KR20160076931A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent light-emitting ability and hole transporting ability, and relates to an organic electroluminescent device comprising the same in at least one organic matter layer, thereby having improved properties such as the light emitting efficiency, the driving voltage, the durability, and the like. The compound is represented by chemical formula 1.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

The light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The dopant material can 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 such a phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with that of fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq ₃ and the like are widely known as a hole blocking layer and an electron transporting layer, and an anthracene derivative as a luminescent material is reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in terms of efficiency improvement of a light emitting material, a metal complex compound containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like is a blue, green, It is used as a material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of light emitting properties, but their glass transition temperature is low and their thermal stability is not very good, which is not satisfactory in terms of lifetime in an organic EL device.

Korea Patent Publication No. 10-2011-0066763

It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and which has excellent hole injecting, transporting ability, and light emitting ability.

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

In order to achieve the above object, the present invention provides a compound represented by the following formula (1)

(In the formula 1,

A ₁ to A ₈ are each independently N or C (R ₁ ), wherein when R ₁ is plural, they are the same or different,

Provided that at least one of A ₁ and A ₂ , A ₂ and A _3, and A ₃ and A ₄ are both C (R ₁ ), wherein R ₁ is bonded to adjacent R ₁ to form To form any of the condensed rings to be displayed;

The dotted line is the part where the condensation occurs;

X ₁ is selected from the group consisting of O, S, C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ );

Y ₁ and Y ₂ are each independently N or C (R ₂ ), wherein when R ₂ is plural, they are the same or different from each other;

Either not form a condensed ring in R ₁ of Formula 2 to 4 and, R ₂ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group , A C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, the number of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C of 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 group, and a C ₆ ~ arylamine group of C ₆₀ of selected from the group consisting of or, or another R _1, R ₁ and R ₂ in which the R ₁ adjacent to each other, And at least one of the other R ₂ and the adjacent R ₂ are bonded to each other condensed aromatic ring or a N, O, S, may form a fused heteroaromatic ring containing at least one of Si and;

Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ is selected from the group consisting of an aryl amine;

In the above R ₁ , R ₂ and Ar ₁ to Ar ₅ , the alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ aryl amine, or is unsubstituted, but the When the substituent is plural, these may be the same or different from each other).

The present invention also provides an organic electroluminescent device comprising (i) a positive electrode, (ii) a negative electrode, and (iii) at least one organic material layer interposed between the positive electrode and the negative electrode, One is an organic electroluminescent device comprising a compound represented by the general formula (1).

According to an example, the organic compound layer containing the compound of Formula 1 is a light emitting layer, and the compound of Formula 1 is preferably a phosphorescent host of the light emitting layer.

According to another example, the organic material layer containing the compound of Formula 1 is a hole transport layer, and the compound of Formula 1 is preferably the hole transport layer material.

According to another example, the organic material layer including the compound represented by Formula 1 is a light-emission-assisting layer, and the compound represented by Formula 1 is preferably the light-emitting layer.

Since the compound according to the present invention has excellent hole transporting property, thermal stability and light emitting property, it can be used as a material of an organic material layer of an organic electroluminescent device. Particularly, when the compound according to the present invention is used as a phosphorescent host, a hole transporting layer material, a light emitting auxiliary layer material or a life improving layer material, the organic electroluminescent material having excellent light emitting performance, low driving voltage, high efficiency, It is possible to manufacture a full color display panel in which devices can be manufactured and performance and lifetime are further improved.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The compounds of the present invention are characterized in that the condensed heteroaromatic moiety consisting of a nitrogen-containing heteroaromatic ring and a heteroaromatic heteroaromatic ring containing 5 heteroaromatic rings other than nitrogen is fused to a naphthalene moiety-condensed basic skeleton And is characterized by being represented by the above formula (1). The compound represented by Chemical Formula 1 has a higher molecular weight than conventional organic EL device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], and thus has a high glass transition temperature, But it is excellent in carrier transport ability and light emission performance. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

Generally, in the phosphorescent light emitting layer of the organic electroluminescent device, the host material must have a triplet energy gap higher than that of the dopant. That is, when the lowest excitation state of the host is higher in energy than the lowest emission state of the dopant, the phosphorescence efficiency of the organic electroluminescent device can be improved. In the compound of formula (1) according to the present invention, a nitrogen-containing 5-membered heteroaromatic ring such as pyrrole, imidazole, pyrazole, triazole and the like and a 5-membered heteroaromatic heteroaromatic ring such as oxygen and sulfur are condensed The resulting condensed heteroaromatic moiety has a high triplet energy level and a broad singlet energy level. Therefore, the compound of the present invention having the basic structure in which the condensed heteroaromatic moiety is condensed to the naphthalene moiety can be used as a host material of the light emitting layer, since the energy level can be controlled higher than that of the dopant.

Further, since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the exciton generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Therefore, when an organic layer (hereinafter, referred to as a 'light emission-assisting layer') is formed between the hole transporting layer and the light emitting layer using the compound of Formula 1, the compound prevents diffusion of the excitons from the light emitting layer to the hole transporting layer, Unlike the conventional organic electroluminescent device not including the light emitting auxiliary layer, the number of excitons contributing to light emission in the light emitting layer can be substantially increased, thereby improving the luminous efficiency of the device. Also, when an organic material layer (hereinafter, referred to as a 'life improving layer') is formed between the light emitting layer and the electron transporting layer using the compound of Formula 1, the exciton diffusion from the light emitting layer to the electron transporting layer The durability and stability of the organic electroluminescent device can be improved, and the half life of the device can be efficiently increased. Thus, the compound represented by the formula (1) may be used as a light-emitting auxiliary layer material or a life improving layer material other than the host of the light emitting layer.

In addition, since the compound of Formula 1 can control the HOMO and LUMO energy levels according to the type of the substituent introduced into the basic skeleton, the compound of Formula 1 can have a wide band gap and a high carrier transportability. For example, the compound of Formula 1 has an electron withdrawing group (EWG) having a high electron absorbing property such as a nitrogen-containing heterocycle (for example, pyridine group, pyrimidine group, triazine group, etc.) When combined, since the entire molecule has a bipolar characteristic, the bonding force between holes and electrons can be increased. As described above, since the compound of the present invention having EWG introduced into the above basic skeleton has excellent carrier transporting property and light emitting property, it can be used as an electron injection / transport layer material or a life improving layer material other than the light emitting layer material of the organic electroluminescence device . When an electron donating group (EDG) is bonded to an electron donor such as an arylamine group, a carbazole group, a terphenyl group or a triphenylene group in the basic skeleton of the compound according to the present invention, Transporting can be carried out smoothly, so that it can be usefully used as a hole injecting / transporting layer or a light emitting auxiliary layer material other than the light emitting layer material.

In addition, the compound of formula (1) according to the present invention has a remarkably increased molecular weight of the compound as a result of introducing various substituents, especially an aryl group and / or a heteroaryl group, into the basic skeleton, Of the light emitting material (e.g., CBP). The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer.

Thus, the compound represented by Formula 1 can improve the luminescent characteristics of the organic electroluminescent device and improve the hole injection / transport ability, electron injection / transport ability, luminous efficiency, driving voltage, lifetime characteristics, . Accordingly, the compound of formula (I) according to the present invention is useful as an organic electroluminescent device, preferably an organic layer material, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / A light-emitting layer, a light-emitting layer, a light-emitting layer, a light-emitting layer, a light-emitting layer, and a life-improving layer. The performance and lifetime characteristics of the organic electroluminescent device including the compound of the present invention can be greatly improved, and the performance of the full-color organic electroluminescent panel to which such an organic electroluminescent device is applied can also be maximized.

In the compounds represented by formula (I) according to the present invention, A ₁ to A ₈ each independently is N or C (R ₁ ), preferably one of A ₁ to A ₈ is N and the others are all C (R ₁ ) Or A ₁ to A ₈ may all be C (R ₁ ). Here, when a plurality of R < ₁ > s are the same or different from each other.

Provided that at least one of A ₁ and A ₂ , A ₂ and A _3, and A ₃ and A ₄ are both C (R ₁ ), wherein R ₁ is bonded to other adjacent R ₁ , To form a condensed ring represented by the following formula.

According to one example, among A ₁ and A ₂ , A ₂ and A ₃ and A ₃ and A ₄ , A ₁ and A ₂ are both C (R ₁ ), wherein R ₁ is bonded to another adjacent R ₁ To form a condensed ring represented by any one of formulas (2) to (4), the compound may be represented by any of the following formulas (C-4) to (C-6).

According to another example, among A ₁ and A ₂ , A ₂ and A ₃ and A ₃ and A ₄ , A ₂ and A ₃ are both C (R ₁ ), and R ₁ is adjacent to other adjacent R ₁ When any one of the condensed rings represented by the formulas (2) to (4) is combined, the compound may be represented by any one of the following formulas (C-1) to (C-3).

According to another example, among A ₁ and A ₂ , A ₂ and A ₃ and A ₃ and A ₄ , A ₃ and A ₄ are both C (R ₁ ), wherein R ₁ is adjacent to another adjacent R ₁ , When any one of the condensed rings represented by the formulas (2) to (4) is bonded to each other, the compound may be represented by any one of the following formulas (C-7) to (C-9).

In the above formulas C-1 to C-9,

X ₁ , Ar ₁ , Y ₁ , Y ₂ , and A ₁ to A ₈ are the same as defined in Formula 1, respectively.

X ₁ is selected from the group consisting of O, S, C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ), preferably O, S, and C (Ar ₂ ) (Ar < ₃ >).

In Formula 1, Ar ₁ to Ar ₅ are the same or different, each independently represent a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and C ₆ of the ~ C ₆₀ is selected from the group consisting of an aryl amine preferably of, each independently represent a C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and C ₆ of the ~ of And an arylamine group of C ₄₀ . For example, each of Ar ₁ to Ar ₅ may independently be selected from the group consisting of a methyl group, a phenyl group, a biphenyl group, and a pyridinyl group, but is not limited thereto.

Y ₁ and Y ₂ are each independently N or C (R ₂ ), preferably Y ₁ and Y ₂ are both C (R ₂ ), or one of Y ₁ and Y ₂ is N and the remainder is C (R < ₂ >). At this time, when a plurality of R < ₂ > are present, they are the same as or different from each other.

In Formula 1, at least one of R ₁ , R ₂ , and Ar ₁ to Ar ₅ , which are not condensed rings of any of Formulas 2 to 4, is independently a C ₁ to C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms and be selected from the group consisting of 5 to 60 heteroaryl group, and a C ₆ ~ with an aryl amine of the C ₆₀ preferably each independently represents a C alkyl group of ₁ ~ C _20, C ₆ ~ it is more preferably a C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 is a heteroaryl group and a C ₆ ~ selected from the group consisting of C ₄₀ arylamines.

The alkyl, aryl, heteroaryl and arylamine groups of R ₁ , R ₂ , and Ar ₁ to Ar ₅ are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group (preferably, C ₁ ~ C ₂₀ alkyl group), (preferably an aryl group of _{C 6 ~ C 60, C 6} ~ C 40 aryl group), nuclear atoms aryl of from 5 to 60 heteroaryl group (preferably, the number of nuclear atoms of 5 to heteroaryl groups of 40), C ₆ to C ₆₀ aryl amine groups (preferably, substituted by C ₆ to more selected from the group consisting of an arylamine group) of ₄₀ C 1 or more substituents is unsubstituted. At this time, when there are a plurality of substituents, they may be the same or different.

For example, at least one of R ₁ , R ₂ , and Ar ₁ to Ar ₅ , which does not form a condensed ring of any one of formulas (2) to (4), independently represents a substituent represented by the following formula A substituted phenyl group or the like, and the rest are the same as defined in the above formula (1). However, the present invention is not limited thereto.

In the above formulas (5) and (6)

* Represents a moiety bonded to Formula 1;

L ₁ and L ₂ are the same or different and are each independently a single bond or a group selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms, Or a phenylene group, a biphenylene group or a carbazolyl group;

Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₁ )

With the proviso that at least one of Z ₁ to Z ₅ is N, and when R ₁₁ is plural, they are the same as or different from each other;

R ₁₁ is hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group (preferably, C ₁ ~ alkyl group of _{C 20), C 2 ~ C} 40 alkenyl group (preferably a, C ₂ ~ C ₂₀ alkenyl group), an alkynyl group of C ₂ ~ C ₄₀ (group preferably, C of ₂ ~ C ₂₀ of the alkynyl group), C ₆ ~ C ₄₀ aryl group (preferably, C ₆ ~ C ₂₀ aryl) (Preferably a heteroaryl group having 5 to 20 nuclear atoms), a C ₆ to C ₄₀ aryloxy group (preferably a C ₆ to C ₂₀ aryloxy group), a heteroaryl group having 5 to 40 nuclear atoms , A C ₁ to C ₄₀ alkyloxy group (preferably a C ₁ to C ₂₀ alkyloxy group), a C ₃ to C ₄₀ cycloalkyl group (preferably a C ₃ to C ₂₀ cycloalkyl group) (Preferably a heterocycloalkyl group having 3 to 20 nucleus atoms), a C ₆ to C ₄₀ arylamine group (preferably a C ₆ to C ₂₀ arylamine group), a C ₁ to C ₄₀ arylamine group alkylsilyl groups of C ₄₀ (preferably group, C ₁ ~ C ₂₀ alkyl silyl), C ₁ ~ C ₄ (Preferably, C ₁ ~ C ₂₀ alkyl boron group) ₀ alkylboronic group of, C ₆ ~ C ₄₀ aryl boron group (preferably, an aryl boronic a _{C 6 ~ C 20), C} 6 ~ C 40 an aryl phosphine group (preferably, C ₆ ~ C ₂₀ aryl phosphine group), C ₆ ~ (preferably, C ₆ ~ aryl phosphine oxide groups of the C ₂₀₎ C ₄₀ aryl phosphine oxide group and a C ₆ ~ C aryl silyl group of ₄₀ (preferably, C ₆ ~ C ₂₀ aryl silyl group) selected from the group consisting of or, or an adjacent combination with L ₁ or other R ₁₁ to form a condensed ring, and that;

R ₁₃ and R ₁₄ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, and a C ₆ to C ₆₀ aryl An amine group, or R ₁₃ and R ₁₄ may be bonded to each other to form a condensed ring;

In this case, the alkyl group of said R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic An arylphosphine group, an arylphosphine oxide group, and an arylsilyl group; And the alkyl, aryl, heteroaryl and arylamine groups of R ₁₃ and R ₁₄ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl (preferably C ₁ to C ₂₀ alkyl), C ₂ ~ C ₄₀ alkenyl group (preferably, C ₂ ~ C ₂₀ alkenyl group), C alkynyl group of ₂ ~ C ₄₀ alkynyl group (preferably, C ₂ ~ C ₂₀ of), C ₆ ~ (preferably, C ₆ ~ C ₂₀ aryl group), C ₄₀ aryl group (the heteroaryl group of preferably, the nuclear atoms of 5 to 20), the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ (Preferably C ₆ to C ₂₀ aryloxy groups), C ₁ to C ₄₀ alkyloxy groups (preferably C ₁ to C ₂₀ alkyloxy groups), C ₆ to C ₄₀ aryl (Preferably an arylamine group of C ₆ to C ₂₀ ), a C ₁ to C ₄₀ cycloalkyl group (preferably a C ₁ to C ₂₀ cycloalkyl group), a heterocycloalkyl group of 3 to 40 nuclear atoms Preferably, heterocycloalcohols having 3 to 20 nuclear atoms Kilgi), C ₁ to alkyl silyl group of C ₄₀ (group preferably, C ₁ to C ₂₀ alkyl silyl), C ₁ to C ₄₀ groups of the alkyl boron (preferably, C group _{of 1} to alkylboronic of C ₂₀₎ , C ₆ ~ C ₄₀ aryl group (preferably, C ₆ ~ arylboronic group of C ₂₀₎ boron group, C ₆ ~ C ₄₀ aryl phosphine group of the (preferably, C ₆ ~ C ₂₀ aryl phosphine group), C _6-aryl phosphine oxide of a C ₄₀ group (group, preferably, C ₆ to silyl aryl of C ₂₀₎ (preferably, C ₆ to C ₂₀ aryl phosphine oxide group), and C ₆ to C ₄₀ aryl silyl group of , And when the substituent is plural, they may be the same or different from each other.

Examples of the substituent represented by the above-mentioned formula (5) include a heterocyclic ring shown by the following A-1 to A-15, but the present invention is not limited thereto.

In the above A-1 to A-15,

L ₁ and R ₁₁ are the same as defined in Formula 5 above;

n is an integer of 0 to 4, and when n is 0, hydrogen means that hydrogen is not substituted with substituent R ₁₂ ; and when n is an integer of 1 to 4, R ₁₂ represents deuterium, halogen, cyano, nitro of the group, C ₁ ~ C ₄₀ alkyl group (preferably, C ₁ ~ C ₂₀ alkyl group), C ₂ ~ C ₄₀ alkenyl group (preferably, C ₂ ~ C ₂₀ alkenyl group), C ₂ ~ C ₄₀ of (Preferably C ₂ to C ₂₀ alkynyl groups), C ₃ to C ₄₀ cycloalkyl groups (preferably C ₃ to C ₂₀ cycloalkyl groups), heterocyclic alkyl groups having 3 to 40 nuclear atoms (Preferably a C ₆ to C ₂₀ aryl group), a heteroaryl group having 5 to 40 nuclear atoms (preferably a heterocycloalkyl group having 3 to 20 nuclear atoms), a C ₆ to C ₄₀ aryl group (Preferably a heteroaryl group having 5 to 20 nuclear atoms), a C ₆ to C ₄₀ aryloxy group (preferably a C ₆ to C ₂₀ aryloxy group), a C ₁ to C ₄₀ alkyloxy group ₁ ~ C ₂₀ alkyloxy group of), C (Preferably, C ₆ ~ C ₂₀ aryl amine group) ₆ ~ C ₄₀ aryl amine group of, C ₁ ~ C ₄₀ alkyl (group, preferably, C ₁ ~ C ₂₀ alkyl silyl) silyl group, C ₁ ~ C ₄₀ groups of the alkyl boron (preferably, C ₁ ~ alkyl boronic groups of the C _20), C ₆ ~ aryl boronic of C ₄₀ (group preferably, the aryl boronic of _{C 6 ~ C 20), C} 6 ~ C 40 an aryl phosphine group (preferably, C ₆ ~ C ₂₀ aryl phosphine group), C ₆ ~ C ₄₀ aryl phosphine oxide groups (preferably, C ₆ ~ aryl phosphine oxide of the C ₂₀ group), and C ₆ ~ (Preferably C ₆ to C ₂₀ arylsilyl group) of C ₄₀ or an arylsilyl group of C ₄₀ (preferably C ₆ to C ₂₀ arylsilyl group), or may be bonded to an adjacent group (for example, adjacent L ₁ , R ₁₁ or other R ₁₂ ) To form a condensed ring;

In this case, the alkyl group of said R _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group (preferably a C ₁ to C ₂₀ alkyl group), a C ₂ to C ₂₀ alkyl group (preferably a C ₁ to C ₂₀ alkyl group), an arylphosphine oxide group ~ C ₄₀ alkenyl group (preferably, C ₂ ~ C ₂₀ alkenyl group), C alkynyl group of ₂ ~ C ₄₀ (preferably, C ₂ ~ alkynyl group of _{C 20), C 6 ~ C} 40 aryl group (Preferably a C ₆ to C ₂₀ aryl group), a heteroaryl group having 5 to 40 nuclear atoms (preferably a heteroaryl group having 5 to 20 nuclear atoms), a C ₆ to C ₄₀ aryloxy group (Preferably a C ₆ to C ₂₀ aryloxy group), a C ₁ to C ₄₀ alkyloxy group (preferably a C ₁ to C ₂₀ alkyloxy group), a C ₆ to C ₄₀ arylamine group , C ₆ -C ₂₀ In the arylamine group), C of ₃ ~ C ₄₀ cycloalkyl group (preferably, C ₃ ~ C ₂₀ cycloalkyl group), the nuclear atoms of 3 to 40 heterocycloalkyl group (preferably, the number of nuclear atoms of 3 to 20 hetero cycloalkyl group), an alkyl silyl group of C ₁ ~ C ₄₀ (preferably, C ₁ ~ C alkyl silyl group of _20), C ₁ ~ C ₄₀ groups of the alkyl boron (preferably, C ₁ ~ alkyl boron C ₂₀ group ), C ₆ ~ C ₄₀ aryl boron group (preferably, C ₆ ~ C ₂₀ of the arylboronic group), C ₆ ~ C to ₄₀ aryl phosphine group (preferably of, C ₆ ~ C ₂₀ aryl phosphine group of a), A C ₆ to C ₄₀ arylphosphine oxide group (preferably a C ₆ to C ₂₀ arylphosphine oxide group) and a C ₆ to C ₄₀ arylsilyl group (preferably a C ₆ to C ₂₀ arylsilyl group ), Provided that when the substituent is plural, they may be the same or different from each other.

The compounds represented by formula (1) according to the present invention may be represented by the following compounds, but are not limited thereto.

In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and may be a linear, branched or cyclic structure . ≪ / RTI > Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

In the present invention, "alkylboron group" means a boron group substituted with alkyl having 1 to 40 carbon atoms, "arylboron group" means a boron group substituted with aryl having 6 to 60 carbon atoms, Means a phosphine group substituted with aryl of 1 to 60, and the term "arylphosphine oxide group" means a phosphine oxide group substituted with aryl having 1 to 60 carbon atoms.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic electroluminescent device

The present invention also provides an organic electroluminescent device comprising the compound represented by the above-mentioned formula (1).

More specifically, the present invention relates to an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes an organic electric field A light emitting device is provided. At this time, the compound represented by the formula (1) may be used singly or in combination of two or more.

According to an example, the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and the light emitting layer may include a compound represented by Formula 1. At this time, the compound represented by Formula 1 may be included in an organic electroluminescent device as a light emitting layer material, preferably a phosphorescent host, a fluorescent host or a dopant material, more preferably a phosphorescent host. In this case, the organic electroluminescent device of the present invention can improve luminous efficiency, brightness, power efficiency, thermal stability, and device lifetime.

According to another example, the one or more organic compound layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the hole transport layer may include a compound represented by Formula 1. [ At this time, the compound represented by Formula 1 may be included in the organic electroluminescent device as a hole transport layer material. In this case, the organic electroluminescent device of the present invention can improve the luminous efficiency, luminance, power efficiency, thermal stability, and device lifetime because holes are smoothly transported by the above compound.

According to another example, the one or more organic material layers include a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. . At this time, the compound represented by Formula 1 may be included in the organic electroluminescent device as a light-emitting auxiliary layer material. In this case, since the exciton is prevented from diffusing from the light emitting layer into the hole transporting layer by the above compound, the light emitting efficiency of the organic electroluminescent device of the present invention is improved as compared with the conventional organic electroluminescent device not including the light emitting auxiliary layer , Brightness, power efficiency, thermal stability, and device lifetime can also be improved.

According to another example, the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting layer, a life improving layer, an electron transporting layer, and an electron injecting layer. . At this time, the compound represented by Formula 1 may be included in the organic electroluminescent device as the lifetime enhancing layer material. In this case, the organic electroluminescent device of the present invention prevents diffusion of the exciton from the light emitting layer to the electron transporting layer by the above compound, so that the half life of the device can be increased, and the luminous efficiency, luminance, .

The structure of the organic electroluminescent device of the present invention is not particularly limited. For example, a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated on a substrate, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer .

According to an example, the organic electroluminescent device may have a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked on a substrate. Alternatively, the light-emitting auxiliary layer may be inserted between the hole transporting layer and the light emitting layer, or the life improving layer may be interposed between the light emitting layer and the electron transporting layer, or an electron injecting layer may be interposed between the electron transporting layer and the cathode .

The organic electroluminescent device of the present invention can be used in the art, except that at least one of the organic layers (for example, a light emitting layer, a hole transporting layer, a light emitting auxiliary layer or a life improving layer) Can be produced by forming organic layers and electrodes using known materials and methods.

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 examples thereof include silicon wafers, quartz or glass plates, metal plates, plastic films and sheets, and the like.

Examples of the positive electrode 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), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The material used for the light emitting layer, the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer is not particularly limited as long as it is a conventional material known in the art.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Preparation Example 1] Synthesis of Compound 1-1-A and 1-1-B

[Step 1] Synthesis of 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-

(55.87 g, 220.0 mmol) and KOAc (58.88 g, 600.0 mmol) and DMF (500 ml) were placed in a nitrogen stream and stirred , PdCl ₂ (dppf) (7.32 g, 10.0 mmol) was added thereto, and the mixture was stirred at 153 캜 for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 30.89 g (yield: 80%) of 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -pyrrole.

GC-Mass (theory: 193.05 g / mol, measured: 193 g / mol)

^{1 H-NMR: δ 1.20 (} t, 12H), δ 6.22 (m, 1H), δ 6.85 (m, 2H), δ 9.50 (b, 1H)

[Step 2] Synthesis of 3- (3- (methylthio) naphthalen-2-yl) -1H-pyrrole

(4,9,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrrole (28.96 g, 150.0 mmol) obtained in the above [step 1] (60.0 g, 150.0 mmol), K ₂ CO ₃ (62.19 g, 450.0 mmol) and Toluene / H ₂ O / EtOH (600 ml / 150 ml / 150 ml) after put into the _{Pd (PPh 3) 4 (8.67} g, 7.50 mmol), and stirred at 100 ℃ for 5 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 30.52 g (yield: 85%) of 3- (3- (methylthio) naphthalen-2-yl) -1H-pyrrole was obtained by column chromatography.

GC-Mass (calculated: 239.34 g / mol, measured: 239 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (d, 1H), δ 7.15 (m, 1H), δ 7.50 (m, 2H), δ 7.89 (s, 1H),? 7.95 (m, 2H),? 8.27 (s,

[Step 3] Synthesis of 3- (3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole

3- (3- (methylthio) naphthalen-2-yl) -1H-pyrrole (23.93 g, 100.0 mmol) synthesized in the above Step 2 was added to acetic acid (200 ml) under nitrogen atmosphere and stirred at room temperature. Subsequently, hydrogen peroxide (3.74 g, 110.0 mmol) was dissolved in acetic acid (20 ml), slowly added dropwise to the reactor, and stirred for 6 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, and 19.66 g (yield: 77%) of 3- (3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole was obtained by column chromatography.

GC-Mass (calculated: 255.33 g / mol, measured: 255 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (m, 1H), δ 7.15 (m, 1H), δ 7.60 (m, 2H), δ 8.02 (m, 1H),? 8.11 (m, 1H),? 8.67 (m, 2H),? 9.67 (brs,

[Step 4] Synthesis of Compound 1-1-A and 1-1-B

3- (3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole (25.53 g, 100.0 mmol) synthesized in the above step 3 was added to trifluoromethanesulfonic acid under a nitrogen stream and stirred at room temperature for 24 hours , H ₂ O / pyridine (80 ml / 10 ml) was slowly added thereto, and the mixture was stirred at 100 ° C for 30 minutes. After completion of the reaction, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 5.36 g (yield: 24%) of compound 1-1-A and 7.82 g (yield: 35%) of compound 1-1-B were obtained by column chromatography.

GC-Mass of the compound 1-1-A (theoretical value: 223.29 g / mol, measured value: 223 g / mol)

Of the compound ^{1-1-A 1 H-NMR:} δ 7.69 (m, 1H), δ 7.78 (m, 2H), δ 7.90 (m, 3H), δ 8.11 (d, 1H), δ 8.28 (d, 1H ), [delta] 11.12 (brs, IH)

GC-Mass of the compound 1-1-B (theoretical value: 223.29 g / mol, measured value: 223 g / mol)

Of the compound ^{1-1-B 1 H-NMR:} δ 7.69 (m, 1H), δ 7.78 (m, 2H), δ 7.90 (m, 3H), δ 8.11 (d, 1H), δ 8.28 (d, 1H ), [delta] 11.12 (brs, IH)

[Preparation Example 2] Synthesis of Compound 1-1-C

[Step 1] Synthesis of 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-

The procedure of Preparation Example 1 was repeated except that 2-bromo-1H-pyrrole (29.21 g, 200.0 mmol) was used instead of 3-bromo-1H-pyrrole used in [Step 1] of [Preparation Example 1] (Yield: 70%) of 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrrole was obtained by carrying out the same procedure as in [Step 1] .

GC-Mass (theory: 193.05 g / mol, measured: 193 g / mol)

^{1 H-NMR: δ 1.20 (} t, 12H), δ 6.15 (t, 1H), δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 11.94 (brs, 1H)

[Step 2] Synthesis of 2- (3- (methylthio) naphthalen-2-yl) -1H-pyrrole

The same procedure as in [Step 1] was repeated except for using 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Preparation Example 1] was repeated except that 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrrole (28.96 g, 150.0 mmol) (Yield: 72%) of 2- (3- (methylthio) naphthalen-2-yl) -1H-pyrrole was obtained in the same manner as in [Step 2].

GC-Mass (calculated: 239.34 g / mol, measured: 239 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.15 (m, 1H), δ 6.48 (d, 1H), δ 6.95 (m, 1H), δ 7.50 (m, 2H), δ 7.89 (s, 1H), 8 7.95 (m, 2H), 8 8.27 (s, 1 H), 8 11.94 (brs,

[Step 3] Synthesis of 2- (3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole

(3- (methylthio) naphthalen-2-yl) -1H-pyrrole obtained in [Step 2] was used instead of 3- (3- (yield: 70%) of 2- ((4-fluorophenyl) -1H-pyrrole- 3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole.

GC-Mass (calculated: 255.33 g / mol, measured: 255 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.15 (m, 1H), δ 6.48 (d, 1H), δ 6.95 (m, 1H), δ 7.60 (m, 2H), δ 8.02 (m, 1H), 8 8.11 (m, 1 H), 8 8.67 (m, 2H), 8 11.94 (brs,

[Step 4] Synthesis of Compound 1-1-C

(3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole obtained in [Step 3] instead of 3- (3- (methylsulfinyl) (yield: 60%) of compound 1- (4-fluorophenyl) -1H-pyrrole (25.53 g, 100.0 mmol) was used in the same manner as in [Step 4] of [Preparation Example 1] 1-C.

GC-Mass (calculated: 223.29 g / mol, measured: 223 g / mol)

^{1 H-NMR: δ 7.69 (} m, 1H), δ 7.78 (m, 2H), δ 7.90 (m, 3H), δ 8.11 (d, 1H), δ 8.28 (d, 1H), δ 11.12 (brs, 1H)

[Preparation Example 3] Synthesis of Compound 2-1-A

Synthesis of 3- (2-bromo-1H-pyrrol-3-yl) naphthalen-2-ol and 3- (3-bromo-1H-

2,3-dibromo-1H-pyrrole (44.98 g, 200.0 mmol), 3-hydroxynaphthalen-2-yl boronic acid (37.60 g, 200.0 mmol), K ₂ CO ₃ and then Toluene / H ₂ O / EtOH stirred for (800 ml / 200 ml / 200 ml), placed _{Pd (PPh 3) 4 (11.56} g, 10.0 mmol), and stirred at 100 ℃ for 5 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 23.05 g (yield: 40%) of 3- (2-bromo-1H-pyrrol-3-yl) naphthalen- yield: 30%) of 3- (3-bromo-1H-pyrrol-2-yl) naphthalen-2-ol (B).

GC-Mass (A) (calculated: 288.10 g / mol, measured: 288 g / mol)

^{1 H-NMR (A):} δ 6.68 (d, 1H), δ 7.25 (d, 1H), δ 7.50 (m, 3H), δ 8.02 (m, 3H), δ 9.61 (s, 1H), δ 12.04 (br s, 1H)

GC-Mass (B) (288.10 g / mol, measured: 288 g / mol)

^{1 H-NMR (B):} δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.51 (m, 3H), δ 8.01 (m, 3H), δ 9.61 (s, 1H), δ 11.94 (br s, 1H)

[Step 2] Synthesis of Compound 2-1-A

3-yl) naphthalen-2-ol (28.81 g, 100.0 mmol) synthesized in the above Step 1 and sodium 2,4,6-trimethylbenzoate (9.31 g, , 50.0 mmol), Pd (OAc ) 2 (1.12 g, 5.0 mmol), 1,3-Bis (2,6-diisopropylphenyl) imidazol-2-ylidene (IPr) (3.89 g, 10.0 mmol), K 2 CO 3 (27.64 g, 200.0 mmol) and mesitylene (500 ml), and the mixture was stirred at 120 ° C for 24 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.64 g (yield: 90%) of compound 2-1-A was obtained by column chromatography.

GC-Mass (207.20 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.42 (} m, 2H), δ 7.49 (s, 1H), δ 7.73 (m, 2H), δ 7.92 (d, 1H), δ 8.11 (d, 1H), δ 8.28 (d, 1H), [delta] 11.12 (brs, IH)

[Preparation Example 4] Synthesis of Compound 2-1-B

[Step 1] Synthesis of 3- (4-bromo-1H-pyrrol-3-yl) naphthalen-2-ol

Except that 3,4-dibromo-1H-pyrrole (44.98 g, 200.0 mmol) was used instead of 2,3-dibromo-1H-pyrrole used in [Step 1] of [Preparation Example 3] (Yield: 80%) of 3- (4-bromo-1H-pyrrol-3-yl) naphthalen-2-ol was obtained by carrying out the same procedure as in [Step 1] of [

GC-Mass (theory 288.10 g / mol, measurement 288 g / mol)

^{1 H-NMR: δ 7.00 (} s, 1H), δ 7.16 (s, 1H), δ 7.50 (m, 3H), δ 8.02 (m, 3H), δ 9.61 (br, 2H)

[Step 2] Synthesis of Compound 2-1-B

Bromo-1H-pyrrole-3-yl) naphthalen-2-ol synthesized in [Step 1] was used instead of 3- (2-bromo- (yield: 85%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 3], except that the title compound was obtained as a pale-yellow solid (28.81 g, 100.0 mmol) ) Of 2-1-B.

GC-Mass (207.20 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.42 (} s, 1H), δ 7.49 (s, 1H), δ 7.73 (m, 2H), δ 7.92 (s, 2H), δ 8.11 (d, 1H), δ 8.28 (d, 1H), [delta] 11.12 (brs, IH)

[Preparation Example 5] Synthesis of Compound 2-1-C

Was prepared in the same manner as in 3- ((2-bromo-1H-pyrrol-3-yl) naphthalen-2-ol used in [Step 1] of [Preparation Example 3] The same procedure as in [Step 2] of [Preparation Example 3] was carried out except that 28.81 g (100.0 mmol) of 3-bromo-1H-pyrrol-2-yl) naphthalen- (yield: 88%) of 2-1-C.

GC-Mass (207.20 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.42 (} s, 1H), δ 7.49 (s, 1H), δ 7.55 (d, 1H), δ 7.73 (m, 2H), δ 7.92 (d, 1H), δ 8.11 (d, 1H),? 8.28 (d, 1H),? 11.12 (brs, 1H)

[Preparation Example 6] Synthesis of Compound 3-1-A

[Step 1] Synthesis of 3 - ((1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H)

(32.0 g, 200.0 mmol), 1- (1,4-dihydronaphthalen-2-yl) pyrrolidine (43.85 g, 220.0 mmol) and dioxane (500 ml) Followed by heating and stirring at 100 DEG C for 18 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 31.54 g (yield: 70%) of 3 - ((1H-pyrrol-2-yl) methyl) -3,4- dihydronaphthalen- one.

GC-Mass (calculated: 225.30 g / mol, measured: 225 g / mol)

^{1 H-NMR: δ 2.67 (} m, 2H), δ 2.97 (m, 2H), δ 3.29 (m, 1H), δ 3.72 (m, 2H), δ 5.88 (d, 1H), δ 6.11 (t, (M, 2H), 8 7.38 (m, 2H), 8 11.44 (brs,

[Step 2] Synthesis of 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole

(1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one (33.80 g, 150.0 mmol) obtained in the above step 1 and CH ₂ Cl ₂ / CH ₃ SO ₃ H (450 ml / 50 ml) was added thereto, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the filtrate was added with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.48 g (yield: 60%) of 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole was obtained by column chromatography.

GC-Mass (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR: δ 3.96 (} s, 1H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.52 (m, 2H), δ 7.79 (s, 1H), δ 8.00 (m, 2H),? 8.28 (s, 1H),? 11.94 (brs, 1H)

[Step 3] Synthesis of Compound 3-1-A

1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole (20.53 g, 100.0 mmol) and THF (300 ml) obtained in the above Step 2 were placed under a nitrogen stream and stirred at -78 ° C. The solution obtained by dissolving n-BuLi (7.05 g, 110.0 mmol) in hexane (70 ml) was slowly added dropwise. After 1 hour, CH ₃ I (17.15 g, 130.0 mmol) was added and stirred at room temperature for 1 hour. Then, n-BuLi (7.05 g, 110.0 mmol) was dissolved in hexane (70 ml) The solution was slowly added dropwise, and after 1 hour, CH ₃ I (17.15 g, 130.0 mmol) was added thereto, followed by stirring at room temperature for 15 hours. After completion of the reaction, recrystallization from hexane gave 12.36 g (yield: 53%) of Compound 3-1-A.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.80 (} t, 6H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.49 (m, 2H), δ 7.79 (s, 1H), δ 7.95 (m, 2H), [delta] 8.31 (s, IH), 11.94 (brs, IH)

[Preparation Example 7] Synthesis of Compound 3-1-B

[Step 1] Synthesis of 3 - ((1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-2 (1H)

Except that 3- (bromomethyl) -1H-pyrrole (32.0 g, 200.0 mmol) was used instead of 2- (bromomethyl) -1H-pyrrole used in [Step 1] of [Preparation Example 6] (1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one was obtained in a yield of 38.30 g (yield: 85% .

GC-Mass (calculated: 225.30 g / mol, measured: 225 g / mol)

^{1 H-NMR: δ 2.68 (} m, 2H), δ 2.94 (m, 2H), δ 3.29 (m, 1H), δ 3.71 (m, 2H), δ 6.02 (d, 1H), δ 6.53 (s, 1H), 8 6.65 (d, 1 H), 8 7.20 (m, 2H),? 7.35 (m, 2H)

[Step 2] 2,10- dihydrobenzo [5,6] indeno [1,2-c] pyrrole , And 1,4-dihydrobenzo [5,6] indeno [1,2-b] pyrrole

(3- (1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one used in [Step 2] of [Preparation Example 6] [Step 2] of [Preparation Example 6] was repeated except that (1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one (33.80 g, 150.0 mmol) (Yield: 40%) of 2,10-dihydrobenzo [5,6] indeno [1,2-c] pyrrole (A) and 10.47 g (yield: 34%) of 1,4 -dihydrobenzo [5,6] indeno [1,2-b] pyrrole (B).

GC-Mass (A) (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR (A):} δ 3.80 (s, 2H), δ 6.67 (d, 1H), δ 6.83 (d, 1H), δ 7.53 (m, 2H), δ 7.79 (d, 1H), δ 7.99 (m, 2H), 8 8.28 (d, IH), 8 9.60 (brs, IH)

GC-Mass (B) (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR (B):} δ 3.80 (s, 2H), δ 6.28 (d, 1H), δ 6.75 (d, 1H), δ 7.53 (m, 2H), δ 7.79 (d, 1H), δ 7.99 (m, 2H), 8 8.28 (d, IH), 8 11.94 (brs, IH)

[Step 3] Synthesis of Compound 3-1-B

Dihydrobenzo [5,6] pyridine obtained in [Step 2] was used instead of 1,10-dihydrobenzo [5,6] indeno [2,1- b] pyrrole used in [Step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was performed, except that 20.53 g (100.0 mmol) of indeno [1,2-c] pyrrole was used, yielding 13.30 g (yield: 57% 3-1-B.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.75 (} s, 6H), δ 6.67 (d, 1H), δ 6.83 (d, 1H), δ 7.49 (m, 2H), δ 7.79 (s, 1H), δ 7.96 (m, 2H), [delta] 8.31 (s, IH), [delta] 9.60 (brs, IH)

[Preparation Example 8] Synthesis of Compound 3-1-C

Obtained in [Step 2] of [Preparation Example 7] instead of 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [Step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was performed except that [5,6] indeno [1,2-b] pyrrole (20.53 g, 100.0 mmol) 51%) of 3-1-C.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.75 (} s, 6H), δ 6.28 (d, 1H), δ 6.75 (d, 1H), δ 7.49 (m, 2H), δ 7.79 (s, 1H), δ 7.96 (m, 2H),? 8.31 (s, 1H),? 11.94 (brs, 1H)

[Preparation Example 9] Synthesis of Compound 1-2-A

[Step 1] Synthesis of 3- (7-bromo-3- (methylthio) naphthalen-2-yl) -1H-pyrrole

(6-bromo-3-iodonaphthalen-2-yl) (methyl) sulfane (56.87 g, 150.0 mmol) was used instead of (3-iodonaphthalen-2-yl) (methyl) sulfane used in [Step 2] of [Preparation Example 1] (Yield: 67%) of 3- (7-bromo-3- (methylthio) naphthalen-2 (2)) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 1] -yl) -1H-pyrrole. < / RTI >

GC-Mass (theory: 318.20 g / mol, measured: 318 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (d, 1H), δ 7.15 (m, 1H), δ 7.39 (d, 1H), δ 7.73 (s, 1H), 8 7.97 (d, IH), 8 8.27 (s, IH)

[Step 2] Synthesis of 3- (7-bromo-3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole

3- (7-bromo-3- ((methylthio) naphthalen-2-yl) -1H-pyrrole was prepared in the same manner as in [Step 1] (yield: 68%) was obtained by carrying out the same procedure as in [Step 3] of [Preparation Example 1], except that methylthio naphthalen-2-yl) ) Of 3- (7-bromo-3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole.

GC-Mass (theory: 334.20 g / mol, measured: 334 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (d, 1H), δ 7.15 (d, 1H), δ 7.48 (d, 1H), δ 8.03 (d, 1H),? 8.52 (s, IH),? 8.67 (s, 2H),? 9.60 (brs,

[Step 3] 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole, thieno [2,3-c] pyrrole

(7-bromo-3- (3-methylpyridyl) -1H-pyrrolo [2,3-c] The same procedure as in [Step 4] of [Preparation Example 1] was performed, except that 33.42 g (100.0 mmol) of methylsulfinyl naphthalen-2-yl) (Yield: 34%) of 8-bromo-2H-naphtho (2, 3 ': 4,5] thieno [2,3- [2 ', 3': 4,5] thieno [2,3-c] pyrrole (B).

GC-Mass (A) (calculated: 302.2 g / mol, measured: 302 g / mol)

^{1 H-NMR (A):} δ 7.16 (d, 1H), δ 7.48 (d, 1H), δ 7.78 (s, 1H), δ 7.89 (m, 2H), δ 8.03 (d, 1H), δ 8.67 (s, IH), [delta] 11.12 (brs, IH)

GC-Mass (B) (theoretical value: 302.2 g / mol, measurement: 302 g / mol)

^{1 H-NMR (B):} δ 7.48 (d, 1H), δ 7.78 (s, 1H), δ 7.86 (s, 1H), δ 7.92 (d, 2H), δ 8.03 (d, 1H), δ 8.67 (s, IH), [delta] 11.12 (brs, IH)

[Step 4] Synthesis of Compound 1-2-A

(30.22 g, 100.0 mmol), iodobenzene (24.48 g, 100.0 mmol), which was synthesized in the above step 3, in a nitrogen stream, , 120.0 mmol), Pd (OAc) ₂ (1.12 g, 5.0 mmol), K ₃ PO ₄ (63.7 g, 300.0 mmol) and Toluene (400 ml) 50% toluene solution (9 ml) was added thereto, followed by stirring at 110 ° C for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 28.00 g (yield: 74%) of Compound 1-2-A was obtained by column chromatography.

GC-Mass (theory: 378.3 g / mol, measured: 378 g / mol)

^{1 H-NMR: δ 6.38 (} d, 1H), δ 7.26 (d, 1H), δ 7.49 (m, 3H), δ 7.60 (m, 3H), δ 7.78 (s, 1H), δ 7.86 (s, 1H), 8 8.03 (d, 1 H), 8 8.67 (s, 1 H)

[Preparation Example 10] Synthesis of Compound 1-2-B

[Step 3] of [Preparation Example 9] was used instead of 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole used in [Step 4] of [Preparation Example 9] , Except that 8-bromo-2H-naphtho [2 ', 3': 4,5] thieno [2,3-c] pyrrole (30.22 g, 100.0 mmol) ] To obtain 29.51 g (yield: 78%) of Compound 1-2-B.

GC-Mass (theory: 378.3 g / mol, measured: 378 g / mol)

^{1 H-NMR: δ 7.06 (} s, 2H), δ 7.49 (m, 3H), δ 7.60 (m, 3H), δ 7.78 (s, 1H), δ 7.86 (s, 1H), δ 8.03 (d, 1H), [delta] 8.67 (s, IH)

[Preparation Example 11] Synthesis of Compound 1-2-C

[Step 1] Synthesis of 2- (7-bromo-3- (methylthio) naphthalen-2-yl) -1H-pyrrole

(4,4,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrrole used in [Step 2] of [Preparation Example 1] Iodonaphthalen-2-yl) (methyl) sulfane was used instead of (3-iodonaphthalen-2-yl) The same procedure as in [Step 2] of [Preparation Example 1] was carried out except that bromo-3-iodonaphthalen-2-yl) (methyl) sulfane (56.87 g, : 63%) of 2- (7-bromo-3- (methylthio) naphthalen-2-yl) -1H-pyrrole.

GC-Mass (theory: 318.20 g / mol, measured: 318 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.15 (t, 1H), δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.39 (d, 1H), δ 7.73 (s, 1H), 8 7.97 (d, IH), 8 8.27 (s, IH)

[Step 2] Synthesis of 2- (7-bromo-3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole

2- (7-bromo-3- ((methylthio) naphthalen-2-yl) -1H-pyrrole was prepared in the same manner as in [Step 1] (yield: 71%) was obtained by carrying out the same procedure as in [Step 3] of [Preparation Example 1], except that methylthio naphthalen-2-yl) ) Of 2- (7-bromo-3- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole.

GC-Mass (theory: 334.20 g / mol, measured: 334 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.15 (t, 1H), δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.48 (d, 1H), δ 8.03 (d, 1H),? 8.52 (s, 1H),? 8.67 (s, 2H),? 11.94 (brs,

[Step 3] Synthesis of 8-bromo-1H-naphtho [2 ', 3': 4,5] thieno [3,2-b]

2-yl) -1H-pyrrole used in [Step 4] of [Preparation Example 1] instead of 2- (7-bromo-3- ( The same procedure as in [Step 4] of [Preparation Example 1] was carried out, except that 33.42 g (100.0 mmol) of methylsulfinyl naphthalen-2-yl) -1H- %) Of 8-bromo-1H-naphtho [2 ', 3': 4,5] thieno [3,2-b] pyrrole.

GC-Mass (theory: 302.2 g / mol, measurement: 302 g / mol)

^{1 H-NMR: δ 7.48 (} m, 2H), δ 7.78 (s, 1H), δ 7.86 (s, 1H), δ 7.92 (d, 1H), δ 8.03 (d, 1H), δ 8.67 (s, 1H), [delta] 11.12 (brs, IH)

[Step 4] Synthesis of Compound 1-2-C

The 8-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3-b] pyrrole obtained in [Step 3] was used instead of the 6-bromo- [Step 4 of Preparation Example 9] was repeated except for using bromo-1H-naphtho [2 ', 3': 4,5] thieno [3,2- b] pyrrole (30.22 g, ] To obtain 31.02 g (yield: 82%) of Compound 1-2-C.

GC-Mass (theory: 378.3 g / mol, measured: 378 g / mol)

^{1 H-NMR: δ 6.38 (} d, 1H), δ 7.26 (d, 1H), δ 7.49 (m, 3H), δ 7.60 (m, 3H), δ 7.78 (s, 1H), δ 7.86 (s, 1H), 8 8.03 (d, 1 H), 8 8.67 (s, 1 H)

[Preparation Example 12] Synthesis of Compound 2-2-A

[Step 1] 3- (3-bromo-1H-pyrrol-2-yl) -6-chloronaphthalen-2- Synthesis of ol

(7-chloro-3-hydroxynaphthalen-2-yl) boronic acid (44.48 g, 200.0 mmol) was used instead of (3-hydroxynaphthalen-2-yl) boronic acid used in [Step 1] of [Preparation Example 3] (Yield: 42%) of 3- (2-bromo-1H-pyrrol-3-yl) -6-chloronaphthalen- 3- (3-bromo-lH-pyrrol-2-yl) -6-chloronaphthalen-2-ol (B) was obtained in an amount of 17.42 g (yield: 27%).

GC-Mass (A) (calculated: 322.60 g / mol, measured: 322 g / mol)

≪ ¹ > H-NMR (A): [delta] 6.68 (d, IH), [delta] 7.25 (d, IH), [delta] 7.32 (d, IH), 8 8.06 (s, IH),? 9.61 (s, IH),? 12.04 (brs,

GC-Mass (B) (calculated: 322.60 g / mol, measured: 322 g / mol)

^{1 H-NMR (B):} δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.32 (d, 1H), δ 7.48 (s, 1H), δ 7.70 (s, 1H), δ 7.84 (d, IH), 8 8.06 (s, IH), 8 9.61 (s, IH)

[Step 2] Synthesis of 6-chloro-1H-naphtho [2 ', 3': 4,5] furo [2,3-b]

(2-bromo-1H-pyrazol-3-yl) naphthalen-2-ol obtained in [step 1] was used instead of 3- (2-bromo- The same procedure as in [Step 2] of [Preparation Example 3] was performed, except that 32.26 g (100.0 mmol) of pyrrol-3-yl) -6-chloronaphthalen- 88%) of 6-chloro-1H-naphtho [2 ', 3': 4,5] furo [2,3-b] pyrrole.

GC-Mass (theory: 241.70 g / mol, measured: 241 g / mol)

^{1 H-NMR: δ 7.42 (} s, 1H), δ 7.48 (m, 2H), δ 7.55 (d, 1H), δ 7.80 (s, 1H), δ 7.91 (m, 2H), δ 11.12 (brs, 1H)

[Step 3] Synthesis of Compound 2-2-A

Obtained in [Step 2] was used instead of 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole used in [Step 4] of [Preparation Example 9] [Step 4] of [Preparation Example 9] was repeated except that chloro-1H-naphtho [2 ', 3': 4,5] furo [2,3-b] pyrrole (24.17 g, (Yield: 72%) of Compound 2-2-A was obtained.

GC-Mass (theory: 317.80 g / mol, measurement: 317 g / mol)

^{1 H-NMR: δ 6.38 (} d, 1H), δ 7.26 (d, 1H), δ 7.42 (s, 1H), δ 7.49 (m, 4H), δ 7.60 (m, 3H), δ 7.80 (s, 1H), [delta] 7.90 (d, IH)

[Preparation Example 13] Synthesis of Compound 2-2-B

[Step 1] Synthesis of 3- (4-bromo-1H-pyrrol-3-yl) -6-chloronaphthalen-2-ol

3-hydroxynaphthalen-2-yl) boronic acid (44.48 g, 200.0 mmol) was used instead of (3-hydroxynaphthalen-2-yl) boronic acid used in [Step 1] of [Preparation Example 4] (Yield: 82%) of 3- (4-bromo-lH-pyrrol-3-yl) -6-chloronaphthalen-2-ol as a white solid in the same manner as in [Step 1] of [Preparation Example 4] 2-ol. ≪ / RTI >

GC-Mass (calculated: 322.60 g / mol, measured: 322 g / mol)

1 H-NMR:? 7.00 (s, 1H),? 7.16 (s, 1H),? 7.32 (d, ),? 8.06 (s, IH),? 9.60 (brs, 2H)

[Step 2] Synthesis of 8-chloro-2H-naphtho [2 ', 3': 4,5] furo [2,3-c]

Bromo-1H-pyrrole-3-yl) naphthalen-2-ol synthesized in [Step 1] was used instead of 3- (2-bromo- The same procedure as in [Step 2] of [Preparation Example 3] was carried out, except that 32.26 g (100.0 mmol) of 2- : 81%) of 8-chloro-2H-naphtho [2 ', 3': 4,5] furo [2,3-c] pyrrole.

GC-Mass (theory: 241.70 g / mol, measured: 241 g / mol)

1H-NMR:? 7.42 (s, 1H),? 7.49 (m, 2H),? 7.91 (m, 4H)

[Step 3] Synthesis of Compound 2-2-B

Was obtained in the same manner as in [Step 2] except that 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole used in [Step 4] of [Preparation Example 9] [Step 4] of [Preparation Example 9] was repeated, except that chloro-2H-naphtho [2 ', 3': 4,5] furo [2,3-c] pyrrole (24.17 g, (Yield: 79%) of Compound 2-2-B was obtained.

GC-Mass (theory: 317.80 g / mol, measurement: 317 g / mol)

^{1 H-NMR: δ 7.06 (} s, 2H), δ 7.42 (s, 1H), δ 7.49 (m, 4H), δ 7.60 (m, 3H), δ 7.80 (s, 1H), δ 7.90 (d, 1H)

[Preparation Example 14] Synthesis of Compound 2-2-C

[Step 1] Synthesis of 8-chloro-1H-naphtho [2 ', 3': 4,5] furo [3,2-b]

(3- (2-bromo-1H-pyrrol-3-yl) naphthalen-2-ol obtained in [Step 1] of [Preparation Example 12] was used instead of 3- The same procedure as in [Step 2] of [Preparation Example 3] was carried out except that 32.26 g (100.0 mmol) of 2-bromo-1H-pyrrol-2- To obtain 18.37 g (yield: 76%) of 8-chloro-1H-naphtho [2 ', 3': 4,5] furo [3,2-b] pyrrole.

GC-Mass (theory: 241.70 g / mol, measured: 241 g / mol)

1H-NMR:? 7.42 (s, 1H),? 7.48 (m, 2H),? 7.55 (d, 1H),? 7.80 )

[Step 2] Synthesis of compound 2-2-C

Obtained in the above Step 1 was used instead of 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole used in [Step 4] of [Preparation Example 9] [Step 4] of [Preparation Example 9] was repeated except that chloro-1H-naphtho [2 ', 3': 4,5] furo [3,2- b] pyrrole (24.17 g, (Yield: 67%) of Compound 2-2-C was obtained.

GC-Mass (theory: 317.80 g / mol, measurement: 317 g / mol)

^{1 H-NMR: δ 6.38 (} d, 1H), δ 7.26 (d, 1H), δ 7.42 (s, 1H), δ 7.49 (m, 4H), δ 7.60 (m, 3H), δ 7.80 (s, 1H), [delta] 7.90 (d, IH)

[Preparation Example 15] Synthesis of Compound 3-2-A

Synthesis of 3 - ((1H-pyrrol-2-yl) methyl) -7-chloro-3,4-dihydronaphthalen-2 (1H)

1- (6-chloro-1,4-dihydronaphthalen-2-yl) pyrrolidine (51.41 g, prepared as described in Preparation Example 6) was used instead of 1- (1,4- dihydronaphthalen- The same procedure as in [Step 1] of [Preparation Example 6] was repeated to produce 17.40 g (yield: 67%) of 3 - ((1H-pyrrol- 2- yl) methyl) -7-chloro-3,4-dihydronaphthalen-2 (1H) -one.

GC-Mass (theory: 259.70 g / mol, measured: 259 g / mol)

^{1 H-NMR: δ 2.67 (} m, 2H), δ 2.92 (m, 2H), δ 3.29 (m, 1H), δ 3.66 (d, 1H), δ 3.76 (d, 1H), δ 5.88 (d, (D, IH), 8 7.31 (d, IH), 8 7.62 (s, IH), 8 11.84 (brs,

[Step 2] Synthesis of 6-chloro-1,10-dihydrobenzo [5,6] indeno [2,1-b]

(3- (1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one used in [Step 2] of [Preparation Example 6] Preparation Example 6] was repeated except that (1 H-pyrrol-2-yl) methyl) -7-chloro-3,4-dihydronaphthalen-2 (1H) -one (38.96 g, 150.0 mmol) (Yield: 58%) of 6-chloro-1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole was obtained in the same manner as in [Step 2].

GC-Mass (calculated: 239.70 g / mol, measured: 239 g / mol)

^{1 H-NMR: δ 3.96 (} s, 2H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.39 (d, 1H), δ 7.69 (s, 2H), δ 7.85 (d, 1H), 8 8.27 (s, 1 H), 8 11.94 (brs, 1 H)

[Step 3] Synthesis of 6-chloro-10,10-dimethyl-1,10-dihydrobenzo [5,6] indeno [2,1-b]

1, 10-dihydrobenzo [2,1-b] pyrrole obtained in [Step 2] was used instead of 1,10-dihydrobenzo [5,6] 5,6] indeno [2,1-b] pyrrole (23.97 g, 100.0 mmol) was used in the same manner as in [Step 3] of [Preparation Example 6] %) Of 6-chloro-10,10-dimethyl-1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole.

GC-Mass (theory: 267.80 g / mol, measured: 267 g / mol)

^{1 H-NMR: δ 1.80 (} s, 6H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.36 (d, 1H), δ 7.69 (s, 2H), δ 7.80 (d, 1H), [delta] 8.30 (s, IH), 11.94 (brs, IH)

[Step 4] Synthesis of Compound 3-2-A

Obtained in [Step 3] was used instead of 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole used in [Step 4] of [Preparation Example 9] [Step 9] of Preparation Example 9 was repeated except that chloro-10,10-dimethyl-1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole (26.78 g, 4], 23.39 g (yield: 68%) of Compound 3-2-A was obtained.

GC-Mass (theory: 343.90 g / mol, measured: 343 g / mol)

^{1 H-NMR: δ 1.80 (} s, 6H), δ 6.42 (d, 1H), δ 7.30 (d, 1H), δ 7.36 (d, 1H), δ 7.50 (d, 2H), δ 7.60 (m, (S, 3H), 8 7.68 (m, 2H), 8 7.80

[Preparation Example 16] Synthesis of Compound 3-2-B

Synthesis of 3 - ((1H-pyrrol-3-yl) methyl) -7-chloro-3,4-dihydronaphthalen-2 (1H)

(Bromomethyl) -1H-pyrrole (32.0 g, 200.0 mmol) instead of 2- (bromomethyl) -1H-pyrrole used in [Step 1] of [Preparation Example 6] Step 1 of Preparation Example 6 was repeated except that 1- (6-chloro-1,4-dihydronaphthalen-2-yl) pyrrolidine (51.41 g, 220.0 mmol) was used in place of dihydronaphthalen- (1H-pyrrol-3-yl) methyl) -7-chloro-3,4-dihydronaphthalen-2 (1H) -one was obtained in a yield of 35.84 g (yield: 69% .

GC-Mass (theory: 259.70 g / mol, measured: 259 g / mol)

3.26 (d, IH),? 3.66 (d, IH),? 3.76 (d, 1H),? 6.02 (d, IH), 8.45 (d, IH), 8.45 (d, IH)

[Step 2] 6-chloro-2,10-dihydrobenzo [5,6] indeno [1,2-c] pyrrole, 8-chloro-1,4- dihydrobenzo [ Synthesis of pyrrole

(3- (1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one used in [Step 2] of [Preparation Example 6] (38.96 g, 150.0 mmol) was used in place of (1H-pyrrol-3-yl) methyl) -7-chloro-3,4-dihydronaphthalen- (Yield: 38%) of 6-chloro-2,10-dihydrobenzo [5,6] indeno [1,2-c] pyrrole (A) and 12.58 g : 35%) of 8-chloro-1,4-dihydrobenzo [5,6] indeno [1,2-b] pyrrole (B).

GC-Mass (A) (calculated: 239.70 g / mol, measured: 239 g / mol)

1H-NMR (?):? 3.80 (s, 2H),? 6.67 (s, 1H),? 6.83 d, 1 H), 8 8.27 (s, 1 H),? 9.60 (brs, 1 H)

GC-Mass (B) (calculated: 239.70 g / mol, measured: 239 g / mol)

(D, 1H), 7.39 (d, 1H), 7.69 (s, 2H), 7.85 (d, d, 1 H), 8 8.27 (s, 1 H), 8 11.94 (brs, 1 H)

[Step 3] Synthesis of 6-chloro-10,10-dimethyl-2,10-dihydrobenzo [5,6] indeno [1,2-

The procedure of Example 1 was repeated except that 6-chloro-2,10-dihydrobenzo [2,1-b] pyridine obtained in the above Step 1 was used instead of 1,10-dihydrobenzo [5,6] 5,6] indeno [1,2-c] pyrrole (23.97 g, 100.0 mmol) was used in the same manner as in [Step 3] of [Preparation Example 6] %) Of 6-chloro-10,10-dimethyl-2,10-dihydrobenzo [5,6] indeno [1,2-c] pyrrole.

GC-Mass (theory: 267.80 g / mol, measured: 267 g / mol)

1H-NMR:? 1.75 (s, 6H),? 6.67 (s, IH),? 6.83 (s, IH),? 7.36 ), [delta] 8.30 (s, IH), [delta] 9.60 (brs, IH)

[Step 4] Synthesis of Compound 3-2-B

Obtained in [Step 3] was used instead of 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole used in [Step 4] of [Preparation Example 9] [Step 9] of Preparation Example 9 was repeated except that chloro-10,10-dimethyl-2,10-dihydrobenzo [5,6] indeno [1,2-c] pyrrole (26.78 g, 4] to obtain 25.79 g (yield: 75%) of 3-2-B.

GC-Mass (theory: 343.90 g / mol, measured: 343 g / mol)

^{1 H-NMR: δ 1.75 (} s, 6H), δ 7.01 (d, 2H), δ 7.36 (d, 1H), δ 7.50 (d, 2H), δ 7.60 (m, 3H), δ 7.69 (m, 2H), 8 7.80 (d, 1 H), 8 8.30 (s, 1 H)

[Preparation Example 17] Synthesis of Compound 3-2-C

[Step 1] Synthesis of 8-chloro-4,4-dimethyl-1,4-dihydrobenzo [5,6] indeno [1,2- b]

Obtained in [Step 2] of [Preparation Example 16] was used instead of 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [Step 3] of [Preparation Example 6] [Step 3] of [Preparation Example 6] was carried out, except that 4-dihydrobenzo [5,6] indeno [1,2-b] pyrrole (23.97 g, 100.0 mmol) 4-dimethyl-1,4-dihydrobenzo [5,6] indeno [1,2-b] pyrrole.

GC-Mass (theory: 267.80 g / mol, measured: 26733 g / mol)

(D, IH), 7.36 (d, IH), 7.69 (m, 2H), 7.80 ), [delta] 8.30 (s, IH), [delta] 11.94 (brs, IH)

[Step 2] Synthesis of compound 3-2-C

Obtained in the above Step 1 was used instead of 6-bromo-1H-naphtho [2 ', 3': 4,5] thieno [2,3- b] pyrrole used in [Step 4] of [Preparation Example 9] [Step 9] of Preparation Example 9 was repeated except that chloro-4,4-dimethyl-1,4-dihydrobenzo [5,6] indeno [1,2- b] pyrrole (26.78 g, 4] to obtain 24.42 g (yield: 71%) of the compound 3-2-C.

GC-Mass (theory: 343.90 g / mol, measured: 343 g / mol)

^{1 H-NMR: δ 1.75 (} s, 6H), δ 6.27 (d, 1H), δ 7.06 (d, 1H), δ 7.36 (d, 1H), δ 7.50 (d, 2H), δ 7.60 (m, (S, 3H), 8 7.69 (m, 2H), 8 7.80

[Preparation Example 18] Synthesis of Compound 1-3

[Step 1] Synthesis of 1,2,5-triphenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-

Except that 3-bromo-1,2,5-triphenyl-1H-pyrrole (74.86 g, 200.0 mmol) was used instead of 3-bromo-1H-pyrrole used in [Step 1] of [Preparation Example 1] (Yield: 84%) of 1,2,5-triphenyl-3- (4,4,5,5-tetramethyl-1,3 , 2-dioxaborolan-2-yl) -1H-pyrrole.

GC-Mass (calculated value: 421.30 g / mol, measured: 421 g / mol)

¹ H-NMR:? 1.20 (s, 12H),? 6.47 (s, 1H),? 7.51 (m,

[Step 2] Synthesis of 3- (7-bromo-3- (methylthio) naphthalen-2-yl) -1,2,5-triphenyl-1H-

The same procedure as in [Step 1] was repeated except for using 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrrole (63.20 g, 150.0 mmol) was used as a starting material, and (3) (3,3,5-tetramethyl-1,3,2-dioxaborolan- except that 6-bromo-3-iodonaphthalen-2-yl) (methyl) -l 3 -sulfane (57.02 g, 150.0 mmol) was used in place of diiodonaphthalen-2-yl) (Yield: 88%) of 3- (7-bromo-3- (methylthio) naphthalen-2-yl) -1,2,5-triphenyl-1H -pyrrole.

GC-Mass (calculated: 546.50 g / mol, measured: 546 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.67 (s, 1H), δ 7.39 (d, 1H), δ 7.51 (m, 8H), δ 7.60 (m, 3H), δ 7.73 (s, 1H), 8 7.84 (d, 4H), 8 7.97 (d, 1H), 8 8.27

[Step 3] Synthesis of 3- (7-bromo-3- (methylsulfinyl) naphthalen-2-yl) -1,2,5-triphenyl-1H-

(7-bromo-3- (methylthio) -1H-pyrrole obtained in the above Step 2 was used instead of 3- (3- (methylthio) naphthalen- The same procedure as in [Step 3] of [Preparation Example 1] was carried out except that naphthalen-2-yl) -1,2,5-triphenyl-1H-pyrrole (54.65 g, 100.0 mmol) To obtain 41.63 g (yield: 74%) of 3- (7-bromo-3- (methylsulfinyl) naphthalen-2-yl) -1,2,5-triphenyl-1H-pyrrole.

GC-Mass (calculated: 562.50 g / mol, measured: 562 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.67 (s, 1H), δ 7.51 (m, 9H), δ 7.60 (m, 3H), δ 7.84 (d, 4H), δ 8.03 (d, 1H),? 8.52 (s, 1H),? 8.67 (s, 2H)

[Step 4] Synthesis of Compound 1-3

(Methylsulfinyl) naphthalen-2-yl) -1H-pyrrole used in [Step 4] of [Preparation Example 1] instead of 3- The same procedure as in [Step 4] of [Preparation Example 1] was carried out except that naphthalen-2-yl) -1,2,5-triphenyl-1H-pyrrole (56.25 g, 100.0 mmol) 30.77 g (yield: 58%) of Compound 1-3 was obtained.

GC-Mass (calculated: 530.50 g / mol, measured: 530 g / mol)

^{1 H-NMR: δ 7.51 (} m, 9H), δ 7.60 (m, 3H), δ 7.78 (s, 1H), δ 7.85 (m, 5H), δ 8.03 (d, 1H), δ 8.67 (s, 1H)

[Preparation Example 19] Synthesis of Compound 2-3

[Step 1] Synthesis of 3- (4-bromo-1,2,5-triphenyl-1H-pyrrol-3-yl) -6-chloronaphthalen-

3,4-dibromo-1,2,5-triphenyl-1H-pyrrole (90.64 g, 200.0 mmol) was used instead of 2,3-dibromo-1H-pyrrole used in [Step 1] of [Preparation Example 3] 3-hydroxynaphthalen-2-yl) boronic acid (44.48 g, 200.0 mmol) was used in place of (3-hydroxynaphthalen-2- (Yield: 83%) of 3- (4-bromo-1,2,5-triphenyl-1H-pyrrol-3-yl) -6- chloronaphthalen-2-ol .

GC-Mass (calculated: 550.90 g / mol, measured: 550 g / mol)

^{1 H-NMR: δ 7.32 (} d, 1H), δ 7.51 (m, 9H), δ 7.60 (m, 3H), δ 7.70 (s, 1H), δ 7.84 (m, 5H), δ 8.06 (s, 1H), [delta] 9.61 (s, IH)

[Step 2] Synthesis of Compound 2-3

3-yl) naphthalen-2-ol obtained in [Step 1] was used instead of 3- (2-bromo-lH-pyrrol- The same procedure as in [Step 2] of [Preparation Example 3] was repeated except that 2,5-triphenyl-1H-pyrrol-3-yl) -6-chloronaphthalen- To yield 43.24 g (yield: 92%) of compound 2-3.

GC-Mass (theory: 470.00 g / mol, measurement: 470 g / mol)

^{1 H-NMR: δ 7.42 (} s, 1H), δ 7.51 (m, 10H), δ 7.60 (m, 3H), δ 7.80 (s, 1H), δ 7.84 (d, 4H), δ 7.90 (d, 1H)

[Preparation Example 20] Synthesis of Compound 3-3

Synthesis of 7-chloro-3 - ((1,2,5-triphenyl-1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-

(Bromomethyl) -1,2,5-triphenyl-1H-pyrrole (77.66 g, 200.0 mmol) was used instead of 2- (bromomethyl) -1H-pyrrole used in [Step 1] of [Preparation Example 6] , Except that 1- (6-chloro-1,4-dihydronaphthalen-2-yl) pyrrolidine (51.41 g, 220.0 mmol) was used instead of 1- (1,4- dihydronaphthalen- (Yield: 73%) of 7-chloro-3 - ((1,2,5-triphenyl-1H-pyrrol-3-yl) methyl) thiophene was obtained by carrying out the same processes as in [Step 1] of Preparation Example 6 -3,4-dihydronaphthalen-2 (1H) -one.

GC-Mass (calculated: 488.00 g / mol, measured: 488 g / mol)

1H-NMR:? 2.68 (m, 2H),? 2.93 (m, 2H),? 3.29 (m, 1H),? 3.66 ), 7.14 (d, IH), 7.35 (d, IH), 7.51 (m, 8H)

[Step 2] Synthesis of 6-chloro-1,2,3-triphenyl-2,10-dihydrobenzo [5,6] indeno [1,2-

(1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one used in [Step 2] of [Preparation Example 6] except that 3-chloro-3 - ((1,2,5-triphenyl-lH-pyrrol-3-yl) methyl) -3,4- dihydronaphthalen-2 (1H) -one (73.20 g, 150.0 mmol) (Yield: 57%) of 6-chloro-1,2,3-triphenyl-2,10-dihydrobenzo [5,6] indeno (yield: 57%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 6] [1,2-c] pyrrole.

GC-Mass (calculated: 468.00 g / mol, measured: 468 g / mol)

^{1 H-NMR: δ 3.80 (} s, 2H), δ 7.39 (d, 1H), δ 7.51 (m, 8H), δ 7.60 (m, 3H), δ 7.69 (s, 2H), δ 7.85 (m, 5H), 8 8.27 (s, 1 H)

[Step 3] Synthesis of Compound 3-3

Except that the 6-chloro-1,2,3-thiadiazole obtained in the above Step 2 was used instead of the 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [Step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was carried out except that triphenyl-2,10-dihydrobenzo [5,6] indeno [1,2-c] pyrrole (46.80 g, To obtain 3-3 of 26.21 g (yield: 56%).

GC-Mass (calculated: 468.00 g / mol, measured: 468 g / mol)

^{1 H-NMR: δ 1.75 (} s, 6H), δ 7.36 (d, 1H), δ 7.51 (m, 8H), δ 7.61 (m, 3H), δ 7.69 (m, 2H), δ 7.82 (d, 5H), [delta] 8.30 (s, IH)

[Preparation Example 21] Synthesis of compounds 4-1-A and 4-1-B

[Step 1] Synthesis of 3- (1- (methylthio) naphthalen-2-yl) -1H-pyrrole

(2-iodonaphthalen-1-yl) (methyl) sulfane (45.02 g, 150.0 mmol) instead of (3-iodonaphthalen-2-yl) (methyl) sulfane used in [Step 2] of [Preparation Example 1] (Methylthio) naphthalen-2-yl) -1H-pyrrole (yield: 75%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 1] Respectively.

GC-Mass (calculated: 239.34 g / mol, measured: 239 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (s, 1H), δ 7.15 (d, 1H), δ 7.52 (t, 1H), δ 7.59 (t, (D, 1H), 8 8.0 (d, 1H), 8 8.07 (d,

[Step 2] Synthesis of 3- (1- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole

(Methylthio) naphthalen-2 (2-yl) -1H-pyrrole obtained in the above Step 1 was used instead of 3- (methylthio) naphthalen- (yield: 73%) of 3- (2-fluorophenyl) -1H-pyrrole (23.93 g, 100.0 mmol) was used in the same manner as in [Step 3] of [Preparation Example 1] 1- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole.

GC-Mass (calculated: 255.33 g / mol, measured: 255 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (s, 1H), δ 7.15 (d, 1H), δ 7.41 (t, 1H), δ 7.52 (t, (D, 1H), 8 8.15 (d, 1H), 8.31 (d, 1H), 8.48

[Step 3] Synthesis of compounds 4-1-A and 4-1-B

(Methylsulfinyl) naphthalen-2 (2-yl) -1H-pyrrole obtained in [Step 2] was used instead of 3- (3- (methylsulfinyl) (yield: 20%) of the compound 4- (4-fluorophenyl) -1H-pyrrole (25.53 g, 100.0 mmol) 1-A and 7.37 g (yield: 33%) of compound 4-1-B.

GC-Mass of the compound 4-1-A (theoretical value: 223.29 g / mol, measured value: 223 g / mol)

Of the compound ^{4-1-A 1 H-NMR:} δ 7.64 (m, 2H), δ 7.83 (d, 1H), δ 7.92 (d, 2H), δ 8.03 (m, 2H), δ 8.16 (d, 1H ), [delta] 11.12 (brs, IH)

GC-Mass of the compound 4-1-B (theoretical value: 223.29 g / mol, measured value: 223 g / mol)

¹ H-NMR of the compound 4-1-B: δ 7.64 (m , 2H), δ 7.83 (d, 1H), δ 7.92 (s, 2H), δ 8.03 (m, 2H), δ 8.16 (d, 1H ), [delta] 11.12 (brs, IH)

[Preparation Example 22] Synthesis of Compound 4-1-C

[Step 1] Synthesis of 2- (1- (methylthio) naphthalen-2-yl) -1H-pyrrole

(4,4,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrrole used in [Step 2] of [Preparation Example 1] Iodonaphthalen-2-yl) (methyl) sulfane was used instead of (3-iodonaphthalen-2-yl) The same procedure as in [Step 2] of [Preparation Example 1] was repeated to obtain 24.77 g (yield: 69%) of iodonaphthalen-1-yl (methyl) sulfane (45.02 g, 2- (1- (methylthio) naphthalen-2-yl) -1H-pyrrole.

GC-Mass (calculated: 239.34 g / mol, measured: 239 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.15 (t, 1H), δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.52 (t, 1H), δ 7.59 (t, (D, 1H), 8 8.0 (d, 1H), 8.07 (d,

[Step 2] Synthesis of 2- (1- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole

(Methylthio) naphthalen-2 (2-yl) -1H-pyrrole obtained in [step 1] was used instead of 3- (methylthio) naphthalen- (yield: 76%) of 2- ((4-fluorophenyl) -1H-pyrrole- 1- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole.

GC-Mass (calculated: 255.33 g / mol, measured: 255 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (s, 1H), δ 7.15 (d, 1H), δ 7.41 (t, 1H), δ 7.52 (t, (D, 1H), 8 8.15 (d, 1H), 8.31 (d, 1H), 8.48

[Step 3] Synthesis of compound 4-1-C

(1- (methylsulfinyl) naphthalen-2-yl) -1H-pyrrole obtained in [Step 2] was used instead of 3- (3- (methylsulfinyl) (yield: 58%) of compound 4- (4-fluorophenyl) -1H-pyrrole (25.53 g, 100.0 mmol) was used in the same manner as in [Step 4] of [Preparation Example 1] 1-C.

GC-Mass (calculated: 223.29 g / mol, measured: 223 g / mol)

^{1 H-NMR: δ 7.64 (} t, 2H), δ 7.83 (d, 1H), δ 7.92 (m, 2H), δ 8.03 (m, 2H), δ 8.16 (d, 1H), δ 11.12 (brs, 1H)

[Preparation Example 23] Synthesis of Compound 5-1-A

Synthesis of 2- (2-bromo-1H-pyrrol-3-yl) naphthalen-1-ol and 2- (3-bromo-1H-

Except that (1-hydroxynaphthalen-2-yl) boronic acid (37.6 g, 200.0 mmol) was used instead of (3-hydroxynaphthalen-2-yl) boronic acid used in [Step 1] of [Preparation Example 3] (2-bromo-1H-pyrrol-3-yl) naphthalen-1-ol (A) and 20.16 g (yield: 35%) of [Step 1] of [Preparation Example 3] To obtain 16.14 g (yield: 28%) of 2- (3-bromo-1H-pyrrol-2-yl) naphthalen-1-ol (B).

GC-Mass (A) (calculated: 288.14 g / mol, measured: 288 g / mol)

^{1 H-NMR (A):} δ 6.68 (d, 1H), δ 7.25 (d, 1H), δ 7.67 (m, 2H), δ 7.88 (m, 2H), δ 8.21 (d, 1H), δ 8.32 (d, 1 H),? 10.33 (s, 1H),? 12.04 (brs, 1H)

GC-Mass (B) (288.14 g / mol, measured: 288 g / mol)

^{1 H-NMR (B):} δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.67 (m, 2H), δ 7.88 (m, 2H), δ 8.21 (d, 1H), δ 8.32 (d, 1 H),? 10.33 (s, 1H),? 11.94 (brs, 1H)

[Step 2] Synthesis of Compound 5-1-A

(2-bromo-lH-pyrrolo [3-yl] naphthalen-2-ol obtained in the above Step 1 was used instead of 3- (2-bromo- 18.23 g (yield: 88%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 3], except that 28.81 g (100.0 mmol) of 3- Of Compound 5-1-A.

GC-Mass (207.2 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.48 (} d, 1H), δ 7.68 (m, 2H), δ 7.84 (d, 1H), δ 7.92 (m, 2H), δ 8.14 (m, 2H), δ 11.12 (brs, 1H)

[Preparation Example 24] Synthesis of Compound 5-1-B

[Step 1] Synthesis of 2- (4-bromo-1H-pyrrol-3-yl) naphthalen-1-ol

(44.98 g, 200.0 mmol) was used instead of 2,3-dibromo-1H-pyrrole used in [Step 1] of [Preparation Example 3], and 3-hydroxynaphthalen- The same procedure as in [Step 1] of [Preparation Example 3] was repeated except that 1-hydroxynaphthalen-2-yl boronic acid (37.6 g, 200.0 mmol) yield: 78%) of 2- (4-bromo-1H-pyrrol-3-yl) naphthalen-1-ol.

GC-Mass (288.1 g / mol, measured: 288 g / mol)

^{1 H-NMR: δ 7.00 (} s, 1H), δ 7.16 (s, 1H), δ 7.67 (m, 2H), δ 7.88 (m, 2H), δ 8.21 (d, 1H), δ 8.32 (d, 1H), [delta] 9.60 (brs, IH), [delta] 10.33 (s, IH)

[Step 2] Synthesis of Compound 5-1-B

(4-bromo-lH-pyrrolo [3-yl] naphthalen-2-ol obtained in [Step 1] was used instead of 3- (2-bromo- (yield: 82%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 3], except that 28.81 g (100.0 mmol) of 2- Of compound 5-1-B.

GC-Mass (207.20 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.48 (} d, 1H), δ 7.68 (m, 2H), δ 7.84 (d, 1H), δ 7.92 (s, 2H), δ 8.14 (m, 2H), δ 11.12 (brs, 1H)

[Preparation Example 25] Synthesis of Compound 5-1-C

(2-bromo-1H-pyrrol-3-yl) naphthalen-2-ol obtained in [Step 1] in the above [Preparation Example 23] was used instead of 3- The same procedure as in [Step 2] of [Preparation Example 3] was carried out except that 28.81 g (100.0 mmol) of 3-bromo-1H-pyrrol-2-yl) naphthalen- (yield: 85%) of compound 5-1-C.

GC-Mass (207.20 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.48 (} d, 1H), δ 7.68 (m, 2H), δ 7.84 (d, 1H), δ 7.92 (m, 2H), δ 8.14 (m, 2H), δ 11.12 (brs, 1H)

[Preparation Example 26] Synthesis of Compound 6-1-A

[Step 1] Synthesis of 1 - ((1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H)

Dihydronaphthalen-2-yl) pyrrolidine (43.85 g, 220.0 mmol) instead of 1- (1,4-dihydronaphthalen-2-yl) pyrrolidine used in [Step 1] of [Preparation Example 6] 1 - ((1H-pyrrol-2-yl) methyl) -3, 4 (yield: 62%) was obtained by carrying out the same procedure as in [Step 1] of [Preparation Example 6] -dihydronaphthalen-2 (1H) -one.

GC-Mass (calculated: 225.30 g / mol, measured: 225 g / mol)

^{1 H-NMR: δ 2.73 (} m, 1H), δ 2.83 (m, 3H), δ 3.04 (m, 1H), δ 3.29 (m, 1H), δ 4.02 (m, 1H), δ 5.88 (d, (D, 1H), 6.11 (t, 1H), 6.64 (d, 1H), 7.20

[Step 2] Synthesis of 9,10-dihydrobenzo [4,5] indeno [2,1-b] pyrrole

(LH) -one obtained in the above Step 1 was used instead of 3 - ((lH-pyrrol-2-yl) methyl) -3,4- dihydronaphthalen- [Step 2] of [Preparation Example 6] was repeated except that (1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one (33.80 g, 150.0 mmol) (Yield: 54%) of 9,10-dihydrobenzo [4,5] indeno [2,1-b] pyrrole was obtained.

GC-Mass (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR: δ 4.29 (} s, 2H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.31 (t, 1H), δ 7.61 (t, 1H), δ 8.00 (m, 2H), 8 8.14 (d, 1 H), 8 11.94 (brs, 1 H)

[Step 3] Synthesis of Compound 6-1-A

Dihydrobenzo [4,5] dihydrobenzo [2,1-b] pyrrole obtained in [step 2] was used instead of 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [Step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was conducted, except that 20.53 g (100%) of indeno [2,1-b] pyrrole was used, yielding 10.97 g (yield: 47% 6-1-A.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.87 (} s, 6H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.32 (t, 1H), δ 7.62 (t, 1H), δ 8.04 (m, 3H), [delta] 8.16 (d, IH), 8 11.94 (brs, IH)

[Preparation Example 27] Synthesis of Compound 6-1-B

[Step 1] Synthesis of 1 - ((1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-2 (1H)

(Bromomethyl) -1H-pyrrole (32.0 g, 200.0 mmol) instead of 2- (bromomethyl) -1H-pyrrole used in [Step 1] of [Preparation Example 6] Step 1] of [Preparation Example 6] was repeated except that 1- (3,4-dihydronaphthalen-2-yl) pyrrolidine (43.85 g, 220.0 mmol) was used in place of dihydronaphthalen- (Yield: 80%) of 1 - ((1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one.

GC-Mass (calculated: 225.30 g / mol, measured: 225 g / mol)

^{1 H-NMR: δ 2.73 (} m, 1H), δ 2.84 (m, 4H), δ 3.13 (m, 1H), δ 4.02 (m, 1H), δ 6.02 (d, 1H), δ 6.53 (s, (D, 1H), 8.45 (m, 3H), 8.45

[Step 2] Synthesis of 8,10-dihydrobenzo [4,5] indeno [1,2-c] pyrrole, 7,10-dihydrobenzo [4,5] indeno [

(LH) -one obtained in the above Step 1 was used instead of 3 - ((lH-pyrrol-2-yl) methyl) -3,4- dihydronaphthalen- [Step 2] of [Preparation Example 6] was repeated except that (1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one (33.80 g, 150.0 mmol) (Yield: 38%) of 7,10-dihydrobenzo [4,5] indeno [1,2-c] pyrrole (A) and 11.39 g (yield: 37% -dihydrobenzo [4,5] indeno [1,2-b] pyrrole (B).

GC-Mass (A) (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR (A):} δ 4.13 (s, 2H), δ 6.67 (s, 1H), δ 6.83 (s, 1H), δ 7.31 (t, 1H), δ 7.61 (t, 1H), δ 7.99 (m, 3H), [delta] 8.14 (d, IH), [delta] 9.60 (brs, IH)

GC-Mass (B) (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR (B):} δ 4.13 (s, 2H), δ 6.28 (d, 1H), δ 6.75 (d, 1H), δ 7.31 (t, 1H), δ 7.61 (t, 1H), δ 7.99 (m, 3H), 8 8.14 (d, IH), 8 11.94 (brs, IH)

[Step 3] Synthesis of Compound 6-1-B

Dihydrobenzo [4,5] dihydrobenzo [2,1-b] pyrrole obtained in [Step 2] was used instead of 1,10-dihydrobenzo [5,6] The same procedure as in [Step 3] of [Preparation Example 6] was repeated except that indeno [1,2-c] pyrrole (20.53 g, 100.0 mmol) was used to yield 12.60 g (yield: 54% 6-1-B.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.82 (} s, 6H), δ 6.67 (s, 1H), δ 6.83 (s, 1H), δ 7.32 (t, 1H), δ 7.62 (t, 1H), δ 8.04 (m, 3H), [delta] 8.16 (d, IH), [delta] 9.60 (brs, IH)

[Preparation Example 28] Synthesis of Compound 6-1-C

Obtained in [Step 2] of Preparation Example 27 instead of 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [Step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was performed, except that dihydrobenzo [4,5] indeno [1,2-b] pyrrole (20.53 g, 100.0 mmol) : 50%) of Compound 6-1-C.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.82 (} s, 6H), δ 6.28 (d, 1H), δ 6.75 (d, 1H), δ 7.32 (t, 1H), δ 7.62 (t, 1H), δ 8.04 (m, 3H), [delta] 8.16 (d, IH), 8 11.94 (brs, IH)

[Preparation Example 29] Synthesis of compounds 7-1-A and 7-1-B

[Step 1] Synthesis of 3- (2- (methylthio) naphthalen-1-yl) -1H-pyrrole

(1-iodonaphthalen-2-yl) (methyl) sulfane (45.02 g, 150.0 mmol) was used instead of (3-iodonaphthalen-2-yl) (methyl) sulfane used in [Step 2] of [Preparation Example 1] (Methylthio) naphthalen-1-yl) -1H-pyrrole (yield: 73%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 1] Respectively.

GC-Mass (calculated: 239.34 g / mol, measured: 239 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (s, 1H), δ 7.15 (d, 1H), δ 7.41 (t, 1H), δ 7.50 (t, 1H), 8 7.67 (d, 1H), 8 8.00 (m, 2H), 8 8.91

[Step 2] Synthesis of 3- (2- (methylsulfinyl) naphthalen-1-yl) -1H-pyrrole

(2- (methylthio) naphthalen-1-yl) -1H-pyrrole obtained in the above Step 1 was used instead of 3- (3- (methylthio) naphthalen- (yield: 74%) of 3- (2-fluorophenyl) -1H-pyrrole (23.93 g, 100.0 mmol) was used in the same manner as in [Step 3] of [Preparation Example 1] 2- (methylsulfinyl) naphthalen-1-yl) -1H-pyrrole.

GC-Mass (calculated: 255.33 g / mol, measured: 255 g / mol)

^{1 H-NMR: δ 2.64 (} s, 3H), δ 6.44 (d, 1H), δ 6.87 (s, 1H), δ 7.15 (d, 1H), δ 7.55 (m, 2H), δ 7.77 (d, (D, 1H), 8 8.15 (d, 1H), 8.43 (d,

[Step 3] Synthesis of compounds 7-1-A and 7-1-B

(2- (methylsulfinyl) naphthalen-1-yl) -1H-pyrrole obtained in [Step 2] was used instead of 3- (3- (methylsulfinyl) (yield: 23%) of the compound 7- (4-fluorophenyl) -1H-pyrrole (25.53 g, 100.0 mmol) was used in place of [ 1-A and 8.04 g (yield: 36%) of compound 7-1-B.

GC-Mass of the compound 7-1-A (theoretical value: 223.29 g / mol, measured value: 223 g / mol)

Of the compound ^{7-1-A 1 H-NMR:} δ 7.53 (m, 2H), δ 7.61 (t, 1H), δ 7.79 (m, 2H), δ 7.92 (m, 2H), δ 7.99 (d, 1H ), [delta] 11.12 (brs, IH)

GC-Mass of compound 7-1-B (calculated: 223.29 g / mol, measured: 223 g / mol)

Compound ¹ of the 7-1-B H-NMR: δ 7.53 (t, 1H), δ 7.61 (t, 1H), δ 7.79 (m, 2H), δ 7.92 (s, 2H), δ 7.99 (d, 1H ), 8.54 (d, IH), 8.11 (brs, IH)

[Preparation Example 30] Synthesis of Compound 7-1-C

[Step 1] Synthesis of 2- (2- (methylthio) naphthalen-1-yl) -1H-pyrrole

(4,4,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrrole used in [Step 2] of [Preparation Example 1] Iodonaphthalen-2-yl) (methyl) sulfane was used instead of (3-iodonaphthalen-2-yl) (yield: 67%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 1], except that iodonaphthalen-2-yl) (methyl) sulfane (45.02 g, 2- (2- (methylthio) naphthalen-1-yl) -1H-pyrrole.

GC-Mass (calculated: 239.34 g / mol, measured: 239 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.15 (t, 1H), δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.41 (t, 1H), δ 7.50 (t, 1H), 8 7.67 (d, 1H), 8.01 (m, 2H), 8 8.91

[Step 2] Synthesis of 2- (2- (methylsulfinyl) naphthalen-1-yl) -1H-pyrrole

(2- (methylthio) naphthalen-1-yl) -1H-pyrrole obtained in [Step 1] was used instead of 3- (methylthio) naphthalen- (yield: 80%) of 2- ((4-fluorophenyl) -1H-pyrrole- 2- (methylsulfinyl) naphthalen-1-yl) -1H-pyrrole.

GC-Mass (calculated: 255.33 g / mol, measured: 255 g / mol)

^{1 H-NMR: δ 2.46 (} s, 3H), δ 6.15 (t, 1H), δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.52 (t, 1H), δ 7.59 (t, (D, IH), 8 7.77 (d, IH), 8 8.15 (d, IH), 8.43

[Step 3] Synthesis of Compound 7-1-C

(2- (methylsulfinyl) naphthalen-1-yl) -1H-pyrrole obtained in [Step 2] was used instead of 3- (3- (methylsulfinyl) The same procedure as in [Step 4] of [Preparation Example 1] was repeated, but using 13.17 g (yield: 59%) of compound 7- 1-C.

GC-Mass (calculated: 223.29 g / mol, measured: 223 g / mol)

^{1 H-NMR: δ 7.53 (} t, 1H), δ 7.61 (t, 1H), δ 7.79 (m, 2H), δ 7.92 (m, 2H), δ 7.99 (d, 1H), δ 8.54 (d, 1H), [delta] 11.12 (brs, IH)

[Preparation Example 31] Synthesis of Compound 8-1-A

Synthesis of 1- (2-bromo-1H-pyrrol-3-yl) naphthalen-2-ol and 1- (3-bromo-1H-

Except that 2-hydroxynaphthalen-1-yl boronic acid (37.6 g, 200.0 mmol) was used instead of (3-hydroxynaphthalen-2-yl) boronic acid used in [Step 1] of [Preparation Example 3] (2-bromo-1H-pyrrol-3-yl) naphthalen-2-ol (A) and 21.32 g (yield: 37%) of [Step 1] of [Preparation Example 3] To obtain 17.86 g (yield: 31%) of 1- (3-bromo-1H-pyrrol-2-yl) naphthalen-2-ol (B).

GC-Mass (A) (calculated: 288.14 g / mol, measured: 288 g / mol)

^{1 H-NMR (A):} δ 6.68 (d, 1H), δ 7.23 (m, 2H), δ 7.43 (m, 2H), δ 8.01 (m, 2H), δ 8.91 (d, 1H), δ 9.61 (s, IH), [delta] 12.04 (brs, IH)

GC-Mass (B) (288.14 g / mol, measured: 288 g / mol)

^{1 H-NMR (B):} δ 6.48 (d, 1H), δ 6.95 (d, 1H), δ 7.22 (d, 1H), δ 7.43 (m, 2H), δ 8.01 (m, 2H), δ 9.61 (s, IH), [delta] 11.94 (brs, IH)

[Step 2] Synthesis of Compound 8-1-A

(2-bromo-lH-pyrrolo [3-yl] naphthalen-2-ol obtained in the above Step 1 was used instead of 3- (2-bromo- 18.44 g (yield: 89%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 3], except that n-butyllithium was used instead of 2- Of compound 8-1-A.

GC-Mass (207.2 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.54 (} m, 2H), δ 7.60 (m, 2H), δ 7.92 (m, 2H), δ 7.99 (d, 1H), δ 8.54 (d, 1H), δ 11.12 (brs, 1H)

[Preparation Example 32] Synthesis of Compound 8-1-B

[Step 1] Synthesis of 1- (4-bromo-1H-pyrrol-3-yl) naphthalen-2-ol

(44.98 g, 200.0 mmol) was used instead of 2,3-dibromo-1H-pyrrole used in [Step 1] of [Preparation Example 3], and 3-hydroxynaphthalen- The same procedure as in [Step 1] of [Preparation Example 3] was performed except that 2-hydroxynaphthalen-1-yl) boronic acid (37.6 g, 200.0 mmol) yield: 76%) of 1- (4-bromo-1H-pyrrol-3-yl) naphthalen-2-ol.

GC-Mass (288.1 g / mol, measured: 288 g / mol)

^{1 H-NMR: δ 7.00 (} s, 1H), δ 7.16 (s, 1H), δ 7.22 (d, 1H), δ 7.43 (m, 2H), δ 8.01 (m, 2H), δ 8.91 (d, 1H), [delta] 9.60 (brs, IH), [delta] 9.61 (s,

[Step 2] Synthesis of Compound 8-1-B

(4-bromo-lH-pyrrolo [3-yl] naphthalen-2-ol obtained in the above Step 1 was used instead of 3- (2-bromo- (yield: 86%) was obtained by carrying out the same procedure as in [Step 2] of [Preparation Example 3], except that 28.81 g (100.0 mmol) of 2- Of compound 8-1-B.

GC-Mass (207.20 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.53 (} m, 2H), δ 7.60 (m, 2H), δ 7.92 (s, 2H), δ 7.99 (d, 1H), δ 8.54 (d, 1H), δ 11.12 (brs, 1H)

[Preparation Example 33] Synthesis of Compound 8-1-C

Obtained in [Step 1] of [Preparation Example 31] was used instead of 3- (2-bromo-lH-pyrrol-3-yl) naphthalen-2-ol used in [Step 2] of [Preparation Example 3] The same procedure as in [Step 2] of [Preparation Example 3] was carried out except that 28.81 g (100.0 mmol) of 3-bromo-1H-pyrrol-2-yl) naphthalen- (yield: 85%) of Compound 8-1-C.

GC-Mass (207.20 g / mol, measured: 207 g / mol)

^{1 H-NMR: δ 7.53 (} m, 2H), δ 7.60 (m, 2H), δ 7.92 (m, 2H), δ 7.99 (d, 1H), δ 8.54 (d, 1H), δ 11.12 (brs, 1H)

[Preparation Example 34] Synthesis of Compound 9-1-A

[Step 1] Synthesis of 2 - ((1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-1 (2H)

1- (3,4-dihydronaphthalen-1-yl) pyrrolidine (43.85 g, 220.0 mmol) instead of 1- (1,4-dihydronaphthalen-2-yl) pyrrolidine used in [Step 1] of [Preparation Example 6] (1H-pyrrol-2-yl) methyl) -3, 4 (yield: 60%) was obtained by carrying out the same procedure as in [Step 1] of [Preparation Example 6] -dihydronaphthalen-1 (2H) -one. < / RTI >

GC-Mass (calculated: 225.30 g / mol, measured: 225 g / mol)

^{1 H-NMR: δ 1.63 (} m, 1H), δ 1.88 (m, 1H), δ 2.60 (m, 1H), δ 2.75 (m, 1H), δ 2.85 (m, 2H), δ 3.28 (m, (D, IH), 8.48 (d, IH), 8.48 (t, IH) , [delta] 7.83 (d, IH), [delta] 11.84 (brs, IH)

[Step 2] Synthesis of 7,8-dihydrobenzo [6,7] indeno [2,1-b] pyrrole

2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one used in [Step 2] of [Preparation Example 6] was replaced with 2- [Step 2] of [Preparation Example 6] was repeated except that (1H-pyrrol-2-yl) methyl) -3,4-dihydronaphthalen-1 (2H) (Yield: 53%) of 7,8-dihydrobenzo [6,7] indeno [2,1-b] pyrrole.

GC-Mass (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR: δ 3.96 (} s, 2H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.32 (d, 1H), δ 7.48 (m, 2H), δ 8.04 (d, 2H),? 8.92 (d, 1H),? 11.94 (brs, 1H)

[Step 3] Synthesis of Compound 9-1-A

Dihydrobenzo [6,7] dihydrobenzo [2,1-b] pyrrole obtained in [Step 2] was used instead of the 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [Step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was performed, except that 11,5-dihydro-indeno [2,1-b] pyrrole (20.53 g, 100.0 mmol) 9-1-A.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.80 (} s, 6H), δ 6.28 (d, 1H), δ 6.99 (d, 1H), δ 7.32 (d, 1H), δ 7.44 (m, 2H), δ 8.05 (m, 2H),? 8.87 (d, 1H),? 11.94 (brs, 1H)

[Preparation Example 35] Synthesis of Compound 9-1-B

[Step 1] Synthesis of 2 - ((1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-1 (2H)

(Bromomethyl) -1H-pyrrole (32.0 g, 200.0 mmol) instead of 2- (bromomethyl) -1H-pyrrole used in [Step 1] of [Preparation Example 6] Step 1] of [Preparation Example 6] was repeated except that 1- (3,4-dihydronaphthalen-1-yl) pyrrolidine (43.85 g, 220.0 mmol) was used in place of dihydronaphthalen- To obtain 31.99 g (yield: 71%) of 2 - ((1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-1 (2H) -one.

GC-Mass (calculated: 225.30 g / mol, measured: 225 g / mol)

^{1 H-NMR: δ 1.63 (} m, 1H), 1.88 (m, 1H), 2.63 (m, 1H), 2.75 (m, 1H), 2.86 (m, 2H), 3.28 (m, 1H), δ 6.02 (d, 1 H),? 6.53 (s, 1H),? 6.65 (s, 1H),? 7.24 , ≪ / RTI > 1H), # 9.50 (brs, 1H)

Step 2 Synthesis of 7,9-dihydrobenzo [6,7] indeno [1,2-c] pyrrole, 7,10-dihydrobenzo [6,7] indeno [1,2- b]

2-yl) methyl) -3,4-dihydronaphthalen-2 (1H) -one used in [Step 2] of [Preparation Example 6] was replaced with 2- [Step 2] of [Preparation Example 6] was repeated except that (1H-pyrrol-3-yl) methyl) -3,4-dihydronaphthalen-1 (2H) (Yield: 34%) of 7,9-dihydrobenzo [6,7] indeno [1,2-c] pyrrole (A) and 9.55 g (yield: 31% -dihydrobenzo [6,7] indeno [1,2-b] pyrrole (B).

GC-Mass (A) (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR (A):} δ 3.80 (s, 2H), δ 6.67 (s, 1H), δ 6.83 (s, 1H), δ 7.32 (d, 1H), δ 7.48 (m, 2H), δ 8.04 (m, 2H), [delta] 8.92 (d, IH), [delta] 9.60 (brs, IH)

GC-Mass (B) (calculated: 205.30 g / mol, measured: 205 g / mol)

^{1 H-NMR (B):} δ 3.80 (s, 2H), δ 6.28 (d, 1H), δ 6.78 (d, 1H), δ 7.32 (d, 1H), δ 7.48 (m, 2H), δ 8.04 (m, 2H), [delta] 8.92 (d, IH), [delta] 11.94 (brs, IH)

[Step 3] Synthesis of Compound 9-1-B

Dihydrobenzo [6,7] dihydrobenzo [2,1-b] pyrrole obtained in [step 2] was used instead of the 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was conducted, except that 20.53 g (100.0 mmol) of indeno [1,2-c] pyrrole was used, yielding 12.13 g (yield: 52% 9-1-B.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.75 (} s, 6H), δ 6.67 (s, 1H), δ 6.83 (s, 1H), δ 7.32 (d, 1H), δ 7.45 (m, 2H), δ 8.05 (m, 2H), [delta] 8.87 (d, IH), [delta] 9.60 (brs, IH)

[Preparation Example 36] Synthesis of Compound 9-1-C

Obtained in [Step 2] of Preparation Example 35 instead of 1,10-dihydrobenzo [5,6] indeno [2,1-b] pyrrole used in [Step 3] of [Preparation Example 6] The same procedure as in [Step 3] of [Preparation Example 6] was performed except that dihydrobenzo [6,7] indeno [1,2-b] pyrrole (20.53 g, 100.0 mmol) : 47%) of compound 9-1-C.

GC-Mass (calculated: 233.30 g / mol, measured: 233 g / mol)

^{1 H-NMR: δ 1.75 (} s, 6H), δ 6.28 (d, 1H), δ 6.75 (d, 1H), δ 7.32 (d, 1H), δ 7.45 (m, 2H), δ 8.05 (m, 2H),? 8.87 (d, 1H),? 11.94 (brs, 1H)

[Synthesis Example 1] Synthesis of compound 1

11.16 g (50.0 mmol) compound 1-1-A, 16.21 g (50.0 mmol) 4-bromo-N, N-diphenylaniline, 1.37 g Pd 2 (dba) of (1.5 mmol) _3, 1.01 g of a nitrogen stream (5.0 mmol) of P (t-bu) ₃ , 12.01 g (125.0 mmol) of NaO (t-bu) and 500 ml of toluene were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 15.4 g (yield: 66%) of compound 1 was obtained by column chromatography.

GC-Mass (calculated: 466.6 g / mol, measured: 466 g / mol)

[Synthesis Example 2] Synthesis of compound 4

The same procedure as in [Synthesis Example 1] was carried out except that Compound 2-1-A (10.36 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1 to obtain 15.99 g (yield: 71%).

GC-Mass (theory: 450.54 g / mol, measurement: 450 g / mol)

[Synthesis Example 3] Synthesis of compound 14

Instead of 4-bromo-N, N-diphenylaniline, compound 2-1-B (10.36 g, 50.00 mmol) was used instead of compound 1-1-A used in Synthesis Example 1, 16.6 g (yield: 74%) of compound 14 was obtained in the same manner as in [Synthesis Example 1], except that 9H-carbazole (16.11 g, 50.00 mmol) was used.

GC-Mass (calculated: 448.53 g / mol, measured: 448 g / mol)

[Synthesis Example 4] Synthesis of compound 16

Instead of 4-bromo-N, N-diphenylaniline, compound 3-1-A (11.67 g, 50.00 mmol) was used instead of compound 1-1-A used in Synthesis Example 1, 15.66 g (yield: 66%) of compound 16 was obtained in the same manner as in [Synthesis Example 1], except that 9H-carbazole (16.11 g, 50.00 mmol) was used.

GC-Mass (calculated: 474.61 g / mol, measured: 474 g / mol)

[Synthesis Example 5] Synthesis of compound 23

Instead of 4-bromo-N, N-diphenylaniline, Compound 2-1-B (10.36 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1, -biphenyl] -4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine (23.82 g, 50.00 mmol) The compound 23 of 19.59 g (yield: 65%) was obtained.

GC-Mass (theory: 602.74 g / mol, measured: 602 g / mol)

[Synthesis Example 6] Synthesis of compound 27

Instead of 4-bromo-N, N-diphenylaniline, compound 3-1-C (11.67 g, 50.00 mmol) was used in place of compound 1-1-A used in [Synthesis Example 1] -biphenyl] -4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine (23.82 g, 50.00 mmol) The compound 27 of 22.95 g (yield: 73%) was obtained.

GC-Mass (theory: 628.82 g / mol, measurement: 628 g / mol)

[Synthesis Example 7] Synthesis of compound 32

Instead of 4-bromo-N, N-diphenylaniline, Compound 2-1-B (10.36 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1, Synthesis Example 1] was repeated except for using 2-bromo-1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4-amine (27.63 g, 50.00 mmol) The compound 32 of 22.4 g (yield: 66%) was obtained.

GC-Mass (theory: 678.84 g / mol, measured: 678 g / mol)

[Synthesis Example 8] Synthesis of compound 36

Instead of 4-bromo-N, N-diphenylaniline, Compound 3-1-C (11.67 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1, Synthesis Example 1] was repeated except for using 2-bromo-1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4-amine (27.63 g, 50.00 mmol) The compound 36 of 25.73 g (yield: 73%) was obtained.

GC-Mass (calculated: 704.92 g / mol, measured: 704 g / mol)

[Synthesis Example 9] Synthesis of compound 37

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline (18.06 g, 50.00 mmol) was used instead of 4-bromo-N, N- diphenylaniline used in [Synthesis Example 1] , 18.38 g (yield: 73%) of compound 37 was obtained in the same manner as in [Synthesis Example 1].

GC-Mass (calculated: 503.62 g / mol, measured: 503 g / mol)

[Synthesis Example 10] Synthesis of compound 42

Instead of 4-bromo-N, N-diphenylaniline, compound 2-1-C (10.36 g, 50.00 mmol) was used in place of compound 1-1-A used in [Synthesis Example 1] 17.8 g (yield: 73%) of compound 42 (yield: 73%) was obtained by following the same procedure as in [Synthesis Example 1], except that 4- .

GC-Mass (calculated: 487.56 g / mol, measured: 487 g / mol)

[Synthesis Example 11] Synthesis of compound 44

Instead of 4-bromo-N, N-diphenylaniline, compound 3-1-B (11.67 g, 50.00 mmol) was used instead of compound 1-1-A used in [Synthesis Example 1] 18.49 g (yield: 72%) of compound 44 was obtained by following the same procedure as in [Synthesis Example 1], except that 18.06 g (50.0 mmol) of 2- .

GC-Mass (theory: 513.64 g / mol, measured: 513 g / mol)

[Synthesis Example 12] Synthesis of compound 48

(11.16 g, 50.00 mmol) was used in place of the compound 1-1-C used in Synthesis Example 1 and 2-bromo-4- (4-bromo-N, 18.55 g (yield: 67%) of compound 48 was obtained by carrying out the same procedure as in [Synthesis Example 1], except that the compound 48 (20.57 g, 50.00 mmol) was used instead of 4- (naphthalen- .

GC-Mass (calculated: 553.68 g / mol, measured: 553 g / mol)

[Synthesis Example 13] Synthesis of compound 50

Instead of 4-bromo-N, N-diphenylaniline, compound 2-1-B (10.36 g, 50.00 mmol) was used instead of compound 1-1-A used in [Synthesis Example 1] 18.55 g (yield: 69%) of compound 50 was obtained by carrying out the same processes as in [Synthesis Example 1], except that naphthalen-1-yl) phenylquinazoline (20.57 g, 50.00 mmol) .

GC-Mass (calculated: 537.62 g / mol, measured: 537 g / mol)

[Synthesis Example 14] Synthesis of compound 58

Instead of 4-bromo-N, N-diphenylaniline, compound 2-1-A (10.36 g, 50.00 mmol) was used in place of the compound 1-1-A used in Synthesis Example 1 and 2- (3-bromophenyl) triphenylene (Yield: 74%) of compound 58 was obtained in the same manner as in [Synthesis Example 1], except that the compound 58 (19.16 g, 50.00 mmol) was used.

GC-Mass (calculated: 509.61 g / mol, measured: 509 g / mol)

[Synthesis Example 15] Synthesis of compound 62

Instead of 4-bromo-N, N-diphenylaniline was used the compound 3-1-B (11.67 g, 50.00 mmol) instead of the compound 1-1-A used in Synthesis Example 1 and 2- (3-bromophenyl) triphenylene (Yield: 68%) of compound 62 was obtained by following the same procedure as in [Synthesis Example 1], except that the title compound (19.16 g, 50.00 mmol) was used.

GC-Mass (calculated: 535.69 g / mol, measured: 535 g / mol)

[Synthesis Example 16] Synthesis of compound 65

Instead of 4-bromo-N, N-diphenylaniline, Compound 1-1-B (11.16 g, 50.00 mmol) was used instead of Compound 1-1-A used in Synthesis Example 1, 19.37 g (yield: 73%) of compound was obtained by carrying out the same procedure as in [Synthesis Example 1], except that 4,6-diphenyl-1,3,5-triazine (19.41 g, 50.00 mmol) 65 was obtained.

GC-Mass (calculated: 530.65 g / mol, measured: 530 g / mol)

[Synthesis Example 17] Synthesis of compound 67

Instead of 4-bromo-N, N-diphenylaniline, Compound 2-1-B (10.36 g, 50.00 mmol) was used instead of Compound 1-1-A used in Synthesis Example 1, (Yield: 69%) of compound (4) was obtained in the same manner as in [Synthesis Example 1], except that 4,6-diphenyl-1,3,5-triazine (19.41 g, 50.00 mmol) 67.

GC-Mass (calculated: 514.59 g / mol, measured: 514 g / mol)

[Synthesis Example 18] Synthesis of compound 72

Instead of 4-bromo-N, N-diphenylaniline, compound 3-1-C (11.67 g, 50.00 mmol) was used instead of compound 1-1-A used in [Synthesis Example 1] 19.46 g (yield: 72%) of compound (4) was obtained by following the same procedure as in [Synthesis Example 1], except that 4,6-diphenyl-1,3,5-triazine (19.41 g, 72 was obtained.

GC-Mass (calculated: 540.67 g / mol, measured: 540 g / mol)

[Synthesis Example 19] Synthesis of compound 75

Instead of 4-bromo-N, N-diphenylaniline, Compound 1-1-C (11.16 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1, -biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- 2 -amine (29.63 g, 50.00 mmol ) Was used to obtain compound 75 of 25.36 g (yield: 69%) by the same procedure as in [Synthesis Example 1].

GC-Mass (734.96 g / mol, measured: 734 g / mol)

[Synthesis Example 20] Synthesis of compound 76

Instead of 4-bromo-N, N-diphenylaniline, Compound 2-1-A (10.36 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1, -biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- 2 -amine (29.63 g, 50.00 mmol ), 24.08 g (yield: 67%) of compound 76 was obtained in the same manner as in [Synthesis Example 1].

GC-Mass (718.9 g / mol, measured: 718 g / mol)

[Synthesis Example 21] Synthesis of compound 80

Instead of 4-bromo-N, N-diphenylaniline, Compound 3-1-B (11.67 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1, -biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- 2 -amine (29.63 g, 50.00 mmol ) Was used to obtain 25.7 g (yield: 69%) of compound 80 by performing the same procedure as in [Synthesis Example 1].

GC-Mass (744.98 g / mol, measured: 744 g / mol)

[Synthesis Example 22] Synthesis of compound 84

(50.00 mmol) of compound 3-2-A, 14.46 g (50.00 mmol) of 4- (diphenylamino) phenyl boronic acid, 20.73 g (150.00 mmol) of K ₂ CO ₃ , 200 ml / 50 ml / 50 ml of toluene / H ₂ O / EtOH were added and stirred. 2.89 g (2.50 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C, and the mixture was stirred at 100 ° C for 5 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, and then filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 17.96 g (yield: 65%) of compound 84 was obtained by column chromatography.

GC-Mass (calculated: 552.72 g / mol, measured: 552 g / mol)

[Synthesis Example 23] Synthesis of compound 87

The same procedure as in [Synthesis Example 22] was conducted, except that the compound 2-2-A (15.89 g, 50.00 mmol) was used in place of the compound 3-2-A used in [Synthesis Example 22] to obtain 18.43 g (yield: 70%) of compound 87 was obtained.

GC-Mass (calculated: 526.64 g / mol, measured: 526 g / mol)

[Synthesis Example 24] Synthesis of compound 90

The same procedure as in [Synthesis Example 22] was conducted, except that Compound 1-2-A (18.91 g, 50.00 mmol) was used in place of Compound 3-2-A used in [Synthesis Example 22] (yield: 74%).

GC-Mass (calculated: 542.7 g / mol, measured: 542 g / mol)

[Synthesis Example 25] Synthesis of compound 92

(4- (9H-carbazole) was used instead of (4- (diphenylamino) phenyl) boronic acid by using Compound 3-2-B (17.19 g, 50.00 mmol) (Yield: 66%) of compound 92 was obtained by following the same procedure as in [Synthesis Example 22], except that the compound 92 was used instead of 4- .

GC-Mass (calculated: 550.71 g / mol, measured: 550 g / mol)

[Synthesis Example 26] Synthesis of compound 94

(4- (9H-carbazol-2-yl) phenyl) boronic acid was used instead of the compound 2-2-C (15.89 g, 50.00 mmol) (Yield: 66%) of compound 94 was obtained in the same manner as in [Synthesis Example 22], except that the compound 94 was used instead of 4- .

GC-Mass (calculated: 524.63 g / mol, measured: 524 g / mol)

[Synthesis Example 27] Synthesis of compound 104

(4- (di [(4-fluorophenyl) boronic acid] was obtained in the same manner as in [Synthesis Example 22], except that Compound 2-2-B (15.89 g, 50.00 mmol) The yield was 24.1 g (yield: 50%) as a colorless powder, using the same procedure as in [Synthesis Example 22], except that 22.07 g (50.00 mmol) of 1,1'-biphenyl] -4- 71%) of compound 104 were obtained.

GC-Mass (theory: 678.84 g / mol, measured: 678 g / mol)

[ Synthetic example  28] Synthesis of compound 110

(4 '- (di ((4-hydroxyphenyl) phenyl) boronic acid was used instead of the compound 3-2-B (17.19 g, 50.00 mmol) 4-yl) amino] - [1,1'-biphenyl] -4-yl) boronic acid (25.87 g, 50.00 mmol) 22], 28.51 g (yield: 73%) of compound 110 was obtained.

GC-Mass (theory: 781.02 g / mol, measured: 781 g / mol)

[Synthesis Example 29] Synthesis of compound 117

(4 '- (di ((4-fluorophenyl) phenyl) boronic acid was obtained in the same manner as in [Synthesis Example 22], except that Compound 1-2- 4-yl) amino] - [1,1'-biphenyl] -4-yl) boronic acid (25.87 g, 50.00 mmol) 22], 26.21 g (yield: 68%) of compound 117 was obtained.

GC-Mass (calculated: 771 g / mol, measured: 771 g / mol)

[Synthesis Example 30] Synthesis of compound 121

(4- (diphenylamino) phenyl) boronic acid was used instead of the compound 2-2-C (15.89 g, 50.00 mmol) instead of the compound 3-2-A used in the synthesis example 22, The same procedure as in [Synthesis Example 22] was repeated but using 20.29 g (yield: 40%) of the title compound as a colorless oil, 72%) of compound 121 were obtained.

GC-Mass (calculated: 563.66 g / mol, measured: 563 g / mol)

[Synthesis Example 31] Synthesis of compound 126

(4- (diphenylamino) phenyl) boronic acid was used instead of the compound 1-2-A (18.91 g, 50.00 mmol) instead of the compound 3-2-A used in [Synthesis Example 22] The same procedure as in [Synthesis Example 22] was repeated, but using 19.71 g (yield: 50%) of the title compound as a colorless oil, but using as the starting material a [1'-biphenyl] -4-yl) quinazolin- 68%) of compound 126 were obtained.

GC-Mass (calculated: 579.72 g / mol, measured: 579 g / mol)

[Synthesis Example 32] Synthesis of compound 127

(4- (4- ((4-fluorophenyl) phenyl) boronic acid was used instead of the compound 3-2-C (17.19 g, 50.00 mmol) (yield: 65%) was obtained by following the same procedure as in [Synthesis Example 22], except that the starting material was used as the starting material, but using naphthalen-1-yl) phenyl) quinazolin- ) Compound 127 was obtained.

GC-Mass (calculated: 639.8 g / mol, measured: 639 g / mol)

[Synthesis Example 33] Synthesis of compound 135

(4- (4- ((4-fluorophenyl) phenyl) boronic acid was obtained in the same manner as in [Synthesis Example 22], except that Compound 1-2- (yield: 68%) was obtained by following the same procedure as in [Synthesis Example 22] above, but using 2- (naphthalen-1-yl) phenyl) quinazolin- ) Compound 135 was obtained.

GC-Mass (calculated: 629.78 g / mol, measured: 629 g / mol)

[Synthesis Example 34] Synthesis of compound 140

(3- (diphenylamino) phenyl) boronic acid was used instead of compound 2-2-B (15.89 g, 50.00 mmol) instead of the compound 3-2-A used in [Synthesis Example 22] (yield: 68%) of compound 140 was obtained by following the same procedure as in [Synthesis Example 22], except that the title compound was obtained as a white amorphous solid (17.41 g, 50.00 mmol).

GC-Mass (calculated: 585.71 g / mol, measured: 585 g / mol)

[Synthesis Example 35] Synthesis of compound 150

(4- (diphenylamino) phenyl) boronic acid was used instead of (4- (diphenylamino) phenyl) boronic acid instead of compound 2-2-A (15.89 g, 50.00 mmol) The same procedure as in [Synthesis Example 22] was repeated, except that 21.66 g (yield: 95%) of the title compound was obtained, : 72%).

GC-Mass (calculated: 590.69 g / mol, measured: 590 g / mol)

[Synthesis Example 36] Synthesis of compound 155

(4 '- ([1 (S) - (4-methylphenyl) boronic acid] was obtained in the same manner as in [Synthesis Example 22], except that Compound 3-2-B (17.19 g, 50.00 mmol) -Biphenyl] -4-yl) boronic acid (27.88 g, 50.00 mmol) in DMF (10 mL) , 28.74 g (yield: 70%) of compound 155 was obtained in the same manner as in [Synthesis Example 22].

GC-Mass (calculated: 821.08 g / mol, measured: 821 g / mol)

[Synthesis Example 37] Synthesis of compound 164

(23.5 g, 50.00 mmol) was used in place of the compound 3-2-A used in [Synthesis Example 22], 22.06 g (yield : 65%).

GC-Mass (theory: 678.84 g / mol, measured: 678 g / mol)

[ Synthetic example  38] Synthesis of compound 166

(4- (9H-carbazol-9-yl) phenyl) boronic acid was used instead of the compound 3-3 (24.8 g, 50.00 mmol) 25.3 g (yield: 72%) of compound 166 was obtained by following the same procedure as in [Synthesis Example 22], except that the compound 166 was used as the starting material.

GC-Mass (calculated: 702.91 g / mol, measured: 702 g / mol)

[Synthesis Example 39] Synthesis of compound 171

(4- (di ([1, < / RTI > 2-diethylamino) phenyl) boronic acid was prepared in the same manner as in [Synthesis Example 22] (Yield: 72%) was obtained by following the same procedure as in [Synthesis Example 22], except that 2-amino-1'-biphenyl] -4-yl) amino) phenyl) boronic acid (22.07 g, ) Of compound 171 were obtained.

GC-Mass (calculated: 847.09 g / mol, measured: 847 g / mol)

[Synthesis Example 40] Synthesis of compound 179

(4- (4- (4- (naphthalen-2-yl) phenyl) boronic acid was used instead of the compound 2-3 (23.5 g, 50.00 mmol) (Yield: 66%) was obtained by following the same procedure as in [Synthesis Example 22] above, but using 1-yl) phenyl) quinazolin-2-yl) boronic acid compound 179 was obtained.

GC-Mass (calculated: 765.92 g / mol, measured: 765 g / mol)

[Synthesis Example 41] Synthesis of compound 181

(3- (diphenylamino) phenyl) boronic acid was used instead of the compound 3-3 (24.8 g, 50.00 mmol) instead of the compound 3-2-A used in [Synthesis Example 22] (yield: 72%) of compound 181 was obtained by following the same procedure as in [Synthesis Example 22], except that phenyl boronic acid (17.41 g, 50.00 mmol)

GC-Mass (calculated: 763.99 g / mol, measured: 763 g / mol)

[Synthesis Example 42] Synthesis of compound 186

(26.52 g, 50.00 mmol) was used in place of the compound 3-2-A used in [Synthesis Example 22], and instead of (3- (4,6-diphenyl -1,3,5-triazin-2-yl) phenyl) boronic acid (17.66 g, 50.00 mmol) was used in the same manner as in [Synthesis Example 22] %) Of compound 186 was obtained.

GC-Mass (calculated: 758.94 g / mol, measured: 758 g / mol)

[Synthesis Example 43] Synthesis of compound 199

Instead of 4-bromo-N, N-diphenylaniline, compound 4-1-A (11.16 g, 50.00 mmol) was used in place of compound 1-1-A used in [Synthesis Example 1] -biphenyl] -4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine (23.82 g, 50.00 mmol) The compound 199 of 22.9 g (yield: 74%) was obtained.

GC-Mass (theory: 618.8 g / mol, measured: 618 g / mol)

[Synthesis Example 44] Synthesis of compound 209

Instead of 4-bromo-N, N-diphenylaniline, compound 4-1-B (11.16 g, 50.00 mmol) was used in place of compound 1-1-A used in [Synthesis Example 1] (yield: 66%) of compound 209 (yield: 66%) was obtained by following the same procedure as in [Synthesis Example 1], except that the compound 209 (18.06 g, 50.00 mmol) .

GC-Mass (calculated: 503.62 g / mol, measured: 503 g / mol)

[Synthesis Example 45] Synthesis of compound 226

The same procedure as in [Synthesis Example 1] was conducted except that Compound 5-1-A (10.36 g, 50.00 mmol) was used in place of Compound 1-1-A used in Synthesis Example 1 to obtain 14.64 g (yield: 65%) of compound 226 was obtained.

GC-Mass (theory: 450.54 g / mol, measurement: 450 g / mol)

[Synthesis Example 46] Synthesis of compound 273

Instead of 4-bromo-N, N-diphenylaniline, compound 6-1-C (11.67 g, 50.00 mmol) was used in place of compound 1-1-A used in [Synthesis Example 1] -biphenyl] -4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine (23.82 g, 50.00 mmol) The compound 273 of 21.69 g (yield: 69%) was obtained.

GC-Mass (theory: 628.82 g / mol, measurement: 628 g / mol)

[ Synthetic example  47] Synthesis of compound 280

Instead of 4-bromo-N, N-diphenylaniline was used instead of compound 6-1-A (11.67 g, 50.00 mmol) instead of compound 1-1-A used in [Synthesis Example 1] 17.21 g (yield: 67%) of compound 280 was obtained by carrying out the same procedure as in [Synthesis Example 1], except that the starting material was used as the starting material, but using 18.06 g (50.00 mmol) of 2- .

GC-Mass (theory: 513.64 g / mol, measured: 513 g / mol)

[Synthesis Example 48] Synthesis of compound 322

Instead of 4-bromo-N, N-diphenylaniline was used the compound 7-1-A (11.16 g, 50.00 mmol) instead of the compound 1-1-A used in [Synthesis Example 1] (Yield: 65%) of compound (4) was obtained by following the same procedure as in [Synthesis Example 1], except that 4,6-diphenyl-1,3,5-triazine (19.41 g, 322 < / RTI >

GC-Mass (calculated: 530.65 g / mol, measured: 530 g / mol)

[Synthesis Example 49] Synthesis of compound 349

Bromo-N, N-diphenylaniline was used instead of 4-bromo-N, diphenyllaniline by using Compound 8-1-A (10.36 g, 50.00 mmol) instead of Compound 1-1-A used in [Synthesis Example 1] (yield: 70%) was obtained by carrying out the same processes as in [Synthesis Example 1], except using 20.02 g (20.02 g, 50.00 mmol) of 1- Of compound 349 was obtained.

GC-Mass (calculated: 526.64 g / mol, measured: 526 g / mol)

[Synthesis Example 50] Synthesis of compound 352

Instead of 4-bromo-N, N-diphenylaniline, compound 8-1-A (10.36 g, 50.00 mmol) was used in place of compound 1-1-A used in [Synthesis Example 1] 18.04 g (yield: 74%) of compound 352 (yield: 74%) was obtained by following the same procedure as in [Synthesis Example 1], except that 4- .

GC-Mass (calculated: 487.56 g / mol, measured: 487 g / mol)

[Synthesis Example 51] Synthesis of compound 378

Instead of 4-bromo-N, N-diphenylaniline, compound 9-1-C (11.67 g, 50.00 mmol) was used in place of compound 1-1-A used in [Synthesis Example 1] 17.12 g (yield: 65%) of compound 378 was obtained in the same manner as in [Synthesis Example 1], except that N-phenylnaphthalen-2-amine (18.71 g, 50.00 mmol) was used.

GC-Mass (calculated: 526.68 g / mol, measured: 526 g / mol)

[Example 1] Production of organic electroluminescent device

Compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then an organic electroluminescent device was prepared as follows.

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

(60 nm) / compound 1 (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (30 nm) on an ITO transparent substrate 1 nm) / Al (200 nm) in this order to form an organic electroluminescent device.

DS-522 and DS-501 used are products of Doosan Electronics Co., Ltd., and the structures of the m-MTDATA and BCP are as follows.

[Examples 2 to 28] Preparation of Organic Electroluminescent Device

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that each compound described in Table 1 was used in place of the compound 1 used as the hole transport layer material in Example 1.

[Comparative Example 1] Production of organic electroluminescent device

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that NPB was used in place of the compound 1 used as the hole transport layer material in Example 1.

The structure of the NPB is as follows.

[Experimental Example 1]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 1 to 28 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 1 compound 1 4.8 21.2 Example 2 compound 4 4.1 20.3 Example 3 compound 14 4.9 19.6 Example 4 compound 16 4.4 21.3 Example 5 compound 23 4.3 20.0 Example 6 compound 27 4.9 18.2 Example 7 compound 32 4.3 20.9 Example 8 compound 36 4.5 20.4 Example 9 compound 75 4.6 18.3 Example 10 compound 76 4.8 19.7 Example 11 compound 80 4.3 19.1 Example 12 compound 84 4.2 19.6 Example 13 compound 87 4.2 19.1 Example 14 compound 90 4.7 20.1 Example 15 compound 92 4.8 18.6 Example 16 compound 94 4.5 19.3 Example 17 compound 104 4.6 18.9 Example 18 compound 110 4.8 18.4 Example 19 compound 117 4.2 20.4 Example 20 compound 155 4.7 21.5 Example 21 compound 164 4.7 20.2 Example 22 compound 166 4.4 19.2 Example 23 compound 171 4.6 19.0 Example 24 compound 199 5.1 21.7 Example 25 compound 226 4.3 18.5 Example 26 compound 273 5.1 19.4 Example 27 compound 349 4.9 21.3 Example 28 compound 378 4.3 18.3 Comparative Example 1 NPB 5.2 18.1

As shown in Table 1, the organic electroluminescent devices of Examples 1 to 28 using the compound according to the present invention as an organic material layer had higher current efficiency and driving voltage than the organic electroluminescent device of Comparative Example 1 using NPB as an organic material layer I was able to confirm that it was excellent.

[Example 29] Production of green organic electroluminescent device

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

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

(60 nm) / TCTA (80 nm) / compound 1 (40 nm) / CBP + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ on the ITO transparent substrate 30 nm) / LiF (1 nm) / Al (200 nm) in this order to obtain a green organic electroluminescent device.

The structures of m-MTDATA and BCP used are as described in Example 1, and the structures of TCTA, Ir (ppy) ₃ and CBP are as follows.

[Examples 30 to 56] Preparation of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 29 except that each compound described in Table 2 was used in place of compound 1 used as the light-emission-assisting layer material in Example 29. [

[Comparative Example 2] Production of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 29, except that the compound 1 used as the light-emission-assisting layer material in Example 29 was not used.

[Experimental Example 2]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 29 to 56 and Comparative Example 2, respectively, and the results are shown in Table 2 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 29 compound 1 6.8 42.8 Example 30 compound 4 6.9 42.2 Example 31 compound 14 6.9 41.2 Example 32 compound 16 6.9 42.9 Example 33 compound 23 6.8 40.1 Example 34 compound 27 6.9 40.8 Example 35 compound 32 6.9 42.8 Example 36 compound 36 6.7 41.0 Example 37 compound 75 6.9 43.5 Example 38 compound 76 6.8 41.7 Example 39 compound 80 6.7 42.5 Example 40 compound 84 6.8 41.0 Example 41 compound 87 6.8 40.1 Example 42 compound 90 6.9 44.0 Example 43 compound 92 6.9 44.3 Example 44 compound 94 6.91 42.3 Example 45 compound 104 6.8 44.3 Example 46 compound 110 6.9 41.8 Example 47 compound 117 6.8 41.3 Example 48 compound 155 6.7 44.4 Example 49 compound 164 6.9 40.3 Example 50 compound 166 6.8 44.0 Example 51 compound 171 6.7 44.1 Example 52 compound 199 6.6 40.6 Example 53 compound 226 6.2 40.3 Example 54 compound 273 6.2 42.1 Example 55 compound 349 6.5 40.8 Example 56 compound 378 6.2 40.3 Comparative Example 2 - 6.9 38.2

As shown in Table 2, the green organic electroluminescent devices of Examples 29 to 56, in which the compound according to the present invention was used for the organic material layer, exhibited higher current efficiency and lower power consumption than the green organic electroluminescent device of Comparative Example 2, It was confirmed that the driving voltage was excellent.

[Example 57] Production of red organic electroluminescent device

Compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and red organic electroluminescent devices were prepared as follows.

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

M-MTDATA (60 nm) / TCTA (80 nm) / compound 1 (40 nm) / CBP + 10% (piq) ₂ Ir (acac) on the ITO transparent substrate (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to manufacture a red organic electroluminescent device.

The structures of m-MTDATA and BCP used are as described in Example 1, the structure of CBP and TCTA is as described in Example 29, and the structure of (piq) ₂ Ir (acac) is as follows.

[Examples 58 to 84] Preparation of red organic electroluminescent device

A red organic electroluminescent device was fabricated in the same manner as in Example 57, except that each compound described in Table 3 was used in place of compound 1 used as the light-emission-assisting layer material in Example 57.

[Comparative Example 3] Production of red organic electroluminescent device

A red organic electroluminescent device was prepared in the same manner as in Example 57 except that the compound 1 used as the light emitting auxiliary layer material in Example 57 was not used.

[Experimental Example 3]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples 57 to 84 and Comparative Example 3, respectively, and the results are shown in Table 3 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 57 compound 1 4.93 10.0 Example 58 compound 4 4.98 12.7 Example 59 compound 14 5.09 10.9 Example 60 compound 16 4.94 13.7 Example 61 compound 23 4.99 11.5 Example 62 compound 27 5.01 13.6 Example 63 compound 32 5.23 11.7 Example 64 compound 36 5.08 14.0 Example 65 compound 75 5.22 13.5 Example 66 compound 76 5.11 9.9 Example 67 compound 80 5.18 14.1 Example 68 compound 84 4.98 11.8 Example 69 compound 87 5.06 8.5 Example 70 compound 90 5.01 13.4 Example 71 compound 92 5.19 12.2 Example 72 compound 94 5.21 8.9 Example 73 compound 104 5.08 10.8 Example 74 compound 110 5.07 10.7 Example 75 compound 117 5.00 9.1 Example 76 compound 155 5.20 11.4 Example 77 compound 164 4.96 9.5 Example 78 compound 166 5.02 9.9 Example 79 compound 171 5.07 8.6 Example 80 compound 199 5.04 11.0 Example 81 compound 226 4.90 11.7 Example 82 compound 273 5.11 10.4 Example 83 compound 349 4.87 12.3 Example 84 compound 378 5.09 10.8 Comparative Example 3 - 5.25 8.2

As shown in Table 3, the red organic electroluminescent devices of Examples 57 to 84, in which the compound according to the present invention was used in the organic material layer, had higher current efficiency and lower power consumption than the red organic electroluminescent device of Comparative Example 3, It was confirmed that the driving voltage was excellent.

[Example 85] Production of blue organic electroluminescent device

The compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was prepared as follows.

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

(15 nm) / compound 1 (15 nm) / ADN + 5% DS-405 (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) on an ITO transparent substrate (electrode) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce a blue organic electroluminescent device.

DS-205 and DS-405 used were products of Doosan Heavy Industries, Ltd., the structure of NPB was as described in Comparative Example 1, the structure of BCP was as described in Example 1, and the structure of ADN was as follows.

[Examples 86 to 112] Preparation of blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 85, except that each compound described in Table 4 was used in place of compound 1 used as the light-emission-assisting layer material in Example 85.

[Comparative Example 4] Production of blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 85 except that compound 1 used as the light-emission-assisting layer material in Example 85 was not used.

[Experimental Example 4]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 85 to 112 and Comparative Example 4, respectively, and the results are shown in Table 4 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 85 compound 1 5.24 7.5 Example 86 compound 4 5.43 7.3 Example 87 compound 14 5.41 7.0 Example 88 compound 16 5.43 5.6 Example 89 compound 23 5.46 7.5 Example 90 compound 27 5.42 6.7 Example 91 compound 32 5.21 7.6 Example 92 compound 36 5.38 5.6 Example 93 compound 75 5.52 5.5 Example 94 compound 76 5.58 6.3 Example 95 compound 80 5.54 6.4 Example 96 compound 84 5.26 6.9 Example 97 compound 87 5.55 6.2 Example 98 compound 90 5.16 4.9 Example 99 compound 92 5.30 7.1 Example 100 compound 94 5.46 7.0 Example 101 compound 104 5.31 4.9 Example 102 compound 110 5.42 7.1 Example 103 compound 117 5.27 4.9 Example 104 compound 155 5.12 6.7 Example 105 compound 164 5.51 7.2 Example 106 compound 166 5.29 6.4 Example 107 compound 171 5.13 6.9 Example 108 compound 199 5.48 6.6 Example 109 compound 226 5.26 5.8 Example 110 compound 273 5.01 5.0 Example 111 compound 349 5.33 5.9 Example 112 compound 378 5.33 7.3 Comparative Example 4 - 5.60 4.8

As shown in Table 4, the blue organic electroluminescent devices of Examples 85 to 112 using the compound according to the present invention as the organic material layer are superior to the blue organic electroluminescent devices of Comparative Example 4, It was confirmed that the driving voltage was excellent.

[ Example  113] Green organic Field  Manufacturing of light emitting device

The compound 14 synthesized in Synthesis Example 3 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was prepared as follows.

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

(60 nm) / TCTA (80 nm) / compound 14 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (30 nm) on the ITO transparent substrate 1 nm) / Al (200 nm) in this order to obtain a green organic electroluminescent device.

The structures of m-MTDATA and BCP used are as described in Example 1, and the structures of TCTA and Ir (ppy) ₃ are as described in Example 29. [

[Examples 114 to 127] Preparation of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 113 except that each compound described in Table 5 was used in place of compound 14 used as a light emitting host material in Example 113. [

[Comparative Example 5] Production of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 113 except that CBP was used in place of the compound 14 used as the light emitting host material in Example 113.

The structure of CBP used here is as follows.

[Experimental Example 5]

The driving voltage, the current efficiency and the emission peak at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 113 to 127 and Comparative Example 5, respectively, and the results are shown in Table 5 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 113 Synthesis of compound 14 6.54 39.1 Example 114 compound 16 6.68 39.5 Example 115 compound 58 6.77 41.0 Example 116 compound 62 6.46 40.2 Example 117 compound 65 6.83 40.6 Example 118 compound 67 6.63 41.0 Example 119 compound 72 6.49 40.9 Example 120 compound 92 6.92 40.8 Example 121 compound 94 6.78 39.4 Example 122 compound 140 6.62 43.3 Example 123 compound 150 6.71 43.4 Example 124 compound 166 6.70 41.4 Example 125 compound 181 6.47 43.4 Example 126 compound 186 6.84 40.9 Example 127 compound 322 6.58 39.2 Comparative Example 5 - 6.93 38.2

As shown in Table 5, the green organic electroluminescent devices of Examples 113 to 127, in which the compound according to the present invention was used for the organic material layer, compared with the green organic electroluminescent device of Comparative Example 5 using conventional CBP, .

[Example 128] Production of red organic electroluminescent device

Compound 37 synthesized in Synthesis Example 9 was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / compound 37 + 10% (piq) ₂ Ir (acac) (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structures of m-MTDATA and BCP used herein are as described in Example 1, the structure of TCTA is as described in Example 29, and the structure of (piq) ₂ Ir (acac) is as described in Example 57 .

[Examples 129 to 140] Preparation of red organic electroluminescent device

A red organic electroluminescent device was fabricated in the same manner as in Example 128 except that each compound described in Table 6 was used in place of the compound 37 used as a light emitting host material in forming the light emitting layer in Example 128.

[Comparative Example 6] Production of red organic electroluminescent device

A red organic electroluminescent device was fabricated in the same manner as in Example 128 except that CBP was used instead of the compound 37 used as a light emitting host material in the formation of the light emitting layer. The structure of CBP used here is as described in Comparative Example 5.

[Evaluation Example 6]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 128 to 140 and Comparative Example 6, respectively, and the results are shown in Table 6 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 128 compound 37 4.91 9.5 Example 129 compound 42 5.08 10.2 Example 130 compound 44 5.24 8.6 Example 131 compound 48 4.76 8.9 Example 132 compound 50 4.96 10.1 Example 133 compound 121 4.84 9.3 Example 134 compound 126 5.18 10.3 Example 135 compound 127 4.93 8.6 Example 136 compound 135 4.81 8.4 Example 137 compound 179 5.24 9.8 Example 138 compound 209 5.07 9.5 Example 139 compound 280 5.08 10.7 Example 140 compound 352 4.99 8.7 Comparative Example 6 - 5.25 8.2

As shown in Table 6, the red organic electroluminescent devices of Examples 128 to 130, in which the compound according to the present invention was used for the organic material layer, compared with the red organic electroluminescent device of Comparative Example 6 using CBP in the prior art, .

Claims (9)

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

(In the formula 1,
A ₁ to A ₈ are each independently N or C (R ₁ ), wherein when R ₁ is plural, they are the same or different,
Provided that at least one of A ₁ and A ₂ , A ₂ and A ₃ , and A ₃ and A ₄ are both C (R ₁ ), wherein R ₁ is bonded to adjacent R ₁ to form To form one of the condensed rings represented by R < 1 >
(2)

(3)

[Chemical Formula 4]

The dotted line is the part where the condensation occurs;
X ₁ is selected from the group consisting of O, S, C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ );
Y ₁ and Y ₂ are each independently N or C (R ₂ ), wherein when R ₂ is plural, they are the same or different from each other;
R ₁ and R ₂ which are not the condensed rings are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 of the heteroaryl A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in, or the other R _1, R ₁ and R ₂ in which the R ₁ adjacent to each other, And at least one of the other R ₂ and the adjacent R ₂ are bonded to each other condensed aromatic ring or a N, O, S, may form a fused heteroaromatic ring containing at least one of Si and;
Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ is selected from the group consisting of an aryl amine;
In the above R ₁ , R ₂ and Ar ₁ to Ar ₅ , an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, each independently, an alkynyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ aryl phosphonium pingi of C _60, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ aryl amine, or is unsubstituted, wherein the substituent When there are multiple, they are the same as or different from each other). The method according to claim 1,
A compound represented by any one of the following formulas C-1 to C-9:

(In the above formulas C-1 to C-9,
X ₁ , Ar ₁ , Y ₁ , Y ₂ , and A ₁ to A ₈ are as defined in claim 1, respectively. The method according to claim 1,
At least one of R ₁ , R ₂ , and Ar ₁ to Ar ₅ , in which the condensed ring is not formed, is each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A heteroaryl group, and an arylamine group of C ₆ to C ₆₀ , with the remainder being as defined in claim 1,
The alkyl group, aryl group, heteroaryl group and arylamine group in each of R ₁ , R ₂ and Ar ₁ to Ar ₅ in which the condensed ring is not formed are each independently selected from deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₆ ~ substituted by one substituent at least one selected from the group consisting of an aryl amine of the C ₆₀ or is unsubstituted, wherein the above substituent And when they are plural, they are the same or different from each other). The method according to claim 1,
At least one of R ₁ , R ₂ and Ar ₁ to Ar ₅ in which the condensed ring is not formed is independently selected from the group consisting of a substituent represented by the following formula (5), a substituent represented by the following formula (6) And the remainder is as defined in claim 1:
[Chemical Formula 5]

[Chemical Formula 6]

(In the above formulas 5 to 6,
* Represents a moiety bonded to Formula 1;
L ₁ and L ₂ are the same or different and are each independently a single bond or a heteroarylene group having 5 to 18 nucleus atoms and a C ₆ to C ₁₈ arylene group;
Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₁ )
With the proviso that at least one of Z ₁ to Z ₅ is N, and when R ₁₁ is plural, they are the same as or different from each other;
R ₁₁ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, nuclear atoms heteroaryl of 5 to 40 group, C ₆ ~ aryloxy C ₄₀ C ₁ ~ C ₄₀ alkyloxy group, the C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, A C ₆ to C ₄₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₄₀ or aryl silyl, or adjacent to, combined with L ₁ or other R ₁₁ to form a condensed ring, and that;
R ₁₃ and R ₁₄ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms and a C ₆ to C ₆₀ aryl An amine group, or R ₁₃ and R ₁₄ may be bonded to each other to form a condensed ring;
In this case, the alkyl group of said R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic An arylphosphine group, an arylphosphine oxide group, and an arylsilyl group; And R ₁₃ and the alkyl group of R _14, an aryl group, a heteroaryl group, arylamine group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ substituted from the group consisting arylsilyl of C ₄₀ of at least one selected more substituents, or And when the substituent is plural, they may be the same or different from each other). 5. The method of claim 4,
Wherein the substituent represented by the general formula (5) is one of the substituents represented by the following general formulas (A-1) to (A-15):

(In the above A-1 to A-15,
L ₁ And R < ₁₁ > are as defined in claim 4, respectively,
n is an integer of 0 to 4, and when n is an integer of 1 to 4, R ₁₂ is a group selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, an alkynyl group of ₂ ~ C _40, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 aryl group, C ₆ ~ aryloxy C _{40 60} C ₁ - C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or in, or near the L ₁ to , R < ₁₁ > and the other R < ₁₂ > to form a condensed ring;
In this case, the alkyl group of said R _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an arylboronic A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, an aryloxycarbonyl group, an aryloxycarbonyl group, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ with arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of Substituted or unsubstituted, provided that when the substituent is plural, they may be the same or different from each other). 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers comprises a compound represented by the general formula (1) according to any one of claims 1 to 5. The method according to claim 6,
The organic material layer including the compound represented by Formula 1 is a light emitting layer,
Wherein the compound represented by Formula 1 is a phosphorescent host of the light emitting layer. The method according to claim 6,
The organic material layer containing the compound represented by Formula 1 is a hole transport layer,
Wherein the compound represented by Formula 1 is the hole transport layer material. The method according to claim 6,
The organic material layer containing the compound represented by the formula (1) is an emission auxiliary layer,
Wherein the compound represented by Formula 1 is the light-emitting auxiliary layer material.