KR20160036158A - 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 an organic electroluminescent device comprising the same. The organic electroluminescent device applying the organic light emitting compound according to the present invention has high brightness and long lifespan compared with 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 been sufficiently developed yet. Therefore, the development of new materials is continuously required.

Accordingly, it is an object of the present invention to provide a novel organic light emitting compound and an organic electroluminescent device including the organic electroluminescent compound included in the organic compound layer of the device, in order to enable the organic electroluminescent device to have improved brightness and long life.

In order to solve the above-described problems, the present invention provides an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device including the same in an organic material layer.

[Chemical Formula 1]

The structures, substituents and characteristics of the above formula (1) will be described later.

The present invention also provides a method for producing a hole injection layer, a hole transport layer, a hole injecting and transporting layer, an electron transporting layer, an electron injecting layer, The organic electroluminescent device includes an organic electroluminescent compound represented by Formula

The organic electroluminescent device employing the organic electroluminescent compound according to the present invention has high brightness and excellent lifetime characteristics and can be used for various display devices, monochromatic or white illumination, and the like.

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.

The present invention relates to an organic luminescent compound characterized by the following formula (1).

[Chemical Formula 1]

In the above formula (1)

Z ₁ to Z ₆ Are each a carbon atom, Z ₁ and Z ₂ , Z ₃ and Z _4, and Z ₅ and Z ₆ are each bonded to '*' of Q to form a condensed ring, n is an integer of 0 to 3, and Z ₁ and Z ₂ , Z ₃ and Z _4, and at least one of the condensed rings formed at Z ₅ and Z ₆ is characterized in that n is 1 or more.

That is, at least one of the condensed rings formed is a ring in which three or more rings are condensed, such as a 5-membered (or 6-membered) to 5-membered (or 6-membered) .

According to one embodiment of the present invention, the compound represented by the formula (1) can be specifically represented by the following formulas (1-1) to (1-3). However, the present invention is not limited thereto and may be a structure in which various condensed rings are formed.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

X is a single bond or is selected from the group consisting of S, O, NR ₁ , SiR ₂ R ₃ , GeR ₄ R ₅ , CR ₆ R ₇ , Se and Te, , And at least one of the plurality of X's is NR < _{1 &} gt ;.

W is CR or N.

R and R ₁ to R ₇ are the same or different from each other 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 a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, 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-C30 alkyl group A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, 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 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 A cyano group, a hydroxy group, a nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group and an ester group.

The "substitution" in the above "substituted or unsubstituted" means that the substituent defined by R and R ₁ to R ₇ can be further substituted by one or more substituents, and the one or more substituents A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 A substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio 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 aryl group, a substituted or unsubstituted aryl group, 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 and an ester group.

In the formula (1) according to the present invention, R and R ₁ to R ₇ Is a substituent represented by Structural Formula 1 to Structural Formula 2 below.

[Structural formula 1]

[Structural formula 2]

In the above Structural Formulas 1 to 2,

L ₁ and L ₂ each independently represent a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which at least one unsubstituted or substituted unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms is fused.

n and m are each independently an integer of 0 to 4, and when n and m are 2 or more, a plurality of L ₁ and L ₂ may be the same or different from each other.

Ar ₁ , Ar ₂ and Ar ₃ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, A substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl substituted or unsubstituted aryl group having 5 to 50 carbon atoms and / A substituted or unsubstituted C2 to C50 heteroaryl group in which one or more substituted or unsubstituted C3 to C30 cycloalkyl is fused.

Ar ₁ , Ar ₂ and Ar ₃ may be bonded to each other or may be connected with adjacent substituents to form a single alicyclic or aromatic ring or a polycyclic ring, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring formed May be substituted with any one or more heteroatoms selected from N, S and O.

P and q are integers of 0 to 3, and when p and q are 2 or more, a plurality of * - () may be the same or different from each other.

In addition, the aryl group contained in the organic luminescent compound according to the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, 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 for R ₁ to R ₇ .

In addition, the heteroaryl group contained in the organic luminescent compound according to the present invention may be any one selected from the following Structural Formulas 3 to 12:

[Structural Formula 3] [Structural Formula 4] [Structural formula 5] [Structural formula 6]

[Structural Formula 7] [Structural formula 8] [Structural Formula 9]

[Structural Formula 10] [Structural Formula 11] [Structural Formula 12]

In the above Structural Formulas 3 to 12,

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;

In addition, the above-mentioned [formula 5] may include a compound represented by the following formula [5-1] by a resonance structure according to the movement of electrons.

[Structural formula 5-1]

In the above Structural Formula 5-1, T ₁ to T ₇ are the same as defined in Structural Formula 3 to Structural Formula 12 above.

According to a preferred embodiment of the present invention, the above Structural Formulas 3 to 12 can be selected from the following Structural Formula 13.

[Structural Formula 13]

In the above structural formula 13,

X is the same as defined for R ₁ to R ₇ in the above formula (1), m is an integer of 1 to 11, and when m is 2 or more, plural Xs may be the same as or different from each other.

The organic luminescent compound of Formula 1 according to the present invention may be represented by the following compounds 1 to 48 more specifically as an embodiment although the scope of the present invention is not limited thereto. It can be utilized as a luminescent compound for various purposes.

In particular, 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 substituents into the core structure represented by the formula (1).

For example, by introducing substituents used for the hole injection layer material, the hole transport layer material, the host or dopant emission layer material, and the electron transport layer material as the phosphorescent material into the core structure, it is possible to realize a material that satisfies the conditions required in each organic layer, Materials that satisfy the requirements of each organic layer may be implemented by introducing a substituent used for the hole injecting layer material, the hole transporting layer material, the host or dopant emitting layer material, and the electron transporting layer material into the core structure.

Further, the present invention relates to 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, At least one organic luminescent compound according to the present invention may be contained.

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 an 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 in addition to the dopant and the compound according to the present invention.

The light emitting layer may include various dopant compounds in addition to the organic light emitting compound according to the present invention, and the dopant compound may be an amine compound represented by the following formula (I).

(I)

In the above formula (I)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, X ₁ to X ₂ are the same X ₁ and X ₂ may be bonded to each other, Y ₁ to Y ₂ may be the same or different from each other, and may be independently selected from the group consisting of independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, A substituted or unsubstituted C2-C24 hetero aryl group, a substituted or unsubstituted C1-C24 alkyl group, a substituted or unsubstituted C6-C24 aryl group, a substituted or unsubstituted C6-C24 aryl group, A substituted or unsubstituted C1 to C24 alkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted C6 to C24 Oxy group, selected from substituted or unsubstituted C 1 -C 40 alkyl silyl group, a substituted or unsubstituted arylsilyl group, a germanium, phosphorus, boron, deuterium and hydrogen having a carbon number of 6 to 30, Y ₁ to Y ₂ is May be combined with adjacent substituents to form aliphatic, aromatic, aliphatic hetero or aromatic hetero condensation rings.

The dopant compound may be an amine compound represented by the following formula (II).

[Formula II]

In the above formula (II)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each may be the same or different and may be in a fused form, (R ₅ ) (R ₆ )] _p -, wherein p is an integer of 1 to 3, and when p is 2 or more, B is a single bond or - [C ₅ and R ₆ are the same or different from each other and each of R ₁ to R ₆ is independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 2 to 60 carbon atoms, A substituted or unsubstituted C1 to C60 A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted 5 to 5 carbon atom A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, (Substituted or unsubstituted C1 to C60 alkyl) amino group, or a substituted or unsubstituted C6 to C60 aryl) amino group, a di (substituted or unsubstituted C6 to C60 aryl) amino group, A substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, a is an integer of 1 to 4, and when a is 2 or more, 2 Or more R ₃ are the same or different, and R ₃ When this is plural, each R < ₃ > may be in fused form.

According to a preferred embodiment, A is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and may be selected from compounds represented by the following formulas (A1) to (A10).

[Chemical Formula A1] [Chemical Formula A2] [Chemical Formula A3] Chemical Formula A4 [Chemical Formula A5]

(A9) a compound of the formula (A10)

In the above formula [A3]

Z ₁ to Z ₂ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C1 to C60 alkylthio group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, and a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1- And a di (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino groups, and may be bonded to adjacent groups to form a condensed ring.

The amine group to be bonded to A may be any one selected from the group consisting of [substituents 1] to [52].

[Substituent 1] [Substituent 2] [Substituent 3] [Substituent 4]

[Substituent 5] [Substituent 6] [Substituent group 7] [Substituent group 8]

[Substituent 9] [Substituent 10] [Substituent group 11] [Substituent group 12]

[Substituent 13] [Substituent 14] [Substituent 15] [Substituent group 16]

[Substituent group 17] [Substituent 18] [Substituent 19] [Substituent 20]

[Substituent 21] [Substituent 22] [Substituent 23] [Substituent 24]

[Substituent 25] [Substituent 26]

[Substituent 27] [Substituent 28] [Substituent group 29] [Substituent group 30]

[Substituent 31] [Substituent group 32] [Substituent group 33] [Substituent 34]

[Substituent 35] [Substituent 36] [Substituent group 37] [Substituent group 38]

[Substituent 39] [Substituent 40] [Substituent 41] [Substituent 42]

[Substituent 43] [Substituent 44] [Substituent 45] [Substituent 46]

[Substituent group 47] [Substituent group 48] [Substituent 49] [Substituent 50]

[Substituent 51] [Substituent 52]

In the above [substituent groups 1] to [substituent group 52]

R is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, Or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted 5 to 60 A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, (Substituted or unsubstituted C1 to C60 alkyl) amino group, or a substituted or unsubstituted C6 to C60 aryl) amino group, a di (substituted or unsubstituted C6 to C60 aryl) amino group, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and is connected to adjacent substituents to form a condensed ring can do.

The light emitting layer may further contain at least one compound represented by any one of the following Chemical Formulas 1A to 1D in addition to the organic light emitting compound of Chemical Formula 1 according to the present invention.

≪ EMI ID =

≪ RTI ID = 0.0 &

[Chemical Formula 1C]

[Chemical Formula 1D]

X 1 to X 10 are the same or different from each other and each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1-30 carbon atoms, a substituted or unsubstituted alkenyl group having 2-30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 6 to 30 carbon atoms A substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group having 1-30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5-30 carbon atoms, a substituted or unsubstituted alkylamine group having 1-30 carbon atoms, An arylamine group having 5-30 carbon atoms, a substituted or unsubstituted aryl group having 5-50 carbon atoms, a heteroaryl group having 3-50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S, Substituted silicon group, substituted or unsubstituted boron , It is selected from substituted or unsubstituted silane group, a carbonyl group, a phosphonium group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group.

In addition, X1 to X10 may form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups adjacent to each other.

In the above formula (1B), Ar17 to Ar20 are the same or different and each independently selected from a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms and a substituted or unsubstituted heteroaromatic linking group having 2 to 60 carbon atoms.

R60 to R63 are the same or different and each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, A substituted or unsubstituted alkyl group having 1-60 carbon atoms, a substituted or unsubstituted alkenyl group having 2-60 carbon atoms, a substituted or unsubstituted alkynyl group having 2-60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, An unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2-60 carbon atoms, -Si (R21) (R22) (R23), and -N (R24) (R25).

R 21 to R 25 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1-60 carbon atoms, a substituted or unsubstituted alkenyl group having 2-60 carbon atoms, a substituted or unsubstituted group having 2-60 carbon atoms A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, an alkynyl group, a substituted or unsubstituted alkoxy group having 1-60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3-60 carbon atoms, a substituted or unsubstituted aryl group having 5-60 carbon atoms, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

W and ww are the same or different from each other, and x and xx are the same or different from each other, w + ww and x + xx are the same or different from each other and independently an integer of 0 to 3;

Y and yy are the same or different, and z and zz are the same or different from each other, y + yy to z + zz are not more than 2, and each is an integer of 0 to 2;

In the above formula (1C), Ar 21 to Ar 24 are the same or different and are independently selected from the group consisting of a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms and a substituted or unsubstituted heteroaromatic linking group having 2 to 60 carbon atoms.

R64 to R67 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, A substituted or unsubstituted alkyl group having 1-60 carbon atoms, a substituted or unsubstituted alkenyl group having 2-60 carbon atoms, a substituted or unsubstituted alkynyl group having 2-60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, An unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2-60 carbon atoms, -Si (R21) (R22) (R23), and -N (R24) (R25).

R 21 to R 25 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1-60 carbon atoms, a substituted or unsubstituted alkenyl group having 2-60 carbon atoms, a substituted or unsubstituted group having 2-60 carbon atoms A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted 5- to 5- A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

Ee to hh are the same as or different from each other, and each independently is an integer of 1 to 4, and ii to 11 are the same or different and independently an integer of 0 to 4;

In the above formula (1D), Ar 25 to Ar 27 are the same or different and each independently selected from a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms and a substituted or unsubstituted heteroaromatic linking group having 2 to 60 carbon atoms.

R 68 to R 73 are the same or different from each other and each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, A substituted or unsubstituted alkyl group having 1-60 carbon atoms, a substituted or unsubstituted alkenyl group having 2-60 carbon atoms, a substituted or unsubstituted alkynyl group having 2-60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, An unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2-60 carbon atoms, -Si (R21) (R22) (R23), and -N (R24) (R25).

R 21 to R 25 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1-60 carbon atoms, a substituted or unsubstituted alkenyl group having 2-60 carbon atoms, a substituted or unsubstituted group having 2-60 carbon atoms A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted 5- to 5- A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

Each of R21 to R25 may be connected to adjacent substituents to form a saturated or unsaturated cyclic structure.

Also, mm to ss are the same as or different from each other, and each independently an integer of 0 to 4.

According to a preferred embodiment, the formula (1A) may be selected from compounds represented by the following formulas (1Aa) to (1Ae).

≪ RTI ID = 0.0 &

≪ RTI ID = 0.0 &

[Chemical Formula 1 Ac]

[Formula 1Ad]

≪ RTI ID = 0.0 &

In the formula [1Aa], Ar7 and Ar8 are the same or different and are each independently selected from substituted or unsubstituted aromatic linking groups having 5-60 carbon atoms and substituted or unsubstituted heteroaromatic linking groups having 2-60 carbon atoms.

R 21 to R 30 are the same as or different from each other and each independently represent the same definitions as defined for X 1 to X 10, and e and f are the same or different and independently an integer of 0 to 4;

Wherein Ar9 and Ar10 are the same as or different from each other, and each independently is the same as defined in the above Ar7 to Ar8, and R31 to R40 are the same as or different from each other, and each independently is the same as defined in X1 to X10 G and h are the same or different and each independently an integer of 0 to 4, and each of the substituents may be connected to adjacent substituents to form a saturated or unsaturated cyclic structure, Each independently substituted substituent is bonded to the 9-position and the 10-position of the anthracene, so that the symmetrical group is not bonded to the anthracene phase.

In the above formula (1), Ar11 to Ar12 are the same as or different from each other, and each independently is the same as defined in the above Ar7 to Ar8, i and j are the same as or different from each other, and each independently is an integer of 1 to 4.

In addition, one of the substituents of c1 to c4 binds to the * moiety of the formula Ac and X is selected from -O-, -S-, -N (R50) - and -N (R51R52) And k is an integer of 1 to 4. When k is 2 or more, the two or more R42 to R49 are the same as or different from each other.

Wherein Ar13 and Ar14 are the same as or different from each other and each independently is the same as defined in Ar7 to Ar8, R53 and R54 are as defined in X1 to X10, L and m are the same as or different from each other, And P and q are the same or different from each other and each independently an integer of 0 to 4;

Is a single bond, -O-, -S-, -N (R55) -, an alkylene group or an arylene group, and r is 2 or 3, and in this case, They may be the same or different, and * the sites are connected to each other.

And R < 59 > are the same or different from each other and each independently is the same as defined in X1 to X10, and u is an integer of 1 to 3, And s and t are independently an integer of 0 to 4, and when s, t, u, and v are each independently 2 or more, A15 And A16 and R56 to R59 may be the same or different.

According to a more preferred embodiment, the compounds represented by the formulas (IA) to (1D) may be any one selected from the following compounds [1] to [310].

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 1

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

  [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 an 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%) of a compound represented by [Intermediate 1-a].

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

[Intermediate 1-b]

40 g (134 mmol) of the intermediate [1-a] obtained in the above Reaction Scheme-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 71%) of the compound represented by [Intermediate 1-b].

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

[Intermediate 1-c]

A 2 L reactor was charged with 100 g (465 mmol) of methyl 2-bromobenzoate, 129 g (605 mmol) of 5-bromobenzo [b] thiophene, 1 g (5 mmol) of dipalladium acetate, 930 mmol) and dimethylformamide (500 mL), and the mixture was refluxed for 12 hours. The reaction solution was filtered, concentrated under reduced pressure, and then separated by column chromatography to obtain 135 g (yield: 84%) of the compound represented by [Intermediate 1-c].

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

[Intermediate 1-d]

135 g (389 mmol) of [Intermediate 1-c] obtained in the above Scheme 1-3 and 1350 mL of tetrahydrofuran were added to a 2 L reactor and stirred. After cooling to 0 ° C, 324 mL (972 mmol) of 3M-methylmagnesium bromide was added dropwise and the mixture was refluxed for 3 hours. Saturated ammonium chloride aqueous solution was added, and organic layer was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and 405 mL of phosphoric acid was added thereto, followed by stirring for 12 hours. The organic layer was extracted with methylene chloride and distilled water, and then concentrated under reduced pressure, followed by separation by column chromatography to obtain 78 g (yield: 60%) of a compound represented by [Intermediate 1-d].

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

[Intermediate 1-e]

78 g (237 mmol) of Intermediate 1-d obtained in the above Scheme 1-4, 51.4 g (308 mmol) of 2-nitrophenylboronic acid and 8.2 g of tetrakis (triphenylphosphine) palladium (7.0 mmol), potassium carbonate (82 g, 592 mmol), 1,4-dioxane (390 mL), toluene (390 mL) and distilled water (156 mL). After cooling to room temperature, the organic layer was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 71 g (yield 80%) of a compound represented by [Intermediate 1-e].

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

[Intermediate 1-f]

71 g (191 mmol) of the compound represented by [Intermediate 1-e] obtained in the above Scheme 1-5, 150.4 g (573 mmol) of triphenylphosphine and 355 mL of dichlorobenzene were placed and refluxed for 12 hours. When the reaction was completed, the reaction mixture was filtered under reduced pressure in a hot state. The solution was dried under reduced pressure and then separated by column chromatography to obtain 57 g (yield: 88%) of the compound represented by [Intermediate 1-f].

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

[Intermediate 1-g]

57 g (168 mmol) of Intermediate 1-f obtained in the above Reaction Scheme 1-6, 41.1 g (202 mmol) of iodobenzene, 2.9 g (8.0 mmol) of copper iodide and 74.9 g 353 mmol), 1,2-cyclohexyldiamine (40.3 g, 353 mmol) and 1,4-dioxane (570 mL) were added and the mixture was stirred at 100 ° C for 12 hours. After filtration at a high temperature, the product was separated by column chromatography to obtain 57 g (yield 82%) of a compound represented by [Intermediate 1-g].

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

[Intermediate 1-h]

57 g (137 mmol) of Intermediate 1-g obtained in the above Reaction Scheme 1-7 and 450 mL of tetrahydrofuran were added to a 2 L reactor and stirred. After cooling to -78 ° C, 103.0 mL (165 mmol) of en-butyllithium (1.6M hexane solution) was added dropwise, and the mixture was warmed to room temperature and stirred for 12 hours. 41.8 g (165 mmol) of iodine was added, the temperature was raised to room temperature, and the mixture was stirred for 2 hours. An aqueous solution of sodium thiosulfate was added, and the organic layer was extracted with ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 45.0 g of [intermediate 1-h] (yield: 61%).

[Reaction Scheme 1-9] Synthesis of [Intermediate 1-i]

[Intermediate 1-i]

45 g (84 mmol) of the compound represented by [Intermediate 1-h], 18 g (105 mmol) of 2-bromoaniline and 0.2 g (1 mmol) of dipalladium acetate were added to a 2 L reactor. ), 1.8 g (3 mmol) of zincphosphate, 40.9 g (126 mmol) of cesium carbonate and 450 mL of toluene were placed and refluxed for 12 hours. After filtration at a high temperature, the filtrate was concentrated under reduced pressure and then separated by column chromatography to obtain 35 g (yield 71%) of a compound represented by [Intermediate 1-i].

[Reaction Scheme 1-10] Synthesis of [Intermediate 1-j]

   [Intermediate 1-j]

35 g (60 mmol) of the compound represented by [Intermediate 1-i] obtained in the above Reaction Scheme 1-9, 0.4 g (1 mmol) of tricyclohexylphosphine tetrafluoroborate, 0.1 g (1 mmol), potassium carbonate (16.5 g, 120 mmol) and toluene (350 mL), 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 19 g (yield: 63%) of a compound represented by [Intermediate 1-j].

[Reaction Scheme 1-11] Synthesis of [Compound 1]

[Compound 1]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Scheme 1-7], except that [Intermediate 1-j] obtained in the above [Reaction Scheme 1-10] was used instead of [Intermediate 1-f] 7.0 g (yield: 60.8%) of a compound was obtained.

[Synthesis Example 2] Synthesis of [Compound 2]

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

[Compound 2]

10.0 g (20 mmol) of the compound represented by [Intermediate 1-j] obtained in the above Reaction Scheme 1-10 and 7.2 g (30 mmol) of Intermediate 1-b obtained in Reaction Scheme 1-2 were added to a 300- , 0.4 g (0.4 mmol) of tris (dibenzylideneacetone) dipalladium, 0.6 g (2 mmol) of tritiated butylphosphonium tetrafluoroborate, 3.8 g (40 mmol) of sodium tertiary butoxide, mL, and refluxed for 12 hours. After filtration at a high temperature, the filtrate was concentrated under reduced pressure and then separated by column chromatography to obtain 8.5 g (yield: 60%) of a compound represented by [Compound 2].

[Synthesis Example 3] Synthesis of [Compound 9]

Synthesis of [Reaction Scheme 3-1] [Intermediate 3-a]

[Intermediate 3-a]

Synthesis Example 1 [Intermediate 1-h] obtained in the above Reaction Scheme 1-8 was used instead of [Intermediate 1-h] in [Reaction Scheme 1-9], except that methylanthranilate was used instead of 2-bromoaniline Synthesis was conducted in the same manner to obtain 44.0 g (yield 70%) of the compound represented by [Compound 3-a].

Synthesis of [Reaction Scheme 3-2] [Intermediate 3-b]

[Intermediate 3-b]

Synthesis Example 1 [Intermediate 3-b] was prepared in the same manner as in [Scheme 1-4] except that [Intermediate 3-a] obtained in the above Reaction Scheme 3-1 was used instead of [Intermediate 1-d] 26.0 g (yield: 61%) of the compound to be displayed was obtained.

Synthesis of [Scheme 3-3] [Compound 9]

[Compound 9]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Formula 1-7], except that [Intermediate 1-g] was used instead of [Intermediate 3-b] obtained in [Reaction Scheme 3-2] 7.5 g (yield 66%) of the compound was obtained.

[Synthesis Example 4] Synthesis of [Compound 10]

[Reaction Scheme 4-1] Synthesis of [Compound 10]

[Compound 10]

Synthesis Example 2 Except for using [Intermediate 3-b] obtained in [Reaction Scheme 3-2] above instead of [Intermediate 1-j] in [Reaction Scheme 2-1], the title compound 8.5 g (yield 62%) of the compound was obtained.

[Synthesis Example 5] Synthesis of [Compound 16]

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

[Intermediate 5-a]

50 g (92 mmol) of the intermediate [1-h] obtained in the above Reaction Scheme 1-8, 55.0 g (102 mmol) of benzophenone hydrazone, 2.1 g (9 mmol) of dipalladium acetate, 5.8 g (9 mmol) of 2'-bis (diphenylphosphino) -1,1-binaphthyl, 12.4 g (129 mmol) of sodium thiosylbutoxide and 400 mL of toluene were placed 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 41 g (yield: 73%) of a compound represented by [Intermediate 5-a].

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

  [Intermediate 5-b]

41 g (67 mmol) of Intermediate 5-a obtained in the above Reaction Scheme 5-1, 12.9 g (81 mmol) of 3,3-dimethylindan-1-one, para-toluenesulfonic acid 38.4 g (202 mmol) and 410 mL of ethanol, and the mixture was refluxed for 48 hours. The reaction solution was concentrated under reduced pressure and purified by column chromatography to obtain 10.0 g (yield 30%) of a compound represented by [Intermediate 5-b].

[Reaction Scheme 5-3] Synthesis of [Compound 16]

[Compound 16]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Scheme 1-7], except that [Intermediate 5-b] obtained in the above Reaction Scheme 5-2 was used instead of [Intermediate 1-f] 8.0 g (yield 70%) of the compound was obtained.

[Synthesis Example 6] Synthesis of [Compound 17]

Synthesis of [Reaction Scheme 6-1] [Compound 17]

[Compound 17]

Synthesis Example 2 Except for using [Intermediate 5-b] obtained in the above Reaction Scheme 5-2 instead of [Intermediate 1-j] in [Reaction Scheme 2-1], the title compound 10.0 g (yield 71%) of the compound was obtained.

[Synthesis Example 7] Synthesis of [Compound 19]

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

[Intermediate 7-a]

Synthesis Example 5 Synthesis was conducted in the same manner as in [Intermediate 7-a] except that [Intermediate 1-d] obtained in the above Reaction Scheme 1-4 was used instead of [Intermediate 1-h] in [Reaction Scheme 5-1] 96 g (yield 71%) of the compound to be displayed was obtained.

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

[Intermediate 7-b]

Synthesis Example 5 Synthesis was conducted in the same manner as in [Intermediate 7-b] except that [Intermediate 7-a] obtained in the above Reaction Scheme 7-1 was used instead of [Intermediate 5-a] in [Reaction Scheme 5-2] 27.0 g (yield: 31%) of the compound to be displayed was obtained.

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

[Intermediate 7-c]

Synthesis Example 1 [Intermediate 7-b] 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-f in Reaction Scheme 1-7 23.0 g (yield: 72%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 7-4] [Intermediate 7-d]

[Intermediate 7-d]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 7-d] except that [Intermediate 7-c] obtained in the above Reaction Scheme 7-3 was used instead of [Intermediate 1-g] in [Reaction Scheme 1-8] To obtain 24.0 g (yield: 71%) of the compound to be displayed.

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

[Intermediate 7-e]

Synthesis Example 5 Synthesis was conducted in the same manner as in [Intermediate 7-e] except that [Intermediate 7-d] obtained in the above Reaction Scheme 7-4 was used instead of [Intermediate 1-h] in [Reaction Scheme 5-1] 14.0 g (yield: 72%) of the compound to be displayed was obtained.

[Synthesis of Reaction Formula 7-6] [Intermediate 7-f]

[Intermediate 7-f]

Synthesis Example 5 Synthesis was conducted in the same manner as in [Intermediate 7-f] except that [Intermediate 7-e] obtained in the above Reaction Scheme 7-5 was used instead of [Intermediate 5-a] in [Reaction Scheme 5-2] 4.1 g (yield: 31%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 7-7] [Compound 19]

[Compound 19]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Scheme 1-7], except that [Intermediate 7-f] obtained in the above Reaction Scheme 7-6 was used instead of [Intermediate 1-f] 7.5 g (yield 67%) of the compound was obtained.

[Synthesis Example 8] Synthesis of [Compound 21]

Synthesis of [Formula 8-1] [Compound 21]

[Compound 21]

Synthesis Example 1 [Intermediate 7-f] obtained in the above Reaction Scheme 7-6 was used instead of [Intermediate 1-f] in [Reaction Scheme 1-7], and 2-bromo-9,9-di Was synthesized in the same manner as in Example 1 to obtain 8.2 g (yield 65%) of the compound represented by [Compound 21].

[Synthesis Example 9] Synthesis of [Compound 22]

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

[Intermediate 9-a]

Synthesis Example 1 [Intermediate 1-d] obtained in the above Reaction Scheme 1-4 was used instead of [Intermediate 1-h] in Reaction Scheme 1-9, except that methylanthranilate was used instead of 2-bromoaniline To obtain 30.0 g (yield: 71%) of the compound represented by [Compound 9-a].

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

[Intermediate 9-b]

Synthesis Example 1 [Intermediate 9-b] was prepared in the same manner as in [Scheme 1-4] except that [Intermediate 9-a] obtained in the above-mentioned Reaction Scheme 9-1 was used instead of [Intermediate 1-c] To obtain 20.0 g (yield 70%) of the compound to be displayed.

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

[Intermediate 9-c]

Synthesis Example 1 [Intermediate 9-c] was synthesized in the same manner as Intermediate 9-b except for using [Intermediate 9-b] obtained in the above Reaction Scheme 9-2 instead of [Intermediate 1-f] 16.0 g (yield: 67%) of the compound to be displayed was obtained.

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

[Intermediate 9-d]

Synthesis Example 1 [Intermediate 9-d] was synthesized in the same manner as Intermediate 9-c except for using [Intermediate 9-c] obtained in the above Reaction Scheme 9-3 instead of [Intermediate 1-g] To obtain 14.5 g (yield 71%) of the compound to be displayed.

Synthesis of [Reaction Scheme 9-5] [Intermediate 9-e]

[Intermediate 9-e]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Compound 9-e] except that [Intermediate 9-d] obtained in the above Reaction Scheme 9-4 was used instead of [Intermediate 1-h] in [Reaction Scheme 1-9] 10.5 g (yield 68%) of the compound to be displayed was obtained.

Synthesis of [Reaction Scheme 9-6] [Intermediate 9-f]

[Intermediate 9-f]

Synthesis Example 1 [Intermediate 9-f] was synthesized in the same manner as Intermediate 9-e except that [Intermediate 9-e] obtained in the above Reaction Scheme 9-5 was used instead of [Intermediate 1-i] 6.5 g (yield 71%) of the compound to be displayed was obtained.

Synthesis of [Compound 9-2]

[Compound 22]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Reaction Formula 1-7], except that [Intermediate 9-f] obtained in the above Reaction Scheme 9-6 was used instead of [Intermediate 1-f] 7.5 g (yield 70%) of the compound was obtained.

[Synthesis Example 10] Synthesis of [Compound 25]

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

[Intermediate 10-a]

Synthesis Example 1 [Intermediate 9-d] obtained in the above Reaction Scheme 9-4 was used instead of [Intermediate 1-h] in Reaction Scheme 1-9, except that methylanthranilate was used instead of 2-bromoaniline Was synthesized in the same manner as above to give 30 g (yield 75%) of the compound represented by [Intermediate 10-a].

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

[Intermediate 10-b]

Synthesis Example 1 Synthesis was conducted in the same manner as in [Intermediate 10-b] except that [Intermediate 10-a] obtained in the above Reaction Scheme 10-1 was used instead of [Intermediate 1-c] in [Reaction Scheme 1-4] 17.0 g (yield 60%) of the compound to be displayed was obtained.

Synthesis of [Scheme 10-3] [Compound 25]

[Compound 25]

Synthesis Example 1 [Intermediate 10-b] obtained in the above Reaction Scheme 10-2 was used instead of [Intermediate 1-j] in [Reaction Scheme 2-1], and 2-chloro-4,6 -Diphenyl-1,3,5-triazine was used in place of 4-chloro-4-fluorobenzyl chloride to obtain 8.0 g (yield: 60%) of the compound represented by [Compound 25].

Examples 1 to 11: Preparation of organic light emitting diode

Example 1

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate is mounted in a vacuum chamber, the base pressure is adjusted to 1 × 10 ^-6 torr, and then an organic material is formed on the ITO in the order of DNTPD (700 Å) and the compound represented by the compound 2 (300 Å) . Next, BH1 as a host was mixed with 3% BD1 as a dopant to form a film (250 ANGSTROM), followed by depositing Compound E1: Liq = 1: 1 (250 ANGSTROM), Liq (10 ANGSTROM) mA.

Examples 2 to 9

Examples 2 to 9 were prepared in the same manner as in Example 1 except that the compound described in [Table 1] was used instead of [Compound 2], and the organic light emitting device was measured at 0.4 mA.

<DNTPD>

<BH1> <BD1>

<E1><Liq>

Comparative Example 1

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 base pressure was adjusted to 1 × 10 ^-6 torr, and organic materials were deposited on the ITO in the order of DNTPD (700 Å) and α-NPB (300 Å). Subsequently, host BH1 and dopant BD1 (250 Å), followed by deposition of compounds E1: Liq = 1: 1 (250 Å), Liq (10 Å), and Al (1,000 Å).

<α-NPB>

In Examples 1 to 11, voltage, current, luminance, color coordinate, and lifetime were measured for the organic light-emitting device manufactured, and the results are shown in Table 1 below. T80 represents the time required for the luminance to be reduced to 80% of the initial luminance (3000 cd / m &lt; 2 &gt;).

division compound V Cd / ㎡ CIEx CIEy T ₈₀ (Hrs) (3000 cd / m 2) Comparative Example 1 α-NPB 4.4 630 0.133 0.129 75 Example 1 Compound 1 4.1 750 0.133 0.128 130 Example 2 Compound 9 4.3 780 0.132 0.130 120 Example 3 Compound 16 4.2 760 0.133 0.127 125 Example 4 Compound 19 4.1 800 0.133 0.126 115 Example 5 Compound 22 4.2 790 0.132 0.128 130 Example 6 Compound 35 4.3 820 0.134 0.127 115 Example 7 Compound 37 4.1 780 0.133 0.129 145 Example 8 Compound 40 4.2 840 0.133 0.127 135 Example 9 Compound 43 4.2 750 0.132 0.126 125

As shown in Table 1, the device employing the organic electroluminescent compound according to the present invention has a higher luminance and a better lifetime characteristic than a device using α-NPB, which is widely used as a hole transport layer material .

Claims (8)

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

In the above formula (1)
Z ₁ to Z ₆ Are each a carbon atom, Z ₁ and Z ₂ , Z ₃ and Z _4, and Z ₅ and Z ₆ are each bonded to '*' of Q to form a condensed ring, n is an integer of 0 to 3, and Z At least one of the condensed rings formed from ₁ and Z ₂ , Z ₃ and Z _4, and Z ₅ and Z ₆ is characterized in that n is 1 or more,
X is a single bond or is selected from the group consisting of S, O, NR ₁ , SiR ₂ R ₃ , GeR ₄ R ₅ , CR ₆ R ₇ , Se and Te, wherein the plural Xs are the same or different, At least one of the plurality of X's is NR &_lt; ₁ &gt;
W is CR or N,
Wherein R and R ₁ to R ₇ are the same or different from each other 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 alkyl 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, 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 and an ester group. 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 (1-1) to (1-3):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In the above formulas (1-1) to (1-3), the definitions of X and W are the same as defined in claim 1. The method according to claim 1,
The above R and R ₁ to R ₇ Is at least one substituent group represented by the following structural formulas 1 to 2:
[Structural formula 1]

[Structural formula 2]

In the above Structural Formulas 1 to 2,
L ₁ and L ₂ each independently represent a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2 to C50 heteroarylene group in which one or more substituted or unsubstituted C 3 -C 30 cycloalkyl is fused,
n and m are each independently an integer of 0 to 4, and when n and m are 2 or more, a plurality of L ₁ and L ₂ are the same or different from each other,
Ar _1, Ar ₂ and a plurality of Ar ₃ are the same or different from each other, each independently represent a substituted or unsubstituted C2 carbon atoms of from 3 to 30 cycloalkyl group, a substituted or unsubstituted alkyl group of 1 to 30, a substituted or unsubstituted A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms substituted or unsubstituted with at least one fused cycloalkyl having 3 to 30 carbon atoms And a substituted or unsubstituted C2 to C50 heteroaryl group in which one or more substituted or unsubstituted Cycloalkyl of 3 to 30 carbon atoms is fused,
Ar ₁ , Ar ₂ and Ar ₃ may be bonded to each other or may be connected with adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the formed alicyclic or aromatic single ring or polycyclic ring may be N , S and &lt; RTI ID = 0.0 &gt; O, &lt; / RTI &gt;
P and q are integers of 0 to 3, and when p and q are 2 or more, a plurality of * - () may be the same or different from each other. The method according to claim 1,
The organic luminescent compound represented by the formula (1) is selected from the following compounds l to 48:

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. 6. The method of claim 5,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes,
Wherein at least one of the layers comprises an organic light-emitting compound represented by the formula (1). 6. The method of claim 5,
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). The method according to claim 6,
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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