KR20150144121A - An organoelectro luminescent compounds and organoelectro luminescent device using the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by chemical formula 1, and to an organic electroluminescent device comprising the same. The organic electroluminescent device applying the organic light emitting compound according to the present invention is driven with a low voltage, improved light emitting efficiency, and high durability compared with a device applying an existing material.

Description

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

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

An organic light emitting phenomenon is a phenomenon that converts electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not yet been sufficiently developed. Therefore, the development of new materials is continuously required.

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic light emitting compound and an organic electroluminescent device including the organic light emitting compound, which can be driven at a lower voltage than conventional materials and have improved luminous efficiency and long life will be.

In order to solve the above-described problems, the present invention provides an organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

The structure and the substituents of the above formula (1) will be described later in detail.

Further, the present invention is a liquid crystal display device comprising a first electrode, a second electrode facing the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, The organic electroluminescent device includes at least one organic electroluminescent compound.

The organic electroluminescent device employing the organic electroluminescent compound according to the present invention has low voltage driving, improved luminous efficiency and long life time characteristics as compared with a device using a conventional material.

1 is a conceptual diagram illustrating an organic electroluminescent device having a multilayer structure according to an embodiment of the present invention.

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

One aspect of the present invention relates to a novel organic electroluminescent compound represented by the following Chemical Formula 1, wherein various substituents are basically bonded to a core structure in which a spiro bond is formed in a 6-ring-5-ring-5-ring- Core structures and substituent groups are realized. In addition, the core structure may have a core structure in which the substituents thereof are connected to each other with adjacent substituents so that at least one ring is further condensed.

[Chemical Formula 1]

The core structure of Formula 1 and the various substituents attached thereto will now be described.

In the above formula (1), * of L is bonded to each of A to form a ring. Thereby forming a core structure in which a spiro bond is formed in a 6-ring-5-ring-5-ring-6 ring.

Z is C, Si or Ge, X and Y each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C3- Or a substituted or unsubstituted aryl group having 5 to 50 carbon atoms. Provided that both X and Y are simultaneously substituted or unsubstituted aryl groups having 5 to 50 carbon atoms.

Q is a linking group connecting X and Y, and is a single bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms or a substituted or unsubstituted group having 2 to 30 carbon atoms Alkenylene group.

Also, at least one carbon atom in X, Y and Q may be substituted with a heteroatom.

According to the definition of X, Y, Z and Q, the formula (1) according to the present invention has a spiro structure. Specifically, indene, benzosilole or benzogermole is a cyclo An alkyl group or an aryl group, a heteroaryl group, a cycloalkyl group, and a heterocycloalkyl group together with a cycloalkyl group to which a fused group is fused.

W is CR ₁ R ₂ , SiR ₃ R ₄ , GeR ₅ R ₆ , NR ₇ , O, S, Se, Te or BR ₈ ; R ₁ and R ₂ , R ₃ and R ₄ , R ₅ and R ₆ May be connected to each other to form a ring.

Wherein R ₁ to R ₈ and E are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 5 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, , A phosphoryl group, an amino group, a thiol group, a cyano group, a hydroxyl group, a nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group, ], [Formula E], [Formula F] and [Formula G] are respectively as follows. The adjacent E may be bonded to each other to form a ring.

(E) [Chemical Formula F]

In the above formulas (E) to (F)

A 1 to A 2 are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms.

In the above-mentioned A1 to A2 Two adjacent ones of the substituents may be bonded to L to form a condensed ring (* denotes a binding site).

In the above formulas (E) to (F) and L,

Each independently A3 is the A1 to A2 defining the same and, Y, Z, W, and Q is the _{NR 9, CR 10 R 11,} O, S, SiR 12 R 13, GeR 14 R 15, BR 16, PR 17 , C = O, Se, Te or Po, and at least one of Y, Z, W and Q is NR ₉ (provided that n is an integer of 0 to 3).

[Formula G]

In the above formula (G)

Y and Q are each independently NR ₂₆ , CR ₂₇ R ₂₈ , O, S, SiR ₂₉ R ₃₀ , GeR ₃₁ R ₃₂ , BR ₃₃ , PR ₃₄ , C═O, Se, 1 to 3).

The adjacent two of R ₁₈ to R ₂₅ may be connected to form an alicyclic hydrocarbon ring, a monocyclic or polycyclic aromatic hydrocarbon ring, and the carbon atom of the alicyclic or aromatic hydrocarbon ring may be N, S, O, Se, Te, Po, NR _{35 ,} SiR ₃₆ R ₃₇ , GeR ₃₈ R ₃₉ , PR ₄₀ and BR ₄₁ .

R ₉ to R ₄₁ have the same definitions as R ₁ to R ₈ , and R ₁₀ , R _{11 ,} R ₁₂ and R _{13 ,} R ₁₄ and R _{15 ,} R ₂₇ and R _{28 ,} R ₂₉ and R _{30 ,} R ₃₁ and R _{32 ,} R ₃₆ and R _{37 , and} R ₃₈ and R ₃₉ may be linked to each other to form a ring.

The 'substituted' in the above 'substituted or unsubstituted' means a case where X, Y, Q, A 1 to A 3, R ₁ to R ₄₁ and substituents thereof are further substituted by one or more substituents , Said one or more substituents are specifically selected from the group consisting of deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, Or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms , A substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a cyano group, A halogen group, a selenium group, a tellurium group, an amide group, an ether group, an ester group, and a group represented by the above formula (E), (F)

The aryl group contained in the organic luminescent compound according to the present invention includes an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms , And when a substituent is present in the aryl group, it may be fused with an adjacent substituent to further form a ring.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, , Aromatic groups such as a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylene group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group.

The aryl group may be further substituted with at least one substituent selected from the substituents described in the definitions of R ₁ to R _5. More specifically, at least one hydrogen atom of the aryl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" are independently of each other an alkyl group having 1 to 10 carbon atoms, An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, A heteroaryl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, .

The heteroaryl group contained in the organic luminescent compound according to the present invention may be any one selected from the following Structural Formulas 1 to 10:

[Structural formula 1] [Structural formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural formula 8] [Structural Formula 9] [Structural Formula 10]

In the above Structural Formulas 1 to 10,

T ₁ to T ₁₂ are the same or different from each other and each independently represent C (R ₄₂ ), C (R ₄₃ ) (R ₄₄ ), N, N (R ₄₅ ), O, S, R ₄₆ ) (R ₄₇ ) and Ge (R ₄₈ ) (R ₄₉ ), and T ₁ to T ₁₂ may not all be carbon atoms at the same time, and R ₄₂ to R ₄₉ may be the same A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C30 aryl group, and a substituted or unsubstituted C1- Or a heteroaryl group having 2 to 30 carbon atoms with unsubstituted and hetero atoms O, N, S, or P;

The above-mentioned [formula 3] may include a compound represented by the following formula [3] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the above structural formula 3-1, T ₁ to T ₇ are the same as defined in [Structural formulas 1] to [Structural formula 10].

According to a preferred embodiment of the present invention, the above Structural Formulas 1 to 10 can be selected from the following Structural Formula 11.

[Structural Formula 11]

In the above structural formula 11,

X is the same as defined for R ₁ to R ₈ in the above formula (1), m is an integer of 1 to 11, and when m is 2 or more, plural Xs are the same as or different from each other, May be connected to substituents of the formulas [E], [F] and [G].

The organic luminescent compound of Formula 1 according to the present invention may be more specifically selected from the following Formulas 2 to 21, but the following specific compounds are specific examples of Formula 1 according to the present invention , Whereby the scope of the present invention is not limited thereto.

As described above, the organic luminescent compound according to the present invention can realize an organic luminescent compound having intrinsic characteristics of the introduced substituent as well as intrinsic properties of the core structure by introducing various substituent groups into the core structure represented by the formula (1) . For example, by introducing a substituent used for the hole injecting layer material, the hole transporting layer material, the light emitting layer material and the electron transporting layer material of the organic electroluminescent device into the core structure, a material meeting the requirements of each organic material layer can be realized.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, ] Of at least one organic light emitting compound according to the present invention.

That is, the organic electroluminescent device according to an embodiment of the present invention may have a structure including a first electrode, a second electrode, and an organic material layer disposed therebetween, and the organic electroluminescent device of Formula 1 according to the present invention Can be produced by using a conventional device manufacturing method and materials, except that the organic material layer is used for the organic material layer of the device.

The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. However, it is not so limited and may include fewer or greater numbers of organic layers.

Therefore, in the organic electroluminescent device of the present invention, the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, 1]. ≪ / RTI >

In the organic electroluminescent device of the present invention, the organic material layer may include at least one of an electron injecting layer, an electron transporting layer, and a layer simultaneously performing electron injection and electron transporting, 1]. ≪ / RTI >

Further, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1). Here, the compound represented by Formula 1 may be included as a host material in the light emitting layer. When the compound represented by Formula 1 is included as a host material in the light emitting layer, the light emitting layer may further include at least one dopant compound. As described above, in the present invention, a dopant material may be used for the light emitting layer in addition to the host. When the light emitting layer comprises a host and a dopant, the dopant content may be selected in the range of about 0.01 to about 20 parts by weight, based on 100 parts by weight of the host.

In the organic compound layer having such a multi-layer structure, the compound represented by the general formula (1) may be used in combination with a light-emitting layer, a layer which simultaneously transports holes and holes, a layer which simultaneously transports light and light, And the like.

Hereinafter, an embodiment of the organic electroluminescent device according to the present invention will be described in more detail with reference to FIG.

The organic electroluminescent device according to the present invention includes an anode 20, a hole transporting layer 40, an organic light emitting layer 50, an electron transporting layer 60, and a cathode (80), and if necessary, may further include a hole injection layer (30) and an electron injection layer (70). In addition, one or two intermediate layers may be further formed, Or an electron blocking layer may be further formed, and an organic layer having various functions may be further included depending on the characteristics of the device.

The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG.

First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, a substrate used in a typical organic electroluminescent device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injecting layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The material for the hole injection layer may be any material that is commonly used in the art besides the organic light emitting compound according to the present invention. Specific examples thereof include 2-TNATA [4,4 ', 4 "-tris ( 2-naphthylphenyl-phenylamino) -triphenylamine], NPD [N, N'-di (1-naphthyl) -N, -methylphenyl) -1,1'-biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'- -biphenyl-4,4'-diamine] or the like can be used.

The hole transport layer material is not particularly limited as long as it is commonly used in the art besides the organic light emitting compound according to the present invention. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenylbenzidine (? -NPD) or a mixture of N, N'-di (naphthalene-1-yl) Etc. may be used.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

Wherein a material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq _2, OXD-7, Liq and [Formula 501] to [Chemical Formula 507] either, but one that can be used is selected from, this limited It is not.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

(501) [502] ≪ EMI ID =

≪ EMI ID = ≪ EMI ID = ≪ EMI ID =

≪ EMI ID =

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

The electron transport layer material serves to stably transport electrons injected from an electron injection electrode, and besides the organic luminescent compound according to the present invention, a known electron transport material can be used. Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- materials such as olate: Bebq2), ADN, [Formula 401], [Formula 402], and oxadiazole derivatives PBD, BMD, BND and the like may be used.

TAZ BAlq

[Compound 401] [Compound 402] BCP

Further, the electron transporting layer used in the present invention can be used as the organometallic compound represented by the following formula (C) alone or in combination with the electron transporting layer material.

≪ RTI ID = 0.0 &

In the above formula (C)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond. M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination bond with M, O is oxygen, A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl, An alkenyl group, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom O, N, or S.

When m is 1 or n = 0 when M is one metal selected from alkali metals and m is 1 or n = 1 when M is a metal selected from alkaline earth metals, or m = 2 and n = 0, and when M is boron or aluminum, m is any one of 1 to 3 and n is any of 0 to 2, and m + n = 3.

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

The Y may be the same or different and independently selected from the following formulas [C1] to [C39], but is not limited thereto.

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

L represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

In the organic electroluminescent device according to the present invention, the organic layer may include a light emitting layer, and the light emitting layer may further include at least one dopant compound. In the organic electroluminescent device of the present invention, May be at least one compound selected from compounds represented by the following general formulas A-1 to J-1, although not particularly limited thereto.

[General Formula A-1]

Wherein M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. L ₁ , L ₂ and L ₃ are the same or different from each other as ligands, and each independently selected from the following structural formula [D], but are not limited thereto. In the following [Structural Formula D], * represents a site binding to the metal ion M.

[Structural formula D]

In the above structural formula D,

A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1- A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms and a substituted or unsubstituted arylsilyl And the like.

Each R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen And may be further substituted with one or more substituents.

Further, the R may be connected to each adjacent substituent by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

As one example, the dopant represented by the above-mentioned [formula A-1] may be any one selected from the following compounds, but is not limited thereto.

[Formula B-1]

In the above general formula B-1,

M ^A1 represents the same metal ion as defined in [formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom, and Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group as defined above, and Q ^A11 and Q ^A12 represent a partial structure containing an atom bonding to M ^A1 .

Exemplary structures of the compound represented by the above-mentioned general formula B-1 are shown below, but the present invention is not limited thereto.

[Formula C-1]

In the above general formula (C-1)

M ^B1 represents the same metal ion as defined from the following formula ^{A-1], Y B11,} Y B14, Y B15 and Y ^B18 each independently represents a carbon atom or a nitrogen ^{atom, Y B12, Y B13, Y} B16 And Y ^B17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom, L ^B11 , L ^B12 , L ^B13 and L ^B14 represent a linking group, Q ^B11 and Q ^B12 represent ^Represents a partial structure containing an atom bonding to M ^B1 .

Exemplary structures of the compound represented by the above-mentioned general formula C-1 are shown below, but the present invention is not limited thereto.

[Formula D-1]

In the above general formula (D-1)

M ^C1 represents a metal ion as defined in [formula A-1], R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is connected to each other to form a 5-membered ring, Each of R ^C13 and R ^C14 independently represents a hydrogen atom, a substituent which is connected to each other to form a 5-membered ring, or a substituent which does not have any one to be connected to each other, and G ^C11 and G ^C12 each independently represent a nitrogen atom, a substituent Or an unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonding to M ^C1 .

Exemplary structures of the compound represented by the above-mentioned general formula (D-1) are shown below, but the present invention is not limited thereto.

[Formula E-1]

In the above general formula E-1,

M ^D1 represents the same metal ion as defined from the following formula A-1], G ^D11, G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, J ^D11, J ^D12, J ^D13 and J ^D14 each independently represents an atomic group necessary for forming a five-membered ring, and L ^D11 and L ^D12 represent a linking group.

Exemplary structures of the compound represented by the above-mentioned formula (E-1) are as follows, but are not limited thereto.

[Formula F-1]

In the above general formula F-1,

M ^E1 represents the same metal ion as defined in [Formula A-1], J ^E11 and J ^E12 each independently represent an atom group necessary for forming a 5-membered ring, and G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

Exemplary structures of the compound represented by the above-mentioned general formula F-1 are shown below, but are not limited thereto.

[Formula G-1]

In the above general formula G-1,

M ^F1 represents the same metal ion as defined in [formula A-1].

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent substituents, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. And Q ^F11 and Q ^F12 represent a partial structure containing an atom bonding to M ^F1 .

Exemplary structures of the compound represented by the above-mentioned general formula G-1 are shown below, but the present invention is not limited thereto.

[Formula H-1] [Formula H-2] [Formula H-3]

In the above formulas H-1 to H-3,

R ¹¹ and R ¹² are substituents of alkyl, aryl or heteroaryl; And q11 and q12 may be an integer of 0 to 4, preferably 0 to 2, and may form a fused ring with substituents adjacent to each other.

When q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different.

L ¹ is a ligand which binds to platinum and is preferably a ligand capable of forming an ortho metal platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand or a halogen ligand, more preferably an ortho metal ) Ligand, a bipyridyl ligand or a phenanthroline ligand, which form a platinum complex.

n ¹ is an integer of 0 to 3, preferably 0, m ¹ is 1 or 2, and preferably 2.

It is preferable that n ¹ and m ¹ denote the metal complex represented by the general formula H-1 as a neutral complex.

In the above-mentioned general formula H-2,

R ²¹ , R ²² , n ² , m ² , q ²² and L ² are respectively the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ , q ²¹ is an integer of 0 to 2 , 0 is preferable.

In the above-mentioned general formula H-3,

R ³¹ , n ³ , m ³ and L ³ are the same as R ¹¹ , n ¹ , m ¹ and L ¹ , q ³¹ is an integer of 0 to 8, preferably 0 to 2, desirable.

Examples of the specific compounds of the above-mentioned general formulas H-1 to H-3 are shown below, but the present invention is not limited thereto.

[Formula I-1]

In the above general formula I-1,

Ring A, ring B, ring C and ring D represents a nitrogen-containing heterocyclic ring which may have a substituent, and the remaining two rings may be substituted with an aryl ring or a hetero ring which may have a substituent And may form a condensed ring with ring A and ring B, ring A and ring C and / or ring B and ring D, respectively. X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them coordinate to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (or a bond), but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. ^{Two of} Z ¹ , Z ² , Z ³ and Z ⁴ represent coordinate bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compounds of the above-mentioned general formula I-1 include, but are not limited to, the following.

[Formula J-1]

In the above general formula J-1,

M represents the same metal ion as defined in [formula A-1], Ar1 represents a substituted or unsubstituted cyclic structure, and two azomethine bonds (-C = N-) , The nitrogen atom (N) binds to the M, respectively, and forms a three-coordinate ligand which is bonded to the M at the 3-position as a whole.

Further, in Ar 1, C represents a carbon atom constituting a ring structure represented by Ar 1. R 1 and R 2 may be the same or different and each represents a substituted or unsubstituted alkyl or aryl group, and L represents a one-dimensional ligand.

In the above general formula J-1, it is preferable that M is Pt. The above-mentioned Ar1 is preferably selected from a 5-membered ring, a 6-membered ring and condensed ring group thereof.

Examples of the specific compounds of the above-mentioned general formula J-1 include, but are not limited to, the following.

In addition, the light emitting layer may further include various dopants and various hosts as well as the dopant and the host.

At least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process, Means a method of forming a thin film by evaporating a material used as a material for forming each of the layers by heating or the like under a vacuum or a low pressure state and the solution process is used as a material for forming each of the layers Means a method of forming a thin film by a method such as ink jet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating and the like.

Further, the organic electroluminescent device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel illumination device, and a single color or white flexible illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

[Synthesis Example 1] Synthesis of Compound (2)

Synthesis of [Reaction Scheme 1-1] [Intermediate 1-a]

A 2 L reactor was charged with 45.0 g (232 mmol) of 2-aminobenzonitrile and 450 mL of tetrahydrofuran, and the mixture was stirred. After cooling to 0 占 폚, 88.2 mL (487 mmol) of 3M-phenylmagnesium bromide was added dropwise, and the mixture was refluxed for 3 hours. After cooling to 0 캜, 44.3 g (732 mmol) of ethyl chloroformate was dissolved in 200 mL of tetrahydrofuran, and the mixture was refluxed for 2 hours. After cooling to 0 ° C, a saturated aqueous ammonium chloride solution was added, and then the organic layer was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 46.0 g (yield: 80.0%) of the compound represented by [Intermediate 1-a].

[Synthesis of Reaction Scheme 1-2] [Intermediate 1-b]

40 g (134 mmol) of the intermediate [1-a] obtained in the above Reaction Scheme 1-1 and 500 mL of phosphorus oxychloride were placed in a 2 L reactor and refluxed for 5 hours. After cooling to 0 占 폚, distilled water was added dropwise. After filtration of the reaction solution, the solid was separated by column chromatography to obtain 30.5 g (yield 70.6%) of the compound represented by [Intermediate 1-b].

Synthesis of [Scheme 1-3] [Intermediate 1-c]

A 2 L reactor was charged with 100 g (483 mmol) of 2-bromonaphthalene, 104.3 g (531 mmol) of benzophenone hydrazone, 10.8 g (48 mmol) of dipalladium acetate, -1,1-binaphthyl (30.1 g, 48 mmol), and sodium pentoxide (65.0 g, 676 mmol) and toluene (800 mL) were added and refluxed for 12 hours. After filtration at a high temperature, the filtrate was concentrated under reduced pressure and then purified by column chromatography to obtain 116.7 g (yield 75.0%) of the compound represented by [Intermediate 1-c].

Synthesis of [Reaction Scheme 1-4] [Intermediate 1-d]

116.7 g (362 mmol) of Intermediate 1-c, 71.8 g (543 mmol) of 1-indanone and 206.6 g (1086 mmol) of para-toluenesulfonic acid obtained in the above Reaction Scheme 1-3, 1167 mL was added and the mixture was refluxed for 48 hours. The reaction solution was concentrated under reduced pressure and purified by column chromatography to obtain 56.8 g (yield: 61.5%) of the compound represented by [Intermediate 1-d].

[Reaction Scheme 1-5] Synthesis of [Intermediate 1-e]

7.0 g (27 mmol) of the compound represented by [Intermediate 1-d] obtained in the above Reaction Scheme 1-4 and 8.6 g (36 mmol) of the intermediate 1-b obtained in Reaction Scheme 1-2 were added to a 300- , 0.5 g (0.5 mmol) of tris (dibenzylideneacetone) dipalladium, 0.8 g (2.7 mmol) of tritiated butylphosphonium tetrafluoroborate, 5.3 g (55 mmol) of sodium tertiary butoxide, mL, and refluxed for 12 hours. After filtration at high temperature, the filtrate was concentrated under reduced pressure and then separated by column chromatography to obtain 9.7 g (yield: 72.9%) of the compound represented by [Intermediate 1-e].

[Reaction Scheme 1-6] Synthesis of [Formula 2]

9.7 g (21 mmol) of the intermediate [1-e] obtained in the above Scheme 1-5 and 77 mL of tetrahydrofuran were placed in a 300 mL reactor and cooled to 0 占 폚. 7.1 g (63 mmol) of potassium-aluminum-butoxide is slowly added at 0 ° C and stirred. After 10 minutes, a solution prepared by dissolving 10.3 g (32 mmol) of 1,5-diiodopentane in 10 mL of tetrahydrofuran was added dropwise at 0 DEG C, the temperature was raised to room temperature, and the mixture was stirred for 24 hours. Water was added and the organic layer was extracted and concentrated under reduced pressure. The obtained solid was purified by recrystallization to obtain 4.7 g (yield: 42.2%) of a compound represented by the formula (2).

MS [M] ^< ⁺ & gt ^; : 528.

[Synthesis Example 2] Synthesis of Compound (3)

Synthesis of [Reaction Scheme 2-1] [Intermediate 2-a]

Synthesis Example 1 59.7 g (yield: 73.8%) of a compound represented by [Intermediate 2-a] was obtained by the same method as in [Reaction Scheme 1] except that 1-naphthylmagnesium bromide was used in place of phenylmagnesium bromide .

Synthesis of [Reaction Scheme 2-2] [Intermediate 2-b]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 2-b] except that [Intermediate 2-b] obtained in the above Reaction Scheme 2-1 was used instead of [Intermediate 1-a] in [Reaction Scheme 1-2] 59.4 g (yield 70.1%) of the compound to be displayed was obtained.

Synthesis of [Reaction 2-3] [Intermediate 2-c]

600 g of acetic acid and 30 mL of hydrochloric acid are added to 60 g (375 mmol) of 1-indanone and 87.5 g (450 mmol) of phenylhydrazine hydrochloride, and the mixture is refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain 77.0 g (yield 74.3%) of the compound represented by [Intermediate 2-c].

Synthesis of [Reaction Scheme 2-4] [Intermediate 2-d]

Synthesis Example 1 [Intermediate 2-b] obtained in the above Reaction Scheme 2-2 was used in place of [Intermediate 2-c] in place of [Intermediate 1-d] in [Reaction Scheme 1-5] To obtain 64.5 g (yield 67.3%) of the compound represented by [Intermediate 2-d].

[Synthesis of Reaction Formula 2-5] [Formula 3]

Synthesis Example 1 [Intermediate 2-d] obtained in the above Reaction Scheme 2-4 was used in place of [Intermediate 1-e] in [Reaction Scheme 1-6] using 1,4-diiodobutane instead of 1,5- , To obtain 4.3 g (yield: 45.2%) of a compound represented by the formula (3).

MS [M] ^< ⁺ & gt ^; : 514

[Synthesis Example 3] Synthesis of Compound (4)

[Reaction Scheme 3-1] Synthesis of [Formula 4]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Formula 1-6], except that [Intermediate 2-d] obtained in [Reaction Formula 2-4] was used instead of [Intermediate 1-e] 3.9 g (yield: 38.6%) of the compound was obtained.

MS [M] ^< ⁺ & gt ^; : 528

[Synthesis Example 4] Synthesis of compound (15)

Synthesis of [Reaction Scheme 4-1] [Intermediate 4-a]

50 g (271 mmol) of dibenzothiophene was added to a round bottom flask containing 400 mL of tetrahydrofuran, and the temperature was adjusted to -78 DEG C under a nitrogen atmosphere. After 30 minutes, 178 mL (285 mmol) of n-butyllithium was slowly added dropwise. After 12 hours, 69 g (271 mmol) of iodine was slowly added dropwise and the temperature was raised to room temperature. After stirring for 2 hours, add aqueous sodium thiosulfate solution. The organic layer was collected and distilled under reduced pressure. Hexane, and the resultant solid was filtered to obtain 52.1 g (yield 60%) of the compound represented by [Intermediate 4-a].

Synthesis of [Reaction Scheme 4-2] [Intermediate 4-b]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 4-b] except that [Intermediate 4-a] obtained in the above-mentioned Reaction Scheme 4-1 was used instead of 2-bromonaphthalene in [Reaction Scheme 1-3] (Yield: 74.2%) of the title compound.

Synthesis of [Reaction Scheme 4-3] [Intermediate 4-c]

Synthesis Example 1 [Intermediate 4-c] was synthesized in the same manner as Intermediate 4-b except for using [Intermediate 4-b] obtained in the above Reaction Scheme 4-2 instead of Intermediate 1-c in Scheme 1-4 35.7 g (yield: 68.2%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 4-4] [Intermediate 4-d]

Synthesis Example 1 [Intermediate 4-d] was synthesized in the same manner as Intermediate 4-d except for using [Intermediate 4-c] obtained in the above Reaction Scheme 4-3 instead of [Intermediate 1-d] 28.4 g (yield: 72.6%) of the compound to be displayed was obtained.

[Reaction Scheme 4-5] Synthesis of [Formula 15]

Synthesis Example 1 [Intermediate 4-d] obtained in the above Reaction Scheme 4-4 was used in place of [Intermediate 1-e] in [Reaction Scheme 1-6] using 1,4-diiodobutane instead of 1,5- , To obtain 4.3 g (yield: 45.2%) of a compound represented by the formula (15).

MS [M] ^< ⁺ & gt ^; : 570

[Synthesis Example 5] Synthesis of [Formula 19]

Synthesis of [Reaction Scheme 5-1] [Intermediate 5-a]

A 1 L reactor is charged with nitrogen, and then 35.1 g (297 mmol) of 2-aminobenzonitrile and 350 mL of dimethylformamide are stirred. 55.56 g (312 mmol) of N-bromosuccinimide is then slowly added to the reactor. The mixture was stirred at room temperature for 4 hours. When the reaction was completed, distilled water was added dropwise at room temperature. When brown crystals were formed, the crystals were filtered and separated by column chromatography to obtain 54.2 g (yield 92.6%) of the compound represented by [Intermediate 5-a].

Synthesis of [Reaction Scheme 5-2] [Intermediate 5-b]

12 g (60.72 mmol) of the compound represented by [Intermediate 5-a], 8.88 g (72.8 mmol) of phenylboronic acid and 1.4 g (1.21 mmol) of tetrakis (triphenylphosphine) ), 16.78 g (121.44 mmol) of potassium carbonate, 60 mL of 1,4-dioxane, 60 mL of toluene and 24 mL of distilled water, and the mixture is stirred at 100 DEG C for 12 hours. After the reaction was completed, the temperature was adjusted to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was concentrated and then subjected to column chromatography to obtain 11.4 g (yield 97%) of a compound represented by [Intermediate 5-b].

[Synthesis of Reaction Scheme 5-3] [Intermediate 5-c]

Synthesis Example 1 Synthesis was conducted in the same manner as Intermediate 5-c except for using [Intermediate 5-b] obtained in the above Reaction Scheme 5-2 instead of 2-aminobenzonitrile in Reaction Scheme 1 (Yield: 84.8%).

Synthesis of [Reaction Scheme 5-4] [Intermediate 5-d]

Synthesis Example 1 [Intermediate 5-d] was synthesized in the same manner as Intermediate 5-c except for using [Intermediate 5-c] obtained in the above Reaction Scheme 5-3 instead of [Intermediate 1-a] in [Reaction Scheme 1-2] To obtain 7.8 g (yield: 73.5%) of the compound to be displayed.

Synthesis of [Reaction Scheme 5-5] [Intermediate 5-e]

Synthesis Example 4 Synthesis was conducted in the same manner as in [Reaction Scheme 4-1] except that dibenzofuran was used instead of dibenzothiophene to obtain 129.7 g (yield 78.4%) of the compound represented by [Intermediate 5-e].

Synthesis of [Reaction Scheme 5-6] [Intermediate 5-f]

Synthesis Example 1 The title compound was synthesized in the same manner as Intermediate 5-f except for using Intermediate 5-d obtained in the above Reaction Scheme 5-5 instead of 2-bromonaphthalene in Reaction Scheme 1-3, (Yield: 74.2%) of the title compound.

Synthesis of [Reaction Scheme 5-7] [Intermediate 5-g]

Synthesis Example 1 [Intermediate 5-g] was synthesized in the same manner as Intermediate 5-f except for using [Intermediate 5-f] obtained in the above Reaction Scheme 5-6 instead of [Intermediate 1-c] 57.4 g (yield 75.1%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 5-8] [Intermediate 5-h]

Synthesis Example 1 [Intermediate 5-h] obtained in the above Reaction Scheme 5-7 was used instead of [Intermediate 5-d] in place of [Intermediate 1-b] in [Reaction Scheme 1-5] To obtain 22.4 g (yield 70.6%) of the compound represented by [Intermediate 5-h].

[Synthesis of Reaction Formula 5-9] [Formula 19]

Synthesis Example 1 [Intermediate 5-h] obtained in [Reaction Scheme 5-8] above was reacted with 1,4-diiodobutane instead of 1,5-diiodopentane instead of [Intermediate 1-e] , To obtain 4.3 g (yield: 45.2%) of a compound represented by the formula (19).

MS [M] ^< ⁺ & gt ^; : 630

[Synthesis Example 6] Synthesis of [Formula 21]

Synthesis of [Reaction Scheme 6-1] [Intermediate 6-a]

Synthesis Example 1 [Intermediate 4-c] obtained in the above Reaction Scheme 4-3 was used instead of [Intermediate 5-d] in place of [Intermediate 1-b] in [Reaction Scheme 1-5] To obtain 12.3 g (yield: 68.7%) of the compound represented by [Intermediate 6-a].

[Reaction Scheme 6-2] Synthesis of [Formula 21]

Synthesis Example 1 [Intermediate 6-a] obtained in the above Reaction Scheme 6-1 was used in place of [Intermediate 1-e] in [Reaction Scheme 1-6] by using 1,4-diiodobutane instead of 1,5- , To obtain 5.7 g (yield: 47.6%) of a compound represented by the formula (21).

MS [M] ^< ⁺ & gt ^; : 646

[Synthesis Example 7] Synthesis of [Formula 31]

Synthesis of [Reaction Scheme 7-1] [Intermediate 7-a]

Synthesis Example 2 Synthesis was conducted in the same manner as in [Scheme 2-3] except that 4-bromophenylhydrazine hydrochloride was used instead of phenylhydrazine hydrochloride, to thereby yield 76.1 g (yield: 57.3%) of the compound represented by [Intermediate 7-a] .

Synthesis of [Reaction Scheme 7-2] [Intermediate 7-b]

Synthesis Example 5 The procedure of Synthesis Example 5 was repeated except that 2-naphthylboronic acid was used instead of phenylboronic acid in place of [intermediate 5-a] in [Reaction Scheme 7-1] To obtain 31.8 g (yield 71.3%) of a compound represented by [Intermediate 7-b].

Synthesis of [Reaction Scheme 7-3] [Intermediate 7-c]

Synthesis Example 1 [Intermediate 7-c] was synthesized in the same manner as Intermediate 7-b except for using [Intermediate 7-b] obtained in the above Reaction Scheme 7-2 instead of Intermediate 1-d in Reaction Scheme 1-5 To obtain 12.8 g (yield 69.4%) of the compound to be displayed.

Synthesis of Scheme 7-4 [Chemical Formula 31]

Synthesis Example 1 [Intermediate 7-c] obtained in the above Reaction Scheme 7-3 was used in place of [Intermediate 1-e] in [Reaction Scheme 1-6] using 1,4-diiodobutane instead of 1,5- , To obtain 5.7 g (yield 47.6%) of a compound represented by the formula (31).

MS [M] ^< ⁺ & gt ^; : 590

[Synthesis Example 8] Synthesis of [Formula 43]

Synthesis of [Reaction Scheme 8-1] [Intermediate 8-a]

Synthesis Example 1 [Intermediate 2-c] obtained in the above Reaction Scheme 2-3 was used instead of [Intermediate 1-b] in [Reaction Scheme 1-5] instead of [Intermediate 1-b] The intermediate 5-d] was synthesized in the same manner as above to give 10.5 g (yield 72.8%) of the compound represented by [Intermediate 8-a].

Synthesis of Reaction Scheme 8-2 [Chemical Formula 43]

Synthesis Example 1 [Intermediate 8-a] obtained in the above Reaction Scheme 8-1 was reacted with 1,4-diiodobutane instead of 1,5-diiodopentane in the scheme [1-6] , To obtain 4.5 g (yield: 41.7%) of the compound represented by the formula (43).

MS [M] ^< ⁺ & gt ^; : 540

[Synthesis Example 9] Synthesis of [Formula 44]

Synthesis of [Synthesis 9-1] [Synthesis of Intermediate 9-a]

Synthesis Example 5 The procedure of Synthesis Example 5 was repeated except that 1-naphthylboronic acid was used instead of phenylboronic acid to obtain 27.6 g (yield: 73.4%) of the compound represented by [Intermediate 9-a] .

Synthesis of [Reaction Scheme 9-2] [Intermediate 9-b]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Scheme 1-1], except that [Intermediate 9-b] obtained in the above Reaction Scheme 9-1 was used instead of 2-aminobenzonitrile, and designated as [Intermediate 9-b] (Yield: 69.5%).

Synthesis of [Synthesis 9-3] [Intermediate 9-c]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 9-c], except that [Intermediate 9-b] obtained in the above Reaction Scheme 9-2 was used instead of [Intermediate 1-a] in [Reaction Scheme 1-2] To obtain 15.4 g (yield 70.7%) of the compound to be displayed.

Synthesis of [Reaction Scheme 9-4] [Intermediate 9-d]

Synthesis Example 1 [Intermediate 2-c] obtained in the above Reaction Scheme 2-3 was used instead of [Intermediate 1-b] in [Reaction Scheme 1-5] instead of [Intermediate 1-b] 12.7 g (yield: 67.1%) of the compound represented by [Intermediate 9-d] was obtained by the same method as Intermediate 9-c].

Synthesis of Scheme 9-5 Synthesis of Scheme 44

Synthesis Example 1 [Intermediate 9-d] obtained in the above Reaction Scheme 9-4 was used instead of 1,5-diiodopentane in the reaction scheme 1 - , To obtain 3.9 g (yield: 37.6%) of the compound represented by the formula (44).

MS [M] ^< ⁺ & gt ^; : 590

[Synthesis Example 10] Synthesis of [Formula 45]

Synthesis of [Synthesis 10-1] [Synthesis of Intermediate 10-a]

Synthesis Example 5 Synthesis was conducted in the same manner as in [Scheme 5-2] except that 2-naphthylboronic acid was used instead of phenylboronic acid to obtain 30.7 g (yield 72.6%) of the compound represented by [Intermediate 10-a] .

Synthesis of [Reaction Scheme 10-2] [Intermediate 10-b]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Scheme 1-1], except that [Intermediate 10-a] obtained in the above Reaction Scheme 10-1 was used instead of 2-aminobenzonitrile to synthesize [Intermediate 10-b] (Yield: 79.5%) of the title compound.

Synthesis of [Reaction Scheme 10-3] [Intermediate 10-c]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 10-c], except that [Intermediate 10-b] obtained in the above Reaction Scheme 10-2 was used instead of [Intermediate 1-a] in [Reaction Scheme 1-2] 17.6 g (yield: 72.4%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 10-4] [Intermediate 10-d]

Synthesis Example 1 [Intermediate 2-c] obtained in the above Reaction Scheme 2-3 was used instead of [Intermediate 1-b] in [Reaction Scheme 1-5] instead of [Intermediate 1-b] Intermediate 10-c] was used to synthesize 11.3 g (yield: 68.1%) of the compound represented by [Intermediate 10-d].

[Synthesis of Reaction Formula 10-5] [Formula 45]

Synthesis Example 1 [Intermediate 10-d] obtained in the above Reaction Scheme 10-4 was used instead of 1,5-diiodopentane in the reaction scheme 1 - , To obtain 4.3 g (yield: 38.4%) of the compound represented by the formula (45).

MS [M] ^< ⁺ & gt ^; : 590

[Synthesis Example 11] Synthesis of [Formula 48]

Synthesis of [Intermediate 11-a]

50.0 g (254 mmol) of the intermediate [5-a] obtained in the above Reaction Scheme 5-1 was dissolved in 500 mL of dichloromethane and stirred. 53.2 g (279 mmol) of paratoluenesulfonic acid was dissolved in 60.2 g (761 mmol) of pyridine, and the mixture was stirred at room temperature. After completion of the reaction, the reaction mixture was extracted with dichloromethane and water. The organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography to give 65.3 g (yield: 73.3%) of the compound represented by [Intermediate 11-a].

Synthesis of [Reaction Scheme 11-2] [Intermediate 11-b]

Synthesis Example 1 In the same manner as in [Scheme 1-5] except that pyrrole was used instead of [intermediate 1-d], and [intermediate 11-a] obtained in the above Reaction Scheme 11-1 was used instead of [intermediate 1-b] To obtain 46.7 g (yield 70.6%) of the compound represented by [Intermediate 11-b].

Synthesis of [Reaction Scheme 11-3] [Intermediate 11-c]

Was dissolved in 46.7 g (138 mmol) of the intermediate [11-b], 49.6 g (152 mmol) of cesium carbonate, 280 mL of tetrahydrofuran and 140 mL of methanol obtained in the above Reaction Scheme 11-2 and stirred under reflux. After completion of the reaction, the reaction mixture was extracted with dichloromethane and water. The organic layer was concentrated under reduced pressure, and the residue was separated by column chromatography to obtain 31.2 g (yield: 64.2%) of a compound represented by [Intermediate 11-c].

Synthesis of [Reaction Scheme 11-4] [Intermediate 11-d]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Scheme 1-1] except that 2-aminobenzonitrile was used instead of [Intermediate 11-c] obtained in the above Reaction Scheme 11-3 to obtain [Intermediate 11-d] (Yield: 62.4%).

Synthesis of [Reaction Scheme 11-5] [Intermediate 11-e]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 11-e] except that [Intermediate 11-d] obtained in the above Reaction Scheme 11-4 was used instead of [Intermediate 1-a] in [Reaction Scheme 1-2] To obtain 15.9 g (yield 69.1%) of the compound to be displayed.

Synthesis of [Reaction Scheme 11-6] [Intermediate 11-f]

Synthesis Example 1 [Intermediate 2-c] obtained in the above Reaction Scheme 2-3 was used instead of [Intermediate 1-b] in [Reaction Scheme 1-5] instead of [Intermediate 1-b] Synthesis was carried out in the same way except that Intermediate 11-d] was used to obtain 16.5 g (yield 70.8%) of the compound represented by [Intermediate 11-f].

[Synthesis of Reaction Formula 11-7] [Formula 48]

Synthesis Example 1 [Intermediate 11-f] obtained in [Reaction Scheme 11-6] above was reacted with 1,4-diiodobutane instead of 1,5-diiodopentane instead of [Intermediate 1-e] , To obtain 2.8 g (yield: 30.7%) of a compound represented by the formula (48).

MS [M] ^< ⁺ & gt ^; : 529

[Synthesis Example 12] Synthesis of [Formula 55]

[Synthesis of Intermediate 12-a]

9.2 g (55 mmol) of carbazole was dissolved in 20 mL of tetrahydrofuran in a 300 mL reactor and the temperature was adjusted to -10 DEG C under a nitrogen atmosphere. After 30 minutes, 34.5 mL (55 mmol) of n-butyllithium was slowly added dropwise, and the mixture was stirred at room temperature for 30 minutes. 10.0 g (50 mmol) of 2,4-dichloroquinazoline was dissolved in 50 mL of tetrahydrofuran, and the mixture was slowly added dropwise at -10 ° C, followed by stirring at room temperature for 1 hour. After the reaction, add water. The mixture was extracted with ethyl acetate, and the organic layer was concentrated, and then subjected to column chromatography to obtain 13.4 g (yield: 80.9%) of the compound represented by [Intermediate 12-a].

Synthesis of [Reaction Scheme 12-2] [Intermediate 12-b]

Synthesis Example 1 [Intermediate 2-c] obtained in the above Scheme 2-3 was used instead of [Intermediate 1-b] in [Reaction Scheme 1-5] instead of [Intermediate 1-b] Was synthesized in the same manner as in [Intermediate 12-a] to obtain 11.8 g (yield 67.3%) of the compound represented by [Intermediate 12-b].

Synthesis of [Formula 12-3] [Formula 55]

Synthesis Example 1 [Intermediate 12-b] obtained in the above Reaction Scheme 12-2 was used instead of 1,5-diiodopentane in the reaction scheme 1 - 6 using 1,4-diiodobutane instead of [Intermediate 1-e] Was synthesized in the same manner as above to obtain 4.5 g (yield: 41.8%) of the compound represented by the formula (55).

MS [M] ^< ⁺ & gt ^; : 553.

[Synthesis Example 13] Synthesis of [Formula 64]

[Synthesis of Intermediate 13-a]

A 2 L reactor was charged with 139.8 g (1.236 mol) of ethyl cyanoacetate, 29.5 g (0.453 mol) of potassium cyanide, 46.2 g (0.824 mol) of potassium hydroxide and 920 mL of dimethylformamide under nitrogen, Lt; / RTI > 92 g (412 mol) of 1-nitronaphthalene is then added to the reaction mixture and stirred at 60 ° C for 4 hours. After completion of the reaction, the solvent was concentrated, 600 mL of a 10% sodium hydroxide aqueous solution was added, and the mixture was refluxed with stirring for 1 hour. The solid was filtered and subjected to column chromatography with methylene chloride and heptane to obtain 50 g (yield 60%) of the compound represented by [Intermediate 13-a].

Synthesis of [Reaction Scheme 13-2] [Intermediate 13-b]

Synthesis Example 5 The title compound was synthesized in the same manner as Intermediate 13-b except that 2-aminobenzonitrile was used instead of 2-aminobenzonitrile in Intermediate 13-a obtained in Reaction Scheme 13-2. (Yield: 92.6%).

[Synthesis of Intermediate 13-c]

Synthesis Example 5 Synthesis was conducted in the same manner as in [Intermediate 13-b] except that [Intermediate 13-b] obtained in the above Reaction Scheme 13-2 was used instead of [Intermediate 5-a] in [Reaction Scheme 5-2] 71.3 g (yield 86.4%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 13-4] [Intermediate 13-d]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Scheme 1-1] except that 2-aminobenzonitrile was used instead of [Intermediate 13-c] obtained in the above Reaction Scheme 13-3 to obtain [Intermediate 13-d] (Yield: 68.2%) of the title compound.

Synthesis of [Reaction Scheme 13-5] [Intermediate 13-e]

Synthesis Example 1 [Intermediate 13-e] was synthesized in the same manner as Intermediate 13-d except for using [Intermediate 13-d] obtained in the above Reaction Scheme 13-4 instead of [Intermediate 1-a] in [Reaction Scheme 1-2] 21.6 g (yield: 73.4%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 13-6] [Intermediate 13-f]

Synthesis Example 1 [Intermediate 2-c] obtained in the above Reaction Scheme 2-3 was used instead of [Intermediate 1-b] in [Reaction Scheme 1-5] instead of [Intermediate 1-b] Intermediate 13-d] was used to synthesize 11.9 g (yield: 68.4%) of the compound represented by [Intermediate 13-f].

Synthesis of Scheme 13-7 Synthesis of Scheme 64

Synthesis Example 1 [Intermediate 13-f] obtained in [Reaction Scheme 13-6] above was reacted with 1,4-diiodobutane instead of 1,5-diiodopentane instead of [Intermediate 1-e] Was synthesized in the same manner as above to obtain 4.5 g of the compound represented by the formula (64) (yield: 39.7%).

MS [M] ^< ⁺ & gt ^; : 590

[Synthesis Example 14] Synthesis of [Formula 65]

[Synthesis of Intermediate 14-a]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 14-a] except that [Intermediate 13-d] obtained in the above Reaction Scheme 13-5 was used instead of [Intermediate 1-b] in [Reaction Scheme 1-5] 14.7 g (yield 71.9%) of the compound to be displayed was obtained.

Synthesis of Scheme 14-2 [Chemical Formula 65]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Scheme 1-6] except that [Intermediate 14-a] obtained in [Reaction Scheme 14-1] above was used instead of [Intermediate 1-e] 3.7 g (yield: 35.7%) of a compound was obtained.

MS [M] ^< ⁺ & gt ^; : 654

[Synthesis Example 15] Synthesis of [Formula 89]

[Synthesis of Intermediate 15-a]

Synthesis Example 5 Synthesis was conducted in the same manner as in [Scheme 5-2] except that 2-bromobenzyl alcohol was used instead of [intermediate 5-a], instead of phenylboronic acid, to obtain Intermediate 15 -a] (yield: 71.6%).

Synthesis of [Reaction Scheme 15-2] [Intermediate 15-b]

80.3 g (334 mmol) of the intermediate [15-a] obtained in the above Reaction Scheme 15-1 and 280 mL of phosphoric acid were placed in a 2 L reactor and stirred for 12 hours. The organic layer was extracted with methylene chloride and distilled water, and then concentrated under reduced pressure, followed by column chromatography to obtain 60.7 g (yield: 81.7%) of a compound represented by [Intermediate 15-b].

[Synthesis of Intermediate 15-c]

Synthesis Example 1 [Intermediate 15-b] obtained in the above Reaction Scheme 15-2 was used instead of 1,5-diiodopentane in the reaction scheme 1 - , There was obtained 57.1 g (yield 76.4%) of a compound represented by the formula [Intermediate 15-c]].

Synthesis of Intermediate 15-d

Synthesis Example 4 Synthesis was conducted in the same manner as in [Reaction Scheme 4-1] except that [Intermediate 15-c] obtained in the above Reaction Scheme 15-3 was used instead of dibenzothiophene to synthesize [Intermediate 15-d] 97.3 g (yield: 74.9%) of a compound was obtained.

Synthesis of [Reaction Scheme 15-5] [Intermediate 15-e]

20.0 g (50 mmol) of the compound represented by [Intermediate 15-d] obtained in the above Reaction Scheme 15-4, 10.3 g (60 mmol) of 2-bromoaniline, 0.2 g ), 1.7 g (3 mmol) of zincphosphate, 22.7 g (70 mmol) of cesium carbonate and 160 mL of toluene, and the mixture was refluxed for 12 hours. After filtration at a high temperature, the filtrate was concentrated under reduced pressure and then subjected to column chromatography to obtain 17.2 g (yield 78.0%) of a compound represented by [Intermediate 15-e].

Synthesis of Intermediate 15-f

17.3 g (39 mmol) of the compound [Intermediate 15-e] obtained in the above Reaction Scheme 15-5, 0.3 g (1 mmol) of tricyclohexylphosphine tetrafluoroborate and 0.09 g (0.4 mmol), potassium carbonate (10.7 g, 78 mmol) and toluene (140 mL), and the mixture was refluxed for 12 hours. The mixture was concentrated under reduced pressure and then subjected to column chromatography to obtain 11.3 g (yield: 79.8%) of a compound represented by the formula [Intermediate 15-f].

[Reaction formula 15-7] Synthesis of [Formula 89]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Formula 1-5], except that [Intermediate 15-f] obtained in the above Reaction Scheme 15-6 was used instead of [Intermediate 1-d] 4.8 g (yield 43.8%) of the compound was obtained.

MS [M] ^< ⁺ & gt ^; : 570

[Synthesis Example 16] Synthesis of [Formula 99]

[Synthesis of Intermediate 16-a]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Scheme 1-4] except that 2-indanone was used instead of 1-indanone to obtain 57.9 g (yield 65.3%) of the compound represented by [Intermediate 16-a].

Synthesis of [Reaction Scheme 16-2] [Intermediate 16-b]

Synthesis Example 1 [Intermediate 16-b] was synthesized in the same manner as Intermediate 16-b except for using [Intermediate 16-a] obtained in the above Reaction Scheme [16-2] instead of [Intermediate 1-d] 21.8 g (yield: 63.9%) of the compound to be displayed was obtained.

[Reaction formula 16-3] Synthesis of [Formula 99]

Synthesis Example 1 [Intermediate 16-b] obtained in the above Reaction Scheme 16-2 was used instead of 1,5-diiodopentane in the reaction scheme 1 - 6 using 1,4-diiodobutane instead of [Intermediate 1-e] , 4.1 g (yield: 38.6%) of the compound represented by the above formula (99) was obtained.

MS [M] ^< ⁺ & gt ^; : 514

[Synthesis Example 17] Synthesis of [Formula 161]

[Synthesis of Intermediate 17-a]

Synthesis Example 1 [Intermediate 13-d] obtained in the above Reaction Scheme 13-5 was used in place of [Intermediate 1-b] in [Reaction Scheme 1-5] Was synthesized in the same manner as in [Intermediate 17-a] to obtain 16.3 g (yield 65.1%) of the compound represented by [Intermediate 17-a].

Synthesis of [Formula 17-2] [Formula 161]

Synthesis Example 1 [Intermediate 17-a] obtained in the above scheme [17-1] was used instead of 1,5-diiodopentane in place of [Intermediate 1-e] in [Scheme 1-6] , To obtain 3.5 g (yield: 40.7%) of a compound represented by the formula (161).

MS [M] ^< ⁺ & gt ^; : 640

[Synthesis Example 18] Synthesis of [Formula 176]

Synthesis of [Intermediate 18-a]

Synthesis Example 1 28.3 g (Yield: 70.4%) of the compound represented by [Intermediate 18-a] was synthesized except that 3-bromocarbazole was used in place of [Intermediate 1-d] in [Reaction Scheme 1-6] ≪ / RTI >

Synthesis of [Reaction Scheme 18-2] [Intermediate 18-b]

28.3 g (63 mmol) of Intermediate 18-a obtained in the above Reaction Scheme 18-1, 22.3 g (88 mmol) of bis (pinacolato) diboron and 14.3 g (179 mmol) of potassium acetate, 1.5 g of PdCl2 (dppf), (2 mmol) and 230 mL of toluene were added and refluxed for 12 hours. The reaction solution was filtered using celite, and the filtrate was concentrated under reduced pressure. The filtrate was separated by column chromatography to obtain 21.9 g (yield: 70.1%) of a compound represented by [Intermediate 18-b].

[Synthesis of Intermediate 18-c]

Synthesis Example 2 A compound represented by [Intermediate 18-c] was obtained in the same manner as in [Scheme 2-3] except that 4-bromophenylhydrazine hydrochloride was used instead of phenylhydrazine hydrochloride instead of 1-indanone 63.8 g (yield: 56.1%) was obtained.

Synthesis of [Reaction Scheme 18-4] [Intermediate 18-d]

63.8 g (225 mmol) of Intermediate 18-c obtained in the above Reaction Scheme 18-3, 55.03 g (269 mmol) of iodobenzene, 2.1 g (11 mmol) of copper iodide and 100.1 g 47.8 mmol), 1,2-cyclohexyldiamine (53.8 g, 472 mmol) and 1,4-dioxane (640 mL) were added and the mixture was stirred at 100 ° C for 12 hours. After filtration at high temperature, the product was separated by column chromatography to obtain 62.7 g (yield 77.5%) of a compound represented by [Intermediate 18-d].

Synthesis of [Reaction Scheme 18-5] [Intermediate 18-e]

Synthesis Example 1 [Intermediate 18-d] obtained in the above Reaction Scheme 18-4 was used in place of [Intermediate 1-e] in [Reaction Scheme 1-6] using 1,4-diiodobutane instead of 1,5- Was synthesized in the same manner as above to obtain 21.7 g (yield: 68.4%) of a compound represented by [Intermediate 18-e]].

[Synthesis of Reaction Formula 18-6] [Formula 176]

[Synthesis Example 5] [Intermediate 18-b] obtained in the above Reaction Scheme 18-2 instead of Intermediate 5-a in Reaction Scheme 5-2 was used instead of phenylboronic acid in Intermediate 18- b] was used, to obtain 5.4 g (yield: 60.2%) of a compound represented by the formula [Formula 176].

MS [M] ^< ⁺ & gt ^; : 705

[Synthesis Example 19] Synthesis of [Formula 202]

Synthesis of [Synthesis 19-1] [Intermediate 19-a]

Synthesis Example 11 The procedure of Synthesis Example 11 was repeated except that [Intermediate 2-c] obtained in [Scheme 2-3] above was used instead of [Intermediate 5-a] in [Reaction Scheme 11-1] 67.3 g (yield: 76.9%) of the compound was obtained.

Synthesis of [Reaction Scheme 19-2] [Intermediate 19-b]

Synthesis Example 1 [Intermediate 19-a] obtained in the above scheme [19-1] was used instead of 1,5-diiodo pentane instead of [Intermediate 1-e] in [Reaction Scheme 1-6] (31.7 g, yield: 68.3%) was obtained by a method similar to that of [Intermediate 19-b].

Synthesis of [Reaction Scheme 19-3] [Intermediate 19-c]

Synthesis Example 11 The procedure of Synthesis Example 11 was repeated except that [Intermediate 19-b] obtained in [Reaction Scheme 19-2] above was used instead of [Intermediate 11-b] in [Reaction Scheme 11-3] 15.4 g (yield: 77.5%) of the compound was obtained.

Synthesis of Scheme 19-4 [Chemical Formula 202]

Synthesis Example 1 2,4-dichloroquinazoline was used in place of [Intermediate 1-b] in [Reaction Scheme 1-5], and [Intermediate 19-c] obtained in the above Reaction Scheme 19-3 instead of [Intermediate 1-d] , 5.1 g (yield: 49.3%) of the compound represented by the formula [202] was obtained.

MS [M] ^< ⁺ & gt ^; : 645

Example: Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr. Then, organic substances were injected onto the ITO using DNTPD (700 Å), NPD (300 Å) (300 Å), compound E: Liq = 1: 1 (250 Å), Liq (10 Å) and Al (1,000 Å).

The structures of DNTPD, NPD, RD-1, compound E and Liq are as follows.

<DNTPD> <NPD>

<RD-1><CompoundE><Liq>

Comparative Example

The organic light emitting diode device for the comparative example was fabricated in the same manner except that the compound A and the compound B were used in place of the compound prepared by the invention in the device structure of the embodiment, and the structures of the compound A and the compound B are as follows.

&Lt; Compound A >< Compound B &

The voltage, the current density, the luminance, the color coordinates, and the lifetime of the organic electroluminescent device fabricated according to Example 1 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (3000 cd / m &lt; 2 &gt;) to 95%.

division Host Doping concentration% V Cd / ㎡ CIEx CIEy T ₉₅ (Hr) Comparative Example 1 Compound A 3 5.7 1700 0.665 0.335 150 Comparative Example 2 Compound B 3 3.6 1350 0.665 0.335 50 Example 1 15 3 3.9 2300 0.665 0.335 400

As shown in Table 1, the organic electroluminescent compound according to the present invention has low voltage driving, high luminous efficiency and long life time characteristics as compared with the compounds A and B.

Claims (8)

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
L of * is bonded to A to form a ring, Z is C, Si or Ge, W is CR ₁ R ₂ , SiR ₃ R ₄ , GeR ₅ R ₆ , NR ₇ , O, S, BR ₈ ,
R ₁ and R ₂ , R ₃ and R ₄ , R ₅ and R ₆ may be connected to each other to form a ring,
X and Y each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted An aryl group having 5 to 50 carbon atoms,
Provided that when X and Y are both substituted or unsubstituted aryl groups having 5 to 50 carbon atoms,
Q is a linking group connecting X and Y, and is a single bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms or a substituted or unsubstituted group having 2 to 30 carbon atoms An alkenylene group,
The one or more carbon atoms in X, Y and Q may be substituted with a heteroatom,
Wherein R ₁ to R ₈ and E are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms , A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 5 to 50 carbon atoms A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, , A phosphoryl group, an amino group, a thiol group, a cyano group, a hydroxyl group, a nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group, ], The adjacent E's may be bonded to each other to form a ring,
[Chemical Formula E]

In the above formulas (E) to (F)
A 1 to A 2 are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 carbon atoms, a substituted or unsubstituted C3- A substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms,
In the above-mentioned A1 to A2 Two adjacent ones of the substituents may be bonded to L to form a condensed ring (* denotes a binding site),

In the above formulas (E) to (F) and L,
A3 is the same as the definition of A1 to A2,
Y, Z, W and Q are each independently NR ₉ , CR ₁₀ R ₁₁ , O, S, SiR ₁₂ R ₁₃ , GeR ₁₄ R ₁₅ , BR ₁₆ , PR ₁₇ , C = O, At least one of Y, Z, W and Q is NR &lt; ₉ &gt; (wherein n is an integer of 0 to 3)
[Formula G]

In the above formula (G)
Y and Q are each independently NR ₂₆ , CR ₂₇ R ₂₈ , O, S, SiR ₂₉ R ₃₀ , GeR ₃₁ R ₃₂ , BR ₃₃ , PR ₃₄ , C═O, Se, 1 to 3,
The adjacent two of R ₁₈ to R ₂₅ may be connected to form an alicyclic hydrocarbon ring, a monocyclic or polycyclic aromatic hydrocarbon ring, and the carbon atom of the alicyclic or aromatic hydrocarbon ring may be N, S, O, _{Se, Te, Po, NR 35} , SiR 36 R 37, GeR 38 R 39, PR 40 , and BR ₄₁ may be substituted one or more unsubstituted or substituted heteroatom selected from,
R ₉ to R ₄₁ have the same definitions as R ₁ to R ₈ , and R ₁₀ , R _{11 ,} R ₁₂ and R _13, R ₁₄ and R _{15 ,} R ₂₇ and R _{28 ,} R ₂₉ and R _{30 ,} R ₃₁ and R _{32 ,} R ₃₆ and R _{37 , and} R ₃₈ and R ₃₉ may be linked to each other to form a ring. The method according to claim 1,
The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is selected from the following formulas (2) to (217):

1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic layers comprises an organic electroluminescent compound represented by Formula 1 according to Claim 1. The method of claim 3,
Wherein the organic material layer includes at least one of a hole injection layer, a hole transport layer, and a layer simultaneously injecting holes and transporting holes, wherein at least one of the layers includes an organic light emitting compound represented by Formula 1 To the organic electroluminescent device. The method of claim 3,
Wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises an organic light emitting compound represented by the following formula (1). 6. The method of claim 5,
The organic electroluminescent device according to claim 1, wherein the organic electroluminescent compound represented by Formula 1 is used as a host compound in the light emitting layer. The method of claim 3,
Wherein the organic material layer includes at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously transports electrons and electron injection, and at least one of the layers includes an organic light emitting compound represented by Formula 1 To the organic electroluminescent device. The method of claim 3,
Wherein at least one of the organic light emitting layers emitting red, green or blue light is further included in the organic material layer to emit white light.

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