KR101574704B1 - Novel compounds, organic light emitting device display and organic solar battery using the same - Google Patents

Abstract

상기 화학식 1에서, R₁ 내지 R₆, Ar₁, A, X 및 n은 명세서에서 정의한 바와 같다. The present invention relates to a compound represented by the following general formula (1), an organic electroluminescent device including the same, and an organic solar cell.

In Formula 1, R ₁ to R ₆ , Ar ₁ , A, X and n are as defined in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, an organic electroluminescent device including the same, and an organic solar cell comprising the same. BACKGROUND OF THE INVENTION [0002]

The present invention relates to a novel compound, an organic electroluminescent device including the same, and an organic solar cell.

Recently, development of a high-efficiency, long-life organic electroluminescent device has become an urgent task. Particularly, in consideration of the level of characteristics required for the middle- or large-sized organic electroluminescent device panel, it is urgent to develop a material that is superior to the conventional light-emitting material. Therefore, development of a high-efficiency, long-life RGB light emitting material is an important task for improving the characteristics of the entire organic electroluminescent device.

On the other hand, it is known that a device structure having the best characteristics of a full-color organic electroluminescent device is doped with a host to make a light emitting layer. Therefore, the development of the host material is one of the most important factors to be solved. This is because the host material serves as a solid state solvent and energy transfer agent. Such a host material is preferably high in purity and has a suitable molecular weight to enable vacuum deposition. In addition, the host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability. In addition, the host material requires high electrochemical stability for long life. Further, the host material should be easy to form an amorphous thin film, and have good adhesion to the materials of adjacent layers, but not interlayer migration.

Recently, a system in which a host material is doped with a fluorescent material or a phosphorescent dopant as a light emitting layer of an organic electroluminescent device has been actively studied. The light emitting layer of the host-dopant system facilitates the flow of charge carriers (electrons and holes), thereby lowering the driving voltage of the light emitting device.

For example, in the case of a conventional blue material, many materials have been developed and commercialized since diphenylvinyl-biphenyl (DPVBi, a compound represented by the following formula a) of Idemitsu-Gosan. For example, a blue material system of Idemitsu-Gosan and a system of dinaphthylanthracene (DNA, a compound represented by the following formula b) of Kodak and the like are known. However, a lot of research and development is still required. This is because the distill compound system of Idemitsu-Gosan, which is known to be the most efficient to date, has a power consumption of 6 kW / W and a device lifetime of 30,000 hours or more. However, Due to the fact that when applied to a full color display, the lifetime is only a few thousand hours. Further, the blue light emission is advantageous in light emission efficiency even if the emission wavelength shifts a little toward the long wavelength side, but it can not satisfy the pure blue light, so it is not easy to apply to a high quality display, and there is a problem in color purity, efficiency and thermal stability. .

In addition, TBSA [Kwon, S. K. et. al. Advanced Materials, 2001, 13, 1690; JP2002-121547A] showed relatively good color coordinates of (0.15, 0.11) and a luminous efficiency of 3 keV / A at 7.7 V, but it is known to be insufficient in commercialization level when applied as a single layer material. In addition, TSF [Wu, C. -C., et. al. Advanced Materials, 2004, 16, 61; US2005-0074631A] exhibits a relatively excellent external quantum efficiency of 5.3%, but it is also insufficient for commercialization level. In the case of BTP published by Tsinghua National University in Taiwan [Cheng, C. -H, et. al. Advanced Materials, 2002, 14, 1409; US2004-0076852A] showed a good color coordinate of 2.76 ㏅ / A and a good color coordinate of (0.16, 0.14), but it is insufficient in commercialization level.

As described above, conventional materials do not constitute a host-dopant thin film layer and are composed of a single layer. It is considered that commercialization is difficult in terms of color purity and efficiency, and reliable data on long life is insufficient.

On the other hand, according to US2005-0074631A of Mitsui Chemicals, Japan, the following compounds were found to exhibit luminous efficiency of 4.6 kPa / A.

However, these compounds are designated as bluish green color. Particularly, it is impossible to realize a pure blue color in the symmetrical structure as described above, and it is considered to be insufficient for commercialization for a full color display application as a material which does not have such a pure blue light emission.

The organic luminescent compounds disclosed in the prior art have low thermal stability and the lifetime of the light emitting device manufactured using the organic luminescent compound is not long. Accordingly, the present inventors have found that when anthracene and its substituted side chain groups are formed as rings to improve the thermal stability of a light emitting compound and applied to an organic light emitting device. The life, efficiency and color purity of the organic light emitting device can be significantly increased as compared with the case of applying the conventional light emitting material. Thus, the present invention has been completed.

It is an object of the present invention to provide a compound excellent in thermal stability and excellent in color purity. More specifically, it is an object of the present invention to provide an anthracene compound having an anthracene skeleton and a side chain group in which an anthracene skeleton and a side chain group are maintained in a planar state by forming an anthracene and a substituted side chain group thereof in a ring, Thereby providing an organic compound.

It is another object of the present invention to provide an organic electroluminescent device and an organic solar cell excellent in luminous efficiency and lifetime.

The present invention provides a compound represented by the following formula (1);

In Formula 1,

R ₁ to R ₆ are the same or different from each other and each independently hydrogen; A halogen atom; Adamantyl; Nitro; Hydroxy; Cyano; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Substituted or unsubstituted (C ₅ -C ₆₀₎ heteroaryl; 5 or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si; Substituted or unsubstituted (C ₃ -C ₆₀ ) cycloalkyl; A substituted or unsubstituted tree (C ₁ -C ₆₀₎ alkylsilyl; A substituted or unsubstituted di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl; A substituted or unsubstituted tree (C ₆ -C ₆₀₎ arylsilyl; Substituted or unsubstituted (C ₇ -C ₆₀₎ bicycloalkyl-alkyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkenyl; Substituted or unsubstituted (C ₂ -C _{60 )} alkynyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkoxy; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkylamino; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylamino; Substituted or unsubstituted (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryloxy; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylthio; A substituted or unsubstituted (C ₁ -C ₆₀₎ alkylthio; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkoxycarbonyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylcarbonyl; Or (C ₆ -C ₆₀ ) arylcarbonyl, wherein R ₁ to R ₆ are bonded to adjacent groups to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, or a substituted or unsubstituted (C ₂ -C ₆₀₎ ) alkylene or (C ₂ -C ₆₀₎ connected to each other in the alkenylene to form an aliphatic ring, an aromatic ring, a heteroaromatic ring,

Ar ₁ is a substituted or unsubstituted (C ₆ -C ₆₀ ) aromatic compound having ₁ to 5 rings or a fused ring aromatic compound,

이되,A is adamantyl; Nitro; Hydroxy; Cyano; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Substituted or unsubstituted (C ₂ -C ₆₀ ) heteroaryl; 5 or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si; Substituted or unsubstituted (C ₃ -C ₆₀ ) cycloalkyl; A substituted or unsubstituted tree (C ₁ -C ₆₀₎ alkylsilyl; A substituted or unsubstituted di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl; A substituted or unsubstituted tree (C ₆ -C ₆₀₎ arylsilyl; Substituted or unsubstituted (C ₇ -C ₆₀₎ bicycloalkyl-alkyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkenyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkynyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkoxy; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkylamino; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylamino; Substituted or unsubstituted (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryloxy; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylthio; A substituted or unsubstituted (C ₁ -C ₆₀₎ alkylthio; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkoxycarbonyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylcarbonyl; (C ₆ -C ₆₀ ) arylcarbonyl; or

However,

Ar ₃ is substituted or unsubstituted (C ₁ -C ₆₀ ) alkyleneoxy; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylene-thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryleneoxy; (C ₆ -C ₆₀ ) arylene thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylene; Or (C ₃ -C ₆₀₎ and heteroarylene,

R ₇ is the same as the description of R ₁ to R ₆ ,

n is from 0 to 3,

If n is not a 0, X is _{-O-, -Si (-R 21) (} - R 22) -, -N (-R 21) - or _{-C (-R 21) (- R} 22) - a ,

Wherein R ₂₁ and R ₂₂ are each independently selected from the group consisting of hydrogen; Straight or branched (C ₁ -C ₆₀₎ alkyl; (C ₆ -C ₆₀ ) aryl; (C ₆ -C ₆₀ ) alkoxyaryl; (C ₁ -C ₆₀₎ alkylthio (C ₆ -C ₆₀₎ aryl; (C ₆ -C ₆₀ ) aryl, (C ₁ -C ₆₀ ) alkylsilyl (C ₆ -C ₆₀ ) aryl,

Wherein R ₁ to R _6, Ar _1, and Ar ₃ is A substitution at the same or different, each independently, halogen, (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ aryl, (C ₂ -C ₆₀₎ heteroaryl, N, O, S, and 5-or 6-membered heterocycloalkyl containing one or two or more selected from Si, (C ₃ -C ₆₀₎ cycloalkyl, tri (C ₁ - C ₆₀₎ alkylsilyl, di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl, tri (C ₆ -C ₆₀₎ arylsilyl, adamantyl, (C ₇ -C ₆₀₎ alkyl bicyclo , (C ₂ -C ₆₀₎ alkenyl, (C ₂ -C ₆₀₎ alkynyl, (C ₁ -C ₆₀₎ alkoxy, cyano, (C ₁ -C ₆₀₎ alkylamino, (C ₆ -C ₆₀₎ arylamino, (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ aryloxy, (C ₁ -C ₆₀₎ alkylthio, (C ₆ -C ₆₀₎ arylthio, (C ₁ -C ₆₀ ) alkoxycarbonyl, (C ₁ -C ₆₀ ) alkylcarbonyl, (C ₆ -C ₆₀ ) arylcarbonyl, carboxylic acid, nitro or hydroxy.

The present invention relates to a plasma display panel comprising a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a compound represented by Formula 1.

The present invention relates to a plasma display panel comprising a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a compound represented by Formula 1.

Since the compound of the present invention is excellent in thermal stability, it has a long lifetime when applied to an organic electroluminescent device, and is excellent in luminous efficiency and color coordinates. The compound of the present invention is suitable for an organic film layer material of an organic electroluminescence device of red, green and blue fluorescence and phosphorescence. Particularly, the compound of the present invention is suitable as a blue fluorescent material for a hole transport layer. The organic electroluminescent device of the present invention has a long lifetime, excellent luminous efficiency, and high color purity.

Hereinafter, for a detailed understanding of the present invention, a representative compound of the present invention will be described, for example, a compound according to the present invention, a method for producing the same, and an organic electroluminescent device. However, And are not intended to limit the scope of the invention.

Ⅰ. compound

The present invention provides a compound represented by the following formula (1).

In Formula 1,

R ₁ to R ₆ are the same or different from each other and each independently hydrogen; A halogen atom; Adamantyl; Nitro; Hydroxy; Cyano; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Substituted or unsubstituted (C ₅ -C ₆₀₎ heteroaryl; 5 or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si; Substituted or unsubstituted (C ₃ -C ₆₀ ) cycloalkyl; A substituted or unsubstituted tree (C ₁ -C ₆₀₎ alkylsilyl; A substituted or unsubstituted di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl; A substituted or unsubstituted tree (C ₆ -C ₆₀₎ arylsilyl; Substituted or unsubstituted (C ₇ -C ₆₀₎ bicycloalkyl-alkyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkenyl; Substituted or unsubstituted (C ₂ -C _{60 )} alkynyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkoxy; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkylamino; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylamino; Substituted or unsubstituted (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryloxy; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylthio; A substituted or unsubstituted (C ₁ -C ₆₀₎ alkylthio; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkoxycarbonyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylcarbonyl; Or (C ₆ -C ₆₀ ) arylcarbonyl, wherein R ₁ to R ₆ are bonded to adjacent groups to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, or a substituted or unsubstituted (C ₂ -C ₆₀₎ ) alkylene or (C ₂ -C ₆₀₎ connected to each other in the alkenylene to form an aliphatic ring, an aromatic ring, a heteroaromatic ring,

Ar ₁ is a substituted or unsubstituted (C ₆ -C ₆₀ ) aromatic compound having ₁ to 5 rings or a fused ring aromatic compound,

이되,A is adamantyl; Nitro; Hydroxy; Cyano; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Substituted or unsubstituted (C ₂ -C ₆₀ ) heteroaryl; 5 or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si; Substituted or unsubstituted (C ₃ -C ₆₀ ) cycloalkyl; A substituted or unsubstituted tree (C ₁ -C ₆₀₎ alkylsilyl; A substituted or unsubstituted di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl; A substituted or unsubstituted tree (C ₆ -C ₆₀₎ arylsilyl; Substituted or unsubstituted (C ₇ -C ₆₀₎ bicycloalkyl-alkyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkenyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkynyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkoxy; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkylamino; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylamino; Substituted or unsubstituted (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryloxy; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylthio; A substituted or unsubstituted (C ₁ -C ₆₀₎ alkylthio; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkoxycarbonyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylcarbonyl; (C ₆ -C ₆₀ ) arylcarbonyl; or

However,

Ar ₃ is substituted or unsubstituted (C ₁ -C ₆₀ ) alkyleneoxy; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylene-thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryleneoxy; (C ₆ -C ₆₀ ) arylene thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylene; Or (C ₃ -C ₆₀₎ and heteroarylene,

R ₇ is the same as the description of R ₁ to R ₆ ,

n is from 0 to 3,

If n is not a 0, X is _{-O-, -Si (-R 21) (} - R 22) -, -N (-R 21) - or _{-C (-R 21) (- R} 22) - a ,

Wherein R ₂₁ and R ₂₂ are each independently selected from the group consisting of hydrogen; Straight or branched (C ₁ -C ₆₀₎ alkyl; (C ₆ -C ₆₀ ) aryl; (C ₆ -C ₆₀ ) alkoxyaryl; (C ₁ -C ₆₀₎ alkylthio (C ₆ -C ₆₀₎ aryl; (C ₆ -C ₆₀ ) aryl, (C ₁ -C ₆₀ ) alkylsilyl (C ₆ -C ₆₀ ) aryl,

Wherein R ₁ to R _6, Ar _1, and Ar ₃ is A substitution at the same or different, each independently, halogen, (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ aryl, (C ₂ -C ₆₀₎ heteroaryl, N, O, S, and 5-or 6-membered heterocycloalkyl containing one or two or more selected from Si, (C ₃ -C ₆₀₎ cycloalkyl, tri (C ₁ - C ₆₀₎ alkylsilyl, di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl, tri (C ₆ -C ₆₀₎ arylsilyl, adamantyl, (C ₇ -C ₆₀₎ alkyl bicyclo , (C ₂ -C ₆₀₎ alkenyl, (C ₂ -C ₆₀₎ alkynyl, (C ₁ -C ₆₀₎ alkoxy, cyano, (C ₁ -C ₆₀₎ alkylamino, (C ₆ -C ₆₀₎ arylamino, (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ aryloxy, (C ₁ -C ₆₀₎ alkylthio, (C ₆ -C ₆₀₎ arylthio, (C ₁ -C ₆₀ ) alkoxycarbonyl, (C ₁ -C ₆₀ ) alkylcarbonyl, (C ₆ -C ₆₀ ) arylcarbonyl, carboxylic acid, nitro or hydroxy.

The compound represented by Formula 1 is preferably a compound represented by Formula 1A below.

In the above formula (1A)

R ₁ to R ₆ are the same as defined in Formula 1,

A is a substituted or unsubstituted (C ₆ -C ₆₀ ) aryl or a substituted or unsubstituted (C ₂ -C ₆₀ ) heteroaryl,

n is from 0 to 1,

When n is 1, X is -N (-R ₂₁ ) - or -C (-R ₂₁ ) (-R ₂₂ ) -,

R ₂₁ and R ₂₂ are the same as defined in Formula 1,

The adjacent groups of R ₁₇ to R ₂₀ are bonded to each other to form one or more aromatic or aliphatic rings.

The compound represented by the formula (1) is preferably selected from the following formulas (2) to (13).

&Lt; Formula 2 > < EMI ID =

&Lt; Formula 5 > < EMI ID =

&Lt; Formula 8 > < EMI ID =

&Lt; Formula 11 > < EMI ID =

In the above Chemical Formulas 2 to 13,

A, R ₁ to R ₆ are the same as defined in the above formula (1)

R ₉ to R ₁₆ each independently represent a group selected from the group consisting of R ₁ To R &lt; ₆ &gt;

R ₂₁ and R ₂₂ are each independently hydrogen; Straight or branched (C ₁ -C ₆₀₎ alkyl; (C ₆ -C ₆₀ ) aryl; (C ₆ -C ₆₀ ) alkoxyaryl; (C ₁ -C ₆₀₎ alkylthio (C ₆ -C ₆₀₎ aryl; Amino (C ₆ -C ₆₀ ) aryl; Or (C ₁ -C ₆₀ ) alkylsilyl (C ₆ -C ₆₀ ) aryl.

Specific examples of R ₁ to R ₆ include hydrogen, chloro, fluoro, adamantyl, carboxylic acid, nitro, cyano, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, benzyl, trifluoromethyl, perfluoroethyl, N-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, morpholino, thiomorpholino, phenyl, naphthyl, biphenyl, naphthyl, cyclopentyl, cyclohexyl, 9-dimethylfluorenyl, 9,9-diphenylfluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenyleney, pyryl, klycenyl, naphthacenyl, Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkenyl, alkynyl, alkynyl, alkynyl, alkynyl, (T-butyl) silyl, t-butyldimethylsilyl, t-butyldimethylsilyl, t-butyldimethylsilyl, tributylsilyl, tri Heptyl, bicyclo [2.2.2] octyl, bicyclo [3.2.1] octyl, bicyclo [5.2.0] nonyl, bicyclo [4.2 2] decyl, bicyclo [2.2.2] octyl, 4-pentylbicyclo [2.2.2] octyl, ethenyl, phenylethenyl, ethynyl, phenylethynyl, dimethylamino, diphenylamino, monomethylamino , Monophenylamino, phenyloxy, phenylthio, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, methylcarbonyl, ethylcarbonyl, benzylcarbonyl or phenyl Carbonyl, and the like. R ₁ to R ₆ may be the same or different from each other and are independent from each other.

Specific examples of the Ar ₁ include substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, anthracene, pyrene, triphenylene, tetracene, and chrysene. Ar ₁ may combine with an element of a ring containing - (X) _n - at an arbitrary carbon position 2 or more to form a fused ring.

형태의 치환체일 수 있다. 이때, Ar₃는 치환 또는 비치환된 (C₁-C₆₀)알킬렌옥시; 치환 또는 비치환된 (C₁-C₆₀)알킬렌티오; 치환 또는 비치환된 (C₆-C₆₀)아릴렌옥시; (C₆-C₆₀)아릴렌티오; 치환 또는 비치환된 (C₆-C₆₀)아릴렌; 또는 (C₃-C₆₀)헤테로아릴렌이고, R₇은 R₁ 내지 R₆은와 동일하다. On the other hand, substituent A may be the same as R ₁ and R ₆ , except that it can not be a hydrogen atom or a halogen atom. However, the substituent A is additionally

Lt; / RTI &gt; Wherein Ar ₃ is substituted or unsubstituted (C ₁ -C ₆₀ ) alkyleneoxy; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylene-thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryleneoxy; (C ₆ -C ₆₀ ) arylene thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylene; Or (C ₃ -C ₆₀ ) heteroarylene, and R ₇ is the same as R ₁ to R ₆ .

Specific examples of the substituent A may be as follows, but are not limited thereto.

On the other hand, when the substituents relating to the compound represented by the formula (1) substituted, same or different, each independently, halogen, (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ aryl, (C ₂ - C ₆₀₎ heteroaryl, N, O, 5-or 6-membered heterocycloalkyl of, containing one or two or more selected from S and Si (C ₃ -C ₆₀₎ cycloalkyl, tri (C ₁ -C ₆₀₎ alkylsilyl, di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl, tri (C ₆ -C ₆₀₎ arylsilyl, adamantyl, (C ₇ -C ₆₀₎ alkyl, bicycloalkyl, (C ₂ -C ₆₀₎ alkenyl, (C ₂ -C ₆₀₎ alkynyl, (C ₁ -C ₆₀₎ alkoxy, cyano, (C ₁ -C ₆₀₎ alkylamino, (C ₆ -C ₆₀₎ aryl amino, (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ aryloxy, (C ₁ -C ₆₀₎ alkylthio, (C ₆ -C ₆₀₎ arylthio, ( C ₁ -C ₆₀₎ alkoxycarbonyl, (C ₁ -C ₆₀₎ may be substituted with alkylcarbonyl, (C ₆ -C ₆₀₎ arylcarbonyl, carboxylic acid, nitro, or hydroxy. Each substituent may be the same or different from each other.

More specific examples of the compound represented by the formula (1) may be as follows, but are not limited thereto.

In the present invention, on the other hand, alkyl, alkoxy and other alkyl-related substituents mean straight-chain or branched-chain forms.

In the present invention, aryl is an organic radical derived from aromatic hydrocarbons by removal of one hydrogen, and includes a single or fused ring system, suitably containing from 4 to 7, preferably 5 or 6, ring atoms in each ring do. Specific examples include phenyl, naphthyl, biphenyl, atrile, tetrahydronaphthyl, indanyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, And the like. However, the present invention is not limited thereto.

In the present invention, heteroaryl means an aryl group having at least one hetero atom selected from N, O, S and Si as the aromatic ring skeletal atom and the remaining aromatic skeletal atom carbon, 6-membered monocyclic heteroaryl, and condensed polycyclic heteroaryl with one or more benzene rings, and may be partially saturated. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt. Specific examples include furyl, thiophenyl, pyrrolyl, pyranyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, tri Monocyclic heteroaryl such as aziridinyl, tetrazinyl, triazolyl, tetrazolyl, purafanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, isobenzofuranyl, benzoimidazolyl, benzo Benzothiadiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazole, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinolizinyl, But are not limited to, polycyclic heteroaryls such as quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl and the like and their corresponding N-oxides quaternary salts thereof.

The compound of the present invention described above is excellent in thermal stability, has a long lifetime, and is excellent in luminous efficiency and color coordinates. Particularly, the compound of the present invention is suitable as a material for blue and green fluorescence.

Ⅱ. Organic electroluminescent device

The present invention also relates to a liquid crystal display comprising a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a compound represented by the formula (1).

The organic layer may be one or more selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and may be one or two selected from the group consisting of a hole injection layer, Or more. This is because the compound of Formula 1 is excellent in hole injecting and hole transporting properties and is useful as a hole injecting layer or a hole transporting layer material. Among them, the hole transporting property is excellent, and it is more useful as the hole transporting layer material. The compound of formula (1) is excellent in the property of transferring energy from the light emitting layer to the dopant and is useful as a host material for blue, green, red fluorescence and phosphorescent devices. The compound of Formula 1 is more useful as a host material of a fluorescent device than a phosphorescent device.

The organic layer may further include a compound selected from the group consisting of a compound represented by the following formula (14), a compound represented by the following formula (15), and a mixture thereof in addition to the compound represented by the formula (1).

&Lt; Formula 14 > < EMI ID =

In the above Formulas 14 and 15,

Ar ₅ is (C ₆ -C ₆₀ ) aryl or (C ₄ -C ₆₀ ) heteroaryl,

Ar ₆ and Ar _{7, which} may be the same or different, each independently represent a substituted or unsubstituted (C ₆ -C ₆₀ ) aryl, substituted or unsubstituted (C ₄ -C ₆₀ ) heteroaryl, (C ₆ - C ₆₀₎ arylamino, N, O and (C ₃ -C ₆₀ unsubstituted 5-6 membered heterocycloalkyl or a substituted or unsubstituted, including at least one selected from the S), and cycloalkyl, wherein Ar ₆ and Ar ₇ May form an alicyclic ring, a monocyclic or polycyclic aromatic ring with or without a fused ring,

Ar ₈ is, independently of each other, (C ₆ -C ₆₀ ) arylene or (C ₄ -C ₆₀ ) heteroarylene, wherein Ar ₈ is an alicyclic ring with or without a fused ring, a monocyclic or polycyclic An aromatic ring may be formed,

a is from 1 to 4, b is from 1 to 4, and c is from 0 to 1.

Examples of the above-mentioned formulas (14) and (15) include, but are not limited to, the following compounds.

The organic film may further include one species selected from the group consisting of an arylamine compound, a styrylarylamine compound, and a mixture thereof in addition to the above compound.

In addition, the organic film may further include one or more species selected from the group consisting of Group 1, Group 2, Group 4, Periodic transition metal, Lanthanide series metal and d- .

The organic layer containing the compound of Formula 1 may be a hole injection layer, a hole transport layer, or a light emitting layer, and may be a single layer having both a hole injection function and a hole transport function at the same time. Or an organic layer containing a heterocyclic compound represented by the general formula (1) may be a light emitting layer. At this time, the compound represented by the formula (1) can be used as a blue, green or red fluorescent or phosphorescent host material. More preferably, it is used as a blue fluorescent host material.

Preferably, the organic layer containing the compound of Formula 1 is a hole injection layer or a hole transport layer. The organic electroluminescent device may further include at least one of a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer and an electron injecting layer, The organic layers may be formed of two organic layers.

For example, the organic electroluminescent device according to the present invention includes a first electrode / a hole injection layer / a light emitting layer / a second electrode, a first electrode / a hole injection layer / a hole transport layer / a light emitting layer / an electron transport layer / / Hole injection layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / second electrode structure. Alternatively, the organic electroluminescent device may include a single film / light emitting layer / electron transporting layer / second electrode having a first electrode / hole injecting function and a hole transporting function, or a single electrode / hole transporting layer having a first electrode / hole injecting function and a hole transporting function, Emitting layer / electron transporting layer / electron injecting layer / second electrode structure.

The organic electroluminescent device according to the present invention can be applied to various structures such as a top emission type and a bottom emission type.

A method of manufacturing an organic electroluminescent device according to the present invention is as follows.

First, a first electrode material having a high work function is formed on a substrate by a vapor deposition method, a sputtering method, or the like to form a first electrode. The first electrode may be an anode or a cathode. Here, the substrate used in a typical organic electroluminescent device is preferably a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. As the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), Al, Ag, Mg, Or a reflective electrode.

Next, a hole injection layer (HIL) may be formed on the first electrode by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal characteristics of the desired hole injection layer, and the like. In general, A degree of vacuum of 10 &lt; ^-8 &gt; to 10 &lt; ^-3 &gt; torr, a deposition rate of 0.01 to 100 ANGSTROM / sec and a film thickness of 10 ANGSTROM to 5 mu m.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is preferably from about 2000 rpm to 5000 rpm , And the heat treatment temperature for removing the solvent after coating is suitably selected within a temperature range of about 80 캜 to 200 캜.

As the hole injection layer material, a compound represented by Formula 1 as described above may be used, or a known hole injection layer material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 TCAD, m-MTDATA, m-MTDAPB, starburst amine derivatives as described in Advanced Material, 6, p. 677 (1994), and polyaniline / dodecylbenzenesulfonic acid / dodecylbenzene sulfonate (DBI), a soluble conductive polymer Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / camphor sulfonic acid: polyaniline / camphorsulfonic acid) or PANI / PSS (polyaniline) / poly (4-styrene-sulfonate): polyaniline) / poly (4-styrenesulfonate).

The thickness of the hole injection layer may be about 100 Å to 10000 Å, preferably 100 Å to 1000 Å. If the thickness of the hole injection layer is less than 100 angstroms, the hole injection characteristics may be degraded. If the thickness of the hole injection layer exceeds 10000 angstroms, the driving voltage may increase.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method. In the case of forming the hole transporting layer by the vacuum deposition method and the sputtering method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The hole transport layer material may be a compound represented by the general formula (1) or a known hole transport layer material may be used. For example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, (NPB), N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl ] -4,4'-diamine (TPD), and N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine Is selected from the same range of conditions as the formation of the injection layer used.

The thickness of the electron injection layer may be about 1 to about 100, preferably about 5 to about 90. If the thickness of the electron injection layer is less than 1 angstrom, the electron injection characteristics may be degraded. If the thickness of the electron injection layer exceeds 100 angstroms, the driving voltage may increase.

Finally, the second electrode can be formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like. The second electrode may be used as a cathode or an anode. As the material for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, or a mixture thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- . A transparent cathode using ITO or IZO may also be used to obtain a front light emitting device.

The organic electroluminescent device according to the present invention may be provided in various types of flat panel display devices, for example, a passive matrix organic light emitting display device and an active matrix organic light emitting display device. In particular, when the active matrix organic light emitting display device is provided, the first electrode provided on the substrate side may be electrically connected to the source electrode or the drain electrode of the thin film transistor as the pixel electrode. In addition, the organic electroluminescent device may be provided in a flat panel display device capable of displaying a screen on both sides.

The organic electroluminescent device of the present invention has a long lifetime, excellent luminous efficiency, and high color purity.

Ⅲ. Solar cell

The present invention relates to a plasma display panel comprising a first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a compound represented by the general formula (1).

The compound of Formula 1 is useful as a hole transport layer material having excellent hole injection properties and hole transport properties. The organic film containing the compound of formula (1) may be a hole injection layer, a hole transporting layer, or a single film having both a hole injection function and a hole transport function simultaneously in the solar cell of the present invention. Preferably, the organic layer containing the compound of Formula 1 is a hole injection layer or a hole transport layer.

The solar cell of the present invention may further include at least one layer of a hole injecting layer, a hole transporting layer, an electron blocking layer, a buffer layer, a hole blocking layer, an electron transporting layer and an electron injecting layer, It is also possible to form the organic layer as two layers.

Hereinafter, the present invention will be described in more detail with reference to Examples.

The present invention is intended to more specifically illustrate the present invention, and the scope of the present invention is not limited to these embodiments.

<Examples>

Synthetic example  1: Preparation of compound 1

Compound 1 was synthesized via the reaction path of Scheme 1 below.

<Reaction Scheme 1>

(1) Production of Compound 1-1

9-bromo-anthracene 10g (39㏖), 2- formyl-phenylboronic acid 7g (47m㏖), Pd (PPh 3) 4 4.5g (3.9m㏖) and K ₂ CO ₃ 10.5 g (76 mmol) of the compound was dissolved in toluene / ethanol / distilled water (200 ml / 50 ml / 40 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 8 g (73%) of the desired compound 1-1.

(2) Preparation of Compound 1-2

IPy₂BF₄ 21g (56mmol) was dissolved in dichloromethane and then cooled to -78 ° C. HBF₄ 18.2 g (112 mmol) of the mixture was added, and the mixture was stirred at -78 캜 for 10 minutes. The solid was filtered, and the filtrate was cooled to -60 DEG C, followed by slowly adding 8 g (28 mmol) of Compound 1-1. When the reaction was completed, the organic material was extracted with ice water after completion of the reaction. The organics were dissolved in MgSO4₄, The solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 4.7 g (60%) of the desired compound 1-2.

(3) Preparation of Compound 1-3

4.7 g (17 mmol) of Compound 1-2 was dissolved in 100 ml of diethyl ether, and 2.7 g (20.4 mmol) of AlCl ₃ was added slowly. It was stirred for 15 minutes, then cooled to 0 ° C and 1 g (26 mmol) of lithium aluminum hydride (LAH) was slowly added. This was refluxed for 1 hour. After the reaction was completed, the reaction mixture was slowly cooled to room temperature, and EA was slowly added thereto until no bubbles were formed. Then, 20 ml of 6N HCl was added thereto, and the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 1-3.4 g (90%) of the compound.

(4) Preparation of compounds 1-4

4 g (15 mmol) of Compound 1-3 was dissolved in 40 ml of DMSO, 10.7 g (112 mmol) of sodium tert-butoxide was added at room temperature, and the mixture was stirred at 70 ° C for 15 minutes. 19 g (132 mmol) of methyl iodide was slowly added thereto and further stirred for 1 hour. When the reaction was completed, the reaction mixture was cooled at room temperature, and distilled water was added thereto, followed by stirring for 20 minutes. At this time, a solid was formed. The solid was filtered and the resulting solid was recrystallized from ethanol and acetone to obtain 2.6 g (60%) of the desired compound 1-4.

(5) Preparation of compounds 1-5

2.6 g (8.8 mmol) of Compound 1-4 was dissolved in 30 ml of DMF, and 1.6 g (8.8 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic material was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 2.6 g (80%) of the desired compound 1-5.

(6) Production of Compound 1

Compound 1-5 10g (26.8m㏖), phenylboronic acid 3.9g (32m㏖), Pd (PPh 3) 4 4.5g (3.1m㏖) and K ₂ CO ₃ 7.4g (53.6m㏖) toluene / ethanol / Distilled water (200 ml / 50 ml / 40 ml), followed by stirring at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic material was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was purified by column chromatography using dichloromethane and hexane as eluent to obtain 8.4 g (85%) of the final compound, Compound 1.

Synthetic example  2: Preparation of compound 42

Compound 42 was synthesized via the reaction path of Reaction Scheme 2 below.

<Reaction Scheme 2>

(1) Production of Compound 2-1

Compound 1-5 10g (26.8m㏖), 4- bromo-phenyl boronic acid 6.4g (32m㏖), Pd (PPh 3) 4 4.5g (2.7m㏖) and K ₂ CO ₃ 7.4g (53.6m㏖) Was dissolved in toluene / ethanol / distilled water (200 ml / 50 ml / 40 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was removed by column chromatography using dichloromethane and hexane as eluent to obtain 10.7 g (80%) of the target compound 2-1.

(2) Preparation of Compound 42

Compound 2-1 5g (11.1m㏖), 9,9- dimethyl-fluorene-2-boronic acid walk 3.2g (13.3m㏖), Pd (PPh3 ) 4 1.3g (1.1m㏖) and K ₂ CO ₃ 3.1 g (22.2 mmol) was dissolved in toluene / ethanol / distilled water (100 ml / 25 ml / 20 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off using dichloromethane and hexane as eluent to give 42 g of the final compound (80%).

Synthetic example  3: Preparation of compound 77

Compound 77 was synthesized via the reaction path of Reaction Scheme 3 below.

<Reaction Scheme 3>

(1) Preparation of Compound 3-1

9-bromo-anthracene 20g (78m㏖), 2- methoxyphenyl boronic acid 14.2g (93m㏖), Pd (PPh3 ) 4 7.8g (7.8m㏖) and K ₂ CO ₃ 21.5g (156m㏖) toluene / Ethanol / distilled water (390 ml / 97 ml / 78 ml), followed by stirring at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 20 g (90%) of the target compound 3-1.

(2) Preparation of compound 3-2

13 g (45.7 mmol) of the compound 3-1 was dissolved in 130 ml of dichloromethane and then cooled to 0 占 폚. 92 ml (92 mmol) of boron tribromide was slowly added thereto. The temperature was warmed to room temperature and then stirred. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO 4, and the solvent was removed using a rotary evaporator. The mixture was stirred in a toluene solvent and filtered to obtain 11 g (89%) of the target compound 3-2.

(3) Preparation of compound 3-3

11 g (40 mmol) of the compound 3-2 was dissolved in dichloromethane, 7.1 ml (61 mmol) of 2,6-lutidine was added, and the mixture was cooled to -30 ° C and stirred. To this was added slowly 8.2 ml (49 mmol) of trifluoromethanesulfonic anhydride. The temperature was raised to 0 ° C and stirred for 1 hour. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 15 g (93%) of the target compound 3-3.

(4) Preparation of compound 3-4

Compound 3-3 15g (37.3m㏖), Pd ( PPh 3) 2 Cl 2 2.6g (3.7m㏖), lithium chloride 4.7g (112m㏖) and DBU 6.7㎖ the mid-dimethylformamide to 190 (44.7m㏖) Ml, followed by stirring at 140 占 폚. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 7.5 g (80%) of the target compound 3-4.

(5) Preparation of compound 3-5

7.5 g (30 mmol) of the compound 3-4 was dissolved in 100 ml of DMF, and 5.5 g (30 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO 4, and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 7.4 g (75%) of the target compound 3-5.

(6) Preparation of Compound 77

Compound 3-5 5g (15m㏖), dibe joti carbonyl-2-boronic acid 4.1g (18m㏖), Pd (PPh 3) 4 1.7g (1.5m㏖) and K ₂ CO ₃ 4.1g (30m㏖) Was dissolved in toluene / ethanol / distilled water (100 ml / 25 ml / 20 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure using dichloromethane and hexane as eluent to give 77 g (85%) of the final compound 77.

Synthetic example  4: Preparation of compound 169

Compound 169 was synthesized via the reaction path of Reaction Scheme 4 below.

<Reaction Scheme 4>

(1) Preparation of compound 4-1

9-bromo-anthracene 20g (78m㏖), 2- nitro-phenyl boronic acid 15.5g (93m㏖), Pd (PPh 3) 4 9g (7.8m㏖) and K ₂ CO ₃ 21.5g (156m㏖) toluene / Dissolved in ethanol / distilled water (390 ml / 97 ml / 78 ml) and stirred at 100 ?. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 20 g (85%) of the target compound 4-1.

(2) Preparation of compound 4-2

20 g (67 mmol) of the compound 4-1 was mixed with 100 ml of triethyl phosphite, and the mixture was stirred at 180 캜 for 4 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. Crystallization with methanol gave 12.5 g (75%) of the desired compound 4-2.

(3) Preparation of compound 4-3

(17.6 mmol) of Compound 4-2, 0.6 g (8.8 mmol) of copper, 0.2 g (0.9 mmol) of 18-crown-6, 4.8 g (35.1 mmol) of K ₂ CO _3, 100 ml of dichlorobenzene were mixed and stirred under reflux at 180 占 폚 for 12 hours. Cooled to room temperature, distilled under reduced pressure, extracted with MC and washed with distilled water. Dried over anhydrous MgSO ₄ and distilled under reduced pressure. The obtained residue was subjected to column separation to obtain Compound 4-3 3.6 (60%).

(4) Preparation of compound 4-4

3 g (7.1 mmol) of the compound 4-3 was dissolved in 40 ml of DMF, and 1.3 g (7.1 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 2.7 g (90%) of the target compound 4-4.

(5) Preparation of compound 169

Compound 4-4 6.3g (15m㏖), phenylboronic acid 2.2g (18m㏖), Pd (PPh 3) 4 1.7g (1.5m㏖) and K ₂ CO ₃ 4.1g (30m㏖) toluene / ethanol / Dissolved in distilled water (100 ml / 25 ml / 20 ml), and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave the desired compound 169 (5.5 g, 88%).

Synthetic example  5: Preparation of compound 225

Compound 225 was synthesized via the reaction path of Scheme 5 below.

<Reaction Scheme 5>

(1) Preparation of Compound 5-1

9-bromo-anthracene 20g (78m㏖), 2- methoxy-naphthalene-boronic acid 18.8g (93m㏖), Pd (PPh 3) 4 7.8g (7.8m㏖) and K ₂ CO ₃ 21.5g (156m㏖) Dissolved in toluene / ethanol / distilled water (390 ml / 97 ml / 78 ml), and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was then purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 23 g (89%) of the target compound 5-1.

(2) Preparation of Compound 5-2

23 g (68.8 mmol) of the compound 5-1 was dissolved in 230 ml of dichloromethane and then cooled to 0 ° C. 138 ml (138 mmol) of boron tribromide was slowly added thereto. The temperature was warmed to room temperature and then stirred. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The mixture was stirred in a toluene solvent and filtered to obtain 38 g (86%) of the target compound 5-2.

(3) Preparation of compound 5-3

10 g (22 mmol) of the compound 5-2 was dissolved in dichloromethane, 3.9 ml (33 mmol) of 2,6-lutidine was added, and the mixture was cooled to -30 ° C and stirred. 4.5 ml (27 mmol) of trifluoromethanesulfonic anhydride was slowly added thereto. The temperature was raised to 0 &lt; 0 &gt; C and stirred for one hour. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 9.4 g (95%) of the desired compound 5-3.

(4) Preparation of compound 5-4

Compound 5-3 9.4g (21m㏖), Pd ( PPh 3) 2 Cl 2 2.9g (4.2m㏖), lithium chloride 2.7g (63m㏖) and DBU 9.4㎖ (63m㏖) to dimethylformamide imide 150㎖ Followed by stirring at 140 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.7 g (75%) of the target compound 3-4.

(5) Preparation of compound 5-5

4 g (13.2 mmol) of the compound 5-4 was dissolved in 80 ml of DMF, and 2.4 g (13.2 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.5 g (90%) of the target compound 5-5.

(6) Preparation of Compound 225

Compound 5-5 4.5g (11.8m㏖), 2- naphthyl boronic acid 2.5g (14.2m㏖), Pd (PPh 3) 4 1.4g (1.2m㏖) and K ₂ CO ₃ 4.9g (35.4m㏖ ) Was dissolved in toluene / ethanol / distilled water (100 ml / 25 ml / 20 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.3 g (85%) of 225 as the final compound.

Synthetic example  6: Preparation of compound 287

Compound 287 was synthesized via the reaction path of Scheme 6 below.

<Reaction Scheme 6>

(1) Preparation of Compound 6-1

Compound 9-bromo-anthracene 20g (78m㏖), 1- methoxy-2-naphthalene boronic acid 18.8g (93m㏖), Pd (PPh 3) 4 7.8g (7.8m㏖) and K ₂ CO _3, 21.5g (156 mmol) was dissolved in toluene / ethanol / distilled water (390 ml / 97 ml / 78 ml), followed by stirring at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 23 g (89%) of the target compound 6-1.

(2) Preparation of Compound 6-2

23 g (68.8 mmol) of the compound 6-1 was dissolved in 230 ml of dichloromethane and then cooled to 0 占 폚. 138 ml (138 mmol) of boron tribromide was slowly added thereto. The temperature was warmed to room temperature and then stirred. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under a toluene solvent and filtered to obtain 38 g (86%) of the target compound 6-2.

(3) Preparation of Compound 6-3

10 g (22 mmol) of the compound 6-2 was dissolved in dichloromethane, and 3.9 ml (33 mmol) of 2,6-lutidine was added. The mixture was cooled to -30 ° C and stirred. 4.5 ml (27 mmol) of trifluoromethanesulfonic anhydride was slowly added thereto. The temperature was raised to 0 &lt; 0 &gt; C and stirred for one hour. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 9.4 g (95%) of the desired compound 6-3.

(4) Preparation of compound 6-4

2.9 g (4.2 mmol) of Pd (PPh ₃ ) ₂ Cl ₂ , 2.7 g (63 mmol) of lithium chloride and 9.4 ml (63 mmol) of DBU were added to a solution of dimethyl formamide 150 Ml, followed by stirring at 140 占 폚. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 4.7 g (75%) of the target compound 6-4.

(5) Preparation of Compound 6-5

4 g (13.2 mmol) of the compound 6-4 was dissolved in 80 ml of DMF, and 2.4 g (13.2 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 4.5 g (90%) of the target compound 6-5.

(6) Preparation of Compound 287

Compound 6-5 4.5g (11.8m㏖), 2- naphthyl boronic acid 2.5g (14.2m㏖), Pd (PPh 3) 4 1.4g (1.2m㏖), and K ₂ CO _3, 4.9g (35.4 mmol) were dissolved in toluene / ethanol / distilled water (100 ml / 25 ml / 20 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.3 g (85%) of the desired compound 287.

Synthetic example  7: Preparation of compound 337

Compound 337 was synthesized via the reaction path of Scheme 7 below.

<Reaction Scheme 7>

(1) Preparation of Compound 7-1

Compound 9-bromo -10-methoxy-phenanthrene (9-bromo-10-methoxy -Phenanthrene) 22.4g (78m㏖), 9- anthracene boronic acid 20.7g (93m㏖), Pd (PPh 3) 4 7.8g (7.8 mmol) and K ₂ CO ₃ (21.5 g, 156 mmol) were dissolved in toluene / ethanol / distilled water (390 ml / 97 ml / 78 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 6.9 g (23%) of the target compound 7-1.

(2) Preparation of Compound 7-2

26.5 g (68.8 mmol) of the compound 7-1 was dissolved in 270 ml of dichloromethane and then cooled to 0 占 폚. 138 ml (138 mmol) of boron tribromide was slowly added thereto. The temperature was warmed to room temperature and then stirred. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed by a rotary evaporator. The solvent was then stirred in toluene solvent and filtered to obtain 19.1 g (75%) of the target compound 7-2.

(3) Preparation of Compound 7-3

8.1 g (22 mmol) of the compound 7-2 was dissolved in dichloromethane, and 3.9 ml (33 mmol) of 2,6-lutidine was added. The mixture was cooled to -30 캜 and stirred. 4.5 ml (27 mmol) of trifluoromethanesulfonic anhydride was slowly added thereto. The temperature was raised to 0 &lt; 0 &gt; C and stirred for one hour. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 9.1 g (85%) of the desired compound 7-3.

(4) Preparation of Compound 7-4

Compound 7-3 10.6g (21m㏖), Pd ( PPh 3) 2 Cl 2 2.9g (4.2m㏖), lithium chloride 2.7g (63m㏖), and DBU 9.4㎖ the mid-dimethylformamide to 200 a (63m㏖) Ml, followed by stirring at 140 占 폚. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 2.6 g (35%) of the desired compound 7-4.

(5) Preparation of Compound 7-5

4.6 g (13.2 mmol) of the compound 7-4 was dissolved in 100 ml of DMF, and 2.4 g (13.2 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for 17 hours. When the reaction was completed, the reaction mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 5.1 g (90%) of the target compound 7-5.

(6) Preparation of Compound 337

Compound 7-5 5.1g (11.8m㏖), 2- naphthyl boronic acid 2.5g (14.2m㏖), Pd (PPh 3) 4 1.4g (1.2m㏖), and K ₂ CO _3, 4.9g (35.4 mmol) were dissolved in toluene / ethanol / distilled water (100 ml / 25 ml / 20 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 4.2 g (75%) of the desired compound 337.

Synthetic example  8: Preparation of compound 352

Compound 352 was synthesized via the reaction path of Scheme 8 below.

<Reaction Scheme 8>

(1) Preparation of Compound 8-1

10 g (37.5 mmol) of Compound 1-3 and 19.2 g (94 mmol) of iodobenzene were dissolved in 100 ml of toluene. 1.2 g (0.4 mmol) of tricyclohexylphosphine, 0.9 g (4 mmol) of Pd (OAc) _{2 and} 2.7 g (63 mmol) of potassium t-butoxide lithium chloride were refluxed for 12 hours or more. After cooling to room temperature, water was poured and organic matter was extracted. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 12.5 g (80%) of the target compound 8-1.

(2) Preparation of Compound 8-2

10 g (20 mmol) of the compound 8-1 was dissolved in 150 ml of DMF, and 3.6 g (20 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. Thereafter, purification was carried out by column chromatography using dichloromethane and hexane as eluent, to obtain 8.9 g (90%) of the desired compound 8-2.

(3) Preparation of compound 352

Compound 8-2 8g (16.1m㏖), 2- naphthyl, 4-phenyl-boronic acid 4.8g (19.3m㏖), Pd (PPh 3) 4 1.8g (1.6m㏖) and K ₂ CO ₃ 4.5g ( 32.2 mmol) was dissolved in toluene / ethanol / distilled water (160 ml / 32 ml / 32 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was then purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 8.5 g (85%) of Compound 352 as a final compound.

Synthetic example  9: Preparation of compound 393

Compound 393 was synthesized via the reaction path of Scheme 9 below.

<Reaction Scheme 9>

(1) Production of Compound 9-1

Compound 9-bromo-anthracene 10g (39mol), (2- formyl-1-yl) boronic acid ((2-formylnaphthalen-1- yl) boronic acid) 9.4g (47m㏖), Pd (PPh 3) 4 4.5 g (3.9 mmol) of K ₂ CO _{3 and} 10.5 g (76 mmol) of K ₂ CO ₃ were dissolved in toluene / ethanol / distilled water 200 ml / 50 ml / 40 ml and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 5.8 g (45%) of the desired compound 9-1.

(2) Preparation of Compound 9-2

21 g (56 mmol) of IPy ₂ BF ₄ was dissolved in dichloromethane and cooled to -78 ° C. 18.2 g (112 mmol) of HBF ₄ was added, and the mixture was stirred at -78 캜 for 10 minutes. After filtering the solid, the filtrate was cooled to -60 DEG C and then 5.8 g (17.5 mmol) of 9-1 was added slowly. When the reaction was completed, the organic layer was extracted with ice water after completion of the reaction. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 3.0 g (52%) of the desired compound 9-2.

(3) Preparation of Compound 9-3

5.6 g (17 mmol) of the compound 9-2 was dissolved in 100 ml of diethyl ether, and 2.7 g (20.4 mmol) of AlCl ₃ was added slowly. It was stirred for 15 minutes, then cooled to 0 ° C and 1 g (26 mmol) of lithium aluminum hydride (LAH) was slowly added. This was refluxed for 1 hour. After the reaction was completed, the reaction mixture was slowly cooled to room temperature, and EA was slowly added thereto until no bubbles were formed. Then, 20 ml of 6N HCl was added thereto, and the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure to give 4.3 g (80%) of compound 9-3 as a developing solvent.

(4) Preparation of Compound 9-4

4.7 g (15 mmol) of the compound 9-3 was dissolved in 40 ml of DMSO, 10.7 g (112 mmol) of sodium tert-butoxide was added at room temperature, and the mixture was stirred at 70 ° C for 15 minutes. 26.9 g (132 mmol) of benzene iodide was slowly added thereto, and the mixture was further stirred for 1 hour. When the reaction was completed, the reaction mixture was cooled at room temperature, and distilled water was added thereto, followed by stirring for 20 minutes. At this time, a solid was formed, which was filtered, and the resulting solid was recrystallized from ethanol and acetone to obtain 4.2 g (60%) of Compound 9-4.

(5) Preparation of Compound 9-5

4.1 g (8.8 mmol) of Compound 9-4 was dissolved in 30 ml of DMF, and 1.6 g (8.8 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 4.3 g (90%) of the target compound 9-5.

(6) Preparation of compound 393

Compound 9-5 14.7g (26.8m㏖), (9 -phenyl-9H-carbazol-3-yl) boronic acid 9.2g (32m㏖), Pd (PPh 3) 4 4.5g (3.1m㏖) and K ₂ 7.4 g (53.6 mmol) of CO ₃ was dissolved in toluene / ethanol / distilled water (200 ml / 50 ml / 40 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as eluent to obtain 13.3 g (70%) of the desired compound 393.

Synthetic example  10: Preparation of compound 414

Compound 414 was synthesized via the reaction path of Scheme 10 below.

<Reaction formula 10>

(1) Preparation of Compound 10-1

Compound 9-bromo-anthracene 10g (39mol), (1- formylnaphthalen-2-yl) boronic acid 9.4g (47m㏖), Pd (PPh 3) 4 4.5g (3.9m㏖) and K ₂ CO ₃ 10.5g ( 76 mmol) was dissolved in toluene / ethanol / distilled water (200 ml / 50 ml / 40 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 1.9 g (15%) of the target compound 10-1.

(2) Preparation of Compound 10-2

21 g (56 mmol) of IPy ₂ BF ₄ was dissolved in dichloromethane and cooled to -78 ° C. 18.2 g (112 mmol) of HBF ₄ was added, and the mixture was stirred at -78 캜 for 10 minutes. After filtering the solid, the filtrate was cooled to -60 DEG C and then 5.8 g (17.5 mmol) of 10-1 was slowly added.

When the reaction was completed, the organic layer was extracted with ice water after completion of the reaction. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 3.0 g (52%) of the target compound 10-2.

(3) Preparation of Compound 10-3

5.6 g (17 mmol) of the compound 10-2 was dissolved in 100 ml of diethyl ether, and 2.7 g (20.4 mmol) of AlCl ₃ was slowly added. It was stirred for 15 minutes, then cooled to 0 ° C and 1 g (26 mmol) of lithium aluminum hydride (LAH) was slowly added. This was refluxed for 1 hour. After the reaction was completed, the reaction mixture was slowly cooled to room temperature, and EA was slowly added thereto until no bubbles were formed. Then, 20 ml of 6N HCl was added thereto, and the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure to give 3.8 g (70%) of compound 10-3 as a developing solvent.

(4) Preparation of compound 10-4

After dissolving 4.7 g (15 mmol) of the compound 10-3 in 40 ml of DMSO, 10.7 g (112 mmol) of sodium tert-butoxide was added at room temperature, and the mixture was stirred at 70 캜 for 15 minutes. 26.9 g (132 mmol) of benzene iodide was slowly added thereto, and the mixture was further stirred for 1 hour. When the reaction was completed, the reaction mixture was cooled at room temperature, and distilled water was added thereto, followed by stirring for 20 minutes. At this time, a solid was formed, which was filtered, and the obtained solid was recrystallized from ethanol and acetone to obtain 4.2 g (60%) of Compound 10-4.

(5) Preparation of Compound 10-5

4.1 g (8.8 mmol) of Compound 10-4 was dissolved in 30 ml of DMF, and 1.6 g (8.8 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 4.3 g (90%) of the target compound 10-5.

(6) Preparation of compound 414

Compound 10-5 14.7g (26.8m㏖), dibe joti carbonyl-2-boronic acid 7.3g (32m㏖), Pd (PPh 3) 4 4.5g (3.1m㏖) and K ₂ CO ₃ 7.4g (53.6 ml) was dissolved in toluene / ethanol / distilled water (200 ml / 50 ml / 40 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was then purified by column chromatography using dichloromethane and hexane as eluent to obtain 13.3 g (70%) of the desired compound 414.

Synthetic example  11: Preparation of compound 472

Compound 472 was synthesized via the reaction path of Scheme 11 below.

<Reaction Scheme 11>

(1) Production of Compound 11-1

Compound 10-Bromo-9-phenanthrene carboxylic aldehyde (10-Bromo-9-phenanthrenecarboxaldehyde ) 11.1g (39mol), 9- anthracene boronic acid 9.4g (47m㏖), Pd (PPh 3) 4 4.5g (3.9 and 10.5 g (76 mmol) of K ₂ CO ₃ were dissolved in toluene / ethanol / distilled water (200 ml / 50 ml / 40 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 3.7 g (25%) of the desired compound 11-1.

(2) Preparation of Compound 11-2

21 g (56 mmol) of IPy ₂ BF ₄ was dissolved in dichloromethane and cooled to -78 ° C. 18.2 g (112 mmol) of HBF ₄ was added, and the mixture was stirred at -78 캜 for 10 minutes. After filtering the solid, the filtrate was cooled to -60 DEG C and then 11-1 (6.7 g, 17.5 mmol) was added slowly. When the reaction was completed, the organic layer was extracted with ice water after completion of the reaction. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 3.5 g (52%) of the desired compound 11-2.

(3) Production of Compound 11-3

6.5 g (17 mmol) of the compound 11-2 was dissolved in 100 ml of diethyl ether, and 2.7 g (20.4 mmol) of AlCl ₃ was added slowly. It was stirred for 15 minutes, then cooled to 0 ° C and 1 g (26 mmol) of lithium aluminum hydride (LAH) was slowly added. This was refluxed for 1 hour. After the reaction was completed, the reaction mixture was slowly cooled to room temperature, and EA was slowly added thereto until no bubbles were formed. Then, 20 ml of 6N HCl was added thereto, and the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.4 g (70%) of compound 11-3.

(4) Preparation of compound 11-4

5.5 g (15 mmol) of the compound 11-3 was dissolved in 40 ml of DMSO, 10.7 g (112 mmol) of sodium tert-butoxide was added at room temperature, and the mixture was stirred at 70 ° C for 15 minutes. 26.9 g (132 mmol) of benzene iodide was slowly added thereto, and the mixture was further stirred for 1 hour. When the reaction was completed, the reaction mixture was cooled at room temperature, and distilled water was added thereto, followed by stirring for 20 minutes. At this time, a solid was formed. The solid was filtered and the obtained solid was recrystallized from ethanol and acetone to obtain 4.7 g (60%) of Compound 11-4.

(5) Preparation of compound 11-5

4.6 g (8.8 mmol) of the compound 11-4 was dissolved in 30 ml of DMF, and 1.6 g (8.8 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 4.7 g (90%) of the desired compound 11-5.

(6) Preparation of compound 472

9.2 g (32 mmol) of Compound 11-5, 16 g (26.8 mmol) of 9-phenyl-9H-carbazol-3-yl) boronic acid, Pd (PPh ₃₎ was stirred at ₄ 4.5g (3.1m㏖) and K ₂ CO ₃ 7.4g following 100 ℃ (53.6m㏖) dissolved in a toluene / ethanol / distilled water 200㎖ / 50㎖ / 40㎖. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 11.4 g (60%) of the target compound 472.

Synthetic example  12: Preparation of compound 509

Compound 509 was synthesized via the reaction path of Scheme 12 below.

<Reaction Scheme 12>

(1) Preparation of Compound 12-1

Compound 9-bromo-anthracene 20g (78m㏖), (2-nitro-1-yl) boronic acid ((2-nitronaphthalen-1- yl) boronic acid) 20g (93m㏖), Pd (PPh 3) 4 9 g (7.8 mmol) of K ₂ CO _{3 and} 21.5 g (156 mmol) of K ₂ CO ₃ were dissolved in 390 ml / 97 ml / 78 ml of toluene / ethanol / distilled water and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 13.6 g (50%) of the target compound 12-1.

(2) Preparation of Compound 12-2

23.4 g (67 mmol) of the compound 12-1 was added to 100 ml of triethyl phosphite, and the mixture was stirred at 180 占 폚 for 17 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. Crystallization with methanol gave 8.5 g (40%) of the desired compound 12-2.

(3) Preparation of compound 12-3

Compound 12-2 5.6g (17.6m㏖), copper 0.6g (8.8m㏖), 18- crown _{-6 0.2g (0.9m㏖), K 2} CO 3 4.8g (35.1m㏖) and 1,2 100 ml of dichlorobenzene were mixed, and the mixture was refluxed and stirred at 180 占 폚 for 17 hours. Cooled to room temperature, distilled under reduced pressure, extracted with MC and washed with distilled water. Dried over anhydrous MgSO ₄ and distilled under reduced pressure. The resulting residue was subjected to column separation to obtain 4.2 g (60%) of Compound 12-3.

(4) Preparation of compound 12-4

2.8 g (7.1 mmol) of the compound 12-3 was dissolved in 40 ml of DMF, and 1.3 g (7.1 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 3.0 g (90%) of the target compound 12-4.

(5) Preparation of Compound 509

Compound 12-4 7.1g (15m㏖), 2- naphthalenesulfonic acid 3.1g (18m㏖), Pd (PPh 3) 4 1.7g (1.5m㏖), and _{K 2 CO 3, 4.1g (30m㏖} ) the Dissolved in toluene / ethanol / distilled water 100 ml / 25 ml / 20 ml, and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 5 g (65%) of the target compound 509.

Synthetic example  13: Preparation of compound 510

Compound 510 was synthesized via the reaction path of Scheme 13 below.

<Reaction Scheme 13>

(1) Preparation of Compound 13-1

Compound 9-bromo-10-nitrophenanthrene 23.6g (78m㏖), (2-phenylanthracen-9-yl) boronic acid 27.7g (93m㏖), Pd (PPh 3) 4 9g (7.8m㏖) and K ₂ CO ₃ 21.5 g (156 mmol) of the compound was dissolved in 390 ml / 97 ml / 78 ml of toluene / ethanol / distilled water, followed by stirring at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 3.7 g (10%) of the desired compound 13-1.

(2) Preparation of Compound 13-2

31.7 g (67 mmol) of the compound 13-1 was mixed with 320 ml of triethyl phosphite, and the mixture was stirred at 180 캜 for 17 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. Crystallization with ethanol gave 17.8 g (60%) of the desired compound 13-2.

(3) Production of compound 13-3

Compound 13-2 7.8g (17.6m㏖), copper 0.6g (8.8m㏖), 18- crown _{-6 0.2g (0.9m㏖), K 2} CO 3 4.8g (35.1m㏖) and 1,2 100 ml of dichlorobenzene were mixed, and the mixture was refluxed and stirred at 180 占 폚 for 17 hours. Cooled to room temperature, distilled under reduced pressure, extracted with MC and washed with distilled water. Dried over anhydrous MgSO ₄ and distilled under reduced pressure. The obtained residue was subjected to column separation to obtain 4.6 g (50%) of Compound 13-3.

(4) Preparation of compound 13-4

3.7 g (7.1 mmol) of the compound 13-3 was dissolved in 40 ml of DMF, and 1.3 g (7.1 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 3.6 g (85%) of the target compound 13-4.

(5) Preparation of compound 510

Compound 13-4 9g (15m㏖), [1,1' -biphenyl] -3-ylboronic acid 3.6g (18m㏖), Pd (PPh 3) 4 1.7g (1.5m㏖), and K ₂ CO ₃ 4.1 g (30 mmol) was dissolved in toluene / ethanol / distilled water (100 ml / 25 ml / 20 ml) and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and then purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.8 g (50%) of the desired compound 510.

Synthetic example  14: Preparation of compound 531

Compound 531 was synthesized via the reaction path of Scheme 14 below.

<Reaction Scheme 14>

(1) Preparation of Compound 14-1

Compound 9-bromo-anthracene 20g (78m㏖), (1-nitro-naphthalene-2-yl) boronic acid ((1-nitronaphthalen-2- yl) boronic acid) 20g (93m㏖), Pd (PPh 3) 4 9 g (7.8 mmol) of K ₂ CO _{3 and} 21.5 g (156 mmol) of K ₂ CO ₃ were dissolved in 390 ml / 97 ml / 78 ml of toluene / ethanol / distilled water and stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 8.2 g (30%) of the target compound 14-1.

(2) Preparation of Compound 14-2

23.4 g (67 mmol) of the compound 14-1 was mixed with 100 ml of triethyl phosphite, and the mixture was stirred at 180 占 폚 for 17 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. Crystallization with ethanol gave 12.8 g (60%) of the desired compound 14-2.

(3) Preparation of Compound 14-3

(17.6 mmol) of Compound 14-2, 0.6 g (8.8 mmol) of copper, 0.2 g (0.9 mmol) of 18-crown-6, 4.8 g (35.1 mmol) of K ₂ CO _3, 100 ml of dichlorobenzene were mixed, and the mixture was refluxed and stirred at 180 占 폚 for 17 hours. Cooled to room temperature, distilled under reduced pressure, extracted with MC and washed with distilled water. Dried over anhydrous MgSO ₄ , distilled under reduced pressure, and the obtained residue was subjected to column separation to obtain 4.2 g (60%) of Compound 14-3.

(4) Preparation of compound 14-4

2.8 g (7.1 mmol) of the compound 14-3 was dissolved in 40 ml of DMF, and 1.3 g (7.1 mmol) of N-bromosuccinimide was added slowly. The reaction mixture was stirred at room temperature for one day and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 3.0 g (90%) of the target compound 14-4.

(5) Preparation of compound 531

Compound 14-4 to 7.1g (15m㏖), 2- naphthalenesulfonic acid 3.1g (18m㏖), Pd (PPh 3) 4 1.7g (1.5m㏖), and K ₂ CO ₃ 4.1g (30m㏖) toluene / Ethanol / distilled water (100 ml / 25 ml / 20 ml), followed by stirring at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 3.8 g (50%) of the target compound 531.

NMR and mass-spectrum data of the compounds according to the present invention are shown in Table 1 below. The compound numbers are the same as those of the compounds described above.

< Example  1 > Using the compound of the present invention OLED Production

First, a transparent electrode ITO thin film 2 obtained from an OLED glass (manufactured by Samsung Corning) (1) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol Respectively.

Next, an ITO substrate was placed in a substrate folder of a vacuum deposition equipment, and N, N'-bis (α-naphthyl) -N, N'-diphenyl- (N, N'-bis (? -Naphthyl) -N, N'-diphenyl-4,4'-diamine: NPB) was added to the reactor and the reactor was evacuated until the degree of vacuum in the chamber reached 10 -6 torr. Thereafter, a current was applied to the cell to evaporate NPB to deposit a hole injection layer 3 having a thickness of 200 A on the ITO substrate.

Then, 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (4,4' 2-TNATA was evaporated by applying current to the cell to deposit a hole transport layer 4 having a thickness of 600 Å on the hole injection layer.

A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. A compound according to the present invention (for example, Compound 235) was put into one cell in a vacuum vapor deposition apparatus as a light emitting material. Dopant 1 having the following structure was doped into another cell, and then the two cells were heated together to deposit the dopant 1 at a deposition rate of 5 wt%, thereby forming a 400 Å (host: dopant = 95: 5 weight ratio) thickness on the hole transport layer Emitting layer 5 was deposited.

<Compound 235>

<Dopant 1>

Subsequently, tris (8-hydroxyquinoline) aluminum (III) (tris (8-hydroxyquinoline) aluminum (III): Alq3) having the following structure was vapor-deposited as the electron transport layer 6 to a thickness of 200 Å. Then, lithium fluoride (LiF) having the following structure was deposited as the electron injecting layer 7 to a thickness of 10 Å, and then an Al cathode 8 was deposited to a thickness of 1,000 Å to prepare an OLED.

All the organic compounds required for OLED fabrication were vacuum sublimated and purified at 10-6 to 10-8 torr for each material, and used for OLED fabrication.

< Example  &Lt; 2 &gt; OLED  Device fabrication

A hole injection layer and a hole transport layer were formed in the same manner as in Example 1, and Compound 235 according to the present invention was added as a light emitting material to one cell in the vacuum vapor deposition equipment, and dopant 2 having the following structure was added to another cell Then, the two materials were evaporated at different rates and doped with 5 wt% based on the host, thereby depositing a 400Å thick light emitting layer on the hole transport layer.

<Dopant 2>

&Lt; Examples 3 to 290 > Production of OLED device using the compound of the present invention

An OLED was prepared in the same manner as in Example 1 except that the host and the dopant described in Table 2 were used.

< Comparative Example  1 to 4> Using conventional organic luminescent compounds OLED Production

A hole injecting layer 3 and a hole transporting layer 4 were formed in the same manner as in Example 1 above. Thereafter, two isomers of dinaphthylthracene (ADN) (Comparative Compounds 1 and 2) were used as light emitting host materials in the other cells in the vacuum vapor deposition equipment, dopants 1 as in Example 1 were placed in another cell, A light emitting layer 5 with a thickness of 30 nm was deposited on the hole transporting layer.

&Lt; Comparative Compound 1 > < Comparative Compound 2 >

Subsequently, an electron transport layer 6 and an electron injection layer 7 were deposited in the same manner as in Example 1, and then an Al cathode 8 was vapor-deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to produce an OLED .

< Experimental Example > OLED Characterization of

The efficiency and characteristics of the OLED were evaluated and are shown in Table 2 below. The time until the efficiency drops to cd / A and the lifetime drops to 50% is shown in Table 2 below.

Referring to Table 2, it can be seen that the device manufactured using the compound of the present invention is superior in efficiency, lifetime and thermal stability as compared with the comparative example.

Claims (11)

A compound represented by the following formula (1):

In Formula 1,
R ₁ to R ₆ are the same or different from each other and each independently hydrogen; A halogen atom; Adamantyl; Nitro; Hydroxy; Cyano; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Substituted or unsubstituted (C ₅ -C ₆₀₎ heteroaryl; 5 or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si; Substituted or unsubstituted (C ₃ -C ₆₀ ) cycloalkyl; A substituted or unsubstituted tree (C ₁ -C ₆₀₎ alkylsilyl; A substituted or unsubstituted di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl; A substituted or unsubstituted tree (C ₆ -C ₆₀₎ arylsilyl; Substituted or unsubstituted (C ₇ -C ₆₀₎ bicycloalkyl-alkyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkenyl; Substituted or unsubstituted (C ₂ -C ₆₀₎ alkynyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkoxy; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkylamino; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylamino; Substituted or unsubstituted (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryloxy; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylthio; A substituted or unsubstituted (C ₁ -C ₆₀₎ alkylthio; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkoxycarbonyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylcarbonyl; Or (C ₆ -C ₆₀₎ aryl-carbonyl,
Wherein R ₁ to R ₆ are bonded to adjacent groups to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, or a substituted or unsubstituted (C ₂ -C ₆₀ ) alkylene or (C ₂ -C ₆₀ ) alkenylene To form an aliphatic ring, an aromatic ring, a heteroaromatic ring,
Ar ₁ is a substituted or unsubstituted (C ₆ -C ₆₀ ) aromatic compound or fused ring aromatic compound having 1 to 5 rings,
A is adamantyl; Nitro; Hydroxy; Cyano; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Substituted or unsubstituted (C ₂ -C ₆₀ ) heteroaryl; 5 or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si; Substituted or unsubstituted (C ₃ -C ₆₀ ) cycloalkyl; A substituted or unsubstituted tree (C ₁ -C ₆₀₎ alkylsilyl; A substituted or unsubstituted di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl; A substituted or unsubstituted tree (C ₆ -C ₆₀₎ arylsilyl; Substituted or unsubstituted (C ₇ -C ₆₀₎ bicycloalkyl-alkyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkenyl; Substituted or unsubstituted (C ₂ -C ₆₀ ) alkynyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkoxy; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkylamino; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylamino; Substituted or unsubstituted (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryloxy; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylthio; A substituted or unsubstituted (C ₁ -C ₆₀₎ alkylthio; Substituted or unsubstituted (C ₁ -C ₆₀ ) alkoxycarbonyl; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylcarbonyl; (C ₆ -C ₆₀ ) arylcarbonyl; or

However,
Ar ₃ is substituted or unsubstituted (C ₁ -C ₆₀ ) alkyleneoxy; Substituted or unsubstituted (C ₁ -C ₆₀₎ alkylene-thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryleneoxy; (C ₆ -C ₆₀ ) arylene thio; Substituted or unsubstituted (C ₆ -C ₆₀ ) arylene; Or (C ₃ -C ₆₀₎ and heteroarylene,
R ₇ is the same as the description of R ₁ to R ₆ ,
n is 1,
X is _{-O-, -Si (-R 21) (} - R 22) -, -N (-R 21) - or _{-C (-R 21) (- R} 22) - a,
Wherein R ₂₁ and R ₂₂ are each independently selected from the group consisting of hydrogen; Straight or branched (C ₁ -C ₆₀₎ alkyl; (C ₆ -C ₆₀ ) aryl, unsubstituted or substituted with methoxy; (C ₆ -C ₆₀ ) heteroaryl substituted or unsubstituted with a phenyl group; (C ₆ -C ₆₀ ) alkoxyaryl; (C ₁ -C ₆₀₎ alkylthio (C ₆ -C ₆₀₎ aryl; Amino (C ₆ -C ₆₀ ) aryl; Or (C ₁ -C ₆₀₎ alkyl silyl (C ₆ -C ₆₀₎ aryl,
Wherein R ₁ to R _6, Ar _1, A, and Ar ₃ is substituted at the same or different and independently selected from, halogen, (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ each aryl, (C ₂ - C ₆₀₎ heteroaryl, N, O, 5-or 6-membered heterocycloalkyl of, containing one or two or more selected from S and Si (C ₃ -C ₆₀₎ cycloalkyl, tri (C ₁ -C ₆₀₎ alkylsilyl, di (C ₁ -C ₆₀₎ alkyl (C ₆ -C ₆₀₎ arylsilyl, tri (C ₆ -C ₆₀₎ arylsilyl, adamantyl, (C ₇ -C ₆₀₎ alkyl, bicycloalkyl, (C ₂ -C ₆₀₎ alkenyl, (C ₂ -C ₆₀₎ alkynyl, (C ₁ -C ₆₀₎ alkoxy, cyano, (C ₁ -C ₆₀₎ alkylamino, (C ₆ -C ₆₀₎ aryl amino, (C ₆ -C ₆₀₎ aralkyl (C ₁ -C ₆₀₎ alkyl, (C ₆ -C ₆₀₎ aryloxy, (C ₁ -C ₆₀₎ alkylthio, (C ₆ -C ₆₀₎ arylthio, ( C ₁ -C ₆₀₎ alkoxycarbonyl, (C ₁ -C ₆₀₎ alkylcarbonyl, (C ₆ -C ₆₀₎ arylcarbonyl, carboxylic acid, substituted or unsubstituted nitro, methyl by hydroxy or trifluoromethyl . The compound according to claim 1, wherein the compound represented by Formula 1 is a compound represented by Formula 1A:

In the above formula (1A)
A is substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Or substituted or unsubstituted (C ₂ -C ₆₀ ) heteroaryl,
R ₁ is hydrogen; Substituted or unsubstituted (C ₆ -C ₆₀ ) aryl; Or substituted or unsubstituted (C ₅ -C ₆₀₎ heteroaryl,
R ₂ to R ₆ are hydrogen,
n is 1,
X is -N (-R ₂₁ ) - or -C (-R ₂₁ ) (-R ₂₂ ) -,
R ₂₁ and R ₂₂ are each independently a straight or branched (C ₁ -C ₆₀ ) alkyl; (C ₆ -C ₆₀ ) aryl, unsubstituted or substituted with methoxy; Or a heteroaryl group unsubstituted or substituted with a phenyl group (C ₆ -C _60),
The adjacent groups of R ₁₇ to R ₂₀ are bonded to each other to form one or more aromatic or aliphatic rings. The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the group consisting of compounds represented by Chemical Formulas 3, 4, 6, 7, 9, 10, 12, Wherein said compound:
&Lt; Formula 3 >< Formula 4 >

&Lt; Formula 6 >< EMI ID =

&Lt; Formula 9 &gt;&lt; EMI ID =

&Lt; Formula 12 >< EMI ID =

In Formula 3, Formula 4, Formula 6, Formula 7, Formula 9, Formula 10, Formula 12 and Formula 13,
A, R ₁ to R ₆ are the same as defined in the formula (1)
R ₉ to R ₁₆ are each independently the same as those of R ₁ to R ₆ ,
R ₂₁ and R ₂₂ are each independently hydrogen; Straight or branched (C ₁ -C ₆₀ ) alkyl; (C ₆ -C ₆₀ ) aryl, unsubstituted or substituted with methoxy; (C ₆ -C ₆₀ ) heteroaryl substituted or unsubstituted with a phenyl group; (C ₆ -C ₆₀ ) alkoxyaryl; (C ₁ ~ C ₆₀₎ alkylthio (C ₆ -C ₆₀₎ aryl; Amino (C ₆ -C ₆₀ ) aryl; Or (C ₁ ~ C ₆₀₎ alkyl silyl (C ₆ -C ₆₀₎ aryl. The compound according to claim 1, wherein the compound represented by the formula (1) is any one of compounds represented by the following structural formulas:

A first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode, the organic layer including a compound represented by the general formula (1). The organic electroluminescent device according to claim 5, wherein the organic layer is one or more selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. The organic electroluminescent device according to claim 5, wherein the organic layer is one or more selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer. delete The organic electroluminescent device according to claim 5, wherein the organic layer further comprises one selected from the group consisting of an arylamine compound, a styrylarylamine compound, and a mixture thereof. 10. The organic electroluminescent device according to any one of claims 5 to 7 and 9, wherein the organic film is formed from a group consisting of organic metals of group 1, group 2, group 4, group 5 transition metal, lanthanide series and d- Wherein the organic electroluminescent device further comprises at least one selected from the group consisting of the organic electroluminescent device and the organic electroluminescent device. A first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a compound represented by the general formula (1).