4.40 (s, 2H), 7.12-7.16 (m, 4H), 7.45 (t, 2H), 7.70 (d, 2H)

<Step 2> Synthesis of dibenzo [b, f] thiepin-10 (11H) -one

1a, 10b-dihydrodibenzo [b, f] oxireno [2,3-d] thiepine (80.7 g, 356.7 mmol) and lithium iodide (57.3.0 g, 428.0 mmol) obtained in <Step 1> of Preparation Example 8 under nitrogen stream ) And chloroform (800 ml) were mixed and stirred at 60 ° C for 1 hour.

After completion of the reaction, the organic layer was extracted with ethyl acetate, water was removed with MgSO ₄ and recrystallized from ethanol to obtain dibenzo [b, f] thiepin-10 (11H) -one (59.7 g, 74% yield).

¹ H-NMR: δ 3.61 (d, 1H), 4.47 (d, 1H), 7.03-7.07 (m, 2H), 7.30-7.33 (m, 2H), 7.44-7.52 (m, 2H), 7.65 (d , 1H), 7.74 (d, 1H)

Step 3 Synthesis of Compound IAz-8

Dibenzo [b, f] thiepin-10 (11H) -one (59.7 g, 263.9 mmol) and phenylhydrazine obtained in <Step 2> of Preparation Example 8 under nitrogen stream (31.4 g, 290.3 mmol), and acetic acid (600 ml) were mixed and then stirred at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give the compound IAz-8 (42.7 g, 54% yield).

¹ H-NMR of IAz-8: δ 7.09-7.10 (m, 2H), 7.21-7.25 (m, 4H), 7.44-7.59 (m, 6H), 11.36 (b, 1H)

Preparation Example 9 Synthesis of Compound IAz-9

Dibenzo [b, f] thiepin-10 (11H) -one (59.7 g, 263.9 mmol) and biphenyl-2-ylhydrazine obtained in <Step 2> of Preparation Example 8 under nitrogen stream (53.5 g, 290.3 mmol), and acetic acid (600 ml) were mixed and then stirred at 120 ° C. for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain a compound IAz-9 (50.5 g, 51% yield).

¹ H-NMR of IAz-9: δ 7.14-7.25 (m, 7H), 7.41-7.59 (m, 8H), 7.78 (d, 1H), 11.36 (b, 1H)

Synthesis Example 1 Synthesis of Compound A-1

IAz-1 (2.4 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 1 under a nitrogen stream, P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain Compound A-1 (2.5 g, 64% yield).

Mass (Theoretical value: 587.24, Measured value: 587 g / mol)

Synthesis Example 2 Synthesis of Compound A-2

A compound was prepared in the same manner as in Synthesis Example 1, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. A-2 (2.4 g, yield 61%) was obtained.

Mass (Theoretical value: 587.24, Measured value: 587 g / mol)

Synthesis Example 3 Synthesis of Compound A-3

A compound was prepared in the same manner as in Synthesis Example 1, except that 2-bromo-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. A-3 (2.7 g, yield 69%) was obtained.

Mass (Theoretical value: 588.23, Measured value: 588 g / mol)

Synthesis Example 4 Synthesis of Compound A-4

A compound was prepared in the same manner as in Synthesis Example 1, except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. A-4 (2.9 g, yield 73%) was obtained.

Mass (Theoretical value: 588.23, Measured value: 588 g / mol)

Synthesis Example 5 Synthesis of Compound A-5

Synthesis example except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-5 (2.8 g, yield 70%) was obtained in the same manner as 1.

Mass (Theoretical value: 589.23, Measured value: 589 g / mol)

Synthesis Example 6 Synthesis of Compound A-6

The same procedure as in Synthesis Example 1 except for using 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-6 (3.0 g, yield 68%) was obtained.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 7 Synthesis of Compound A-7

The same procedure as in Synthesis Example 1 except for using 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 The compound A-7 (2.7 g, 61% yield) was obtained by operation.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 8 Synthesis of Compound A-8

The same procedure as in Synthesis Example 1 except for using 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-8 (3.1 g, yield 70%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

[ Synthesis Example  9] Synthesis of Compound A-9

The same procedure as in Synthesis Example 1 except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-9 (3.3 g, yield 74%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 10 Synthesis of Compound A-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Was obtained in the same manner as in Synthesis example 1 to obtain compound A-10 (2.9 g, yield 65%).

Mass (Theoretical value: 665.26, Measured value: 665 g / mol)

Synthesis Example 11 Synthesis of Compound A-11

The same procedure as in Synthesis Example 1 except for using 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-11 (2.8 g, yield 62%) was obtained.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 12 Synthesis of Compound A-12

The same procedure as in Synthesis Example 1 except for using 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-12 (3.0 g, yield 68%) was obtained.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 13 Synthesis of Compound A-13

The same procedure as in Synthesis Example 1 except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-13 (2.9 g, yield 66%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 14 Synthesis of Compound A-14

The same procedure as in Synthesis Example 1 except for using 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-14 (3.2 g, yield 73%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 15 Synthesis of Compound A-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Was obtained in the same manner as in Synthesis example 1 to obtain compound A-15 (3.2 g, yield 71%).

Mass (Theoretical value: 665.26, Measured value: 665 g / mol)

Synthesis Example 16 Synthesis of Compound A-16

Compound A- was prepared by the same procedure as in Synthesis Example 1, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. 16 (2.6 g, yield 68%) was obtained.

Mass (Theoretical value: 562.22, Measured value: 562 g / mol)

Synthesis Example 17 Synthesis of Compound A-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1, Compound A-17 (3.1 g, yield 67%) was obtained in the same manner as in Synthesis example 1.

Mass (Theoretical value: 688.26, Measured value: 688 g / mol)

Synthesis Example 18 Synthesis of Compound A-18

The same procedure as in Synthesis Example 1 except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. The procedure was carried out to obtain compound A-18 (3.2 g, yield 78%).

Mass (Theoretical value: 616.20, Measured value: 616 g / mol)

Synthesis Example 19 Synthesis of Compound A-19

A compound was prepared in the same manner as in Synthesis Example 1, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. A-19 (2.5 g, yield 71%) was obtained.

Mass (Theoretical value: 524.19, Measured value: 524 g / mol)

Synthesis Example 20 Synthesis of Compound A-20

Compound A was carried out in the same manner as in Synthesis Example 1, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. -20 (3.3 g, yield 75%) was obtained.

Mass (Theoretical value: 660.26, Measured value: 660 g / mol)

Synthesis Example 21 Synthesis of Compound A-21

The same procedure as in Synthesis Example 1 was performed except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. Compound A-21 (2.2 g, yield 64%) was obtained.

Mass (Theoretical value: 512.20, Measured value: 512 g / mol)

Synthesis Example 22 Synthesis of Compound A-22

Compound A was carried out in the same manner as in Synthesis Example 1, except that 3'-bromobiphenyl-4-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1. -22 (2.4 g, yield 68%) was obtained.

Mass (Theoretical value: 535.21, Measured value: 535 g / mol)

Synthesis Example 23 Synthesis of Compound A-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 1 Compound A-23 (3.1 g, yield 62%) was obtained in the same manner as the example 1.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 24 Synthesis of Compound B-1

Compounds IAz-2 (2.4 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 2 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound B-1 (2.6 g, 66% yield).

Mass (Theoretical value: 587.24, Measured value: 587 g / mol)

Synthesis Example 25 Synthesis of Compound B-2

A compound was prepared in the same manner as in Synthesis Example 24, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. B-2 (2.7 g, yield 69%) was obtained.

Mass (Theoretical value: 587.24, Measured value: 587 g / mol)

Synthesis Example 26 Synthesis of Compound B-3

A compound was prepared in the same manner as in Synthesis Example 24, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. B-3 (2.4 g, yield 62%) was obtained.

Mass (Theoretical value: 588.23, Measured value: 588 g / mol)

Synthesis Example 27 Synthesis of Compound B-4

A compound was prepared in the same manner as in Synthesis Example 24, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. B-4 (2.8 g, yield 72%) was obtained.

Mass (Theoretical value: 588.23, Measured value: 588 g / mol)

Synthesis Example 28 Synthesis of Compound B-5

Synthesis example except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 Compound B-5 (2.4 g, yield 61%) was obtained in the same manner as the 24.

Mass (Theoretical value: 589.23, Measured value: 589 g / mol)

Synthesis Example 29 Synthesis of Compound B-6

Same procedure as in Synthesis Example 24, except that 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 Compound B-6 (2.9 g, yield 65%) was obtained.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 30 Synthesis of Compound B-7

The same process as in Synthesis Example 24, except that 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. To give compound B-7 (3.3 g, yield 74%).

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 31 Synthesis of Compound B-8

Same procedure as in Synthesis Example 24, except that 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 To give compound B-8 (3.5 g, yield 78%).

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 32 Synthesis of Compound B-9

Same procedure as in Synthesis Example 24, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 Compound B-9 (3.1 g, yield 70%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 33 Synthesis of Compound B-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 Was obtained in the same manner as in Synthesis Example 24 to obtain Compound B-10 (2.7 g, 61% yield).

Mass (Theoretical value: 665.26, Measured value: 665 g / mol)

Synthesis Example 34 Synthesis of Compound B-11

The same procedure as in Synthesis Example 24, except that 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. Compound B-11 (3.0 g, yield 61%) was obtained.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 35 Synthesis of Compound B-12

The same procedure as in Synthesis Example 24, except that 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. The compound B-12 (2.8 g, yield 64%) was obtained by the following.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 36 Synthesis of Compound B-13

The same procedure as in Synthesis Example 24, except that 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. Compound B-13 (2.9 g, yield 65%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 37 Synthesis of Compound B-14

The same procedure as in Synthesis Example 24, except that 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. Compound B-14 (3.1 g, yield 70%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 38 Synthesis of Compound B-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 Was obtained in the same manner as in Synthesis Example 24 to obtain Compound B-15 (3.3 g, 73% yield).

Mass (Theoretical value: 665.26, Measured value: 665 g / mol)

Synthesis Example 39 Synthesis of Compound B-16

Compound B- was prepared by the same procedure as in Synthesis Example 24, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. 16 (2.7 g, yield 72%) was obtained.

Mass (Theoretical value: 562.22, Measured value: 562 g / mol)

Synthesis Example 40 Synthesis of Compound B-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24, Compound B-17 (3.6 g, yield 77%) was obtained in the same manner as the synthesis example 24.

Mass (Theoretical value: 688.26, Measured value: 688 g / mol)

Synthesis Example 41 Synthesis of Compound B-18

Same as Synthesis Example 24, except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 The procedure was followed to obtain compound B-18 (2.7 g, 66% yield).

Mass (Theoretical value: 616.20, Measured value: 616 g / mol)

Synthesis Example 42 Synthesis of Compound B-19

A compound was prepared in the same manner as in Synthesis Example 24, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. B-19 (2.3 g, yield 65%) was obtained.

Mass (Theoretical value: 524.19, Measured value: 524 g / mol)

Synthesis Example 43 Synthesis of Compound B-20

Compound B was carried out in the same manner as in Synthesis Example 24, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. -20 (3.1 g, yield 69%) was obtained.

Mass (Theoretical value: 660.26, Measured value: 660 g / mol)

Synthesis Example 44 Synthesis of Compound B-21

The same procedure as in Synthesis Example 24 was performed except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. Compound B-21 (2.1 g, yield 61%) was obtained.

Mass (Theoretical value: 512.20, Measured value: 512 g / mol)

Synthesis Example 45 Synthesis of Compound B-22

Compound B was carried out in the same manner as in Synthesis Example 24, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24. -22 (2.2 g, yield 60%) was obtained.

Mass (Theoretical value: 535.21, Measured value: 535 g / mol)

Synthesis Example 46 Synthesis of Compound B-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 24 Compound B-23 (3.5 g, yield 70%) was obtained in the same manner as the Example 24.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 47 Synthesis of Compound C-1

Compounds IAz-3 (3.4 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 3 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound C-1 (3.0 g, 61% yield).

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 48 Synthesis of Compound C-2

Except for using 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) in place of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47, the same procedure as in Synthesis Example 47 was performed. Compound C-2 (3.6 g, yield 73%) was obtained.

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 49 Synthesis of Compound C-3

A compound was prepared in the same manner as in Synthesis Example 47, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. C-3 (3.7 g, yield 75%) was obtained.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 50 Synthesis of Compound C-4

A compound was prepared in the same manner as in Synthesis Example 47, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. C-4 (3.2 g, yield 65%) was obtained.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 51 Synthesis of Compound C-5

Synthesis example except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47 Compound C-5 (3.3 g, yield 66%) was obtained by the same procedure as 47.

Mass (Theoretical value: 741.29, Measured value: 741 g / mol)

Synthesis Example 52 Synthesis of Compound C-6

The same procedure as in Synthesis 47 except that 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. To give C-6 (4.3 g, yield 78%).

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 53 Synthesis of Compound C-7

The same procedure as in Synthesis 47 except that 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. Compound C-7 (3.9 g, yield 71%) was obtained.

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 54 Synthesis of Compound C-8

The same procedure as in Synthesis 47 except for using 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. Compound C-8 (3.8 g, yield 70%) was obtained.

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 55 Synthesis of Compound C-9

The same procedure as in Synthesis 47 except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. Compound C-9 (3.7 g, yield 68%) was obtained.

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 56 Synthesis of Compound C-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47 Was obtained in the same manner as in Synthesis Example 47 to obtain compound C-10 (3.7 g, yield 67%).

Mass (Theoretical value: 817.32, Measured value: 817 g / mol)

Synthesis Example 57 Synthesis of Compound C-11

The same procedure as in Synthesis 47 except for using 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. Was carried out to give compound C-11 (3.3 g, yield 60%).

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 58 Synthesis of Compound C-12

The same procedure as in Synthesis 47 except for using 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. Compound C-12 (3.3 g, yield 61%) was obtained.

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 59 Synthesis of Compound C-13

The same procedure as in Synthesis 47 except that 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. Compound C-13 (3.6 g, yield 65%) was obtained.

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 60 Synthesis of Compound C-14

The same procedure as in Synthesis 47 except for using 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. Compound C-14 (3.9 g, yield 72%) was obtained.

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 61 Synthesis of Compound C-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47 Was obtained in the same manner as in Synthesis Example 47 to obtain compound C-15 (4.2 g, yield 77%).

Mass (Theoretical value: 817.32, Measured value: 817 g / mol)

Synthesis Example 62 Synthesis of Compound C-16

Compound C- was prepared by the same procedure as in Synthesis Example 47, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. 16 (3.6 g, yield 76%) was obtained.

Mass (Theoretical value: 714.28, Measured value: 714 g / mol)

Synthesis Example 63 Synthesis of Compound C-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47, Compound C-17 (3.6 g, yield 64%) was obtained in the same manner as the synthesis example 47.

Mass (Theoretical value: 840.32, Measured value: 840 g / mol)

Synthesis Example 64 Synthesis of Compound C-18

Except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47, The procedure was followed to obtain compound C-18 (3.2 g, yield 62%).

Mass (Theoretical value: 768.26, Measured value: 768 g / mol)

Synthesis Example 65 Synthesis of Compound C-19

A compound was prepared in the same manner as in Synthesis Example 47, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. C-19 (3.1 g, yield 68%) was obtained.

Mass (Theoretical value: 676.25, Measured value: 676 g / mol)

Synthesis Example 66 Synthesis of Compound C-20

Compound C was carried out in the same manner as in Synthesis Example 47, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. -20 (3.9 g, yield 72%) was obtained.

Mass (Theoretical value: 812.32, Measured value: 812 g / mol)

Synthesis Example 67 Synthesis of Compound C-21

Except for using 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47, the same procedure as in Synthesis Example 47 was carried out. Compound C-21 (2.4 g, yield 76%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 68 Synthesis of Compound C-22

Compound C was carried out in the same manner as in Synthesis Example 47, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47. -22 (3.5 g, yield 75%) was obtained.

Mass (Theoretical value: 687.27, Measured value: 687 g / mol)

Synthesis Example 69 Synthesis of Compound C-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 47 Compound C-23 (3.9 g, yield 65%) was obtained in the same manner as the Example 47.

Mass (Theoretical value: 892.35, Measured value: 892 g / mol)

Synthesis Example 70 Synthesis of Compound D-1

Compounds IAz-4 (3.4 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 4 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound D-1 (3.1 g, yield 63%).

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 71 Synthesis of Compound D-2

A compound was prepared in the same manner as in Synthesis Example 70, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. D-2 (3.3 g, yield 66%) was obtained.

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 72 Synthesis of Compound D-3

A compound was prepared in the same manner as in Synthesis Example 70, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. D-3 (3.4 g, yield 68%) was obtained.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 73 Synthesis of Compound D-4

A compound was prepared in the same manner as in Synthesis Example 70, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. D-4 (3.1 g, yield 62%) was obtained.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 74 Synthesis of Compound D-5

Synthesis example except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Compound D-5 (3.4 g, 69% yield) was obtained by the same procedure as 70.

Mass (Theoretical value: 741.29, Measured value: 741 g / mol)

Synthesis Example 75 Synthesis of Compound D-6

The same procedure as in Synthesis Example 70 except for using 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Compound D-6 (3.9 g, yield 71%) was obtained.

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 76 Synthesis of Compound D-7

The same procedure as in Synthesis Example 70 except for using 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Compound D-7 (3.6 g, yield 65%) was obtained.

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 77 Synthesis of Compound D-8

The same procedure as Synthesis Example 70 except for using 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Was carried out to give compound D-8 (3.4 g, yield 63%).

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 78 Synthesis of Compound D-9

The same procedure as in Synthesis Example 70 except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Was carried out to give compound D-9 (3.7 g, yield 67%).

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 79 Synthesis of Compound D-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Was obtained in the same manner as in Synthesis Example 70 to obtain Compound D-10 (3.5 g, 64% yield).

Mass (Theoretical value: 817.32, Measured value: 817 g / mol)

Synthesis Example 80 Synthesis of Compound D-11

The same procedure as in Synthesis Example 70 except for using 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Was carried out to give compound D-11 (3.6 g, yield 66%).

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 81 Synthesis of Compound D-12

The same procedure as in Synthesis Example 70 except for using 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Was carried out to give compound D-12 (3.3 g, yield 60%).

Mass (Theoretical value: 815.33, Measured value: 815 g / mol)

Synthesis Example 82 Synthesis of Compound D-13

The same procedure as in Synthesis Example 70 except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Compound D-13 (3.4 g, yield 62%) was obtained.

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 83 Synthesis of Compound D-14

The same procedure as in Synthesis Example 70, except that 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. Was carried out to give compound D-14 (3.7 g, yield 68%).

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 84 Synthesis of Compound D-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Was prepared in the same manner as in Synthesis Example 70 to obtain Compound D-15 (3.8 g, 70% yield).

Mass (Theoretical value: 817.32, Measured value: 817 g / mol)

Synthesis Example 85 Synthesis of Compound D-16

Compound D- was prepared by the same procedure as in Synthesis Example 70, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. 16 (3.0 g, yield 63%) was obtained.

Mass (Theoretical value: 714.28, Measured value: 714 g / mol)

Synthesis Example 86 Synthesis of Compound D-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70, Compound D-17 (4.0 g, yield 71%) was obtained in the same manner as the synthesis example 70.

Mass (Theoretical value: 840.32, Measured value: 840 g / mol)

Synthesis Example 87 Synthesis of Compound D-18

Synthesis Example 70 Except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine, which was used in Synthesis Example 70 The procedure was followed to obtain compound D-18 (3.8 g, yield 74%).

Mass (Theoretical value: 768.26, Measured value: 768 g / mol)

Synthesis Example 88 Synthesis of Compound D-19

A compound was prepared in the same manner as in Synthesis Example 70, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. D-19 (3.3 g, yield 72%) was obtained.

Mass (Theoretical value: 676.25, Measured value: 676 g / mol)

Synthesis Example 89 Synthesis of Compound D-20

Compound D was carried out in the same manner as in Synthesis Example 70, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. -20 (3.8 g, yield 70%) was obtained.

Mass (Theoretical value: 812.32, Measured value: 812 g / mol)

Synthesis Example 90 Synthesis of Compound D-21

The same procedure as in Synthesis Example 70 was carried out except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. Compound D-21 (2.9 g, yield 65%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 91 Synthesis of Compound D-22

Compound D was carried out in the same manner as in Synthesis Example 70, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70. -22 (2.8 g, yield 61%) was obtained.

Mass (Theoretical value: 687.27, Measured value: 687 g / mol)

Synthesis Example 92 Synthesis of Compound D-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 70 Compound D-23 (3.9 g, yield 66%) was obtained in the same manner as the Example 70.

Mass (Theoretical value: 892.35, Measured value: 892 g / mol)

Synthesis Example 93 Synthesis of Compound E-1

Compound IAz-5 (2.9 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 5 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound E-1 (2.9 g, yield 65%).

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 94 Synthesis of Compound E-2

A compound was prepared in the same manner as in Synthesis Example 93, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. E-2 (3.2 g, yield 71%) was obtained.

Mass (Theoretical value: 663.27, Measured value: 663 g / mol)

Synthesis Example 95 Synthesis of Compound E-3

A compound was prepared in the same manner as in Synthesis Example 93, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. E-3 (2.9 g, yield 66%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 96 Synthesis of Compound E-4

A compound was prepared in the same manner as in Synthesis Example 93, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. E-4 (3.0 g, yield 67%) was obtained.

Mass (Theoretical value: 664.26, Measured value: 664 g / mol)

Synthesis Example 97 Synthesis of Compound E-5

Synthesis example except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93 Compound E-5 (2.7 g, 61% yield) was obtained by the same procedure as 93.

Mass (Theoretical value: 665.26, Measured value: 665 g / mol)

Synthesis Example 98 Synthesis of Compound E-6

The same procedure as in Synthesis Example 93 except that 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Compound E-6 (3.8 g, yield 76%) was obtained.

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 99 Synthesis of Compound E-7

The same procedure as in Synthesis 93 except for using 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. To give compound E-7 (3.4 g, yield 69%).

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 100 Synthesis of Compound E-8

The same procedure as in Synthesis Example 93 except that 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Was carried out to give compound E-8 (3.2 g, yield 64%).

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 101 Synthesis of Compound E-9

The same procedure as in Synthesis Example 93 except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Compound E-9 (3.1 g, yield 62%) was obtained.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 102 Synthesis of Compound E-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93 Was obtained in the same manner as in Synthesis Example 93 to obtain Compound E-10 (3.6 g, 73% yield).

Mass (Theoretical value: 741.29, Measured value: 741 g / mol)

Synthesis Example 103 Synthesis of Compound E-11

The same procedure as in Synthesis Example 93 except that 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Compound E-11 (3.5 g, yield 70%) was obtained.

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 104 Synthesis of Compound E-12

The same procedure as in Synthesis Example 93 except that 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Was carried out to give compound E-12 (3.7 g, yield 75%).

Mass (Theoretical value: 739.30, Measured value: 739 g / mol)

Synthesis Example 105 Synthesis of Compound E-13

The same procedure as in Synthesis Example 93 except that 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Compound E-13 (3.6 g, yield 72%) was obtained.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 106 Synthesis of Compound E-14

The same process as in Synthesis Example 93 except that 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Compound E-14 (3.5 g, yield 71%) was obtained.

Mass (Theoretical value: 740.29, Measured value: 740 g / mol)

Synthesis Example 107 Synthesis of Compound E-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93 Was obtained in the same manner as in Synthesis Example 93 to obtain Compound E-15 (3.4 g, yield 68%).

Mass (Theoretical value: 741.29, Measured value: 741 g / mol)

Synthesis Example 108 Synthesis of Compound E-16

Compound E- was formed by the same procedure as in Synthesis Example 93, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. 16 (2.8 g, yield 65%) was obtained.

Mass (Theoretical value: 638.25, Measured value: 638 g / mol)

Synthesis Example 109 Synthesis of Compound E-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93, Compound E-17 (3.3 g, yield 64%) was obtained in the same manner as the synthesis example 93.

Mass (Theoretical value: 764.29, Measured value: 764 g / mol)

Synthesis Example 110 Synthesis of Compound E-18

Except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93, the same procedure as in Synthesis Example 93 The procedure was carried out to obtain compound E-18 (3.1 g, yield 66%).

Mass (Theoretical value: 692.23, Measured value: 692 g / mol)

Synthesis Example 111 Synthesis of Compound E-19

A compound was prepared in the same manner as in Synthesis Example 93, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. E-19 (2.7 g, yield 68%) was obtained.

Mass (Theoretical value: 600.22, Measured value: 600 g / mol)

Synthesis Example 112 Synthesis of Compound E-20

Compound E was carried out in the same manner as in Synthesis Example 93, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. -20 (3.1 g, yield 62%) was obtained.

Mass (Theoretical value: 736.29, Measured value: 736 g / mol)

Synthesis Example 113 Synthesis of Compound E-21

The same procedure as in Synthesis Example 93 was carried out except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. Compound E-21 (2.5 g, yield 63%) was obtained.

Mass (Theoretical value: 588.23, Measured value: 588 g / mol)

Synthesis Example 114 Synthesis of Compound E-22

Compound E was carried out in the same manner as in Synthesis Example 93, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93. -22 (2.8 g, yield 68%) was obtained.

Mass (Theoretical value: 611.24, Measured value: 611 g / mol)

Synthesis Example 115 Synthesis of Compound E-23

Synthesis except for using 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 93 Compound E-23 (4.0 g, yield 73%) was obtained in the same manner as the Example 93.

Mass (Theoretical value: 816.32, Measured value: 816 g / mol)

Synthesis Example 116 Synthesis of Compound F-1

Compound IAz-6 (1.9g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 6 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the title compound F-1 (1.9 g, yield 62%).

Mass (Theoretical value: 467.19, Measured value: 467 g / mol)

Synthesis Example 117 Synthesis of Compound F-2

A compound was prepared in the same manner as in Synthesis Example 116, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. F-2 (2.1 g, yield 66%) was obtained.

Mass (Theoretical value: 467.19, Measured value: 467 g / mol)

Synthesis Example 118 Synthesis of Compound F-3

A compound was prepared in the same manner as in Synthesis Example 116, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. F-3 (2.3 g, yield 73%) was obtained.

Mass (Theoretical value: 468.18, Measured value: 468 g / mol)

Synthesis Example 119 Synthesis of Compound F-4

A compound was prepared in the same manner as in Synthesis Example 116, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. F-4 (2.1 g, yield 68%) was obtained.

Mass (Theoretical value: 468.18, Measured value: 468 g / mol)

Synthesis Example 120 Synthesis of Compound F-5

Synthesis example except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Compound F-5 (2.0 g, yield 65%) was obtained in the same manner as 116.

Mass (Theoretical value: 469.18, Measured value: 469 g / mol)

Synthesis Example 121 Synthesis of Compound F-6

The same procedure as in Synthesis Example 116 except for using 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 The compound F-6 (2.2 g, 61% yield) was obtained by operation.

Mass (Theoretical value: 543.22, Measured value: 543 g / mol)

Synthesis Example 122 Synthesis of Compound F-7

The same procedure as in Synthesis Example 116 except for using 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Was carried out to give compound F-7 (2.6 g, yield 71%).

Mass (Theoretical value: 543.22, Measured value: 543 g / mol)

Synthesis Example 123 Synthesis of Compound F-8

The same procedure as in Synthesis Example 116 except for using 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Was carried out to give compound F-8 (2.7 g, yield 73%).

Mass (Theoretical value: 544.21, Measured value: 544 g / mol)

Synthesis Example 124 Synthesis of Compound F-9

The same procedure as in Synthesis Example 116 except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Was carried out to give compound F-9 (2.4 g, yield 65%).

Mass (Theoretical value: 544.21, Measured value: 544 g / mol)

Synthesis Example 125 Synthesis of Compound F-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Was obtained in the same manner as in Synthesis Example 116 to obtain Compound F-10 (2.5 g, Yield 68%).

Mass (Theoretical value: 545.21, Measured value: 545 g / mol)

Synthesis Example 126 Synthesis of Compound F-11

The same procedure as in Synthesis Example 116 except for using 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 This carried out the compound F-11 (2.4 g, yield 65%).

Mass (Theoretical value: 543.22, Measured value: 543 g / mol)

Synthesis Example 127 Synthesis of Compound F-12

The same procedure as in Synthesis Example 116 except for using 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 This carried out the compound F-12 (2.3 g, yield 63%).

Mass (Theoretical value: 543.22, Measured value: 543 g / mol)

Synthesis Example 128 Synthesis of Compound F-13

The same procedure as in Synthesis Example 116 except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Compound F-13 (2.5 g, yield 68%) was obtained.

Mass (Theoretical value: 544.21, Measured value: 544 g / mol)

Synthesis Example 129 Synthesis of Compound F-14

The same procedure as in Synthesis Example 116 except for using 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Compound F-14 (2.3 g, yield 63%) was obtained.

Mass (Theoretical value: 544.21, Measured value: 544 g / mol)

Synthesis Example 130 Synthesis of Compound F-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Was obtained in the same manner as in Synthesis Example 116 to obtain Compound F-15 (2.4 g, 65% yield).

Mass (Theoretical value: 545.21, Measured value: 545 g / mol)

Synthesis Example 131 Synthesis of Compound F-16

Compound F- was prepared by the same procedure as in Synthesis Example 116, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. 16 (2.1 g, yield 70%) was obtained.

Mass (Theoretical value: 442.17, Measured value: 442 g / mol)

Synthesis Example 132 Synthesis of Compound F-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116, Compound F-17 (2.3 g, yield 61%) was obtained in the same manner as the synthesis example 116.

Mass (Theoretical value: 568.21, Measured value: 568 g / mol)

Synthesis Example 133 Synthesis of Compound F-18

The same procedure as in Synthesis Example 116 except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. The procedure was carried out to obtain compound F-18 (2.1 g, yield 63%).

Mass (Theoretical value: 496.15, Measured value: 496 g / mol)

Synthesis Example 134 Synthesis of Compound F-19

A compound was prepared in the same manner as in Synthesis Example 116, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. F-19 (1.9 g, yield 69%) was obtained.

Mass (Theoretical value: 404.14, Measured value: 404 g / mol)

Synthesis Example 135 Synthesis of Compound F-20

Compound F was carried out in the same manner as in Synthesis Example 116, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. -20 (2.6 g, yield 71%) was obtained.

Mass (Theoretical value: 540.21, Measured value: 540 g / mol)

Synthesis Example 136 Synthesis of Compound F-21

The same procedure as in Synthesis Example 116 was carried out except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. Compound F-21 (1.9 g, yield 73%) was obtained.

Mass (Theoretical value: 392.15, Measured value: 392 g / mol)

Synthesis Example 137 Synthesis of Compound F-22

Compound F was carried out in the same manner as in Synthesis Example 116, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116. -22 (1.9 g, yield 70%) was obtained.

Mass (Theoretical value: 415.16, Measured value: 415 g / mol)

Synthesis Example 138 Synthesis of Compound F-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 116 Compound F-23 (2.7 g, yield 64%) was obtained in the same manner as the Example 116.

Mass (Theoretical value: 620.24, Measured value: 620 g / mol)

Synthesis Example 139 Synthesis of Compound G-1

Compounds IAz-7 (2.4 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 7 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound G-1 (2.6 g, yield 65%).

Mass (Theoretical value: 588.22, Measured value: 588 g / mol)

Synthesis Example 140 Synthesis of Compound G-2

A compound was prepared in the same manner as in Synthesis Example 139, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. G-2 (2.4 g, yield 62%) was obtained.

Mass (Theoretical value: 588.22, Measured value: 588 g / mol)

Synthesis Example 141 Synthesis of Compound G-3

A compound was prepared in the same manner as in Synthesis Example 139, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. G-3 (2.6 g, yield 67%) was obtained.

Mass (Theoretical value: 589.21, Measured value: 589 g / mol)

Synthesis Example 142 Synthesis of Compound G-4

A compound was prepared in the same manner as in Synthesis Example 139, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. G-4 (2.5 g, yield 64%) was obtained.

Mass (Theoretical value: 589.21, Measured value: 589 g / mol)

Synthesis Example 143 Synthesis of Compound G-5

Synthesis example except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Compound G-5 (2.7 g, 68% yield) was obtained by the same procedure as 139.

Mass (Theoretical value: 590.21, Measured value: 590 g / mol)

Synthesis Example 144 Synthesis of Compound G-6

The same procedure as in Synthesis Example 139 except for using 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Was carried out to give compound G-6 (3.1 g, yield 70%).

Mass (Theoretical value: 664.25, Measured value: 664 g / mol)

Synthesis Example 145 Synthesis of Compound G-7

The same procedure as in Synthesis Example 139 except for using 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Was carried out to give compound G-7 (3.2 g, yield 72%).

Mass (Theoretical value: 664.25, Measured value: 664 g / mol)

Synthesis Example 146 Synthesis of Compound G-8

The same procedure as in Synthesis Example 139 except for using 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Was carried out to give compound G-8 (3.0 g, yield 67%).

Mass (Theoretical value: 665.24, Measured value: 665 g / mol)

Synthesis Example 147 Synthesis of Compound G-9

The same procedure as in Synthesis Example 139 except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 The compound G-9 (2.8 g, yield 63%) was obtained by the following.

Mass (Theoretical value: 665.24, Measured value: 665 g / mol)

Synthesis Example 148 Synthesis of Compound G-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Was obtained in the same manner as in Synthesis Example 139 to obtain compound G-10 (3.1 g, yield 70%).

Mass (Theoretical value: 666.24, Measured value: 666 g / mol)

Synthesis Example 149 Synthesis of Compound G-11

The same procedure as in Synthesis Example 139 except for using 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Was carried out to give compound G-11 (2.8 g, yield 62%).

Mass (Theoretical value: 664.25, Measured value: 664 g / mol)

Synthesis Example 150 Synthesis of Compound G-12

The same procedure as in Synthesis Example 139 except for using 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Was carried out to give compound G-12 (2.9 g, yield 66%).

Mass (Theoretical value: 664.25, Measured value: 664 g / mol)

Synthesis Example 151 Synthesis of Compound G-13

The same procedure as in Synthesis Example 139, except that 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. Compound G-13 (2.9 g, yield 65%) was obtained.

Mass (Theoretical value: 665.24, Measured value: 665 g / mol)

Synthesis Example 152 Synthesis of Compound G-14

The same procedure as in Synthesis Example 139 except for using 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Compound G-14 (3.0 g, yield 68%) was obtained.

Mass (Theoretical value: 665.24, Measured value: 665 g / mol)

Synthesis Example 153 Synthesis of Compound G-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Was obtained in the same manner as in Synthesis Example 139 to obtain Compound G-15 (2.8 g, Yield 63%).

Mass (Theoretical value: 666.24, Measured value: 666 g / mol)

Synthesis Example 154 Synthesis of Compound G-16

Compound G- was prepared by the same procedure as in Synthesis Example 139, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. 16 (2.5 g, yield 65%) was obtained.

Mass (Theoretical value: 563.20, Measured value: 563 g / mol)

Synthesis Example 155 Synthesis of Compound G-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139, Compound G-17 (3.0 g, yield 65%) was obtained in the same manner as the synthesis example 139.

Mass (Theoretical value: 689.24, Measured value: 689 g / mol)

Synthesis Example 156 Synthesis of Compound G-18

The same procedure as in Synthesis Example 139 except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. The procedure was carried out to obtain compound G-18 (2.8 g, yield 68%).

Mass (Theoretical value: 617.18, Measured value: 617 g / mol)

Synthesis Example 157 Synthesis of Compound G-19

A compound was prepared in the same manner as in Synthesis Example 139, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. G-19 (2.1 g, yield 60%) was obtained.

Mass (Theoretical value: 525.17, Measured value: 525 g / mol)

Synthesis Example 158 Synthesis of Compound G-20

Compound G was carried out in the same manner as in Synthesis Example 139, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. -20 (3.1 g, yield 70%) was obtained.

Mass (Theoretical value: 661.24, Measured value: 661 g / mol)

Synthesis Example 159 Synthesis of Compound G-21

The same procedure as in Synthesis Example 139 was performed except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. Compound G-21 (2.2 g, yield 65%) was obtained.

Mass (Theoretical value: 513.18, Measured value: 513 g / mol)

Synthesis Example 160 Synthesis of Compound G-22

Compound G was carried out in the same manner as in Synthesis Example 139, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139. -22 (2.6 g, yield 71%) was obtained.

Mass (Theoretical value: 536.19, Measured value: 536 g / mol)

Synthesis Example 161 Synthesis of Compound G-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 139 Compound G-23 (3.3 g, yield 66%) was obtained in the same manner as the Example 139.

Mass (Theoretical value: 741.27, Measured value: 741 g / mol)

Synthesis Example 162 Synthesis of Compound H-1

Compounds IAz-8 (2.0 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 8 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound H-1 (2.5 g, yield 71%).

Mass (Theoretical value: 528.17, Measured value: 528 g / mol)

Synthesis Example 163 Synthesis of Compound H-2

A compound was prepared in the same manner as in Synthesis Example 162, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. H-2 (2.4 g, yield 69%) was obtained.

Mass (Theoretical value: 528.17, Measured value: 528 g / mol)

Synthesis Example 164 Synthesis of Compound H-3

A compound was prepared in the same manner as in Synthesis Example 162, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. H-3 (2.6 g, yield 73%) was obtained.

Mass (Theoretical value: 529.16, Measured value: 529 g / mol)

Synthesis Example 165 Synthesis of Compound H-4

A compound was prepared in the same manner as in Synthesis Example 162, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. H-4 (2.7 g, yield 76%) was obtained.

Mass (Theoretical value: 529.16, Measured value: 529 g / mol)

Synthesis Example 166 Synthesis of Compound H-5

Synthesis example except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162 Compound H-5 (2.2 g, yield 63%) was obtained in the same manner as 162.

Mass (Theoretical value: 530.16, Measured value: 530 g / mol)

Synthesis Example 167 Synthesis of Compound H-6

The same procedure as in Synthesis Example 162 except for using 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-6 (2.5 g, yield 62%).

Mass (Theoretical value: 604.20, Measured value: 604 g / mol)

Synthesis Example 168 Synthesis of Compound H-7

The same procedure as in Synthesis Example 162 except for using 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-7 (2.8 g, yield 68%).

Mass (Theoretical value: 604.20, Measured value: 604 g / mol)

Synthesis Example 169 Synthesis of Compound H-8

The same procedure as in Synthesis Example 162 except that 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-8 (2.6 g, yield 64%).

Mass (Theoretical value: 605.19, Measured value: 605 g / mol)

Synthesis Example 170 Synthesis of Compound H-9

The same procedure as in Synthesis Example 162, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-9 (2.6 g, yield 64%).

Mass (Theoretical value: 605.19, Measured value: 605 g / mol)

Synthesis Example 171 Synthesis of Compound H-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162 Was obtained in the same manner as in Synthesis Example 162 to obtain Compound H-10 (2.7 g, 66% yield).

Mass (Theoretical value: 606.19, Measured value: 606 g / mol)

Synthesis Example 172 Synthesis of Compound H-11

The same procedure as in Synthesis Example 162 except for using 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-11 (2.8 g, yield 68%).

Mass (Theoretical value: 604.20, Measured value: 604 g / mol)

Synthesis Example 173 Synthesis of Compound H-12

The same procedure as in Synthesis Example 162, except that 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-12 (2.4 g, yield 60%).

Mass (Theoretical value: 604.20, Measured value: 604 g / mol)

Synthesis Example 174 Synthesis of Compound H-13

The same procedure as in Synthesis Example 162 except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-13 (2.5 g, yield 62%).

Mass (Theoretical value: 605.19, Measured value: 605 g / mol)

Synthesis Example 175 Synthesis of Compound H-14

The same procedure as in Synthesis Example 162 except that 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Was carried out to give compound H-14 (3.0 g, yield 73%).

Mass (Theoretical value: 605.19, Measured value: 605 g / mol)

Synthesis Example 176 Synthesis of Compound H-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162 Was obtained in the same manner as in Synthesis Example 162 to obtain Compound H-15 (2.9 g, 71% yield).

Mass (Theoretical value: 606.19, Measured value: 606 g / mol)

Synthesis Example 177 Synthesis of Compound H-16

Compound H- was prepared by the same procedure as in Synthesis Example 162, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. 16 (2.3 g, yield 69%) was obtained.

Mass (Theoretical value: 503.15, Measured value: 503 g / mol)

Synthesis Example 178 Synthesis of Compound H-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162, Compound H-17 (2.8 g, yield 67%) was obtained in the same manner as the synthesis example 162.

Mass (Theoretical value: 629.19, Measured value: 629 g / mol)

Synthesis Example 179 Synthesis of Compound H-18

Same as Synthesis Example 162, except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. The procedure was carried out to obtain compound H-18 (2.7 g, 71% yield).

Mass (Theoretical value: 557.13, Measured value: 557 g / mol)

Synthesis Example 180 Synthesis of Compound H-19

A compound was prepared in the same manner as in Synthesis Example 162, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. H-19 (2.3 g, yield 75%) was obtained.

Mass (Theoretical value: 465.12, Measured value: 465 g / mol)

Synthesis Example 181 Synthesis of Compound H-20

Compound H was carried out in the same manner as in Synthesis Example 162, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. -20 (2.6 g, yield 65%) was obtained.

Mass (Theoretical value: 601.19, Measured value: 601 g / mol)

Synthesis Example 182 Synthesis of Compound H-21

The same procedure as in Synthesis Example 162 was performed except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Compound H-21 (2.1 g, yield 68%) was obtained.

Mass (Theoretical value: 453.13, Measured value: 453 g / mol)

Synthesis Example 183 Synthesis of Compound H-22

Compound H was carried out in the same manner as in Synthesis Example 162, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. -22 (2.2 g, yield 69%) was obtained.

Mass (Theoretical value: 476.14, Measured value: 476 g / mol)

Synthesis Example 184 Synthesis of Compound H-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 162. Compound H-23 (2.9 g, yield 63%) was obtained in the same manner as the Example 162.

Mass (Theoretical value: 681.22, Measured value: 681 g / mol)

Synthesis Example 185 Synthesis of Compound I-1

Compound IAz-9 (2.5 g, 6.7 mmol), 2-bromo-4,6-diphenylpyridine (2.5 g, 8.0 mmol), Pd (OAc) ₂ (0.08 g, 0.34 mmol) synthesized in Preparation Example 9 under nitrogen stream , P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluenen was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain a compound I-1 (2.6 g, yield 65%).

Mass (Theoretical value: 604.20, Measured value: 604 g / mol)

Synthesis Example 186 Synthesis of Compound I-2

A compound was prepared in the same manner as in Synthesis Example 185, except that 4-bromo-2,6-diphenylpyridine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. I-2 (2.5 g, yield 61%) was obtained.

Mass (Theoretical value: 604.20, Measured value: 604 g / mol)

Synthesis Example 187 Synthesis of Compound I-3

A compound was prepared in the same manner as in Synthesis Example 185, except that 2-chloro-4,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. I-3 (2.8 g, yield 68%) was obtained.

Mass (Theoretical value: 605.19, Measured value: 605 g / mol)

Synthesis Example 188 Synthesis of Compound I-4

A compound was prepared in the same manner as in Synthesis Example 185, except that 4-chloro-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. I-4 (2.8 g, yield 70%) was obtained.

Mass (Theoretical value: 605.19, Measured value: 605 g / mol)

Synthesis Example 189 Synthesis of Compound I-5

Synthesis example except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185 Compound I-5 (3.0 g, yield 74%) was obtained in the same manner as 185.

Mass (Theoretical value: 606.19, Measured value: 606 g / mol)

Synthesis Example 190 Synthesis of Compound I-6

The same procedure as in Synthesis Example 185 except for using 2- (4-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. Compound I-6 (3.0 g, yield 65%) was obtained.

Mass (Theoretical value: 680.23, Measured value: 680 g / mol)

Synthesis Example 191 Synthesis of Compound I-7

The same procedure as in Synthesis Example 185 except for using 4- (4-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. To give compound I-7 (2.8 g, 61% yield).

Mass (Theoretical value: 680.23, Measured value: 680 g / mol)

Synthesis Example 192 Synthesis of Compound I-8

The same procedure as in Synthesis Example 185 except for using 2- (4-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. To give compound I-8 (2.9 g, yield 63%).

Mass (Theoretical value: 680.22, Measured value: 680 g / mol)

Synthesis Example 193 Synthesis of Compound I-9

The same procedure as in Synthesis Example 185 except for using 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. Compound I-9 (2.9 g, yield 64%) was obtained.

Mass (Theoretical value: 681.22, Measured value: 681 g / mol)

Synthesis Example 194 Synthesis of Compound I-10

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185 Was obtained in the same manner as in Synthesis Example 185 to obtain Compound I-10 (3.2 g, yield 70%).

Mass (Theoretical value: 682.22, Measured value: 682 g / mol)

Synthesis Example 195 Synthesis of Compound I-11

The same procedure as in Synthesis Example 185 except for using 2- (3-bromophenyl) -4,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. To give compound I-11 (3.5 g, yield 76%).

Mass (Theoretical value: 680.23, Measured value: 680 g / mol)

Synthesis Example 196 Synthesis of Compound I-12

The same procedure as in Synthesis Example 185 except for using 4- (3-bromophenyl) -2,6-diphenylpyridine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. Was carried out to give compound I-12 (3.3 g, yield 73%).

Mass (Theoretical value: 680.23, Measured value: 680 g / mol)

Synthesis Example 197 Synthesis of Compound I-13

The same procedure as in Synthesis Example 185 except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. Compound I-13 (3.2 g, yield 71%) was obtained.

Mass (Theoretical value: 681.22, Measured value: 681 g / mol)

Synthesis Example 198 Synthesis of Compound I-14

The same procedure as in Synthesis Example 185 except for using 4- (3-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. Compound I-14 (3.1 g, yield 68%) was obtained.

Mass (Theoretical value: 681.22, Measured value: 681 g / mol)

Synthesis Example 199 Synthesis of Compound I-15

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185 Was obtained in the same manner as in Synthesis Example 185 to obtain Compound I-15 (3.0 g, 65% yield).

Mass (Theoretical value: 682.22, Measured value: 682 g / mol)

Synthesis Example 200 Synthesis of Compound I-16

Compound I- was prepared by the same procedure as in Synthesis Example 185, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. 16 (2.6 g, yield 66%) was obtained.

Mass (Theoretical value: 579.18, Measured value: 579 g / mol)

Synthesis Example 201 Synthesis of Compound I-17

Except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185, Compound I-17 (3.2 g, yield 67%) was obtained in the same manner as the synthesis example 185.

Mass (Theoretical value: 705.22, Measured value: 705 g / mol)

Synthesis Example 202 Synthesis of Compound I-18

Same as Synthesis Example 185, except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.7 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. The procedure was followed to obtain compound I-18 (3.3 g, yield 77%).

Mass (Theoretical value: 633.16, Measured value: 633 g / mol)

Synthesis Example 203 Synthesis of Compound I-19

A compound was prepared in the same manner as in Synthesis Example 185, except that 2-bromodibenzo [b, d] furan (2.0 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. I-19 (2.7 g, yield 74%) was obtained.

Mass (Theoretical value: 541.15, Measured value: 541 g / mol)

Synthesis Example 204 Synthesis of Compound I-20

Compound I was carried out in the same manner as in Synthesis Example 185, except that 2- (4-bromophenyl) triphenylene (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. -20 (3.3 g, yield 72%) was obtained.

Mass (Theoretical value: 677.22, Measured value: 677 g / mol)

Synthesis Example 205 Synthesis of Compound I-21

The same procedure as in Synthesis Example 185 was carried out except that 5-bromo-2,2'-bipyridine (1.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. Compound I-21 (2.3 g, yield 65%) was obtained.

Mass (Theoretical value: 529.16, Measured value: 529 g / mol)

Synthesis Example 206 Synthesis of Compound I-22

Compound I was carried out in the same manner as in Synthesis Example 185, except that 4'-bromobiphenyl-3-carbonitrile (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185. -22 (2.5 g, yield 68%) was obtained.

Mass (Theoretical value: 552.17, Measured value: 552 g / mol)

Synthesis Example 207 Synthesis of Compound I-23

Synthesis except that 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine (3.4 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 185 Compound I-23 (3.4 g, yield 67%) was obtained in the same manner as the Example 185.

Mass (Theoretical value: 757.25, Measured value: 757 g / mol)

Synthesis Example 208 Synthesis of Compound L-1

Compound IAz-3 (3.4 g, 6.7 mmol), 5'-bromo- (1,1 ', 3', 1 ") terphenyl (2.5 g, 8.0 mmol), CuI (0.13) synthesized in Preparation Example 3 under nitrogen stream g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C. for 3 hours. After the completion of the solid salt was filtered and purified by column chromatography to give the compound L-1 (3.2 g, yield 65%).

Mass (Theoretical value: 738.3, Measured value: 738 g / mol)

Synthesis Example 209 Synthesis of Compound L-2

The same procedure as in Synthesis Example 208 was performed except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 208. Compound L-2 (3.0 g, yield 68%) was obtained.

Mass (Theoretical value: 662.27, Measured value: 662 g / mol)

Synthesis Example 210 Synthesis of Compound L-3

Use of 2-bromo-9,9-dimethyl-9 H- fluorene (2.18 g, 8.0 mmol) instead of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 208 Except for the same procedure as in Synthesis example 208, the compound L-3 (3.4 g, yield 72%) was obtained.

Mass (Theoretical value: 702.3, Measured value: 702 g / mol)

Synthesis Example 211 Synthesis of Compound M-1

Compound IAz-4 (3.4 g, 6.7 mmol), 5'-bromo- (1,1 ', 3', 1 ") terphenyl (2.5 g, 8.0 mmol), CuI (0.13) synthesized in Preparation Example 4 under nitrogen stream g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C. for 3 hours. After the completion of the solid salt was filtered and purified by column chromatography to give the compound M-1 (3.4 g, yield 68%).

Mass (Theoretical value: 738.3, Measured value: 738 g / mol)

Synthesis Example 212 Synthesis of Compound M-2

The same procedure as in Synthesis Example 211 was performed except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 211. To give compound M-2 (2.8 g, yield 63%).

Mass (Theoretical value: 622.27, Measured value: 622 g / mol)

Synthesis Example 213 Synthesis of Compound M-3

Use of 2-bromo-9,9-dimethyl-9 H- fluorene (2.18 g, 8.0 mmol) instead of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 211 Except for the same procedure as in Synthesis example 211, Compound M-3 (3.5 g, yield 75%) was obtained.

Mass (Theoretical value: 702.3, Measured value: 702 g / mol)

Synthesis Example 214 Synthesis of Compound N-1

Compound IAz-6 (1.9 g, 6.7 mmol), 5'-bromo- (1,1 ', 3', 1 ") terphenyl (2.5 g, 8.0 mmol), CuI (0.13) synthesized in Preparation Example 6 under nitrogen stream g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C. for 3 hours. After the completion of the solid salt was filtered and purified by column chromatography to give the compound N-1 (2.5 g, 73% yield).

Mass (Theoretical value: 511.19, Measured value: 511 g / mol)

Synthesis Example 215 Synthesis of Compound N-2

The same procedure as in Synthesis Example 214 was performed except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 214. To give compound N-2 (2.2 g, yield 77%).

Mass (Theoretical value: 435.16, Measured value: 435 g / mol)

Synthesis Example 216 Synthesis of Compound N-3

Use of 2-bromo-9,9-dimethyl-9 H- fluorene (2.18 g, 8.0 mmol) instead of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 214 Except for the same procedure as in Synthesis example 214, compound N-3 (2.3 g, yield 72%) was obtained.

Mass (Theoretical value: 475.19, Measured value: 475 g / mol)

Synthesis Example 217 Synthesis of Compound O-1

Compound IAz-7 (2.4 g, 6.7 mmol), 5'-bromo- (1,1 ', 3', 1 ") terphenyl (2.5 g, 8.0 mmol), CuI (0.13) synthesized in Preparation Example 7 under nitrogen stream g, 0.67 mmol), 1,10-phenanthroline (0.24 g, 1.34 mmol), Cs ₂ CO ₃ (4.37 g, 13.4 mmol) and nitrobenzene (25 ml) were mixed and stirred at 210 ° C. for 3 hours. After the completion of the solid salt was filtered and purified by column chromatography to give the compound O-1 (2.3 g, 66% yield).

Mass (Theoretical value: 511.19, Measured value: 511 g / mol)

Synthesis Example 218 Synthesis of Compound O-2

The same procedure as in Synthesis Example 217 was performed except that 4-bromobiphenyl (1.90 g, 8.0 mmol) was used instead of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 217. To give compound O-2 (1.9 g, yield 64%).

Mass (Theoretical value: 435.16, Measured value: 435 g / mol)

Synthesis Example 219 Synthesis of Compound O-3

Use of 2-bromo-9,9-dimethyl-9 H- fluorene (2.18 g, 8.0 mmol) in place of 5'-bromo- (1,1 ', 3', 1 ") terphenyl used in Synthesis Example 217 Except for the same procedure as in Synthesis example 217, Compound O-3 (2.2 g, yield 69%) was obtained.

Mass (Theoretical value: 475.19, Measured value: 475 g / mol)

Example 1 Fabrication of Green Organic EL Device

After compound A-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, a green organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes And the substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% of Compound A-1 + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) / Alq ₃ (30 nm) on the thus prepared ITO transparent electrode ) / LiF (1 nm) / Al (200 nm) was laminated in order to produce an organic EL device. The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , and BCP used are as follows.

Example 2 ~ Example 189-Fabrication of Green Organic EL Device

Except for using Compounds A-2 to I-23 synthesized in Synthesis Examples 2 to 189, respectively, instead of Compound A-1 used as a light emitting host material when forming the emission layer in Example 1 (see Table 1), In the same manner as in 1, a green organic EL device was manufactured.

Comparative Example 1 Fabrication of Green Organic EL Device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound A-1 as a light emitting host material in forming the emission layer in Example 1. The structure of CBP used is as follows.

[Evaluation Example 1]

For green organic EL devices prepared in Examples 1 to 189 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.

Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 A-1 6.7 517 41.3 Example 2 A-2 6.7 515 43.1 Example 3 A-3 6.51 518 43.5 Example 4 A-4 6.77 518 41.4 Example 5 A-5 6.46 518 41.3 Example 6 A-6 6.81 517 41.2 Example 7 A-7 6.68 515 41.3 Example 8 A-8 6.66 518 39.7 Example 9 A-9 6.48 518 38.9 Example 10 A-10 6.86 517 41.3 Example 11 A-11 6.77 515 41.3 Example 12 A-12 6.66 518 43.1 Example 13 A-13 6.65 518 43.5 Example 14 A-14 6.71 517 41.4 Example 15 A-15 6.65 518 42.2 Example 16 A-18 6.71 517 42 Example 17 A-19 6.72 515 41.6 Example 18 A-20 6.72 518 41.5 Example 19 A-21 6.73 518 41.4 Example 20 A-22 6.73 518 41.9 Example 21 A-23 6.73 517 41.6 Example 22 B-1 6.48 515 41.5 Example 23 B-2 6.86 518 39.2 Example 24 B-3 6.77 518 41.3 Example 25 B-4 6.66 517 39.7 Example 26 B-5 6.65 518 38.9 Example 27 B-6 6.65 517 41.3 Example 28 B-7 6.64 515 41.3 Example 29 B-8 6.64 518 41.3 Example 30 B-9 6.64 518 41.2 Example 31 B-10 6.63 518 41.2 Example 32 B-11 6.72 518 41.3 Example 33 B-12 6.73 517 41.3 Example 34 B-13 6.73 515 41.2 Example 35 B-14 6.73 518 41.3 Example 36 B-15 6.48 518 39.7 Example 37 B-18 6.86 517 38.9 Example 38 B-19 6.77 518 41.3 Example 39 B-20 6.66 517 41.3 Example 40 B-21 6.77 515 43.1 Example 41 B-22 6.66 518 43.5 Example 42 B-23 6.66 518 41.4 Example 43 C-1 6.81 517 42.2 Example 44 C-2 6.66 515 42 Example 45 C-3 6.81 518 39.7 Example 46 C-4 6.68 518 38.9 Example 47 C-5 6.66 518 41.3 Example 48 C-6 6.7 517 41.3 Example 49 C-7 6.7 515 43.1 Example 50 C-8 6.51 518 43.5 Example 51 C-9 6.77 518 41.4 Example 52 C-10 6.46 518 42.2 Example 53 C-11 6.81 517 42 Example 54 C-12 6.68 515 41.8 Example 55 C-13 6.66 518 41.3 Example 56 C-14 6.48 518 41.2 Example 57 C-15 6.86 517 41.2 Example 58 C-18 6.77 515 41.4 Example 59 C-19 6.66 518 42.2 Example 60 C-20 6.81 518 39.7 Example 61 C-21 6.68 518 38.9 Example 62 C-22 6.66 518 41.3 Example 63 C-23 6.7 517 41.3 Example 64 D-1 6.7 515 43.1 Example 65 D-2 6.51 518 43.5 Example 66 D-3 6.77 518 41.4 Example 67 D-4 6.46 518 42.2 Example 68 D-5 6.81 517 42 Example 69 D-6 6.68 515 41.8 Example 70 D-7 6.66 515 41.3 Example 71 D-8 6.48 518 41.2 Example 72 D-9 6.66 518 41.3 Example 73 D-10 6.81 517 39.7 Example 74 D-11 6.68 515 38.9 Example 75 D-12 6.66 517 41.3 Example 76 D-13 6.7 515 41.3 Example 77 D-14 6.7 518 43.1 Example 78 D-15 6.51 518 43.5 Example 79 D-18 6.77 517 41.4 Example 80 D-19 6.46 515 42.2 Example 81 D-20 6.81 515 42 Example 82 D-21 6.68 515 41.8 Example 83 D-22 6.66 518 41.3 Example 84 D-23 6.48 518 41.2 Example 85 E-1 6.86 517 41.2 Example 86 E-2 6.77 515 41.4 Example 87 E-3 6.66 518 42.2 Example 88 E-4 6.81 518 39.7 Example 89 E-5 6.7 515 43.1 Example 90 E-6 6.51 518 43.5 Example 91 E-7 6.77 518 41.4 Example 92 E-8 6.46 518 42.2 Example 93 E-9 6.81 517 42 Example 94 E-10 6.68 515 41.8 Example 95 E-11 6.66 518 41.3 Example 96 E-12 6.48 518 41.2 Example 97 E-13 6.86 517 41.3 Example 98 E-14 6.77 515 41.2 Example 99 E-15 6.66 517 41.3 Example 100 E-18 6.65 515 39.7 Example 101 E-19 6.71 518 38.9 Example 102 E-20 6.65 518 41.3 Example 103 E-21 6.71 517 41.3 Example 104 E-22 6.72 515 43.1 Example 105 E-23 6.72 515 43.5 Example 106 F-1 6.73 518 41.4 Example 107 F-2 6.73 518 42.2 Example 108 F-3 6.73 517 42 Example 109 F-4 6.48 515 41.5 Example 110 F-5 6.86 518 39.2 Example 111 F-6 6.77 518 41.3 Example 112 F-7 6.66 517 39.7 Example 113 F-8 6.65 518 38.9 Example 114 F-9 6.65 517 41.3 Example 115 F-10 6.64 515 41.3 Example 116 F-11 6.64 518 41.3 Example 117 F-12 6.64 518 41.2 Example 118 F-13 6.63 517 41.2 Example 119 F-14 6.72 515 41.3 Example 120 F-15 6.73 517 41.3 Example 121 F-18 6.73 515 41.3 Example 122 F-19 6.73 518 41.2 Example 123 F-20 6.48 518 41.2 Example 124 F-21 6.86 517 41.4 Example 125 F-22 6.77 515 42.2 Example 126 F-23 6.66 515 42 Example 127 G-1 6.77 515 41.8 Example 128 G-2 6.66 518 42 Example 129 G-3 6.66 518 42.5 Example 130 G-4 6.81 517 41.3 Example 131 G-5 6.66 515 41.3 Example 132 G-6 6.81 518 41.2 Example 133 G-7 6.68 518 41.3 Example 134 G-8 6.66 518 39.7 Example 135 G-9 6.7 517 38.9 Example 136 G-10 6.7 515 41.3 Example 137 G-11 6.51 518 41.3 Example 138 G-12 6.77 518 43.1 Example 139 G-13 6.46 517 43.5 Example 140 G-14 6.81 515 41.4 Example 141 G-15 6.68 517 42.2 Example 142 G-18 6.66 515 42 Example 143 G-19 6.48 518 41.2 Example 144 G-20 6.86 518 41.2 Example 145 G-21 6.77 517 41.4 Example 146 G-22 6.66 515 42.2 Example 147 G-23 6.81 515 39.7 Example 148 H-1 6.68 518 38.9 Example 149 H-2 6.66 518 41.3 Example 150 H-3 6.7 517 41.3 Example 151 H-4 6.7 515 43.1 Example 152 H-5 6.51 518 43.5 Example 153 H-6 6.77 518 41.4 Example 154 H-7 6.46 518 42.2 Example 155 H-8 6.81 517 42 Example 156 H-9 6.68 515 41.8 Example 157 H-10 6.66 515 41.3 Example 158 H-11 6.48 518 41.2 Example 159 H-12 6.66 518 41.3 Example 160 H-13 6.81 517 39.7 Example 161 H-14 6.68 515 38.9 Example 162 H-15 6.66 517 41.3 Example 163 H-18 6.7 515 41.3 Example 164 H-19 6.7 518 43.1 Example 165 H-20 6.51 518 43.5 Example 166 H-21 6.77 517 41.4 Example 167 H-22 6.46 515 42.2 Example 168 H-23 6.81 515 42 Example 169 I-1 6.68 515 41.8 Example 170 I-2 6.66 518 41.3 Example 171 I-3 6.48 518 41.2 Example 172 I-4 6.86 517 41.2 Example 173 I-5 6.77 515 41.4 Example 174 I-6 6.66 518 42.2 Example 175 I-7 6.81 518 39.7 Example 176 I-8 6.7 515 43.1 Example 177 I-9 6.51 518 43.5 Example 178 I-10 6.77 518 41.4 Example 179 I-11 6.61 517 41.1 Example 180 I-12 6.51 515 42.5 Example 181 I-13 6.77 517 39.2 Example 182 I-14 6.66 515 41.3 Example 183 I-15 6.65 518 39.7 Example 184 I-18 6.65 518 41.1 Example 185 I-19 6.77 517 41.3 Example 186 I-20 6.65 515 39.7 Example 187 I-21 6.77 515 41.1 Example 188 I-22 6.66 515 42.5 Example 189 I-23 6.65 515 42.5 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, in the case of the green organic EL device of Examples 1 to 189 using the compound (A-1 to I-23) according to the present invention as the light emitting layer material, the green organic of Comparative Example 1 using the conventional CBP It was confirmed that the efficiency and driving voltage were superior to those of the EL element.

[ Example  190] Red Organic EL  Manufacture of device

Compound A-16 synthesized in Synthesis Example 16 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes And the substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% Compound A-16 + 10% (piq) ₂ Ir (acac) (30 nm) / BCP (10 nm) / Alq ₃ ( 30 nm) / LiF (1 nm) / Al (200 nm) was laminated to fabricate an organic EL device. The structures of m-MTDATA, TCTA, and BCP used are as described in Example 1, and the structure of (piq) ₂ Ir (acac) is as follows.

Example 191 to Example 207-Fabrication of Red Organic EL Device

Except for using the compounds A-16 to I-17 synthesized in Synthesis Examples 17 to 201 instead of the compound A-16 used as the light emitting host material when forming the emission layer in Example 190 (see Table 2), The red organic EL device was manufactured in the same manner as 190.

Comparative Example 2

A red organic electroluminescent device was manufactured in the same manner as in Example 190, except that CBP was used instead of Compound A-16, which was used as a light emitting host material, to form an emission layer in Example 190. The structure of CBP used was as described in Comparative Example 1.

[ Evaluation example  2]

For the organic electroluminescent devices manufactured in Examples 190 to 207 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

Sample Host Driving voltage (V) Current efficiency (cd / A) Example 190 A-16 4.76 10.1 Example 191 A-17 4.53 11.5 Example 192 B-16 4.65 11.8 Example 193 B-17 4.74 11.5 Example 194 C-16 4.87 11.8 Example 195 C-17 4.56 9.6 Example 196 D-16 4.64 9.7 Example 197 D-17 4.55 9.1 Example 198 E-16 4.68 9.2 Example 199 E-17 4.55 11.5 Example 200 F-16 4.32 11.8 Example 201 F-17 4.74 11.5 Example 202 G-16 4.87 11.8 Example 203 G-17 4.53 9.6 Example 204 H-16 4.65 9.7 Example 205 H-17 4.74 11.8 Example 206 I-16 4.87 9.6 Example 207 I-17 4.76 9.7 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, in the case of the red organic EL device of Examples 190 to 207 using the compound (A-16 to I-17) according to the present invention as the light emitting layer material, the red organic of Comparative Example 1 using the conventional CBP It was confirmed that the efficiency and the driving voltage were superior to the EL device.

Example 208 Fabrication of Green Organic EL Device

Compound L-1 synthesized in Synthesis Example 208 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm) / TCTA (80 nm) / Compound L-1 (40 nm) / CBP + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) / An organic electroluminescent device was manufactured by stacking in order of Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).

Example 209 to Example 219-Fabrication of Green Organic EL Device

Example 208 was the same as in Example 208 except for using the compounds L-2 to 0-3 synthesized in Synthesis Examples 209 to 219 instead of the compound L-1 used as the emission auxiliary layer material in the formation of the emission layer. The green organic electroluminescent element was produced by carrying out.

Comparative Example 3

A green organic electroluminescent device was manufactured in the same manner as in Example 208, except that Compound L-1 was not used as the emission auxiliary layer material in Example 208.

[ Evaluation example  3]

For the organic electroluminescent devices manufactured in Examples 208 to 219 and Comparative Example 3, driving voltage and current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below.

Sample Luminous auxiliary layer Driving voltage (V) Current efficiency (cd / A) Example 208 L-1 6.80 42.9 Example 209 L-2 6.85 42.6 Example 210 L-3 6.80 42.4 Example 211 M-1 6.80 42.0 Example 212 M-2 6.75 42.7 Example 213 M-3 6.90 42.7 Example 214 N-1 6.80 41.8 Example 215 N-2 6.80 42.5 Example 216 N-3 6.90 42.9 Example 217 O-1 6.85 41.9 Example 218 O-2 6.70 42.6 Example 219 0-3 6.85 42.9 Comparative Example 2 _ 6.93 38.2

As shown in Table 3, the green organic electroluminescent device of Examples 208 to 219 using the compounds (L-1 to O-3) represented by the formula (1) according to the present invention as a light emitting auxiliary layer material, the light emitting auxiliary layer It was found that the driving voltage was slightly lower than that of the green organic electroluminescent device of Comparative Example 3, in which no material was used, and the light emission efficiency was greatly improved.

Example 220 Fabrication of Blue Organic EL Device

Compound A-9 synthesized in Synthesis Example 9 was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic EL device was manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / AND + 5% DS-405 (30 nm) / Compound A-9 (5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to prepare an organic EL device.

The structure of NPB, AND and Alq ₃ used at this time is as follows.

[Example 221] to [Example 231]-Fabrication of Blue Organic EL Device

A blue organic EL device was manufactured in the same manner as in Example 220, except that each compound described in Table 4 was used instead of Compound A-9 used as the life improving layer material in Example 220.

Example 232-Fabrication of Blue Organic EL Device

After compound A-3 synthesized in Synthesis Example 3 was subjected to high purity sublimation purification by a conventionally known method, a blue organic electroluminescent device was manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / AND + 5% DS-405 (30 nm) / Compound A-3 (30 nm) / LiF (1 nm) / Al ( 200 nm) was laminated in order to prepare an organic EL device.

[Example 233] to [Example 235]-Fabrication of Blue Organic EL Device

A blue organic EL device was manufactured in the same manner as in Example 232, except that each compound shown in Table 5 was used instead of Compound A-3 used as an electron transporting layer material in Example 232.

Comparative Example 4-Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 220, except that Alq ₃ , which is an electron transport layer material, was deposited at 30 nm instead of 25 nm without including the life improving layer.

Comparative Example 5 Fabrication of Blue Organic Electroluminescent Device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that instead of using Compound A-9, which was used as a life improving layer material in Example 220, but using BCP.

The structure of the BCP used at this time is as follows.

[Evaluation Example 4]

For the organic electroluminescent devices manufactured in Examples 220 to 235 and Comparative Examples 4 and 5, respectively, driving voltage, current efficiency, emission wavelength, and lifetime (T97) at a current density of 10 mA / cm 2 were measured. It is shown in Tables 4 and 5 below.

Sample Life Improvement Layer Driving voltage
(V) Current efficiency
(cd / A) Luminous Peak
(nm) life span
(hr, T ₉₇ ) Example 220 A-9 4.4 6.2 457 45 Example 221 A-10 4.1 6.3 458 62 Example 222 A-15 4.2 6.6 458 55 Example 223 B-10 4.5 6.2 458 75 Example 224 B-15 4.3 6.5 458 59 Example 225 F-9 4.3 6.1 458 78 Example 226 F-14 4.4 6.4 457 60 Example 227 H-9 4.1 6.2 458 64 Example 228 H-14 4.7 6.0 458 50 Example 229 K-6 4.7 6.4 457 85 Example 230 P-1 4.5 6.1 458 55 Example 231 P-5 4.2 6.0 458 75 Comparative Example 4 _ 4.7 5.6 458 32 Comparative Example 5 BCP 5.3 5.9 458 28

Sample Electron transport layer Driving voltage
(V) Current efficiency
(cd / A) Luminous Peak
(nm) Example 232 A-3 4.5 6.3 458 Example 233 A-8 4.4 6.3 458 Example 234 A-21 4.3 6.1 458 Example 235 A-22 4.1 6.5 458 Comparative Example 4 _ 4.7 5.6 458

As can be seen from Table 4, in the case of the blue organic EL device of Examples 220 to 231 using the compounds A-9 to P-5 as the life improving layer material, the blue organic of Comparative Example 4 without using the life improving layer The driving voltage is similar or slightly better than that of the EL element, but the current efficiency and lifetime are greatly improved.

In addition, the blue organic EL device of Examples 220 to 231 is not only excellent in driving voltage and current efficiency, but also has a long life compared to the blue organic EL device of Comparative Example 5, which uses CBP as the hole blocking layer material instead of the life improvement layer. Has been improved.

Furthermore, in the case of the blue organic EL device of Examples 232 to 235 using the compounds A-3 to A-22 as the electron transporting layer material, the driving voltage and current compared to the blue organic EL device of Comparative Example 4 using Alq ₃ as the electron transporting layer. The efficiency is further improved.

As such, when the compound of Formula 1 according to the present invention was used as the life improving layer material or the electron transporting layer material, it was confirmed that the driving voltage and the current efficiency were improved, and further, the life characteristics could be greatly improved.

Claims (10)

A compound represented by any one of the following Formulas 3 to:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 3 to 6,
Y ₁ to Y ₁₂ are C (R ₁ ), wherein when R ₁ is plural, they are the same or different;
Ar ₁ to Ar ₅ are the same as or different from each other, and are each independently selected from the group consisting of a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms;
R ₁ is selected from the group consisting of hydrogen, deuterium, and an aryl group of C ₆ to C ₆₀ ;
The aryl group and heteroaryl group of Ar ₁ to Ar ₅ and the aryl group of R ₁ are each independently deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus aryloxy atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ alkyloxy group, the C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one substituent at least one selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted, wherein when the substituent is plural, they are the same or another Can be different. Compound represented by the following formula (9) or (10):
[Formula 9]

[Formula 10]

In Chemical Formulas 9 and 10,
Y ₁ to Y ₁₂ are C (R ₁ ), wherein when R ₁ is plural, they are the same or different;
Ar ₁ to Ar ₅ are the same as or different from each other, and are each independently selected from the group consisting of a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms;
R ₁ is selected from the group consisting of hydrogen, deuterium, and an aryl group of C ₆ to C ₆₀ ;
The aryl group and heteroaryl group of Ar ₁ to Ar ₅ and the aryl group of R ₁ are each independently deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus aryloxy atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ C ₄₀ alkyloxy group, the C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one substituent at least one selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted, wherein when the substituent is plural, they are the same or another Can be different. The method of claim 2,
Ar ₁ is a substituent represented by Formula 11 or an aryl group of C ₆ to C ₆₀ ,
In this case, the group is aryl of the Ar ₁ deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ A compound which is unsubstituted or substituted with one or more substituents selected from the group consisting of arylamine groups of ˜C ₆₀ , wherein when the substituents are plural, they may be the same or different from each other:
[Formula 11]

In Chemical Formula 11,
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), provided that at least one of Z ₁ to Z ₅ is N, wherein when C (R ₁₁ ) is plural, they are each other; Same or different,
R ₁₁ is hydrogen, deuterium (D), halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5-40 heteroaryl group, C ₆ -C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl,
Alkyl group of the R _11, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group Deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 5 nuclear atoms each independently 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ to C _It may be unsubstituted or substituted with one or more substituents selected from the group consisting of an arylphosphine oxide group of ₄₀ and an arylsilyl group of C ₆ to C ₄₀ , wherein when the substituents are plural, they are It may be the same or different from each other. The method of claim 2,
Ar ₁ is a compound characterized in that the substituent represented by any one of the formulas A-1 to A-15:

In Chemical Formulas A-1 to A-15,
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
When R ₁₁ is plural, they are the same as or different from each other,
R ₁₁ is hydrogen, deuterium (D), halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5-40 heteroaryl group, C ₆ -C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl,
When R ₁₂ is plural, they are the same as or different from each other,
R ₁₂ is hydrogen, deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl,
n is an integer from 1 to 4,
An alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group of R ₁₁ and R ₁₂ and The arylsilyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom from 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atom C ₃ to C ₄₀ heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C substituted with one or more substituents selected from the group consisting of arylsilyl ₄₀ or may be unsubstituted, wherein when the substituent of the plurality, It may be the same or different from each other. The method of claim 1,
Ar ₁ is a substituent represented by Formula 11 or an aryl group of C ₆ to C ₆₀ ,
At this time, the aryl groups of Ar ₁ are each independently deuterium (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C Aryl group of ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , alkylsilyl group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₆₀ group And it may be unsubstituted or substituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ arylamine, wherein, when the substituents are plural, they are the same or different from each other.
[Formula 11]

In Chemical Formula 11,
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), provided that at least one of Z ₁ to Z ₅ is N, wherein when C (R ₁₁ ) is plural, they are each other; Same or different,
R ₁₁ is hydrogen, deuterium (D), halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5-40 heteroaryl group, C ₆ -C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron said group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₄₀ arylsilyl of,
Alkyl group of the R _11, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group Deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 5 nuclear atoms each independently 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ arylboron groups, C ₆ to C ₄₀ arylphosphine groups, C ₆ to C _It may be unsubstituted or substituted with one or more substituents selected from the group consisting of an arylphosphine oxide group of ₄₀ and an arylsilyl group of C ₆ to C ₄₀ , wherein when the substituents are plural, they are It may be the same or different from each other. The method of claim 1,
Ar ₁ is a compound characterized in that the substituent represented by any one of the formulas A-1 to A-15:

In Chemical Formulas A-1 to A-15,
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
When R ₁₁ is plural, they are the same as or different from each other,
R ₁₁ is hydrogen, deuterium (D), halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₆ -C ₄₀ aryl group, nuclear atom 5-40 heteroaryl group, C ₆ -C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl,
When R ₁₂ is plural, they are the same as or different from each other,
R ₁₂ is hydrogen, deuterium (D), halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryl Oxy group C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl,
n is an integer from 1 to 4,
An alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group of R ₁₁ and R ₁₂ and The arylsilyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom from 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atom C ₃ to C ₄₀ heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₄₀ aryl boron group, C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C substituted with one or more substituents selected from the group consisting of arylsilyl ₄₀ or may be unsubstituted, wherein when the substituent of the plurality, It may be the same or different from each other. An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode.
At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 6. The method of claim 7, wherein
The at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer,
At least one organic material layer including the compound is an organic electroluminescent device, characterized in that the light emitting layer or the electron transport layer. The method of claim 7, wherein
The at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer,
At least one organic material layer including the compound is an organic electroluminescent device, characterized in that the light emitting auxiliary layer. The method of claim 7, wherein
The at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer,
At least one organic material layer including the compound is an organic electroluminescent device, characterized in that the life improvement layer.