KR101538502B1 - Organic light compound and organic light device using the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound and an organic light emitting device using the same. More particularly, the present invention relates to an organic light emitting device capable of realizing excellent light emitting efficiency, light emission luminance, And an optical compound used therefor. In particular, 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2-a] (ETM), a light emitting layer (EML), a hole transport layer (HTM), and a hole injection layer (HIL) between the first and second electrodes. And can maximize the capability as an OLED material.

Description

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

The present invention relates to an organic light emitting compound and an organic light emitting device using the same, and more particularly, to a novel organic light emitting compound useful as a blue light emitting material and an organic light emitting device containing the same.

An electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

In an organic EL device, a luminescent material is the most important factor for determining performance such as luminous efficiency and lifetime. Some characteristics required for such a light emitting material are that the fluorescent quantum yield should be high in a solid state, the electron and hole mobility must be high, the organic compound should not be easily decomposed during vacuum deposition, a uniform thin film should be formed, Should be.

Organic light emitting materials can be roughly divided into polymer materials and low molecular materials. Low-molecular-based materials have pure organic light-emitting materials that do not contain metal complexes and metals in terms of molecular structure. As such a luminescent material, there are known luminescent materials such as a chelate complexing agent such as tris (8-hydroxyquinolate aluminum (Alq3)), coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives. It has been reported that visible light emission from blue to red can be obtained, and realization of a color display device is expected.

On the other hand, since blue material has been developed and commercialized since DPVBi of Idemitsu-Gosan, a blue material system of Idemitsu-Gosan, a dinaphthylanthracene, a tetra (t-butyl) perylene tetra (t-butyl) perlyene) system. In addition, it has been reported that the phenanthrene-3,6-diamine derivative has better luminous efficiency and device life than the conventional dopant material, and has an appropriate color coordinate [Korean Patent Publication No. 2011-0121147]. However, much research and development is still required.

The distill compound system of Idemitsu-Gosan, which is known to be the most efficient to date, has a power efficiency of 6 lm / W and a device lifetime of 30,000 hours or more. However, When applied to a full color display, it only lasts a few thousand hours. 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 purple light color and is not easy to apply to a high quality display, and there is a problem in color purity, efficiency and thermal stability, Urgent.

The first technical problem to be solved by the present invention is to provide a novel 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2-a] Based organic light-emitting compound.

A second object of the present invention is to provide an organic electroluminescent compound containing 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2-a] And to provide an organic light emitting device having improved lifetime.

In order to solve the above problems, the present invention is characterized by the 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2-a] acridine organic electroluminescent compound represented by the following formula .

[Chemical Formula F]

In formula (F) above,

R ¹ is selected from the group consisting of a C ₅ -C ₄₀ aryl group, a C ₅ -C ₄₀ heteroaryl group, a C ₃ -C ₄₀ cycloalkyl group, and a C ₃ -C ₄₀ heterocycloalkyl group;

R ² is a hydrogen atom, a deuterium atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C _{3 to} C ₄₀ heterocycloalkyl group ≪ / RTI >

로 이루어진 군으로부터 선택되고;R ³ is a C ₅ -C ₄₀ aryl group, or

≪ / RTI >

R ³¹ and R ³² each independently represent a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C _{3 to} C ₄₀ Or R ³¹ and R ³² are taken together with the nitrogen atom to which they are attached to form a C ₅ -C ₄₀ heteroaryl group or a C ₃ -C ₄₀ heterocycloalkyl group, , Or one of R ³¹ and R ³² may form a condensed C ₅ -C ₄₀ heteroaryl group or a condensed C ₃ -C ₄₀ heterocycloalkyl group by bonding to adjacent adjacent substituents;

X is selected from the group consisting of O, S, Se, NY ¹ , CY ² Y ³ , CY ² Y ³ -CY ² Y ³ , CY ² = CY ³ , and SiY ² Y ³ ;

Y ¹ , Y ² and Y ³ are each independently a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and C _{C 3 to C 40} heterocycloalkyl groups, or Y ² and Y ³ may be bonded to each other to form a C ₅ to C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C ₃ -C ₄₀ heterocycloalkyl group;

The heteroaryl or heterocycloalkyl used in the definition of the substituents R ¹ , R ² , R ³¹ , R ³² , Y ¹ , Y ² , and Y ³ is a heteroaryl or heterocycloalkyl group having a heteroatom selected from O, S, N, To 4,

The aryl, cycloalkyl, heteroaryl, or heterocycloalkyl used in the definition of the substituents R ¹ , R ² , R ³¹ , R ³² , Y ¹ , Y ² , and Y ³ is each monocyclic, Wherein said single or multiple rings are selected from the group consisting of deuterium (D), halo, hydroxy, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₁ -C ₄₀ haloalkyl, C ₁ ~C ₄₀ hydroxyalkyl, C ₁ ~C ₄₀ alkoxy, amino, C ₁ ~C ₄₀ alkylamino, di (C ₁ ~C ₄₀ alkyl) amino, C ₅ ~C ₄₀ alkylamino, di (C ₅ ~ C ₄₀ aryl) amino, mono (C ₁ ~C ₄₀ alkyl) silyl, di (C ₁ ~C ₄₀ alkyl) silyl, tri (C ₁ ~C ₄₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C ₄₀ aryl) silyl, tri (C ₅ ~C ₄₀ aryl) silyl, C ₅ ~C ₄₀ aryl, C ₅ ~C ₄₀ heteroaryl, C ₃ ~C ₄₀ cycloalkyl, and C ₃ ~C ₄₀ heterocycloalkyl, < / RTI >< RTI ID = 0.0 > Or unsubstituted ring may be, also from among the aryl substituent, is deuterium (D), halo, hydroxy, cyano, nitro, C ₁ ~C ₄₀ alkyl, C ₁ ~C ₄₀ haloalkyl, C ₁ ~C ₄₀ hydroxyalkyl, C ₁ ~C ₄₀ alkoxy, amino, C ₁ ~C ₄₀ alkylamino, di (C ₁ ~C ₄₀ alkyl) amino, C ₅ ~C ₄₀ alkylamino, di (C ₅ ~C ₄₀ aryl) amino , mono (C ₁ ~C ₄₀ alkyl) silyl, di (C ₁ ~C ₄₀ alkyl) silyl, tri (C ₁ ~C ₄₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~ C ₄₀ aryl) silyl, tri (C ₅ ~C ₄₀ aryl) silyl, to C ₅ ~C ₄₀ aryl, C ₅ ~C ₄₀ heteroaryl, C ₃ ~C ₄₀ cycloalkyl, and C ₃ ~C ₄₀ heterocycloalkyl Lt; / RTI > may be substituted or unsubstituted with a substituent selected from the group consisting of

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises at least one of 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2-a] acridine-based organic light-emitting compound.

The organic light emitting device including the organic light emitting compound according to the present invention can realize high light emitting efficiency, high light emitting luminance, and remarkably improved light emitting life.

Accordingly, the present invention provides a novel organic light emitting compound and an organic light emitting device comprising the compound.

Hereinafter, the present invention will be described in more detail.

While the present invention has been described in connection with what is presently considered to be the most practical and preferred embodiment, it is to be understood that the invention is not limited to the disclosed embodiments. It is to be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but on the contrary, is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In this application, the terms " comprises, " or " comprising " and the like are used to specify that a feature, a number, a step, an operation, an element, a part, But do not preclude the presence or addition of one or more other features, numbers, steps, operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.

The present invention relates to an organic electroluminescent compound, especially 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2-a] (EML), a hole transport layer (HTM), a hole injection layer (HIL), and the like, and to improve performance such as light emission luminance and luminous efficiency, We want to develop materials that maximize their abilities.

In the present specification, the organic luminescent compound means a compound used in an organic photonic device, and is not necessarily limited in its range of application, and its application range is not limited to the organic luminescent layer but may be an organic luminescent layer such as a charge injection layer and a charge transport layer Can be used for any layer constituting the substrate.

In this specification, the terms 'light emitting compound' and 'light emitting device' are used to cover the case where the present invention is applied to both an organic light emitting device and a device for solar power generation regardless of a dictionary or customary definition It is a selected term.

An organic photonic device according to a first aspect of the present invention includes: a first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode, wherein the organic film includes an organic light emitting compound represented by the following formula (F).

[Chemical Formula F]

In formula (F) above,

R ¹ is selected from the group consisting of a C ₅ -C ₄₀ aryl group, a C ₅ -C ₄₀ heteroaryl group, a C ₃ -C ₄₀ cycloalkyl group, and a C ₃ -C ₄₀ heterocycloalkyl group;

R ² is a hydrogen atom, a deuterium atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C _{3 to} C ₄₀ heterocycloalkyl group ≪ / RTI >

로 이루어진 군으로부터 선택되고;R ³ is a C ₅ -C ₄₀ aryl group, or

≪ / RTI >

R ³¹ and R ³² each independently represent a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C _{3 to} C ₄₀ Or R ³¹ and R ³² are taken together with the nitrogen atom to which they are attached to form a C ₅ -C ₄₀ heteroaryl group or a C ₃ -C ₄₀ heterocycloalkyl group, , Or one of R ³¹ and R ³² may form a condensed C ₅ -C ₄₀ heteroaryl group or a condensed C ₃ -C ₄₀ heterocycloalkyl group by bonding to adjacent adjacent substituents;

X is selected from the group consisting of O, S, Se, NY ¹ , CY ² Y ³ , CY ² Y ³ -CY ² Y ³ , CY ² = CY ³ , and SiY ² Y ³ ;

Y ¹ , Y ² and Y ³ are each independently a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and C _{C 3 to C 40} heterocycloalkyl groups, or Y ² and Y ³ may be bonded to each other to form a C ₅ to C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C ₃ -C ₄₀ heterocycloalkyl group;

The heteroaryl or heterocycloalkyl used in the definition of the substituents R ¹ , R ² , R ³¹ , R ³² , Y ¹ , Y ² , and Y ³ is a heteroaryl or heterocycloalkyl group having a heteroatom selected from O, S, N, To 4,

The aryl, cycloalkyl, heteroaryl, or heterocycloalkyl used in the definition of the substituents R ¹ , R ² , R ³¹ , R ³² , Y ¹ , Y ² , and Y ³ is each monocyclic, Wherein said single or multiple rings are selected from the group consisting of deuterium (D), halo, hydroxy, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₁ -C ₄₀ haloalkyl, C ₁ ~C ₄₀ hydroxyalkyl, C ₁ ~C ₄₀ alkoxy, amino, C ₁ ~C ₄₀ alkylamino, di (C ₁ ~C ₄₀ alkyl) amino, C ₅ ~C ₄₀ alkylamino, di (C ₅ ~ C ₄₀ aryl) amino, mono (C ₁ ~C ₄₀ alkyl) silyl, di (C ₁ ~C ₄₀ alkyl) silyl, tri (C ₁ ~C ₄₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C ₄₀ aryl) silyl, tri (C ₅ ~C ₄₀ aryl) silyl, C ₅ ~C ₄₀ aryl, C ₅ ~C ₄₀ heteroaryl, C ₃ ~C ₄₀ cycloalkyl, and C ₃ ~C ₄₀ heterocycloalkyl, < / RTI >< RTI ID = 0.0 > Or unsubstituted ring may be, also from among the aryl substituent, is deuterium (D), halo, hydroxy, cyano, nitro, C ₁ ~C ₄₀ alkyl, C ₁ ~C ₄₀ haloalkyl, C ₁ ~C ₄₀ hydroxyalkyl, C ₁ ~C ₄₀ alkoxy, amino, C ₁ ~C ₄₀ alkylamino, di (C ₁ ~C ₄₀ alkyl) amino, C ₅ ~C ₄₀ alkylamino, di (C ₅ ~C ₄₀ aryl) amino , mono (C ₁ ~C ₄₀ alkyl) silyl, di (C ₁ ~C ₄₀ alkyl) silyl, tri (C ₁ ~C ₄₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~ C ₄₀ aryl) silyl, tri (C ₅ ~C ₄₀ aryl) silyl, to C ₅ ~C ₄₀ aryl, C ₅ ~C ₄₀ heteroaryl, C ₃ ~C ₄₀ cycloalkyl, and C ₃ ~C ₄₀ heterocycloalkyl Lt; / RTI > may be substituted or unsubstituted with a substituent selected from the group consisting of

In addition, in the present invention, it has been found that a derivative having specific and various changes of R ¹ , R ² , R ³ and X as a substituent of the organic light emitting compound represented by the above Formula F is developed to form an electron transport layer (ETM) An organic light emitting compound that can be used as various organic layers between the first electrode and the second electrode, such as a hole transporting layer (HTM), and an organic light emitting device using the organic light emitting compound are developed. When the organic light emitting device is used as an organic light emitting device, And maximizing the ability as an OLED material. In particular, it has been found that the luminescence lifetime is remarkably improved. When applied to optical devices and optical compound fields for photovoltaic power generation, excellent power generation efficiency can be obtained .

Hereinafter, the organic electroluminescent compound represented by Formula F will be described with reference to the organic electroluminescent device, but the present invention should not be construed as being limited thereto.

The organic luminescent compound represented by Formula F is suitable as a material for forming an organic film interposed between the first electrode and the second electrode in the organic optical device. The organic light emitting compound represented by Formula F is suitable for use in an organic layer of an organic light emitting device, particularly, a hole transporting layer, a hole injecting layer, an electron transporting layer, or a light emitting layer, and is used as a dopant material as well as a host material. The organic electroluminescent compound represented by Formula F provides blue hue and is suitable for use in light emitting devices such as white.

The substituent of the organic luminescent compound represented by the formula (F) is specifically described below.

R ¹ is preferably a phenyl group, a naphthalenyl group, an indenyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group, a benzofluorenyl group, a pyrenyl group, a thienyl group, a furyl group, a pyrrolyl group, A thiazolyl group, an isothiazolyl group, an isoxazolyl group, an indolyl group, an indazolyl group, a carbazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, hexahydro pen fringing group, a piperidinyl group, a page p is selected from the group possess, and mole Poly group the group consisting of, each of deuterium (D), halo, hydroxy, cyano, nitro, C ₁ ~C ₁₀ alkyl, C ₁ ~C ₁₀ haloalkyl, C ₁ ~C ₁₀ hydroxyalkyl, C ₁ ~C ₁₀ alkoxy, amino, C ₁ ~C ₁₀ alkylamino, di (C ₁ ~C ₁₀ alkyl) amino, C ₅ ~C ₁₀ arylamino, di (C ₅ ~C ₁₀ aryl) amino, mono (C ₁ ~C ₁₀ alkyl) silyl, di (C ₁ ~C ₁₀ alkyl) silyl, tri (C ₁ ~C ₁₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C ₄₀ aryl) silyl, tri (C ₅ ~C ₄₀ aryl) silyl, C ₅ ~C ₁₀ aryl, C ₅ ~C ₁₀ C ₁ -C ₁₀ cycloalkyl, and C ₃ -C ₁₀ heterocycloalkyl may be substituted or unsubstituted. The term " heteroaryl "

R < ^{1 >} is more preferably

And X ₁ is selected from the group consisting of NY ¹¹ and CY ¹² Y ¹³ , wherein Y ¹¹ , Y ¹² , and Y ¹³ are each independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a n-propyl group , An isopropyl group, an n-butyl group, a tert-butyl group, a hexyl group, and a phenyl group; Wherein R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are each independently a hydrogen atom or a group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, methyl, ethyl, Butyl, tert-butyl, hexyl, trifluoromethyl, dichloroethyl, difluoroethyl, tetrafluoroethyl, methoxy, ethoxy, tert-butoxy, methylsilyl, dimethylsilyl, trimethylsilyl, phenyl, - naphthalenyl, and 2-naphthalenyl.

The R ² is preferably a hydrogen atom, or represents 1 to 4 substituents selected from the group consisting of a deuterium atom, or a C _{1 to} C ₁₀ alkyl group.

The R < ³ > is preferably

An aryl group selected from the group consisting of, wherein R ^a and R ^b each independently is hydrogen, or deuterium (D), halo, hydroxy, cyano, nitro, C ₁ ~C ₁₀ alkyl, mono (C ₅ ~C ₁₀ aryl) alkyl, di (C ₅ ~C ₁₀ aryl) alkyl, tri (C ₅ ~C ₁₀ aryl) alkyl, C ₁ ~C ₁₀ haloalkyl, C ₁ ~C ₁₀ hydroxyalkyl, C ₁ ~C ₁₀ alkoxy, amino, C ₁ ~C ₁₀ alkylamino, di (C ₁ ~C ₁₀ alkyl) amino, C ₅ ~C ₁₀ alkylamino, di (C ₅ ~C ₁₀ aryl) amino, mono (C ₁ ~C ₁₀ alkyl) silyl, di (C ₁ ~C ₁₀ alkyl) silyl, tri (C ₁ ~C ₁₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C ₄₀ aryl) silyl, tri ( C ₅ ~C ₄₀ aryl) silyl, C ₅ ~C ₁₀ aryl, C ₅ ~C ₁₀ heteroaryl, C ₃ ~C ₁₀ cycloalkyl, and from 1 to selected from the group consisting of C ₃ ~C ₁₀ heterocycloalkyl 10 Lt; / RTI >

R < ³ > is more preferably

Wherein R ^a and R ^b are each independently a hydrogen atom or an aryl group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, methyl, ethyl, Butyl, tert-butyl, hexyl, triphenylmethyl, trifluoromethyl, dichloroethyl, difluoroethyl, tetrafluoroethyl, methoxy, ethoxy, tert-butoxy, methylsilyl, dimethylsilyl, Naphthalen-1-yl-phenyl, and naphthalen-2-yl-phenyl.

Also, R ³ is preferably -NR ³¹ R ^32, wherein R ³¹ and R ³² are each independently a hydrogen atom, a C _{1 to} C ₁₀ alkyl group,

≪ / RTI > Wherein X ₂ is selected from the group consisting of O, S, and NY ²¹ Y ²² CY ^23, wherein Y ^21, Y ^22, and Y ²³ each independently represent a hydrogen atom, C ₁ ~C ₁₀ alkyl group, and a C ₅ ~ selected from the group consisting of a C ₁₀ aryl, and; Wherein R ^a and R ^b are each independently a hydrogen atom or a group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, nitro, C ₁ -C ₁₀ alkyl, mono (C ₅ -C ₁₀ aryl) C ₅ ~C ₁₀ aryl) alkyl, tri (C ₅ ~C ₁₀ aryl) alkyl, C ₃ ~C ₁₀ cycloalkyl, C ₃ ~C ₁₀ heterocycloalkyl, C ₁ ~C ₁₀ haloalkyl, C ₁ ~C ₁₀ hydroxyalkyl, C ₁ ~C ₁₀ alkoxy, amino, C ₁ ~C ₁₀ alkylamino, di (C ₁ ~C ₁₀ alkyl) amino, C ₅ ~C ₁₀ alkylamino, di (C ₅ ~C ₁₀ aryl) amino , mono (C ₁ ~C ₁₀ alkyl) silyl, di (C ₁ ~C ₁₀ alkyl) silyl, tri (C ₁ ~C ₁₀ alkyl) silyl group, a mono (C ₅ ~C ₁₀ aryl) silyl, di (C ₅ ~ C ₁₀ aryl) silyl, tri (C ₅ ~C ₁₀ aryl) silyl, C ₅ ~C ₁₀ aryl, and C ₅ ~C ₁₀ is one to four substituents selected from the heteroaryl group consisting of a number of days.

R ³ is more preferably -NR ³¹ R ^32, wherein R ³¹ and R ³² are each independently

(이때, X_a는 O, S, 또는 C(CH₃)₂임)로 이루어진 군으로부터 선택된 1 내지 3개의 치환체일 수 있다.≪ / RTI > Wherein X ₂ is selected from the group consisting of O, S, NY ²¹ and CY ²² Y ²³ , wherein Y ²¹ , Y ²² , and Y ²³ each independently represent a hydrogen atom, a methyl group, an ethyl group, An n-butyl group, a tert-butyl group, a hexyl group, and a phenyl group; Wherein R ^a and R ^b are each independently a hydrogen atom or a group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, Phenyl, 1-naphthyl, 1-naphthyl, 1-naphthyl, 1-naphthyl, 1-naphthyl, 1-naphthyl 2-naphthalenyl, naphthalen-1-yl-phenyl, naphthalen-2-yl-phenyl, and

(Wherein X _a is O, S, or C (CH ₃ ) ₂ ).

The R ³ is preferably -NR ³¹ R ^32, wherein R ³¹ and R ³² , together with the nitrogen atom to which they are bonded,

To form a condensed ring selected from the group consisting of: Wherein X ₃ is O, S, Se, oxo ^{(= O), NY 31,} CY 32 Y 33, CY 32 Y 33 -CY 32 Y 33, CY 32 = CY 33 and is selected from the group consisting of ³² Y ³³ SiY , Wherein Y ³¹ , Y ³² and Y ³³ each independently represent a hydrogen atom, a C _{1 to} C ₁₀ alkyl group, a C _{5 to} C ₁₀ aryl group, a C _{5 to} C ₁₀ heteroaryl group, a C _{3 to} C ₁₀ cycloalkyl group, And C _{3 to} C ₁₀ heterocycloalkyl groups, or Y ³² and Y ³³ may be bonded to each other to form a C ₅ -C ₁₀ aryl group, a C ₅ -C ₁₀ heteroaryl group, C ₃ ~C ₁₀ cycloalkyl group, to form a C ₃ ~C ₁₀ heterocycloalkyl group; Wherein R ^a and R ^b are each independently a hydrogen atom or a group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, nitro, C ₁ -C ₁₀ alkyl, mono (C ₅ -C ₁₀ aryl) C ₅ ~C ₁₀ aryl) alkyl, tri (C ₅ ~C ₁₀ aryl) alkyl, C ₁ ~C ₁₀ haloalkyl, C ₁ ~C ₁₀ hydroxyalkyl, C ₁ ~C ₁₀ alkoxy, amino, C ₁ ~C ₁₀ alkylamino, di (C ₁ ~C ₁₀ alkyl) amino, C ₅ ~C ₁₀ alkylamino, di (C ₅ ~C ₁₀ aryl) amino, mono (C ₁ ~C ₁₀ alkyl) silyl, di (C ₁ ~ C ₁₀ alkyl) silyl, tri (C ₁ ~C ₁₀ alkyl) silyl group, a C ₅ ~C ₁₀ aryl, C ₅ ~C ₁₀ heteroaryl, C ₃ ~C ₁₀ cycloalkyl, and C ₃ ~C ₁₀ heterocycloalkyl Lt; RTI ID = 0.0 > 1 < / RTI > to 4 substituents selected from the group consisting of

The R ³ is more preferably -NR ³¹ R ^32, wherein R ³¹ and R ³² , together with the nitrogen atom to which they are bonded,

To form a condensed ring selected from the group consisting of: Wherein X ₃ is selected from the group consisting of O, S, oxo (═O), NY ³¹ , and CY ³² Y ^{33 wherein} Y ³¹ , Y ³² , and Y ³³ each independently represent a hydrogen atom, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a hexyl group, and a phenyl group; Wherein R ^a and R ^b are each independently a hydrogen atom or a group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, And examples thereof include fluoromethyl, dichloroethyl, difluoroethyl, tetrafluoroethyl, methoxy, ethoxy, tert-butoxy, methylsilyl, dimethylsilyl, trimethylsilyl, phenyl, 1-naphthalenyl, Lt; RTI ID = 0.0 >

More specifically, according to one embodiment of the present invention, the organic light emitting compound used in the organic light emitting device of the present invention is 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2- (1) to (204) as shown in the following [Table 1], but the present invention is not limited thereto.

[First group (group)]

The organic electroluminescent compound represented by Formula F according to the present invention can be synthesized using a conventional synthetic method, and a more detailed synthesis route of the compound can be described in Representative Synthesis Examples 1 and 2 below. The organic electroluminescent compound represented by Formula F is suitable for use in an organic layer of an organic photonic device, particularly a hole transport layer, a hole injection layer, an electron transport layer, or a light emitting layer. The structure of the organic light emitting device according to the present invention is very diverse. The organic EL device may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron blocking layer, an electron transporting layer, and an electron injecting layer between the first electrode and the second electrode.

More specifically, the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device comprises: a first electrode; A second electrode; And at least one organic compound layer interposed between the first electrode and the second electrode, wherein the organic compound layer comprises at least one organic electroluminescent compound selected from Formula (F).

The organic electroluminescent device according to the present invention comprises the organic compound layer as a light emitting layer, and the light emitting layer comprises at least one phosphorescent dopant as at least one organic electroluminescent compound selected from Formula F, It is not limited.

The organic electroluminescent device of the present invention may further comprise at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound, have.

In addition, in the organic light emitting device of the present invention, in addition to at least one organic electroluminescent compound selected from the above-described formula (F), at least one organic metal compound selected from group 1, group 2, group 4, group 5 transition metal, lanthanide series and d- , And the organic material layer may include a light emitting layer and a charge generating layer.

In addition, an organic electroluminescent device emitting white light by simultaneously including at least one common organic light emitting layer emitting blue, red or green light in addition to the organic light emitting compound may be formed in the organic material layer.

More specifically, in an embodiment of the organic light emitting device according to the present invention, the organic light emitting device may have a structure including a first electrode / a hole injection layer / a light emitting layer / an electron transport layer / an electron injection layer / The organic light emitting device may have a structure including a first electrode / a hole injection layer / a hole transporting layer / a light emitting layer / an electron transporting layer / an electron injecting layer / a second electrode. Further, the organic light emitting device may include a first electrode / a hole injecting layer / / Light emitting layer / hole blocking layer / electron transporting layer / electron injecting layer / second electrode.

At this time, one or more of the electron transporting layer, the light emitting layer, the hole injecting layer, or the hole transporting layer may include an organic light emitting compound according to the present invention.

The light emitting layer of the organic light emitting device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white. The phosphorescent dopant may be an organometallic compound containing at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm. In addition, the compound according to the present invention can also be used as a fluorescent dopant in the light emitting layer.

Hereinafter, a method of manufacturing an organic light emitting device according to the present invention will be described in detail. 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. Here, the substrate used in a typical organic optical 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 material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) or the like which is transparent and excellent in conductivity is used.

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 < ^-5 > to 10 < ^-3 > torr, a deposition rate of 0.01 to 100 ANGSTROM / sec, and a film thickness of 100 ANGSTROM to 1 mu m.

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

The hole injection layer material may be an organic light emitting compound represented by Formula F as described above.

Or a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or TCTA, m-MTDATA, m-MTDAPB, which are starburst type amine induction residues described in Advanced Material, 6, p.677 , 4,4 ', 4 "-tris (N- (naphthyl) -N-phenylamino) triphenylamine (2-TNATA), soluble electroconductive polymer polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA) or (PANI / PSS), polyaniline / camphorsulfonic acid (PANI / CSA) or polyaniline / poly (4-styrenesulfonate) (PANI / PSS) And the like can be used.

The thickness of the hole injection layer may be about 100 A to about 10000 A, and preferably about 100 A to about 1000 A. When the thickness of the hole injection layer is less than 100 ANGSTROM, hole injection characteristics may be degraded. If the thickness of the hole injection layer is more than 10000 ANGSTROM, the driving voltage may increase.

Alternatively, the hole injection layer may be formed by a vacuum vapor deposition method. The specific deposition conditions vary depending on the compound used, but are selected from substantially the same range of conditions as the formation of a general hole injection layer. For example, N, N-bis- [4- (di-methtolylamino) phenyl] -N, N-biphenyl-4,4-diamine (DNTPD) and the like can be used.

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 include an organic light emitting compound represented by Formula (F) as described above. Examples of known hole transporting materials include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'- 1-biphenyl] -4,4'-diamine (TPD), and N, N'-di Conventional amine derivatives and the like. The thickness of the hole transporting layer may be about 50 A to 1000 A, preferably 100 A to 600 A. When the thickness of the hole transporting layer is less than 50 ANGSTROM, the hole transporting property may be deteriorated. When the thickness of the HTL is more than 1000 ANGSTROM, the driving voltage may increase.

Next, a light emitting layer (EML) may be formed on the hole transporting layer by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. When a light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions vary depending on the compound used, but generally, the conditions are substantially the same as those for forming the hole injection layer.

The light emitting layer may include the compound represented by Formula F according to the present invention as described above. At this time, the compound represented by Formula F may be used together with a suitable known host material, or may be used together with a known dopant material, and the compound represented by Formula F may be used alone.

Examples of the host material usable in combination with the compound represented by the formula (F) include an asymmetric anthracene derivative represented by the following formula (i), an asymmetric monoanthracene derivative represented by the following formula (ii), an asymmetric pyrene derivative represented by the following formula An anthracene derivative represented by the following formula (v), an anthracene derivative represented by the following formula (vi), a spirofluorene derivative represented by the following formula (V), a condensed ring-containing compound represented by the following formula A compound having an anthracene center skeleton represented by the following general formula (x), or a compound having an anthracene center skeleton represented by the general formula (xi) wherein A ₁ and A ₂ in the general formula (x) are substituted with different groups, Lt; / RTI >

(I)

(Wherein Ar is a substituted or unsubstituted C ₁₀ to C ₅₀ condensed aryl group, Ar 'is a substituted or unsubstituted C ₆ to C ₅₀ aryl group, X is a substituted or unsubstituted C an aryl group of ₆ ~ C _50, substituted or unsubstituted nuclear atoms of 5 to 50 heteroaryl group, a substituted or unsubstituted C ₁ ~ C ₅₀ alkyl group, a substituted or unsubstituted C ₁ ~ C ₅₀ alkoxy group , A substituted or unsubstituted C ₆ to C ₅₀ aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear atoms, an arylthio group having 6 to 50 substituted or unsubstituted nuclear atoms, hwandoen c ₁ ~ c ₅₀ alkoxy carbonyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a; a, b and c are each independently an integer of 0 to 4; n Is an integer of 1 to 3, and when n is 2 or 3, the symbols in [] may be the same or different)

(Ii)

(In the formula ⅱ, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C ₆ ~ aryl group of C ₅₀ and; wherein m and n are each an integer of 1 to 4, wherein stage m = n = 1, Ar when the binding position of the ^first and the benzene ring of Ar ² is symmetrical, the Ar ¹ and Ar ² are not the same, m or n is for 2 to 4 integer, the m and n are different integers; R ^1, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, a substituted or unsubstituted C ₆ to C ₅₀ aryl group, A substituted or unsubstituted C ₁ to C ₅₀ alkyl group, a substituted or unsubstituted C ₃ to C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₁ to C ₅₀ alkoxy group, group, a substituted or unsubstituted C ₆ ~ C ₅₀ aralkyl group, a substituted or unsubstituted 5 to 50 nuclear atoms aryloxy group, a substituted or unsubstituted nucleus of 6 to 50 atoms inexpensive aryl Import, a substituted or unsubstituted C ₁ ~ C ₅₀ alkoxy carbonyl group, a substituted or unsubstituted silyl group, cyano, carboxyl group, a halogen atom, a ring group, a nitro group or a hydroxyl group.)

(Iii)

Wherein Ar and Ar 'are each independently a substituted or unsubstituted nucleus C ₆ to C ₅₀ aryl group; L and L' are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted aryl group, M is an integer from 0 to 2, n is an integer from 1 to 4, s is an integer from 0 to 2, and R < 2 > is an alkylene group having from 1 to 4 carbon atoms, T is an integer from 0 to 4; and L or Ar is bonded to any one of the C1 to C5 positions of the pyrene, and L 'or Ar' is bonded to any one of the C6 to C10 positions of the pyrene ,

Provided that Ar, Ar ', L and L' satisfy the following (1) or (2) when n + t is an even number:

(1) Ar ≠ Ar 'and / or L ≠ L' (wherein ≠ represents a group of different structure)

(2) when Ar = Ar 'and L = L'

(2-1) m? S and / or n? T, or

(2-2) When m = s and n = t,

(2-2-1) L and L ', or pyrene is bonded to other bonding sites on Ar and Ar'

(2-2-2) When L and L 'or pyrene are bonded at the same bonding positions on Ar and Ar', the substitution positions of L and L 'or Ar and Ar' in the pyrene are C1 and C6 Position, or C2 and C7 positions.)

[Chemical Formula (iv)

(In the formula ⅳ, A ¹ and A ² are each independently a substituted or unsubstituted C ₁₀ ~ C2 ₀ condensed aryl group and; C ₆ Ar ¹ and Ar ² each independently represent a hydrogen atom or a substituted or unsubstituted - an aryl group of C ₅₀ ^{and; R 1, R 2, R} 3, R 4, R 5, R 6, R 7, R 8, R 9 and R ¹⁰ is a ring C each independently represent a hydrogen atom, a substituted or unsubstituted an aryl group of ₆ ~ C _50, substituted or beach heteroaryl group can be unsubstituted nuclear atoms of 5 to 50, a substituted or unsubstituted C ₁ ~ C ₅₀ alkyl group, a substituted or unsubstituted C ₃ ~ C ₅₀ of the cycloalkyl group , A substituted or unsubstituted C ₁ to C ₅₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₅₀ aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear atoms, a substituted or unsubstituted import of nuclear atoms of 6 to 50 aryl Cy, substituted or unsubstituted C ₁ ~ C ₅₀ alkoxy carbonyl group, a substituted or unsubstituted silyl group, a carboxyl group, a halo Atom, a cyano group, a group or a hydroxyl group, nitro; Ar ^1, Ar ^2, R ⁹ and R ¹⁰ may have two or more as a substituent in groups fused aryl plurality may be substituted, all of which are saturated by combining groups that are adjacent to one another Or an unsaturated ring may be formed, provided that a group symmetrical with respect to the XY axis shown in the anthracene phase is bonded to the C9 and C10 positions of the anthracene nucleus,

(V)

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, a C ₁ to C ₅₀ alkyl group, A C ₃ to C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₆ to C ₅₀ aryl group, a substituted or unsubstituted C ₁ to C ₅₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₅₀ arylox A substituted or unsubstituted C ₁ to C ₅₀ alkylamino group, a substituted or unsubstituted C ₂ to C ₅₀ alkenylene group, a substituted or unsubstituted C ₆ to C ₅₀ arylamino group, a substituted or unsubstituted C ₅ ~ C ₅₀ heteroaryl group or a substituted or represents a heterocycle of the unsubstituted C ₅ ~ C _50; a and b independently represent an integer of 1 to 5, when they are at least 2 R ¹ together, or R ² respectively, each other may be the same or different from each other, and may bond to one another to form a ring together with each other R ¹ or R ^2, and R ³ and R ^4, R ⁵ and R ^6, R ⁷ and R ^8, R ⁹ R ¹⁰ a may bond to one another to form a ring and; L ¹ is a single bond, -O-, -S-, -N (R ) - ( wherein R is an alkyl group or a substituted C ₁ ~ C ₅₀ unsubstituted A C ₆ to C ₅₀ aryl group, a C ₂ to C ₅₀ alkylene group or a C ₆ to C ₅₀ arylene group)

(Vi)

(Wherein R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom, a C ₁ to C ₅₀ alkyl group, C aryl group of ₃ ~ C ₅₀ cycloalkyl group, C ₆ ~ C ₅₀ of, C ₁ ~ C ₅₀ alkoxy group, the nuclear atoms of 6 to 50 aryloxy group, C ₁ ~ a C ₅₀ alkylamino group, C ₆ ~ c ₅₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 50 heteroaryl group or a substituted or represents a group of unsubstituted nuclear atoms of 5 to 50 heterocycle; c, d, e and f are each independently R ¹¹ , R ¹² , R ¹⁶ , or R ¹⁷ may be the same or different from each other and R ¹¹ , R ¹² , R ¹⁶ or R ¹⁷ may be the same or different from each other. It may bond to one another to form a ring, and R ¹³ and R ^14, R ¹⁸ and R ¹⁹ that may bond to one another to form a ring and; L ² represents a single bond, -O-, -S-, -N ( R) - (Wherein R is C ₁ ~ C ₅₀ alkyl group or a substituted or unsubstituted C ₆ ~ C ₅₀ of the aryl group), C ₂ ~ C ₅₀ alkylene group or C ₆ ~ C ₅₀ represents an arylene group)

[Chemical Formula I]

(Wherein A ⁵ , A ⁶ , A ⁷ and A ⁸ are each independently a substituted or unsubstituted biphenyl group or a substituted or unsubstituted naphthyl group)

[Chemical Formula I]

Wherein A ⁹ , A ¹⁰ , A ¹¹ , A ¹² , A ¹³ and A ¹⁴ each independently represent a substituted or unsubstituted biphenyl group or a substituted or unsubstituted naphthyl group, at least one of which is a condensed aromatic ring having three or more rings Each of R ²¹ , R ²² and R ²³ is independently a hydrogen atom, a C ₁ to C ₆ alkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₁ to C ₆ alkoxy group, a C ₅ to C ₁₈ An aryloxy group of C ₇ to C ₁₈ , an arylamino group of C ₅ to C ₁₆ , a nitro group, a cyano group, an ester group of C ₁ to C ₆ or a halogen atom)

[Chemical Formula I]

(Wherein R ₁ and R ₂ are each independently a hydrogen atom, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aralkyl group, a substituted or unsubstituted A C ₆ to C ₅₀ aryl group, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted amino group, a cyano group or a halogen atom, and R ₁ may be the same as each other or different from each other and each other, and R _2, such as flu, R ₁ and R ₂ that is bonded to fluorene may be the same or different from each other; R ₃ and R ₄ are each independently a hydrogen atom, substituted or unsubstituted C ₁ ~ C ₅₀ alkyl group, a substituted or unsubstituted C ₆ ~ C ₅₀ aralkyl group, a substituted of unsubstituted or unsubstituted C ₆ ~ aryl group of C ₅₀ or substituted cyclic or represents a group of unsubstituted nucleus atoms 5-50 heterocycle , R ₃ together are bonded to different fluorene R ₄ with each other the same or may be different, such as fluorene groups bond R ₃ and R ₄ may be the same or different from one another and that; Ar ₁ and Ar ₂ is either the sum of the benzene ring substituted with three or more unsubstituted condensed polycyclic Ar ₁ and Ar ₂ may be the same or different from each other, n is an integer of 1 to 3, and n represents an integer of 1 to 3, 1 < / RTI >

[Formula x]

Wherein A ₁ and A ₂ are each independently a substituted or unsubstituted C ₆ -C ₂₀ aryl group or a group derived therefrom, and the aryl group is a substituted or unsubstituted C ₆ -C ₅₀ A substituted or unsubstituted C ₁ to C ₅₀ alkyl group, a substituted or unsubstituted C ₃ to C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₁ to C ₅₀ alkoxy group, a substituted or unsubstituted C An aralkyl group having ₆ to ₅₀ carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, an arylthio group having 5 to 50 substituted or unsubstituted nuclear atoms, a substituted or unsubstituted C ₁ to C ₅₀ An alkoxycarbonyl group of 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and a hydroxyl group, , These substituents may be the same or different from each other. Or may be different, and may be form a substituted cyclic, saturated or unsaturated structure by combining to each other, adjacent to each other; R _1, R _2, R _3, R _4, R _5, R _6, R ₇ and R ₈ each independently represent a hydrogen atom, a substituted or unsubstituted C ₆ to C ₅₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 50 nuclear atoms, a substituted or unsubstituted C ₁ to C ₅₀ alkyl group , A substituted or unsubstituted C ₃ to C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₁ to C ₅₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₅₀ aralkyl group, a substituted or unsubstituted nuclear atom An arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted C ₁ to C ₅₀ alkoxycarbonyl group, a substituted or unsubstituted silyl group, a carboxyl group , A halogen atom, a cyano group, a nitro group and a hydroxyl group)

(Xi)

(Was in the formula _{xi, A 1, A 2,} R 1, R 2, R 3, R 4, R 5, R 6, R 7 and R ₈ are as defined in the general formula x are each independently, just the central The C9 and C10 positions of the anthracene are not bonded to groups symmetrical with respect to the XY axis shown in the anthracene phase)

Among the host materials described above, an anthracene derivative is preferable, a monoanthracene derivative is more preferable, and an asymmetric anthracene derivative is particularly preferable.

IDE102, IDE105, and C545T, available from Idemitsu Co., Ltd., and C545T available from Hayashibara Co., Ltd., may be used as the fluorescent dopant in combination with the compound of the present invention. As the phosphorescent dopant, red phosphorescent dopant PtOEP, A green phosphorescent dopant Ir (PPy) ₃ (PPy is 2-phenylpyridine), a blue phosphorescent dopant F2Irpic, and a red phosphorescent dopant RD 61 of UDC Co., Ltd. can be used. N-methylquinacridone (MQD), coumarine derivatives and the like can also be used. Further, a metal-ligand complex compound represented by the following formula (a) may also be used.

(A)

M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³

(In the above formula a, M ¹ is selected from the group consisting of a metal element 7 Group 8 Group 9 Group, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 the Periodic Table; L ^101, L ¹⁰² and L ¹⁰³ are each selected from the following structures as ligands;

,

또는

이며, R₂₃₁내지 R₂₄₂는 서로 독립적으로 수소, 중수소, 할로젠이 치환되거나 치환되지 않은 C₁~C₃₀의 알킬기, C₁~C₃₀의 알콕시기, 할로젠이 치환 또는 비치환된 C₆~C₃₀의 아릴기, 시아노가 치환 또는 비치환된 C₅~C₃₀의 시클로알킬기이거나, 인접한 치환체와 C₃~C₁₂의 알킬렌 또는 C₃~C₁₂의 알케닐렌으로 연결되어 스피로 고리 또는 축합고리를 형성할 수 있거나, R₂₀₇또는 R₂₀₈과 C₃~C₁₂의 알킬렌 또는 C₃~C₁₂의 알케닐렌으로 연결되어 포화 또는 불포화의 축합고리를 형성할 수 있다.Wherein R ₂₀₁ , R ₂₀₂ and R ₂₀₃ are each a hydrogen atom, a C ₁ to C ₃₀ alkyl group optionally substituted with halogen, a C ₁ to C ₅₀ substituted or unsubstituted C ₁ to C ₃₀ alkyl, An aryl group, or a halogen atom; R ₂₀₄ to R ₂₁₉ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, a substituted or unsubstituted C ₃ to C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ ~ C ₃₀ uial Kane group, a substituted or unsubstituted mono or a substituted or unsubstituted aryl group, a substituted or unsubstituted C ₆ ~ C ₃₀ unsubstituted di (C ₁ ~ C ₃₀ (C ₁ -C ₃₀ alkyl) amino group, a substituted or unsubstituted mono- or di- (C ₆ -C ₃₀ aryl) amino group, SF 5, a substituted or unsubstituted tri (C ₁ -C ₃₀ alkyl) Di (C ₁ to C ₃₀ alkyl) (C ₆ to C ₃₀ aryl) silyl, substituted or unsubstituted tri (C ₆ to C ₃₀ aryl) silyl, cyano or halogen atom; R ₂₂₀ to R ₂₂₃ independently represent a hydrogen atom, a deuterium atom, a C ₁ to C ₃₀ alkyl group optionally substituted by halogen, or a C ₆ to C ₃₀ substituted or unsubstituted C ₁ to C ₃₀ alkyl Lt; / RTI > R ₂₂₄ and R ₂₂₅ independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a halogen atom, or R ₂₂₄ And R ₂₂₅ are connected to a C ₃ to C ₁₂ alkylene or C ₃ to C ₁₂ alkenylene with or without a condensed ring to form an aliphatic ring and a single ring or multiple ring aromatic ring; R ₂₂₆ is a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, or a halogen atom ; R ₂₂₇ to R ₂₂₉ independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a halogen atom; Q is

,

or

, R ₂₃₁ to R ₂₄₂ independently represent hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group, a cyano furnace a substituted or unsubstituted C ₅ ~ of the C ₃₀ or a cycloalkyl group, an alkenylene with the adjacent substituents with C ₃ ~ C ₁₂ alkylene or C ₃ ~ C ₁₂ of the spiro ring or may form a condensed ring, alkenylene of R ₂₀₇ or R ₂₀₈ and C ₃ ~ C ₁₂ alkylene or C ₃ ~ C ₁₂ of the may form a fused ring, saturated or unsaturated.

The doping concentration is not particularly limited, but the content of the dopant is usually 0.01 to 15 parts by weight based on 100 parts by weight of the host. The thickness of the light emitting layer may be about 100 A to 1000 A, preferably 200 A to 600 A, When the thickness of the light emitting layer is less than 100 ANGSTROM, the light emission characteristics may be degraded. When the thickness of the light emitting layer is more than 1000 ANGSTROM, the driving voltage may increase.

When a luminescent compound is used together with a phosphorescent dopant in the luminescent layer, a method such as vacuum deposition, spin coating, casting, LB or the like is performed on the luminescent layer to prevent the triplet excitons or holes from diffusing into the electron transporting layer The hole blocking layer HBL can be formed. When the hole blocking layer is formed by a vacuum deposition method or a spin coating method, the 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. Known hole blocking materials that can be used include oxadiazole derivatives, triazole derivatives (TAZ), phenanthroline derivatives (BCP), and the like.

The thickness of the hole blocking layer may be about 50 Å to 1000 Å, preferably 100 Å to 300 Å. When the thickness of the hole blocking layer is less than 50 ANGSTROM, the hole blocking characteristics may be deteriorated. When the thickness of the hole blocking layer is more than 1000 ANGSTROM, the driving voltage may increase.

Next, an electron transport layer (ETL) is formed by various methods such as a vacuum evaporation method, a spin coating method, and a casting method.

In the case of forming the electron transporting layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but generally, the conditions are substantially the same as those for forming the hole injection layer. The electron transport layer material serves to stably transport electrons injected from an electron injection electrode, and quinoline derivatives, particularly known materials such as Alq3, TAZ, Balq, PBD and the like may be used.

The thickness of the electron transporting layer may be about 100 ANGSTROM to 1000 ANGSTROM, preferably 200 ANGSTROM to 500 ANGSTROM. When the thickness of the electron transporting layer is less than 100 ANGSTROM, the electron transporting property may be degraded. When the thickness of the electron transporting layer is more than 1000 ANGSTROM, the driving voltage may increase.

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited. As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used. The deposition conditions of the electron injection layer 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 thickness of the electron injection layer may be about 1 A to 100 A, preferably 5 A to 50 A. If the thickness of the electron injection layer is less than 1 A, the electron injection characteristics may be deteriorated. If the thickness of the electron injection layer exceeds 100 A, 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. As the metal 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- .

Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic electroluminescent compound according to another embodiment of the present invention is the 11H, 16H-dihydrobenzo [3,4-c] naphtho [1,2-a] More specifically, the compounds 1 to 204 specifically exemplified in the above [first group (s)] can be included. The details of the compounds are the same as those described for the organic foot and the device described above.

Hereinafter, Synthesis Examples and Examples of the present invention will be specifically described, but the present invention is not limited to the following Synthesis Examples and Examples. In the following synthesis examples, the intermediate compounds are indicated by adding the serial number to the final product number. For example, the compound 1 is represented by the compound [1], and the intermediate compound of the compound is represented by [1-1] or the like.

[Example]

Representative Synthesis Example 1. Synthesis of Compound 1

Preparation of intermediate compounds [1-1], [1-2]

In a 3 L reaction flask, 200 g (0.52 mol) of 6,12-dibromocycline, 62.6 mL (0.52 mmol) of 2-aminoacetophenone, 32.9 g (0.52 mmol) of copper powder, 1-L of diphenyl ether was added to 143.2 g (1.03 mol) of potassium and the mixture was heated and stirred at 180 占 폚 for 33 hours. After completion of the reaction, 1 L of methanol was added, stirred, and filtered under reduced pressure. 2 L of acetone and 6 L of distilled water were further added thereto, followed by stirring under reduced pressure. The solid was separated and purified by silica gel chromatography to obtain 95.6 g (yield 42%) of intermediate compound [1-1] as a light yellow solid and 17.9 g (yield 7%) of intermediate compound [1-2].

Preparation of intermediate compound [1-3]

In a 3 L reaction flask, 95.6 g (0.22 mol) of Intermediate Compound [1-1] was dissolved in 1.5 mL of tetrahydrofuran under a nitrogen atmosphere, and 310.2 mL (1.4 M in THF: toluene = 1: 3) of methylmagnesium bromide 0.43 mol) was slowly added dropwise. After stirring for 13 hours, 800 mL of NH ₄ Cl aqueous solution was added to terminate the reaction. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography to obtain a bright yellow 60.4 g (61% yield) of a solid intermediate compound [1-3] was obtained.

Preparation of intermediate compound [1-4]

In a 3 L reaction flask, 60.4 g (0.13 mol) of intermediate compound [1-3] was dissolved in 1.3 L of toluene in a nitrogen atmosphere, and 25.8 mL (0.79 mol) of methanesulfonic acid was added dropwise. After completion of the reaction, 500 mL of tetrahydrofuran and methanol were added, and the mixture was stirred for 1 hour. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography 32.5 g (yield 56%) of intermediate compound [1-4] as a yellow solid was obtained.

Preparation of intermediate compound [1-5]

32.5 g (74.14 mmol) of intermediate compound [1-4], 45.4 g (222.42 mmol) of iodobenzene, 2.4 g (37.07 mmol) of powder copper and 20.5 g (148.28 mmol) of potassium carbonate were added to a 1 L reaction flask under a nitrogen atmosphere. ), 350 mL of diphenyl ether was added and the mixture was heated and stirred at 180 ° C for 18 hours. After completion of the reaction, 300 mL of methanol was added, stirred, and filtered under reduced pressure. Then, 200 mL of acetone and 600 mL of distilled water were added thereto, followed by stirring and filtration under reduced pressure. The solid was separated and purified by silica gel chromatography to obtain 28.6 g (yield 75%) of intermediate compound [1-5] as a light yellow solid.

Preparation of compound [1]

1.0 g (1.94 mmol) of intermediate compound [1-5], 0.43 g (2.53 mmol) of diphenylamine, 0.37 g (3.89 mmol) of sodium tert.butoxide and 0.02 g (0.10 mmol) of palladium acetate were added to a 100 mL reaction flask, And 0.04 g (0.19 mmol) of trimethylbutylphosphine were added 20 mL of toluene, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then purified by silica gel chromatography to obtain 0.84 g (yield 72%) of a yellow solid compound [1].

Representative Synthesis Example 2. Synthesis of Compound [203]

Preparation of compound [203]

To a 100 mL reaction flask was added 1 g (1.94 mmol) of Intermediate Compound [1-5], 0.40 g (3.30 mmol) of phenylboronic acid, 0.04 g (0.04 mmol) of tetrakis (triphenylphosphine) palladium, 4 mL , And 20 mL of 1,4-dioxane were added thereto, followed by stirring under reflux for 5 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then purified by silica gel chromatography to obtain 0.85 g (yield 86%) of a light yellow solid compound [203] .

Compounds 1 to 204 were synthesized according to the methods of Representative Synthesis Examples 1 and 2, and the results of nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS) Respectively.

[Synthesis Example 1] Synthesis of compound [1]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 6H), 6.95 ~ 6.92 (m, 2H), 6H), 6.45 (d, 1H), 1.75 (s, 6H), 6.75 (d,

MS / FAB: 602 (M < ^{+ &} gt ^; ).

[Synthesis Example 2] Synthesis of compound [2]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.92 (m, 2H), 2H), 6.53 (d, 2H), 6.45 (d, 1H), 1.75 (s, 6H)

MS / FAB: 612 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 3] Synthesis of compound [3]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.81 (m, 7H), 6H), 1.75 (s, 6H), 6.75 (d, 2H), 6.71 (d,

MS / FAB: 630 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 4] Synthesis of compound [4]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.91 (m, 6H), 6H), 1.25 (s, 18H), 6.75 (d, 2H), 6.81 (s,

MS / FAB: 714 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 5] Synthesis of compound [5]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 ~ 7.05 (m, 6H), 6.95 ~ 6.92 (m, 2H ), 6.81 (s, 1H), 6.71 (t, 1H), 6.63 (t, 18H)

MS / FAB: 747 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 6] Synthesis of compound [6]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.89 (m, 6H), 1H), 6.63 (t, 1H), 6.63 (s, 1H)

MS / FAB: 638 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 7] Synthesis of compound [7]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 4H), 7.10 (t, 2H), 6.95 ~ 2H), 6.75 (d, 1H), 1.75 (s, 6H), 6.92 (s,

MS / FAB: 652 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 8] Synthesis of compound [8]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 ~ 7.92 (m, 6H), 7.78 ~ 7.72 (m, 4H), 7.47 ~ 7.43 (m, 6H), 7.28 (t, 2H 2H), 6.45 (d, 2H), 6.95 (d, 2H), 6.95-6.88 (m, 4H) 2H), 1.75 (s, 6H)

MS / FAB: 702 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 9] Synthesis of compound [9]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.64 (m, 12H), 7.40 ~ 7.39 (m, 4H), 7.26 (t, 2H), 2H), 6.45 (d, 1H), 1.75 (s, 6H), 6.70 (s, 1H)

MS / FAB: 702 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 10] Synthesis of Compound [10]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.44 ~ 7.31 (m, 14H), 7.10 (t, 2H), 1H), 6.75 (s, 6H), 6.75 (m, 2H), 6.81 (s,

MS / FAB: 754 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 11] Synthesis of compound [11]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 6H), 7.52 (d, 2H), 7.45 (d, 2H), 7.28 ( (m, 2H), 7.18-7.10 (m, 4H), 6.92 (m, 2H), 6.81 6H), 1.62 (s, 12H)

MS / FAB: 835 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 12] Synthesis of compound [12]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.65 (m, 10H), 7.52 (d, 2H), 7.45 (d, 2H), 7.28 ~ 2H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 5H)

MS / FAB: &^lt; / RTI ^& gt ^; 1079 (M ⁺ )

[Synthesis Example 13] Synthesis of compound [13]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 6H), 7.52 (d, 2H), 7.45 (d, 2H), 7.28 ~ 2H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45 (m,

MS / FAB: 1083 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 14] Synthesis of compound [14]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.92 (m, 6H), 2H), 1.75 (s, 6H), 1.10 (s, 1H), 6.71 (d, (s, 12 H)

MS / FAB: 686 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 15] Synthesis of compound [15]

¹ H NMR (300 MHz, CDCl ₃ )? 8.83 (d, 2H), 8.02 (d, 2H), 7.78-7.72 (m, 4H), 7.10-7. ), 6.81 (s, 1 H), 6.71-6.41 (m, 9H), 2.02

MS / FAB: 630 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 16] Synthesis of compound [16]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.92 (m, 2H), 6H), 6.75 (s, 6H), 6.75 (s, 1H), 6.71 (s,

MS / FAB: 662 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 17] Synthesis of Compound [17]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (m, 2H), 8.02 ~ 7.97 (m, 4H), 7.78 ~ 7.72 (m, 4H), 7.45 (m, 2H), 7.10 (m, 2H), 2H), 6.81 (s, 1H), 6.71-6.45 (m, 9H), 1.75 (s, 6H)

MS / FAB: 604 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 18] Synthesis of Compound [18]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (m, 2H), 8.36 (d, 4H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (m, 2H), 6.95 ~ 2H), 6.75 (m, 2H), 6.75 (m, 2H), 6.81 (s,

MS / FAB: 604 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 19] Synthesis of Compound [19]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (m, 2H), 8.02 ~ 7.94 (m, 6H), 7.78 ~ 7.72 (m, 4H), 7.26 (m, 2H), 7.17 ~ 7.10 (m, 4H 2H), 6.75 (m, 2H), 6.75 (s, 1H), 6.75 (m,

MS / FAB: 604 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 20] Synthesis of compound [20]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 ~ 8.80 (m, 4H), 8.40 (s, 4H), 8.02 (m, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (m, 2H), 2H), 6.75 (m, 2H), 6.81 (s, 1H), 6.71-6.63

MS / FAB: 606 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 21] Synthesis of Compound [21]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (m, 4H), 8.35 (s, 4H), 8.02 (m, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (m, 2H), 6.95 ~ 2H), 6.75 (m, 2H), 6.75 (m, 5H), 6.71-6.63

MS / FAB: 606 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 22] Synthesis of compound [22]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (m, 2H), 8.12 (m, 2H), 8.02 (m, 2H), 7.84 ~ 7.59 (m, 10H), 7.47 (d, 2H), 7.27 ( 2H), 6.45 (m, 2H), 6.95-6.92 (m, 2H), 6.81 (s, , 1.75 (s, 6H)

MS / FAB: 704 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 23] Synthesis of compound [23]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.18 (d, 2H), 8.07 ~ 8.02 (m, 4H), 7.78 ~ 7.72 (m, 4H), 7.47 (m, 2H), 2H), 6.53 (d, 2H), 6.45 (m, 2H), 7.31-7.31 (m, 4H) m, 1 H), 1.75 (s, 6 H)

MS / FAB: 704 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 24] Synthesis of compound [24]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (m, 2H), 6.95 ~ 6.92 (m, 2H), 6.82-6.63 (m, 9H), 6.53-6.45 (m, 5H), 1.75 (s, 6H)

MS / FAB: 616 (M < ^{+ &} gt ^; ).

[Synthesis Example 25] Synthesis of compound [25]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (m, 1H), 8.02 (d, 3H), 7.84 ~ 7.72 (m, 5H), 7.65 (s, 1H), 7.53 ( 2H), 6.53 (d, 2H), 6.45 (m, 2H), 7.40 (m, 1H), < / RTI > 1.75 (s, 6H)

MS / FAB: 600 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 26] Synthesis of compound [26]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (m, 2H), 6.95 ~ 6.92 (m, 6H), 6H), 1.62 (s, 6H), 1.62 (s, 1H), 6.81 (s,

MS / FAB: 642 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 27] Synthesis of compound [27]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.23 ~ 6.91 (m, 18H), 6.81 (s, 1H), 2H), 1.75 (s, 6H), 6.71 (m, 2H)

MS / FAB: 766 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 28] Synthesis of compound [28]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.43 (m, 2H), 7.29 (m, 2H), 7.10 ( 2H), 6.75 (m, 2H), 6.81 (m, 3H), 6.71-6.63 (m, 4H)

MS / FAB: 628 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 29] Synthesis of compound [29]

¹ H NMR (300 MHz, CDCl ₃ )? 8.83 (d, 2H), 8.02 (m, 2H), 7.78-7.72 (m, 4H), 7.18-7.10 ), 6.81 (m, 3H), 6.71-6.62 (m, 4H), 6.53

MS / FAB: 652 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 30] Synthesis of compound [30]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (m, 2H), 7.78 ~ 7.72 (m, 4H), 7.27 (d, 4H), 7.10 (m, 2H), 6.95 ~ 2H), 6.81 (s, 1H), 6.71-6.62 (m, 2H), 6.53-6.45 (m,

MS / FAB: 738 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 31] Synthesis of Compound [31]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.35 (m, 2H), 8.02 (m, 2H), 7.88 (m, 2H), 7.78 ~ 7.71 (m, 6H), 7.42 ~ 2H), 6.75 (m, 2H), 6.81 (m, 2H), 6.75 (m, s, 6H)

MS / FAB: 815 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 32] Synthesis of compound [32]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (m, 2H), 7.79 ~ 7.72 (m, 6H), 7.56 (m, 2H), 7.28 ~ 7.10 (m, 8H), 2H), 6.75 (m, 2H), 6.75 (m, 2H), 6.75 (m, 2H) 6H)

MS / FAB: 782 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 33] Synthesis of compound [33]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.11 ~ 7.06 (m, 8H), 6.95 ~ 6.81 (m, 5H ), 6.71 (d, IH), 1.75 (s, 6H)

MS / FAB: 633 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 34] Synthesis of compound [34]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.02 (d, 3H), 7.92 ~ 7.72 (m, 8H), 7.60 ~ 7.53 (m, 6H), 2H), 6.53 (d, 2H), 6.45 (d, 1H), 1.75 (s, 6H), 7.23-7.10 (m, 7H), 6.95-6.92

MS / FAB: 752 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 35] Synthesis of compound [35]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.92 (m, 2H), (S, 3H), 1.75 (s, 6H), 6.73 (s, 1H)

MS / FAB: 633 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 36] Synthesis of compound [36]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.92 (m, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 5H)

MS / FAB: 608 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 37] Synthesis of compound [37]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (d, 4H), 7.10 (t, 4H), 6.95 ~ 6.88 (m, 4H), 3H), 1.75 (s, 6H), 6.81 (s, 1H), 6.71-6.63

MS / FAB: 617 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 38] Synthesis of compound [38]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.91 (m, 4H), 6H), 1.25 (s, 9H), 6.81 (s, 1H), 6.71-6.63

MS / FAB: 659 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 39] Synthesis of compound [39]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 ~ 7.05 (m, 6H), 6.95 ~ 6.92 (m, 2H ), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 7H)

MS / FAB: 675 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 40] Synthesis of compound [40]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (d, 4H), 7.10 (t, 4H), 6.95 ~ 6.89 (m, 4H), 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 7H)

MS / FAB: 621 (M < ^{+ &} gt ^; ).

[Synthesis Example 41] Synthesis of compound [41]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (d, 4H), 7.29 (d, 2H), 7.10 (t, 4H), 6.95 ~ 2H), 6.81 (s, 1H), 6.71-6.63 (m, 5H), 6.53-6.45 (m,

MS / FAB: 628 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 42] Synthesis of compound [42]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 ~ 7.92 (m, 4H), 7.78 ~ 7.72 (m, 4H), 7.47 ~ 7.43 (m, 3H), 7.28 (t, 1H ), 7.10 (t, 4H), 6.95-6.88 (m, 3H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45

MS / FAB: 653 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 43] Synthesis of compound [43]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.64 (m, 8H), 7.40 ~ 7.39 (m, 2H), 7.26 (t, 1H), 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 5H), 1.75

MS / FAB: 653 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 44] Synthesis of compound [44]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (d, 4H), 7.44 ~ 7.31 (m, 7H), 7.10 (t, 4H), 2H), 6.81 (s, 1H), 6.71-6.45 (m, 10H), 1.75 (s, 6H)

MS / FAB: 679 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 45] Synthesis of compound [45]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.28 (t, 1H), (M, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 6H), 1.75 1.62 (s, 6H)

MS / FAB: 719 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 46] Synthesis of compound [46]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.65 (m, 7H), 7.52 ~ 7.45 (m, 2H), 7.28 ~ 7.06 (m, 12H ), 6.95-6.92 (m, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45

MS / FAB: 841 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 47] Synthesis of compound [47]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.28 ~ 7.01 (m, 18H ), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 6H)

MS / FAB: 843 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 48] Synthesis of compound [48]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.98 ~ 7.92 (m, 4H), 7.30 (s, 4H), 7.15 ~ 7.12 (m, 4H), 6H), 1.30 (s, 6 H), 1.95 (s, 3H), 6.91 (s,

MS / FAB: 645 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 49] Synthesis of compound [49]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 ~ 8.06 (m, 3H), 7.87 ~ 7.81 (m, 4H), 7.54 (t, 1H), 7.19 (t, 4H), 2H), 6.90 (s, 1H), 6.80-6.61 (m, 10H), 1.67 (s, 6H)

MS / FAB: 603 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 50] Synthesis of compound [50]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 ~ 8.89 (m, 3H), 8.49 (s, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 (t, 4H), 2H), 6.90 (s, 1H), 6.80-6.44 (m, 8H), 1.67 (s, 6H)

MS / FAB: 604 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 51] Synthesis of compound [51]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.27 ~ 7.19 (m, 6H), 7.04 ~ 7.01 (m, 2H ), 6.90 (s, 2H), 6.80-6.44 (m, 9H), 1.67 (s, 6H)

MS / FAB: 627 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 52] Synthesis of compound [52]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.36 (d, 2H), 7.19 (t, 4H), 7.04 ~ 2H), 6.90 (s, 1H), 6.80-6.44 (m, 10H), 1.67 (s, 6H)

MS / FAB: 670 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 53] Synthesis of compound [53]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.44 (d, 1H), 8.11 (d, 2H), 7.97 (d, 1H), 7.87 ~ 7.80 (m, 5H), 7.51 ~ 7H), 7.04-7.01 (m, 2H), 6.90-6.44 (m, 10H), 1.67 (s, 6H)

MS / FAB: 708 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 54] Synthesis of compound [54]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.44 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 (t, 4H), 7.04 ~ 6.90 (m, 4H), 6.80-6.44 (m, 8H), 1.67 (s, 6H)

MS / FAB: 604 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 55] Synthesis of compound [55]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 (t, 2H), 7.04`7.01 (m, 6H), 6H), 1.34 (s, 9H), 1.19 (s, 6H), 6.90 (s,

MS / FAB: 700 (M @ ⁺ )

[Synthesis Example 56] Synthesis of compound [56]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.45 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 (t, 4H), 7.04 ~ 6H), 6.80 (s, 1H), 6.80-6.44 (m, 8H), 1.67 (s, 6H)

MS / FAB: 603 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 57] Synthesis of compound [57]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.88 ~ 7.81 (m, 5H), 7.65 (d, 1H), 7.37 ~ 7.19 (m, 7H), (M, 3H), 6.90 (s, IH), 6.80-6.44 (m, 8H), 6.38

MS / FAB: 692 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 58] Synthesis of compound [58]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.88 ~ 7.81 (m, 5H), 7.65 (d, 1H), 7.37 ~ 7.19 (m, 5H), (M, 6H), 1.34 (s, 9H), 7.06-7.00 (m, 5H), 6.90

MS / FAB: 748 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 59] Synthesis of compound [59]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.88 ~ 7.81 (m, 5H), 7.65 (d, 1H), 7.38 ~ 7.19 (m, 7H), (M, 3H), 6.90 (s, IH), 6.80-6.44 (m, 7H), 6.38

MS / FAB: &^lt; / RTI ^& gt ^; 717 (M ⁺ )

[Synthesis Example 60] Synthesis of Compound [60]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 ~ 8.03 (m, 4H), 7.87 ~ 7.81 (m, 4H), 7.35 (t, 1H), 7.26 ~ 7.01 (m, 7H ), 6.90 (s, 1 H), 6.80-6.44 (m, 8H), 1.67 (s, 6H)

MS / FAB: 603 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 61] Synthesis of compound [61]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 ~ 7.14 (m, 4H), 7.04 ~ 7.01 (m, 2H ), 6.90 (s, 1H), 6.80-6.44 (m, 11H), 3.82

MS / FAB: 704 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 62] Synthesis of compound [62]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H, 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 ~ 7.01 (m, 6H), 6.90 (s, 1H), 6.80 , 6.54 (m, 7H), 1.67 (s, 6H), 0.24 (s, 9H)

MS / FAB: 679 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 63] Synthesis of compound [63]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 ~ 6.97 (m, 8H), 6.90 (s, 1H), (S, 3H), 1.67 (s, 6H), 0.24 (s, 9H)

MS / FAB: 688 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 64] Synthesis of compound [64]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (d, 2H), 8.11 (d, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 ~ 7.14 (m, 4H), 7.04 ~ 7.00 (m, 4H ), 6.90 (s, 1H), 6.80-6.44 (m, 9H), 1.67 (s, 6H)

MS / FAB: 731 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 65] Synthesis of compound [65]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.93 (d, 2H), 8.12 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 ~ 7.05 (m, 4H), 6.95 ~ 6.89 (m, 4H ), 6.81 (s, 1H), 6.71-6.63 (m, 2H), 6.53-6.45 (m, 7H)

MS / FAB: 692 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 66] Synthesis of compound [66]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 ~ 7.05 (m, 4H), 2H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 5H), 1.75

MS / FAB: 699 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 67] Synthesis of compound [67]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 ~ 7.92 (m, 4H), 7.78 ~ 7.72 (m, 4H), 7.47 ~ 7.43 (m, 3H), 7.28 (t, 1H 2H), 6.53-6.45 (m, 5H), 1.75 (s, 6H), 6.95 (m, 2H) ), 0.15 (s, 9H)

MS / FAB: 725 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 68] Synthesis of compound [68]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.81 ~ 7.67 (m, 8H), 7.40 ~ 7.39 (m, 2H), 7.26 (t, 1H), 2H), 6.53-6.45 (m, 5H), 1.75 (s, 6H), 6.75 (s, 0.15 (s, 9H)

MS / FAB: 725 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 69] Synthesis of compound [69]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.44 ~ 7.41 (m, 6H), 7.31 (m, 1H), 2H), 6.81 (s, 1H), 6.71-6.45 (m, 9H), 1.75 (s, 6H), 0.15 (s, 9H)

MS / FAB: 751 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 70] Synthesis of compound [70]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.38 (t, 1H), (M, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 1.62 (s, 6H), 0.15 (s, 9H)

MS / FAB: 791 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 71] Synthesis of compound [71]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.65 (m, 7H), 7.52 ~ 7.45 (m, 2H), 7.28 ~ 7.05 (m, 12H 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 6H)

MS / FAB: 913 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 72] Synthesis of compound [72]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.28 ~ 6.92 (m, 18H ), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 6H)

MS / FAB: 915 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 73] Synthesis of compound [73]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 ~ 7.05 (m, 4H), 6.95 ~ 6.92 (m, 4H ), 6.81 (s, 1H), 6.71-6.63 (m, 2H), 6.53-6.45 (m, 7H) s, 9H)

MS / FAB: &^lt; / RTI ^& gt ^; 717 (M ⁺ )

[Synthesis Example 74] Synthesis of compound [74]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.18 ~ 7.05 (m, 6H), 6.95 ~ 6.92 (m, 2H ), 6.81 (m, 2H), 6.71-6.62 (m, 3H), 6.53-6.45 (m, 5H)

MS / FAB: 699 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 75] Synthesis of Compound [75]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.27 (d, 2H), 7.10 ~ 7.05 (m, 4H), 6H), 0.15 (s, 9H), 6.75 (m, 2H), 6.81 (s,

MS / FAB: 742 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 76] Synthesis of compound [76]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.35 (m, 1H), 8.02 (d, 2H), 7.88 (m, 1H), 7.78 ~ 7.71 (m, 5H), 7.42 ~ 2H), 7.17-7.05 (m, 5H), 6.95-6.92 (m, 2H), 6.81 (s, 1H), 6.76-6.63 1.75 (s, 6H), 0.15 (s, 9H)

MS / FAB: 781 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 77] Synthesis of compound [77]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.72 (m, 5H), 7.56 (d, 1H), 7.28 ~ 6.92 (m. 10H), 2H), 6.53-6.45 (m, 5H), 6.29 (d, 1H), 1.75 (s, 6H)

MS / FAB: 765 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 78] Synthesis of compound [78]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t. 2H), 6.95 ~ 6.89 (m, 4H), 3H), 1.75 (s, 6H), 6.81 (s, 1H), 6.71-6.63 (m, 4H)

MS / FAB: 650 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 79] Synthesis of compound [79]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t. 2H), 6.95 ~ 6.89 (m, 4H), 2H), 6.53-6.45 (m, 5H), 1.75 (s, 6H), 6.81 (s,

MS / FAB: 625 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 80] Synthesis of compound [80]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t. 2H), 6.95 ~ 6.82 (m, 6H), 2H), 6.53-6.45 (m, 7H), 2.24 (s, 3H), 1.75 (s, 6H)

MS / FAB: 634 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 81] Synthesis of compound [81]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.89 (m, 6H), 2H), 6.53-6.45 (m, 7H), 1.75 (s, 6H), 1.25 (s, 9H)

MS / FAB: 677 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 82] Synthesis of compound [82]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 (t, 2H), 6.95 ~ (M, 4H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45

MS / FAB: 646 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 83] Synthesis of compound [83]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 ~ 7.92 (m, 4H), 7.78 ~ 7.72 (m, 4H), 7.47 ~ 7.44 (m, 3H), 7.28 (t, 1H ), 7.10 (t, 2H), 6.95-6.88 (m, 5H), 6.81 (s, s, 6H)

MS / FAB: 671 (M ^< ^{+ &} gt ^; ).

[Synthetic Example 84] Synthesis of compound [84]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 6H), 7.67 ~ 7.64 (m, 2H), 7.40 ~ 7.39 (t, 2H ), 7.26 (t, IH), 7.10 (t, 2H), 6.95-6.89 (m, 4H), 6.81 (s, IH), 6.71 m, 5H), 1.75 (s, 6H)

MS / FAB: 671 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 85] Synthesis of compound [85]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.44 ~ 7.41 (m, 6H), 7.31 (m, 1H), 2H), 6.95 (s, 2H), 6.95 (m, 2H), 6.95 (s,

MS / FAB: 670 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 86] Synthesis of compound [86]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 (d, 1H), 7.45 (d, 1H), 7.28 ( 2H), 6.95 (m, 2H), 6.81 (s, 1H), 7.18 (t, , 6.53-6.45 (m, 6H), 1.75 (s, 6H), 1.62 (s, 6H)

MS / FAB: 737 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 87] Synthesis of compound [87]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.65 (m, 7H), 7.52 (d, 1H), 7.45 (d, 1H), 7.28 ~ (M, 2H), 6.53 (m, 2H), 7.25 (m, 4H), 7.10-7. 6.45 (m, 6 H), 1.75 (s, 6 H)

MS / FAB: 859 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 88] Synthesis of compound [88]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 (d, 1H), 7.45 (d, 1H), 7.28 ~ 2H), 6.53-6.45 (m, 6H), 1.75 (m, 2H), 7.01 (m, s, 6H)

MS / FAB: 861 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 89] Synthesis of compound [89]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 2H), 6.95 ~ 6.89 (m, 6H), 6H), 1.10 (d, 6H), 6.71 (d, IH), 6.81 (s,

MS / FAB: 663 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 90] Synthesis of Compound [90]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.18 ~ 7.17 (m, 2H), 7.10 (t, 2H), 2H), 6.63 (m, 2H), 6.53-6.45 (m, 5H), 1.75 (s, 6H)

MS / FAB: 646 (M ^< ^{+ &} gt ^; ).

[Synthesis 91] Synthesis of compound [91]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.27 (d, 2H), 7.10 (t, 2H), 6.95 ~ 1H), 6.83 (t, 1H), 6.53-6.45 (m, 7H), 1.75 (s, 6H)

MS / FAB: 689 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 92] Synthesis of compound [92]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.35 (m, 1H), 8.02 (d, 2H), 7.88 (m, 1H), 7.78 ~ 7.71 (m, 5H), 7.42 ~ (M, 2H), 7.17 (t, 1H), 7.10 (t, 2H), 6.95 ~ 6.89 (m, 4H), 6.81 m, 5H), 1.75 (s, 6H)

MS / FAB: 727 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 93] Synthesis of compound [93]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.72 (m, 5H), 7.28 (d, 1H), 7.28 ~ 2.22 (m, 2H), (T, 1H), 6.63 (t, 1H), 6.53-6.45 (m, 2H), 7.15 (m, 5H), 6.29 (d, 1 H), 1.75 (s, 6 H)

MS / FAB: 711 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 94] Synthesis of compound [94]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 (t, 2H), 6.95 ~ 2H), 6.92 (s, 1H), 6.71 (m, 3H), 6.64-6.63 (m, 3H) 3H), < / RTI > 1.75 (s, 6H)

MS / FAB: 658 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 95] Synthesis of compound [95]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 (t, 2H), 6.95 ~ 2H), 6.81 (s, 1H), 6.71 (m, 3H), 6.63 (d,

MS / FAB: 633 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 96] Synthesis of compound [96]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 (t, 2H), 6.95 ~ 2H), 6.45 (m, 3H), 2.24 (s, 3H), 6.83 (d, , 1.75 (s, 6H)

MS / FAB: 642 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 97] Synthesis of compound [97]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 (m, 2H), 6.92 ~ 2H), 6.45 (m, 3H), 1.75 (s, 6H), 1.25 (s, 9H)

MS / FAB: 684 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 98] Synthesis of compound [98]

¹ H NMR (300 MHz, CDCl ₃ )? 8.83 (d, 2H), 8.02-7.92 (m, 4H), 7.78-7.72 (m, 4H), 7.47-7.43 2H), 6.45 (d, IH), 6.71 (d, IH), 6.71 (m, 1.75 (s, 6H)

MS / FAB: 678 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 99] Synthesis of compound [99]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.64 (m, 8H), 7.40 ~ 7.39 (m, 2H), 7.29 ~ 7.26 (m, 3H ), 7.10 (m, 2H), 6.95-6.92 (m, 2H), 6.81 (s, IH), 6.71-6.63 s, 6H)

MS / FAB: 678 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 100] Synthesis of Compound [100]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.41 ~ 7.29 (m, 9H), 7.10 (m, 2H), 2H), 6.81 (s, 1H), 6.71-6.53 (m, 8H), 6.45 (d,

MS / FAB: 704 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 101] Synthesis of compound [101]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.29 (m, 3H), (M, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 5H), 6.53-6.45 1.62 (s, 6H)

MS / FAB: 744 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 102] Synthesis of compound [102]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.65 (m, 7H), 7.52 ~ 7.45 (m, 2H), 7.29 ~ 7.06 (m, 12H 2H), 6.81 (s, 1H), 6.71-6.63 (m, 5H), 6.53-6.45 (m, 4H)

MS / FAB: 866 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 103] Synthesis of compound [20]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.65 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.29 ~ 7.06 (m, 16H 2H), 6.81 (s, 1H), 6.71-6.63 (m, 5H), 6.53-6.45 (m, 4H)

MS / FAB: 868 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 104] Synthesis of compound [104]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 (m, 2H), 6.95 ~ 6H), 1.10 (d, 1H), 6.92 (s, 1H), 6.92 (s, 6H)

MS / FAB: 670 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 105] Synthesis of compound [105]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.18 ~ 7.10 (m, 4H), 2H), 6.81 (m, 2H), 6.71-6.63 (m, 5H), 6.53-6.45 (m,

MS / FAB: 653 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 106] Synthesis of Compound [106]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 ~ 7.27 (d, 4H), 7.10 (m, 2H), (M, 2H), 6.81 (m, 1H), 6.71-6.63 (m, 4H), 6.53-6.45

MS / FAB: 696 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 107] Synthesis of Compound [107]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.35 (d, 1H), 8.02 (d, 2H), 7.88 (d, 1H), 7.78 ~ 7.71 (m, 5H), 7.42 ~ 2H), 7.29 (d, 2H), 7.17-7.10 (m, 3H), 6.95-6.92 (m, 2H), 6.81-6.63 1.75 (s, 6H)

MS / FAB: 734 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 108] Synthesis of Compound [108]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.71 (m, 5H), 7.56 (d, 1H), 7.29 ~ 7.10 (m, 7H), (M, 3H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45

MS / FAB: 718 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 109] Synthesis of Compound [109]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.71 (m, 4H), 7.27 (d, 2H), 7.10 (m, 2H), 6.95 ~ 2H), 6.81 (s, 1H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 7H)

MS / FAB: 701 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 110] Synthesis of Compound [110]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.71 (m, 4H), 7.27 (d, 2H), 7.10 (m, 2H), 6.95 ~ (M, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 2H), 6.53-6.45

MS / FAB: 676 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 111] Synthesis of Compound [111]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.71 (m, 4H), 7.27 (d, 2H), 7.10 (m, 2H), 6.95 ~ 2H), 6.53-6.45 (m, 7H), 2.24 (s, 3H), 1.75 (s, 6H)

MS / FAB: 685 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 112] Synthesis of Compound [112]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.71 (m, 4H), 7.27 (d, 2H), 7.10 (m, 2H), 6.95 ~ 2H), 6.53-6.45 (m, 7H), 1.75 (s, 6H), 1.25 (s, 9H)

MS / FAB: 727 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 113] Synthesis of Compound [113]

¹ H NMR (300 MHz, CDCl ₃ )? 8.83 (d, 2H), 8.02-7.92 (m, 4H), 7.78-7. 72 (m, 4H), 7.47-7.43 (M, 2H), 7.10 (t, 2H), 6.95-6.88 (m, 3H), 6.81 )

MS / FAB: 720 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 114] Synthesis of Compound [114]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.64 (m, 8H), 7.40 ~ 7.39 (m, 2H), 7.27 ~ 7.26 (m, 3H 2H), 6.95-6.92 (m, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 2H), 6.53-6.45

MS / FAB: 720 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 115] Synthesis of Compound [115]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.44 ~ 7.27 (m, 9H), 7.10 (t, 2H), 2H), 6.81 (s, 1H), 6.71-6.45 (m, 9H), 1.75 (s, 6H)

MS / FAB: 746 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 116] Synthesis of Compound [116]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.28 ~ 7.27 (m, 3H ), 7.18-7.10 (m, 3H), 6.95-6.92 (m, 2H), 6.81 (s, 1H), 6.71-6.63 ), 1.62 (s, 6H)

MS / FAB: 786 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 117] Synthesis of Compound [117]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.65 (m, 7H), 7.52 ~ 7.45 (m, 2H), 7.28 ~ 7.10 (m, 12H ), 6.95-6.92 (m, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45

MS / FAB: 909 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 118] Synthesis of Compound [118]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 5H), 7.52 ~ 7.45 (m, 2H), 7.28 ~ 6.92 (m, 18H ), 6.81 (s, 1 H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 911 (M ⁺ )

[Synthesis Example 119] Synthesis of Compound [119]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.27 (d, 2H), 7.10 (t, 2H), 6.95 ~ 6H), 1.10 (d, 2H), 6.92 (m, 2H), 6.92 (s, 6H)

MS / FAB: 712 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 120] Synthesis of Compound [120]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.27 (d, 2H), 7.18 ~ 7.10 (m, 4H), 2H), 6.81 (m, 2H), 6.71-6.62 (m, 3H), 6.53-6.45 (m, 5H)

MS / FAB: 695 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 121] Synthesis of Compound [121]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.35 (d, 1H), 8.02 (d, 2H), 7.88 (d, 1H), 7.78 ~ 7.71 (m, 5H), 7.42 ~ 2H), 7.27 (d, 2H), 7.17-7.10 (m, 3H), 6.95-6.92 (m, 2H), 6.81-6.63 1.75 (s, 6H)

MS / FAB: 776 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 122] Synthesis of Compound [122]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.72 (m, 5H), 7.56 (d, 1H), 7.28 ~ 7.10 (m, 7H), (M, 2H), 6.53-6.45 (m, 5H), 6.29 (d, 1H), 1.75 (s, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 760 (M ⁺ )

[Synthesis Example 123] Synthesis of compound [123]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.02 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), (S, 6H), 7.51-7.45 (m, 3H), 7.10-7. 07 (m, 5H), 6.99-6.92

MS / FAB: 753 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 124] Synthesis of Compound [124]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.02 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), 2H), 6.81-6.63 (m, 6H), 6.53-6.45 (m, 5H), 1.75 (s, 6H), 7.51-7.44 (m, 4H)

MS / FAB: 796 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 125] Synthesis of Compound [125]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.71 (m, 7H), 7.56 (d, 1H), 7.44 (s, 1H), 7.28 ~ 2H), 6.81-6.63 (m, 6H), 6.53-6.45 (m, 5H), 1.75 (s, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 836 (M ⁺ )

[Synthesis Example 126] Synthesis of Compound [126]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.02 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), 2H), 6.81-6.45 (m, 12H), 1.75 (s, 6H), 7.51-7.45 (m, 3H)

MS / FAB: 746 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 127] Synthesis of Compound [127]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.71 (m, 7H), 7.56 (d, 1H), 7.28 ~ 7.22 (m, 3H), (M, 3H), 6.81 (s, 1H), 6.71-6.45 (m, 9H), 1.75

MS / FAB: 793 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 128] Synthesis of Compound [128]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.71 (m, 7H), 7.56 (d, 1H), 7.44 (s, 1H), 7.28 ~ 2H), 6.81-6.63 (m, 6H), 6.53-6.45 (m, 5H), 1.75 (s, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 836 (M ⁺ )

[Synthesis Example 129] Synthesis of Compound [129]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.99 ~ 7.91 (m, 7H), 7.76 (d, 1H), 7.48 ~ 7.42 (m, 3H), 2H), 7.30 (s, 4H), 7.15-7.12 (m, 2H), 7.01-6.63

MS / FAB: 786 ^< RTI ID ⁼ 0.0 >

[Synthesis Example 130] Synthesis of Compound [130]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 8.10 ~ 7.92 (m, 7H), 7.83 (d, 1H), 7.69 ~ 7.68 (m, 3H), (M, 3H), 7.01 (s, 1H), 6.91-6.65 (m, 9H), 1.95

MS / FAB: 753 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 131] Synthesis of Compound [131]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 8.10 ~ 7.92 (m, 7H), 7.83 (d, 1H), 7.69 ~ 7.64 (m, 4H), 2H), 7.01-6.83 (m, 6H), 6.73-6.65 (m, 5H), 1.95 (s, 6H)

MS / FAB: 796 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 132] Synthesis of Compound [132]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 8.10 ~ 7.92 (m, 7H), 7.83 (d, 1H), 7.69 ~ 7.68 (m, 3H), 2H), 7.30 (s, 4H), 7.15-7.12 (m, 2H), 7.01-6.63

MS / FAB: 746 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 133] Synthesis of Compound [133]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.98 ~ 7.92 (m, 4H), 7.62 ~ 7.51 (m, 8H), 7.33 ~ 7.18 (m, 6H ), 7.18-7.12 (m, 4H), 7.01 (s, 1H), 6.91-6.83 (m, 3H), 6.73-6.65

MS / FAB: 772 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 134] Synthesis of compound [134]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.98 ~ 7.92 (m, 4H), 7.83 (s, 1H), 7.62 ~ 7.51 (m, 9H), (M, 3H), 6.73-6.65 (m, 5H), 1.95 (s, 6H), 7.30 (s, 4H), 7.18-7.12

MS / FAB: 779 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 135] Synthesis of compound [135]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.99 ~ 7.92 (m, 5H), 7.62 ~ 7.51 (m, 9H), 7.30 (s, 4H), (M, 3H), 6.73-6.65 (m, 5H), 1.95 (s, 6H)

MS / FAB: 822 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 136] Synthesis of compound [136]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.98 ~ 7.92 (m, 4H), 7.30 (s, 4H), 7.15 ~ 7.11 (m, 4H), 6H), 1.45 (s, 9H), 7.01 (s, 1H), 6.91-6.83 (m, 3H)

MS / FAB: 658 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 137] Synthesis of compound [137]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.98 ~ 7.92 (m, 4H), 7.38 ~ 7.30 (m, 4H), 7.15 ~ 7.11 (m, 4H ), 7.01 (s, 2H), 6.91-6.82 (m, 3H), 6.73 (d, 2H), 6.65

MS / FAB: 683 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 138] Synthesis of Compound [138]

¹ H NMR (300 MHz, CDCl ₃ )? 9.03 (s, 2H), 8.22 (s, 2H), 7.98-7.92 (m, 4H), 7.30-7. ), 6.73-6.65 (m, 6H), 1.95 (s, 6H), 1.45 (s, 9H)

MS / FAB: 726 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 139] Synthesis of compound [139]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.98 ~ 7.92 (m, 4H), 7.30 ~ 7.28 (m, 3H), 7.15 ~ 7.11 (m, 4H 6H), 1.45 (s, 9H), 7.01 (s, 1H), 6.91-6.83 (m, 2H), 6.73-6.65

MS / FAB: 676 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 140] Synthesis of Compound [140]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 ~ 8.17 (m, 4H), 7.98 ~ 7.92 (m, 4H), 7.65 (t, 2H), 7.15 ~ 7.11 (m, 4H ), 7.01 (s, 1H), 6.83-6.65 (m, 8H), 1.95 (s, 6H)

MS / FAB: 660 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 141] Synthesis of Compound [141]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.65 (t, 1H), 8.52 (d, 1H), 8.22 ~ 8.14 (m, 4H), 7.98 ~ 7.92 (m, 4H), (M, 3H), 7.19-7.11 (m, 5H), 7.01 (s, 1H), 6.91-6.73 1.95 (s, 6 H), 1.45 (s, 9 H)

MS / FAB: 810 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 142] Synthesis of Compound [142]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.65 (t, 1H), 8.52 (d, 1H), 8.22 ~ 8.14 (m, 4H), 7.98 ~ 7.92 (m, 4H), 2H), 6.73 (t, 2H), 7.71-7.64 (m, 4H) 6.65 (m, 3H), 1.95 (s, 6H), 1.45 (s, 9H)

MS / FAB: &^lt; / RTI ^& gt ^; 853 (M ⁺ )

[Synthesis Example 143] Synthesis of compound [143]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.65 (t, 1H), 8.52 (d, 1H), 8.22 ~ 8.14 (m, 4H), 7.98 ~ 7.92 (m, 4H), 2H), 7.15-7.11 (m, 4H), 6.98-6.93 (m, 11H), 1.95 (s, 6H)

MS / FAB: 803 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 144] Synthesis of compound [144]

^{1 H NMR (300 MHz, CDCl} 3) δ 9.03 (s, 2H), 8.22 (s, 2H), 7.98 ~ 7.92 (m, 4H), 7.30 ~ 7.25 (m, 6H), 7.15 ~ 7.12 (m, 2H ), 7.01 (s, 1H), 6.91-6.83 (m, 3H), 6.73-6.65 (m, 7H)

MS / FAB: 674 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 145] Synthesis of Compound [145]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.18 ~ 7.05 (m, 6H), 6.95 ~ 6.92 (m, 2H ), 6.81 (m, 2H), 6.71-6.62 (m, 3H), 6.53-6.45 (m, 5H)

MS / FAB: 699 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 146] Synthesis of Compound [146]

¹ H NMR (300 MHz, CDCl ₃ )? 8.83 (d, 2H), 8.02 (d, 2H), 7.78-7. 72 (m, 4H), 7.10-6.81 ), 6.53-6.45 (m, 6H), 1.75 (s, 6H), 0.15 (s, 9H)

MS / FAB: 742 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 147] Synthesis of compound [147]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 ~ 7.05 (m, 5H), 6.95 ~ 6.92 (m, 2H ), 6.81 (s, 1H), 6.71-6.63 (m, 2H), 6.53-6.45 (m, 7H)

MS / FAB: 692 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 148] Synthesis of Compound [148]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 ~ 7.97 (m, 4H), 7.78 ~ 7.72 (m, 4H), 7.45 (t, 2H), 7.05 (d, 2H), (M, 2H), 6.81 (s, 1H), 6.63-6.45 (m, 8H)

MS / FAB: 676 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 149] Synthesis of Compound [149]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.02 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), 6H), 0.15 (s, 9H), 7.51-7.45 (m, 3H), 7.10-6.92 (m, 8H)

MS / FAB: 826 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 150] Synthesis of Compound [150]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.02 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), 2H), 6.81-6.79 (m, 2H), 6.71-6.63 (m, 2H), 6.53-6.45 (m, , 5H), 1.75 (s, 6H), 0.15 (s, 9H)

MS / FAB: 869 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 151] Synthesis of compound [151]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.02 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), 2H), 6.81-6.43 (m, 11H), 1.75 (s, 6H), 0.15 (s, 9H), 7.51-7.45 (m, 3H)

MS / FAB: 819 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 152] Synthesis of Compound [152]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.79 ~ 7.72 (m, 5H), 7.56 (d, 1H), 7.28 ~ 6.92 (m, 10H), 2H), 6.53-6.45 (m, 5H), 6.29 (d, 1H), 1.75 (s, 6H)

MS / FAB: 765 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 153] Synthesis of compound [153]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.27 (d, 2H), 7.10 (t, 4H), 6.95 ~ 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 7H)

MS / FAB: 670 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 154] Synthesis of compound [154]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.29 (d, 2H), 7.10 (t, 4H), 6.95 ~ 2H), 6.81 (s, 1H), 6.71-6.63 (m, 5H), 6.53-6.45 (m,

MS / FAB: 627 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 155] Synthesis of compound [155]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.89 (m, 4H), 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 7H)

MS / FAB: 620 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 156] Synthesis of Compound [156]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.18 ~ 7.10 (m, 6H), 6.95 ~ 6.92 (m, 2H ), 6.81 (m, 2H), 6.71-6.62 (m, 4H), 6.53-6.45 (m, 5H)

MS / FAB: 627 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 157] Synthesis of compound [157]

¹ H NMR (300 MHz, CDCl ₃ )? 8.83 (d, 2H), 8.02 (d, 2H), 7.78-7.72 (m, 4H), 7.10-6.84 ), 6.53-6.45 (m, 6H), 1.75 (s, 6H)

MS / FAB: 670 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 158] Synthesis of Compound [158]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 ~ 7.08 (m, 5H), 6.95 ~ 6.92 (m, 2H ), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 7H)

MS / FAB: 620 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 159] Synthesis of Compound [159]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.72 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.92 (m, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45 (m, 5H)

MS / FAB: 607 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 160] Synthesis of Compound [160]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.02 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), 2H), 6.81-6.43 (m, 12H), 1.75 (s, 6H), 7.51-7.45 (m, 3H)

MS / FAB: 746 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 161] Synthesis of Compound [161]

¹ H NMR (300 MHz, CDCl ₃ )? 8.92 (m, 2H), 8.11? 8.03 (m, 4H), 7.87-7.81 2H), 6.90 (s, 1H), 6.80-6.72 (m, 3H), 6.62-6.44 (m, 5H), 1.84

MS / FAB: 603 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 162] Synthesis of compound [162]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.45 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 (m, 4H), 7.04 ~ (S, 6H), 6.98 (m, 2H), 6.90 (s,

MS / FAB: 603 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 163] Synthesis of compound [163]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.53 ~ 7.40 (m, 7H), 7.19 (m, 4H), 2H), 6.90 (s, 1H), 6.80-6.44 (m, 10H), 1.84 (s, 6H)

MS / FAB: 678 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 164] Synthesis of Compound [164]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 5H), 7.61 ~ 7.54 (m, 2H), 7.37 (m, 1H), 2H), 6.90 (s, 1H), 6.80-6.72 (m, 4H), 6.62-6.44 (m, 6H), 1.84 1.71 (s, 6 H)

MS / FAB: 718 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 165] Synthesis of Compound [165]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.51 ~ 7.40 (m, 6H), 7.19 (m, 4H), (M, 2H), 6.88-6.72 (m, 6H), 6.62-6.44 (m, 6H)

MS / FAB: 678 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 166] Synthesis of Compound [166]

¹ H NMR (300 MHz, CDCl ₃ )? 8.92 (m, 2H), 8.11-8.01 (m, 4H), 7.87-7.81 (m, 4H), 7.56-7.52 6H), 7.19 (m, 4H), 7.04-6.97 (m, 3H), 6.90 (s,

MS / FAB: 652 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 167] Synthesis of Compound [167]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.82 ~ 7.73 (m, 8H), 7.49 ~ 7.48 (m, 2H), 7.35 (m, 1H), 2H), 6.90 (s, 1H), 6.80-6.72 (m, 3H), 6.62-6.44 (m, 5H), 1.84

MS / FAB: 652 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 168] Synthesis of Compound [168]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.54 (m, 1H), 8.41 (m, 1H), 8.11 ~ 8.03 (m, 4H), 7.87 ~ 7.81 (m, 4H), (M, 3H), 7.19-7.16 (m, 5H), 7.08-7.01 (m, 3H), 6.90

MS / FAB: 753 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 169] Synthesis of Compound [169]

¹ H NMR (300 MHz, CDCl ₃ )? 8.92 (m, 2H), 8.84 (m, 1H), 8.41 2H), 6.89-6.72 (m, 6H), 6.62-6.44 (m, 5H), 1.84 (s, 6H)

MS / FAB: 796 (M ^< ^{+ &} gt ^; ) [

[Synthesis Example 170] Synthesis of Compound [170]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 ~ 8.89 (m, 3H), 8.49 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.19 (m, 4H), 2H), 6.90 (s, 1H), 6.80-6.72 (m, 3H), 6.62-6.44 (m, 5H), 1.84

MS / FAB: 604 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 171] Synthesis of Compound [171]

¹ H NMR (300 MHz, CDCl ₃ )? 8.92-8.51 (m, 2H), 8.11 (m, 2H), 7.87-7.81 ), 7.05-7.01 (m, 4H), 6.90 (s, IH), 6.84-6.80 (m, 5H), 6.72 (m, s, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 907 (M ⁺ )

[Synthesis Example 172] Synthesis of Compound [172]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.54 (m, 4H), 8.41 (m, 4H), 8.11 ~ 8.03 (m, 10H), 8.41 ~ 7.81 (m, 4H), (M, 2H), 7.05-7.01 (m, 4H), 6.90 (s, 1H), 6.84-6.72 m, 1 H), 1.84 (s, 6 H)

MS / FAB: &^lt; / RTI ^& gt ^; 1107 (M ⁺ )

[Synthesis Example 173] Synthesis of Compound [173]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.99 ~ 7.81 (m, 16H), 7.72 (m, 4H), 7.58 ~ 7.57 (m, 12H), (M, 2H), 6.54 (m, 1H), 1.84 (s, 1H), 6.84 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 1107 (M ⁺ )

[Synthesis Example 174] Synthesis of Compound [174]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.54 ~ 8.21 (m, 4H), 8.41 (m, 4H), 8.11 ~ 8.03 (m, 10H), 7.87 ~ 7.81 (m, 4H ), 7.60 ~ 7.54 (m, 12H), 7.24 ~ 7.19 (m, 18H), 7.05 ~ 7.01 (m, 4H), 6.90 ), 6.62 (m, 2H), 6.54 (m, IH), 1.84 (s, 6H)

MS / FAB: 1411 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 175] Synthesis of Compound [175]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.99 ~ 7.81 (m, 16H), 7.72 (m, 4H), 7.58 ~ 7.57 (m, 12H), 1H), 6.62 (m, 2H), 6.54 (m, 2H), 7.24-7.19 (m, m, 1 H), 1.84 (s, 6 H)

MS / FAB: 1411 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 176] Synthesis of Compound [176]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.65 (m, 6H), 7.53 ~ 7.40 (m, 24H), (M, 2H), 7.04 (m, 2H), 6.90 (s, 1H), 6.80-6.62

MS / FAB: 1059 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 177] Synthesis of Compound [177]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.54 (d, 4H), 8.41 (d, 4H), 8.11 ~ 8.03 (m, 10H), 7.87 ~ 7.81 (m, 4H), 2H), 7.09-7.01 (m, 2H), 6.90 (s, 1H), 6.80-6.44 (m, 9H), 1.84

MS / FAB: &^lt; / RTI ^& gt ^; 1259 (M ⁺ )

[Synthesis Example 178] Synthesis of Compound [178]

¹ H NMR (300 MHz, CDCl ₃ )? 8.92 (m, 2H), 8.11 (m, 2H), 7.87-7.81 (m, 4H), 7.51-7.40 (M, 3H), 6.90 (s, 1H), 6.84-6.44 (m, 10H), 1.84

MS / FAB: 754 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 179] Synthesis of Compound [179]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.54 (d, 2H), 8.41 (d, 2H), 8.11 ~ 8.03 (m, 6H), 7.87 ~ 7.81 (m, 4H), 6H), 7.19 (m, 4H), 7.05-7.01 (m, 3H), 6.90 (s,

MS / FAB: &^lt; / RTI ^& gt ^; 855 (M ⁺ )

[Synthesis Example 180] Synthesis of Compound [180]

¹ H NMR (300 MHz, CDCl ₃ )? 8.92 (m, 2H), 8.11 (m, 2H), 7.99-7.72 (m, 12H), 7.58-7.57 (M, 3H), 6.90 (s, 1H), 6.84-6.44 (m, 10H), 1.84

MS / FAB: &^lt; / RTI ^& gt ^; 855 (M ⁺ )

[Synthesis Example 181] Synthesis of Compound [181]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.54 (d, 2H), 8.41 (d, 2H), 8.11 ~ 8.03 (m, 6H), 7.87 ~ 7.81 (m, 4H), (M, 4H), 6.62 (m, 2H), 6.62 (m, 2H), 7.60-7.54 (m, 6H), 7.24-7.19 6.54 (d, 1 H), 1.84 (s, 6 H)

MS / FAB: &^lt; / RTI ^& gt ^; 1007 (M ⁺ )

[Synthesis Example 182] Synthesis of Compound [182]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.99 ~ 7.72 (m, 12H), 7.58 ~ 7.57 (m, 6H), 7.24 ~ 7.19 (m, 12H ), 7.06-7.01 (m, 3H), 6.90 (s, 1H), 6.84-6.44 (m,

MS / FAB: &^lt; / RTI ^& gt ^; 1007 (M ⁺ )

[Synthesis Example 183] Synthesis of Compound [183]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.65 (s, 3H), 7.53 ~ 7.40 (m, 12H), 2H), 6.90 (s, 1H), 6.80-6.44 (m, 10H), 1.84 (s, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 831 (M ⁺ )

[Synthesis Example 184] Synthesis of Compound [184]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.54 (m, 2H), 8.41 (m, 2H), 8.11 ~ 8.03 (m, 6H), 7.87 ~ 7.81 (m, 4H), 2H), 6.90 (s, 1H), 6.80-6.44 (m, 10H), 1.84 (s, 6H)

MS / FAB: 931 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 185] Synthesis of compound [185]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.92 ~ 7.76 (m, 10H), 7.62 ~ 7.53 (m, 8H), 7.37 (m, 2H), 2H), 6.90 (s, 1H), 6.80-6.44 (m, 9H), 1.84 (s, 6H), 1.71

MS / FAB: &^lt; / RTI ^& gt ^; 987 (M ⁺ )

[Synthesis Example 186] Synthesis of Compound [186]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.92 ~ 7.76 (m, 7H), 7.62 ~ 7.53 (m, 4H), 7.37 ~ 7.19 (m, 6H ), 7.04-7.11 (m, 2H), 6.90 (s, 1H), 6.80-6.44 (m,

MS / FAB: 795 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 187] Synthesis of Compound [187]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.92 ~ 7.76 (m, 16H), 7.62 ~ 7.54 (m, 8H), 7.37 (m, 4H), 1H), 6.62 (m, 2H), 6.54 (m, 2H), 7.27-7.19 (m, 6H), 7.05-7.01 m, 1 H), 1.84 (s, 6 H), 1.71 (s, 24 H)

MS / FAB: 1371 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 188] Synthesis of Compound [188]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.92 ~ 7.76 (m, 10H), 7.62 ~ 7.54 (m, 4H), 7.37 (m, 2H), (M, 5H), 6.62-6.44 (m, 5H), 1.84 (s, 6H), 7.24-7.19 (m, 6H) 1.71 (s, 12H)

MS / FAB: &^lt; / RTI ^& gt ^; 987 (M ⁺ )

[Synthesis Example 189] Synthesis of Compound [189]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 4H), 7.87 ~ 7.81 (m, 10H), 7.70 (m, 8H), 7.19 (m, 2H), 7.04 ~ 2H), 6.62 (m, 2H), 6.54 (m, 1H), 1.84 (s, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 851 (M ⁺ )

[Synthesis Example 190] Synthesis of Compound [190]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 4H), 7.87 ~ 7.81 (m, 7H), 7.70 ~ 7.49 (m, 13H), 7.28 ~ 7.19 (m, 3H ), 7.04-7.01 (m, 3H), 6.90 (s, IH), 6.80-6.72 (m, 2H), 6.62 s, 6H)

MS / FAB: 892 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 191] Synthesis of Compound [191]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.32 ~ 7.01 (m, 21H), 6.90 (s, 1H), 6.80-6.72 (m, 5H), 6.62-6.50 (m, 7H), 1.84 (s, 6H)

MS / FAB: 845 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 192] Synthesis of Compound [192]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.92 (m, 2H), 8.11 (m, 2H), 7.87 ~ 7.81 (m, 4H), 7.54 ~ 7.36 (m, 15H), 7.20 ~ 7.19 (m, 6H 2H), 6.90 (s, 1H), 6.80-6.72 (m, 5H), 6.62-6.44 (m, 5H), 1.84

MS / FAB: 861 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 193] Synthesis of Compound [193]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.94 (d, 2H), 7.84 ~ 7.61 (m, 20H), 7.41 (t, 4H), 7.31 ( (m, 2H), 7.10 (t, 2H), 6.95-6.92 (m, 4H), 6.81 , 1.75 (s, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 1003.23 (M ⁺ )

[Synthesis Example 194] Synthesis of Compound [194]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.94 (d, 1H), 7.84 ~ 7.61 (m, 12H), 7.44 ~ 7.31 (m, 10H), 6H), 6.45 (d, IH), 1.75 (s, 6H), 6.90 (s,

MS / FAB: 879.10 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 195] Synthesis of Compound [195]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.94 (d, 1H), 7.84 ~ 7.61 (m, 12H), 7.41 (t, 2H), 7.31 ( (m, 3H), 6.75 (m, 3H), 6.75 (m, 3H) 6H)

MS / FAB: 803 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 196] Synthesis of Compound [196]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 ~ 7.96 (m, 4H), 7.78 ~ 7.72 (m, 5H), 7.61 (s, 4H), 7.10 (t, 4H), (M, 3H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45

MS / FAB: 751.91 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 197] Synthesis of Compound [197]

¹ H NMR (300 MHz, CDCl ₃ )? 8.83 (d, 2H), 8.02-7.96 (m, 4H), 7.78-7.72 2H), 6.45 (d, IH), 6.71 (d, IH), 7.30 (s, 1.75 (s, 6H)

MS / FAB: 1010.30 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 198] Synthesis of Compound [198]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.91 (d, 1H), 7.78 ~ 7.71 (m, 6H), 7.61 (s, 4H), 7.10 ( (m, 3H), 6.75-6.92 (m, 3H), 6.81 (s,

MS / FAB: 794.90 (M ^< ^{+ &} gt ^; ).

[Preparation Example 199] Synthesis of compound [199]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 ~ 8.00 (m, 3H), 7.78 ~ 7.72 (m, 4H), 7.61 ~ 7.53 (m, 5H), 7.43 (t, 1H ), 7.10 (t, 4H), 6.95-6.92 (m, 3H), 6.81 (s, IH), 6.71-6.63

MS / FAB: 744.89 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 200] Synthesis of Compound [200]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.94 (d, 1H), 7.84 ~ 7.72 (m, 6H), 7.61 (s, 4H), 7.10 ( (m, 3H), 6.75-6.92 (m, 3H), 6.81 (s,

MS / FAB: 808.03 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 201] Synthesis of Compound [201]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.16 (s, 2H), 8.02 (d, 2H), 7.78 ~ 7.61 (m, 24H), 7.41 ~ 7.31 (m, 18H), 2H), 6.45 (d, 1H), 1.75 (d, 2H), 7.14 (m, 2H) s, 6H)

MS / FAB: 1307.62 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 202] Synthesis of Compound [202]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.16 (s, 1H), 8.02 (d, 2H), 7.78 ~ 7.61 (m, 14H), 7.41 ~ 7.31 (m, 9H), (M, 2H), 6.81 (s, 1H), 6.71-6.63 (m, 3H), 6.53-6.45

MS / FAB: 955.19 (M ^< ^{+ &} gt ^; ).

[Synthesis Example 203] Synthesis of Compound [203]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.02 (d, 2H), 7.78 ~ 7.69 (m, 7H), 7.41 (t, 2H), 7.31 (t, 1H), 7.10 ( 2H), 6.75 (d, IH), 1.75 (s, 6H), 6.75 (m,

MS / FAB: 511.65 (M ^< ^{+ &} gt ^; ).

[Preparation 204] Synthesis of Compound [204]

^{1 H NMR (300 MHz, CDCl} 3) δ 8.83 (d, 2H), 8.16 (s, 1H), 8.02 (d, 2H), 7.94 (d, 1H), 7.78 ~ 7.61 (m, 14H), 7.41 ~ 2H), 6.75 (d, 1H), 1.75 (s, 2H), 7.31 (m, 6H) 6H)

MS / FAB: 787.98 (M ^< ^{+ &} gt ^; ).

Comparative Example 1

A compound represented by the following formula (a) is used as a fluorescent blue host, and a compound b represented by the following formula (b) is used as a fluorescent blue dopant, and 2-TNATA (4,4 ' 2-yl) -N-phenylamino) -triphenylamine was used as a hole injection layer material and α-NPD (N, N'-di (naphthalene- (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) was used as an organic light emitting device having the following structure: ITO / 2-TNATA (80 nm) /? -NPD ) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate into 50 mm × 50 mm × 0.7 mm size, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, Washed and used. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound (a) represented by Formula (a) and compound (b) represented by Formula (b) (5% doped) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to form an organic light emitting device as shown in the second table group. This was referred to as Comparative Sample 1.

Examples 1 to 204

In Comparative Example 1, except for using Compound 1 as a light emitting layer fluorescent dopant compound instead of compound b as a light emitting layer fluorescent dopant compound in each of Examples 1 to 204 shown in the above Synthesis Example, (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / (30 nm) / [compound a + one of the fluorescent dopants 1 to 204 (5%)] (30 nm) / ITO / 2-TNATA ) / Al (60 nm). These were referred to as Samples 1 to 204, respectively.

Evaluation Example 1: Evaluation of luminescence characteristics of Comparative Sample 1 and Samples 1 to 204

The emission luminance, the luminous efficiency, and the emission peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for the comparative sample 1 and the samples 1 to 204, )]. The samples showed blue emission peak values in the range of 448 to 463 nm.

[Second group (group)]

Samples 1 to 204 exhibited improved luminescence properties as compared to Comparative Sample 1, as shown in the above [second group (s)].

Evaluation Example 2: Evaluation of life characteristics of Comparative Sample 1 and Samples 1 to 204

The comparative sample 1 and samples 1 to 204 were measured for time to reach 97% of life on the basis of 3000 nits by using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ Group)].

[Group 3]

Samples 1 to 204 exhibited improved lifespan characteristics as compared to Comparative Sample 1, as shown in the above [third group (group)] .

Claims (10)

An organic light-emitting compound represented by the following formula (F):
[Chemical Formula F]

In formula (F) above,
R ¹ is selected from the group consisting of a C ₅ -C ₄₀ aryl group, a C ₅ -C ₄₀ heteroaryl group, a C ₃ -C ₄₀ cycloalkyl group, and a C ₃ -C ₄₀ heterocycloalkyl group;
R ² is a hydrogen atom, a deuterium atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C _{3 to} C ₄₀ heterocycloalkyl group ≪ / RTI >
X is selected from the group consisting of O, S, Se, NY ¹ , CY ² Y ³ , CY ² Y ³ -CY ² Y ³ , CY ² = CY ³ , and SiY ² Y ³ ;
Y ¹ , Y ² and Y ³ are each independently a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and C _{C 3 to C 40} heterocycloalkyl groups, or Y ² and Y ³ may be bonded to each other to form a C ₅ to C ₄₀ aryl group, a C _{5 to} C ₄₀ heteroaryl group, a C _{3 to} C ₄₀ cycloalkyl group, and a C ₃ -C ₄₀ heterocycloalkyl group;
The heteroaryl or heterocycloalkyl used in the definitions of the substituents R ¹ , R ² , Y ¹ , Y ² , and Y ³ may include 1 to 4 hetero atoms selected from O, S, N, and Si ,
The aryl, cycloalkyl, heteroaryl, or heterocycloalkyl used in the definition of the above substituents R ¹ , R ² , Y ¹ , Y ² , and Y ³ is each monocyclic or is substituted with 2 to 7 rings a multi-ring (polycyclic) consisting of the monocyclic or multiple ring deuterium (D), halo, hydroxy, cyano, nitro, C ₁ ~C ₄₀ alkyl, C ₁ ~C ₄₀ haloalkyl, C ₁ ~C ₄₀ Hyde hydroxyalkyl, C ₁ ~C ₄₀ alkoxy, amino, C ₁ ~C ₄₀ alkylamino, di (C ₁ ~C ₄₀ alkyl) amino, C ₅ ~C ₄₀ alkylamino, di (C ₅ ~C ₄₀ aryl) amino, mono (C ₁ ~C ₄₀ alkyl) silyl, di (C ₁ ~C ₄₀ alkyl) silyl, tri (C ₁ ~C ₄₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C (C ₅ -C ₄₀ aryl) silyl, tri (C ₅ -C ₄₀ aryl) silyl, C ₅ -C ₄₀ aryl, C ₅ -C ₄₀ heteroaryl, C ₃ -C ₄₀ cycloalkyl, and C ₃ -C ₄₀ heterocycloalkyl. Substituted or unsubstituted with a substituent selected from May hwandoel, also aryl, among the above substituents is deuterium (D), halo, hydroxy, cyano, nitro, C ₁ ~C ₄₀ alkyl, C ₁ ~C ₄₀ haloalkyl, C ₁ ~C ₄₀ hydroxyalkyl , C ₁ ~C ₄₀ alkoxy, amino, C ₁ ~C ₄₀ alkylamino, di (C ₁ ~C ₄₀ alkyl) amino, C ₅ ~C ₄₀ alkylamino, di (C ₅ ~C ₄₀ aryl) amino, mono ( C ₁ ~C ₄₀ alkyl) silyl, di (C ₁ ~C ₄₀ alkyl) silyl, tri (C ₁ ~C ₄₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C ₄₀ aryl ) silyl, tri (C ₅ ~C ₄₀ aryl) silyl, from C ₅ ~C ₄₀ aryl, C ₅ ~C ₄₀ heteroaryl, C ₃ ~C ₄₀ cycloalkyl, and C ₃ ~C ₄₀ heterocycloalkyl group consisting of alkyl Which may be substituted or unsubstituted with the selected substituents,
R ³ is:

Or an NR ³¹ R ³² group,
Wherein R ³ In this case, the aryl group, the aryl group of R ^a and R ^b each independently is hydrogen, or deuterium (D), halo, hydroxy, cyano, nitro, C ₁ ~C ₁₀ alkyl, mono (C ₅ -C ₁₀ aryl) alkyl, di (C ₅ -C ₁₀ aryl) alkyl, tri (C ₅ -C ₁₀ aryl) alkyl, C ₁ -C ₁₀ haloalkyl, C ₁ -C ₁₀ hydroxyalkyl, C ₁ ~C ₁₀ alkoxy, amino, C ₁ ~C ₁₀ alkylamino, di (C ₁ ~C ₁₀ alkyl) amino, C ₅ ~C ₁₀ alkylamino, di (C ₅ ~C ₁₀ aryl) amino, mono (C ₁ ~C ₁₀ alkyl) silyl, di (C ₁ ~C ₁₀ alkyl) silyl, tri (C ₁ ~C ₁₀ alkyl) silyl group, a mono (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C ₄₀ aryl) silyl , tri (C ₅ ~C ₄₀ aryl) silyl, C ₅ ~C ₁₀ aryl, C ₅ ~C ₁₀ heteroaryl, C ₃ ~C ₁₀ cycloalkyl, and C ₃ ~C ₁₀ heterocycloalkyl selected from the group consisting of alkyl 1 To 5 substituents,
When R ³ is -NR ³¹ R ³² , R ³¹ and R ³² each independently represent a hydrogen atom, a C ₁ -C ₁₀ alkyl group,

≪ / RTI > Wherein X ₂ is selected from the group consisting of O, S, and NY ²¹ Y ²² CY ^23, wherein Y ^21, Y ^22, and Y ²³ each independently represent a hydrogen atom, C ₁ ~C ₁₀ alkyl group, and a C ₅ ~ selected from the group consisting of a C ₁₀ aryl, and; Wherein R ^a and R ^b are each independently a hydrogen atom or a group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, nitro, C ₁ -C ₁₀ alkyl, mono (C ₅ -C ₁₀ aryl) C ₅ ~C ₁₀ aryl) alkyl, tri (C ₅ ~C ₁₀ aryl) alkyl, C ₃ ~C ₁₀ cycloalkyl, C ₃ ~C ₁₀ heterocycloalkyl, C ₁ ~C ₁₀ haloalkyl, C ₁ ~C ₁₀ hydroxyalkyl, C ₁ ~C ₁₀ alkoxy, amino, C ₁ ~C ₁₀ alkylamino, di (C ₁ ~C ₁₀ alkyl) amino, C ₅ ~C ₁₀ alkylamino, di (C ₅ ~C ₁₀ aryl) amino , mono (C ₁ ~C ₁₀ alkyl) silyl, di (C ₁ ~C ₁₀ alkyl) silyl, tri (C ₁ ~C ₁₀ alkyl) silyl group, a mono (C ₅ ~C ₁₀ aryl) silyl, di (C ₅ ~ C ₁ -C ₁₀ aryl) silyl, tri (C ₅ -C ₁₀ aryl) silyl, C ₅ -C ₁₀ aryl, and C ₅ -C ₁₀ heteroaryl, or
And R < ³¹ > and R < ³² > are bonded to each other together with the nitrogen atom to which they are bonded,

To form a condensed ring. The method according to claim 1,
Wherein R ¹ is a phenyl group, a naphthalenyl group, an indenyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group, a benzofluorenyl group, a pyrenyl group, a thienyl group, a furyl group, a pyrrolyl group, A thiazolyl group, an isothiazolyl group, an isoxazolyl group, an indolyl group, an indazolyl group, a carbazolyl group, a hexahydrophene group, a quinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an imidazolyl group, a pyrazolyl group, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy, aryloxy, aryloxy, aryloxy, aryloxy, aryloxy, C ₁₀ haloalkyl, C ₁ ~C ₁₀ hydroxyalkyl, C ₁ ~C ₁₀ alkoxy, amino, C ₁ ~C ₁₀ alkylamino, di (C ₁ ~C ₁₀ alkyl) amino, C ₅ ~C ₁₀ arylamino, di (C ₅ ~C ₁₀ aryl) amino, mono (C ₁ ~C ₁₀ alkyl) silyl, di (C ₁ ~C ₁₀ alkyl) silyl, tri (C ₁ ~C ₁₀ alkyl) silyl, Mo No (C ₅ ~C ₄₀ aryl) silyl, di (C ₅ ~C ₄₀ aryl) silyl, tri (C ₅ ~C ₄₀ aryl) silyl, C ₅ ~C ₁₀ aryl, C ₅ ~C ₁₀ heteroaryl, C ₃ C 1 to C ₁₀ cycloalkyl, and C _{3 to} C ₁₀ heterocycloalkyl is substituted or unsubstituted. 3. The method of claim 2,
Wherein R < ^{1 &}

And X ₁ is selected from the group consisting of NY ¹¹ and CY ¹² Y ¹³ , wherein Y ¹¹ , Y ¹² , and Y ¹³ are each independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a n-propyl group , An isopropyl group, an n-butyl group, a tert-butyl group, a hexyl group, and a phenyl group; Wherein R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are each independently a hydrogen atom or a group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, methyl, ethyl, Butyl, tert-butyl, hexyl, trifluoromethyl, dichloroethyl, difluoroethyl, tetrafluoroethyl, methoxy, ethoxy, tert-butoxy, methylsilyl, dimethylsilyl, trimethylsilyl, phenyl, Naphthalenyl, 2-naphthalenyl, and 2-naphthalenyl. The method according to claim 1,
Wherein R ² is a hydrogen atom, or is a deuterium atom, or an organic light emitting compound, characterized in that 1 to 4 substituents selected from the group consisting of a C ₁ ~C ₁₀ alkyl group. delete The method according to claim 1,
Wherein R < ^{3 &}

Wherein R ^a and R ^b are each independently a hydrogen atom or an aryl group selected from the group consisting of deuterium (D), halo, hydroxy, cyano, methyl, ethyl, Butyl, tert-butyl, hexyl, triphenylmethyl, trifluoromethyl, dichloroethyl, difluoroethyl, tetrafluoroethyl, methoxy, ethoxy, tert-butoxy, methylsilyl, dimethylsilyl, Phenyl, 1-naphthalenyl, 2-naphthalenyl, naphthalen-1-yl-phenyl, and naphthalen-2-yl- Luminescent compound. delete delete The method according to claim 1,
An organic electroluminescent compound characterized in that it is selected from the group consisting of the following compounds 1 to 204:

A first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode,
Wherein the organic layer comprises an organic light-emitting compound according to any one of claims 1 to 4, 6 and 9.