KR20140083897A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic luminescent compound represented by chemical formula 1 below and an organic electroluminescent device including the same. The organic luminescent compound according to the present invention has excellent luminous efficiency and life characteristics, thereby enabling the manufacture of an organic electroluminescent device which has excellent luminous efficiency and simultaneously has enhanced power efficiency and long life characteristics.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

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

In recent years, organic light emitting devices capable of being driven by a low voltage in a self-emission type are superior in viewing angle and contrast ratio compared to a liquid crystal display, which is a mainstream of a flat panel display device, require no backlight and are lightweight and thin, And has been attracting attention as a next generation display device.

An organic electroluminescent device is a device that injects electric charge into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole.

The organic electroluminescent device can be formed on a transparent substrate that can be made of plastic and can be driven at a voltage as low as 10 V or less as compared with a plasma display panel or an inorganic electroluminescent display and has a relatively low power consumption , And has an advantage of excellent color. In addition, organic electroluminescent devices are capable of displaying three colors of green, blue, and red, and thus are attracting much attention as next-generation rich color display devices.

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, In particular, CBP is the most widely known phosphorescent host material, and an organic electroluminescent device using a BAlq derivative as a host is known.

However, an organic electroluminescent device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material. However, when a material such as BAlq or CBP is used as a host of a phosphorescent material, There is no significant advantage in terms of power efficiency due to a high voltage and satisfactory level of life of the device can not be achieved, and development of a more stable and high-performance host material is required.

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic luminescent compound having a luminescent efficiency higher than that of a conventional material, and at the same time having improved power efficiency and longevity.

The present invention also provides an organic electroluminescent device with high efficiency and long life by employing the organic electroluminescent compound as a light emitting material.

In order to solve the above-described problems, the present invention provides an organic electroluminescent compound represented by the following formula (1), wherein the organic electroluminescent compound includes at least one organic electroluminescent compound Thereby providing a thin film layer.

[Chemical Formula 1]

The definition of each substituent or skeletal atom will be described later.

Also, the present invention provides an organic thin film layer for an organic electroluminescent device comprising at least one organic electroluminescent compound represented by the above formula (1) and an organic electroluminescent device comprising the same.

The organic electroluminescent device according to the present invention can produce an organic electroluminescent device having excellent luminous efficiency and long lifetime characteristics while having excellent luminous efficiency and material life characteristics.

1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention.

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

An aspect of the present invention relates to an organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1)

L is selected from a substituted or unsubstituted aryl group having 6 to 60 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

Y ₁ and Y ₂ represent a single bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 30 carbon atoms, A substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, p and q are each a An integer of 0 to 5, and when p and q are 2 or more, plural Y ₁ and Y ₂ may be the same or different from each other.

Z is a single bond or CR ₁ R ₂ , O, S, SiR ₃ R ₄ And NR ₅ , R ₁ to R _{5 each} represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms Aryl groups, and may combine with each other or adjacent substituents to form a saturated or unsaturated ring.

X ₁ to X ₁₄ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, an amidino group, a hydrazine, a hard lone, a carboxyl group or a salt thereof, Substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, An arylalkylamino group having 1 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Each of X ₁ to X ₁₄ may be bonded to adjacent substituents to form a saturated or unsaturated ring, and m is an integer of 0 to 8;

The 'substituted or unsubstituted' in the above 'substituted or unsubstituted' means a case where L, Y ₁ , Y ₂ , R ₁ to R ₅ and X ₁ to X ₁₄ are further substituted by one or more substituents, One or more substituents include an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, An aryloxy group, an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a hydroxyl group, a nitro group, an amidino group, a hydrazine , Hydrazone, Carbopol Group or a salt thereof, a sulfonic acid group or a salt thereof come, phosphoric acid or a salt thereof, a substituted or unsubstituted aryl having a carbon number of 5 to 60 Im, a cyano group, is selected from deuterium and halogen group.

According to a preferred embodiment of the present invention, Y ₁ and Y ₂ may be any one selected from the following formulas [C1] to [C14].

[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]

In the above Structural Formula C1 to Structural Formula C14, hydrogen or deuterium may be bonded to the carbon position of the ring in each structural formula, and R is X ₁ To X < _{14 &} gt ;.

According to a preferred embodiment of the present invention, L may be a substituted or unsubstituted C2-C60 heteroaryl group containing at least one nitrogen.

According to a preferred embodiment of the present invention, L connected to Y ₂ may be any one selected from the following formulas [1] to [10]. 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 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 the different and are each independently of one _{another, C (R 41), C} (R 42) (R 43), N, N (R 44), O , and is selected from S, wherein R ₄₁ To R < ₄₄ > 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 cycloalkyl group having 3 to 30 carbon atoms, And a heteroaryl group having 2 to 30 carbon atoms having a substituted or unsubstituted hetero atom, O, N, S or P,

According to a preferred embodiment of the present invention, the above-mentioned structural formulas 1 to 10 may be any one selected from the following structural formulas.

[Structural Formula 11]

In the above structural formula 11,

X is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms An amino group, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S, or P as a hetero atom, a cyano group, Is selected from a, m is an integer from 1 to 11, is a plurality of X are the same or different when m is 2 or more.

On the other hand, the aryl group contained in the organic light emitting compound according to the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and is 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, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, Naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, naphthyl group, An aromatic group such as a fluorenyl group, a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a pyrenyl group, a perylene group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group.

At least one hydrogen atom of the aryl group may be replaced by a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R) 'And R''each independently represent an alkyl group having 1 to 10 carbon atoms, which is referred to as an "alkylamino group" in this case), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, A halogenated alkyl 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 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 or a heteroarylalkyl group having 2 to 24 carbon atoms.

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, , An octyl group, a stearyl group, a trichloromethyl group, and a trifluoromethyl group, and at least one hydrogen atom of the alkyl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, (in this case, "alkylsilyl group" hereinafter), a substituted or unsubstituted amino group (-NH _2, -NH (R), -N (R ') (R "), where R, R' and R" are each A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms (preferably an alkyl group having 1 to 24 carbon atoms) A halogenated alkyl group, an alkenyl group having 2 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms Group, may be substituted with a heteroarylalkyl group having 1 to 24 carbon atoms heteroaryl group, having 5 to 24 aryl group, C 6 -C 24 aryl group, a C 3 -C 24 heteroaryl group, or having from 3 to 24 of the.

Specific examples of the alkoxy group used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

The aryloxy group which is a substituent used in the present invention means an -O-aryl radical, wherein the aryl group is as defined above, and specific examples thereof include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy and the like, and at least one hydrogen atom contained in the aryloxy group may be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl and the like.

Specific examples of the alkenyl group used in the present invention include straight chain or branched chain alkenyl groups and include 3-pentenyl, 4-hexenyl, 5-heptenyl, 4-methyl- Dimethyl-pentenyl group, 6-methyl-5-heptenyl group and 2,6-dimethyl-5-heptenyl group.

Further, according to a more preferred embodiment of the present invention, the above-mentioned formula (1) can be selected from the compounds represented by the following formulas (2) to (228).

[Chemical Formula 2] < EMI ID =

[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]

[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]

[Formula 79] [Formula 80] [Formula 81]

[Chemical Formula 82]

[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]

[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 100] [Chemical Formula 100]

[Formula 103] [Formula 103]

[Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Chemical Formula 115]

[Chemical Formula 120] [Chemical Formula 120] [Chemical Formula 120]

[Formula 124] [Formula 124] [Formula 125]

[Formula 126] < EMI ID = 129.1 >

[Formula 130] < EMI ID = 131.0 >

[Formula 135] [Formula 135] [Formula 137]

[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]

[Chemical Formula 144] [Chemical Formula 144] [Chemical Formula 145]

[Chemical Formula 146] [Chemical Formula 148] [Chemical Formula 149]

[Formula 15] [Formula 15] [Formula 15] [Formula 15]

[Chemical Formula 155] [Chemical Formula 156] [Chemical Formula 157]

[Formula 15] [Formula 15] [Formula 15] [Formula 15] [Formula 15]

[166] [165] [165]

[Formula 166] [Formula 169] [Formula 169]

[173] [173] [173]

[Formula 177] [Formula 177] [Formula 177]

[Formula 181] [Formula 181] [Formula 181] [Formula 181]

[Formula 182] [Formula 184] [Formula 184]

[Formula 188] [Formula 188] [Formula 189]

[Formula 19] [Formula 19] [Formula 193] [Formula 193]

[Formula 19] [Formula 19] [Formula 19] [Formula 19] [Formula 19]

[201] [201] [201]

[Chemical Formula 203]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 210] [Chemical Formula 212] [Chemical Formula 213]

[Formula 21] [Formula 21] [Formula 21] [Formula 21]

[Formula 21] < EMI ID =

[Formula 22] < EMI ID =

[228] [228]

Another aspect of the present invention relates to an organic thin film layer for an organic electroluminescence device, which comprises at least one compound according to the formula (1) of the present invention.

According to one embodiment of the present invention, the organic thin film layer is characterized in that it further comprises at least one compound represented by the following formulas [A-1] to [J-1].

[General Formula A-1]

ML ₁ L ₂ L ₃

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 the group consisting of 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 a specific 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 group 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 organic thin film layer may further include various host compounds and various dopant compounds in addition to the organic electroluminescent compound and the dopant compound according to the present invention.

Another aspect of the present invention relates to an organic electroluminescent device including the organic thin film layer, wherein at least one organic thin film layer including a light emitting layer is sandwiched between the cathode and the anode of the organic electroluminescent device, The organic luminescent compound of Formula 1 according to the present invention may be included alone or as a component of a mixture and further include the above-exemplified dopant compounds.

The organic electroluminescent device according to the present invention may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer in addition to the light emitting layer. May be used for the hole injecting layer, the hole transporting layer, the electron injecting layer, and the electron transporting layer in addition to the light emitting layer.

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.

In the present invention, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenylamino) triphenylamine).

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, .

The material of the electron transport layer is not particularly limited as long as it is commonly used in the art, and for example, oxadiazole derivative PBD, BMD, BND, Alq3, or the like can be used.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li2O, and BaO can be used.

The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

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, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO) or the like which is transparent and excellent in conductivity is used.

A hole injection 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.

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.

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.

According to another embodiment of the present invention, 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 is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. It will be clear to those who have knowledge.

<Examples>

Example 1 Synthesis of Compound Represented by Formula 2

(1) Synthesis of Compound Represented by Formula (1-a)

A compound represented by the formula (1-a) was synthesized by the following reaction scheme (1).

[Reaction Scheme 1]

[Chemical Formula 1-a]

186.1 g (640.2 mmol) of 1-bromo-3-iodobenzene, 63.5 g (853.6 mmol) of copper powder, 22.6 g (83.4 mmol) of 18- (1280.4 mmol) were added in this order, 500 mL of 1,2-dichlorobenzene was added, and the mixture was refluxed and stirred at 180 ° C for 1 day. After the completion of the reaction, the solution was concentrated under a high-temperature filter and subjected to column chromatography using hexane alone to obtain 48 g of a compound represented by the formula (1-a). (Yield: 41%)

(2) Synthesis of Compound Represented by Formula (1-b)

[Chemical Formula 1-b] was synthesized by the following Reaction Scheme 2.

[Reaction Scheme 2]

[Chemical Formula 1-a] [Chemical Formula 1-b]

48.0 g (176.4 mmol) of the compound represented by the formula 1-a obtained in the above reaction scheme 1 was dissolved in 480 mL of tetrahydrofuran in a nitrogen stream, and 132 mL of 1.6 M normal-butyl lithium was added thereto while stirring at -78 ° C. 211.6 mmol) is slowly added dropwise, and the mixture is stirred for 1 hour while keeping the temperature at -78 ° C. Then, 25.7 g (246.9 mmol) of trimethyl borate was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. When the reaction is completed, 200 mL of a 1 M aqueous hydrochloric acid solution is added dropwise at room temperature, and the mixture is stirred for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and recrystallized in methylene chloride and hexane to obtain 25.2 g of a compound represented by the formula (1-b). (Yield 60%)

(3) Synthesis of Compound Represented by Formula (1-c)

The compound represented by the formula (1-c) was synthesized by the following reaction scheme [3].

[Reaction Scheme 3]

[Chemical Formula 1-b] [Chemical Formula 1-c]

10.0 g (40.6 mmol) of the compound represented by the formula 1-b obtained from the above-mentioned reaction formula 2, 14.45 g (60.95 mmol) of 3-bromocarbazole and 940 mg (0.8 mmol) of tetrakis (triphenylphosphine) palladium ), 11.23 g (81.27 mmol) of potassium carbonate, 50 mL of 1,4-dioxane, 50 mL of toluene and 20 mL of distilled water, and the mixture is stirred at 100 ° C for 12 hours. When the reaction is complete, extract using methylene chloride and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and acetone to obtain 8.2 g of a compound represented by the formula (1-c). (Yield: 56%)

(4) Synthesis of Compound Represented by Formula 2

A compound represented by the formula (2) was synthesized by the following reaction scheme (4).

[Reaction Scheme 4]

[Chemical Formula 1-c] [Chemical Formula 2]

20.0 g (55.80 mmol) of the compound represented by the formula (1-c) obtained from the above-mentioned scheme 3 and 5.58 g (83.70 mmol) of 60% sodium hydride were placed in 300 mL of dimethylformamide and stirred at room temperature for 30 minutes . 17.93 g (66.96 mmol) of chlorodiphenyltriazine is dissolved in 200 mL of dimethylformamide, and the mixture is slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 22.0 g of a compound represented by the formula (2). (Yield 67%)

MS [M] &lt; ⁺ & gt ^; 589.23

Example 2 Synthesis of Compound Represented by Formula 3

(1) Synthesis of Compound Represented by Formula 3

[Chemical Formula 3] was synthesized by the following Reaction Scheme 5.

[Reaction Scheme 5]

[Chemical Formula 1-c] [Chemical Formula 3]

20.0 g (55.80 mmol) of the compound represented by the formula (1-c) obtained from the above-mentioned scheme 3 and 5.58 g (83.70 mmol) of 60% sodium hydride were placed in 300 mL of dimethylformamide and stirred at room temperature for 30 minutes . Thereafter, 17.86 g (66.96 mmol) of chlorodiphenylpyrimidine is dissolved in 200 mL of dimethylformamide, and the mixture is slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 24.0 g of a compound represented by the formula (3). (Yield: 73%)

MS [M] &lt; ⁺ & gt ^; 588.23

Example 3 Synthesis of Compound Represented by Formula 26

(1) Synthesis of Compound Represented by Formula 3-a

A compound represented by the formula (3-a) was synthesized by the following reaction scheme [6].

[Reaction Scheme 6]

[Formula 3-a]

2.5 g (2.2 mmol) of tetrakis (triphenylphosphine) palladium and 30.1 g (218.0 mmol) of potassium carbonate were added to 20.0 g (109 mmol) of 2,4,6-trichlorotriazine, 17.1 g Is added to a mixed solvent of 600 mL of tetrahydrofuran, 400 mL of toluene and 400 mL of distilled water, and the mixture is refluxed for 9 hours. After completion of the reaction, the organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure and then recrystallized with toluene to obtain 20.7 g of a compound represented by the formula (3-a). (Yield: 84%)

(2) Synthesis of Compound Represented by Formula 3-b

[Chemical Formula 3-b] was synthesized by the following Reaction Scheme 7.

[Reaction Scheme 7]

[Formula 3-a] [Formula 3-b]

20.7 g (91.56 mmol) of the compound represented by the formula 3-a obtained from the above-mentioned scheme 6, 19.4 g (91.56 mmol) of dibenzofuran-2-boronic acid and 2.1 g of tetrakis (triphenylphosphine) palladium (1.8 mmol) of potassium carbonate and 25.3 g (183.1 mmol) of potassium carbonate are added to a mixed solvent of 600 mL of tetrahydrofuran, 400 mL of toluene and 400 mL of distilled water, and the mixture is refluxed for 12 hours. After completion of the reaction, the organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and the residue was recrystallized from methylene chloride and a nucleic acid to obtain 21.9 g of a compound represented by the formula (3-b). (Yield 69%)

(3) Synthesis of Compound Represented by Formula 26

[Chemical Formula 26] was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

[Chemical Formula 1-c] [Chemical Formula 3-b] [Chemical Formula 26]

20.0 g (55.80 mmol) of the compound represented by the formula (1-c) obtained from the above-mentioned scheme 3 and 5.58 g (83.70 mmol) of 60% sodium hydride were placed in 300 mL of dimethylformamide and stirred at room temperature for 30 minutes . 23.96 g (66.96 mmol) of the compound represented by the formula [3-b] obtained from the scheme 7 was dissolved in 200 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 33.7 g of a compound represented by the formula (26). (Yield: 89%)

MS [M] &lt; ⁺ & gt ^; 679.24

Example 4 Synthesis of Compound Represented by Formula 34

(1) Synthesis of Compound Represented by Formula 4-a

A compound represented by the following formula (4-a) was synthesized by the following reaction scheme (9).

[Reaction Scheme 9]

[Chemical Formula 4-a]

18.0 g (89.7 mmol) of 3-bromophenylboronic acid, 1.7 g (1.5 mmol) of tetrakis (triphenylphosphine) palladium and 20.7 g (149.4 mmol ), 100 mL of 1,4-dioxane, 100 mL of toluene, and 50 mL of distilled water, and the mixture is stirred at 100 ° C for 12 hours. When the reaction is complete, extract using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 23.2 g of a compound represented by the following formula (4-a). (Yield: 80%)

(2) Synthesis of Compound Represented by Formula 4-b

[Chemical formula 4-b] was synthesized by the following reaction scheme [Reaction formula 10].

[Reaction Scheme 10]

[Formula 4-a] [Formula 4-b]

23.2 g (59.8 mmol) of the compound represented by the formula 4-a obtained in the above Reaction Scheme 9 was dissolved in 230 mL of tetrahydrofuran in a nitrogen stream and 45 mL of 1.6 M normal-butyl lithium was added thereto with stirring at -78 ° C. 71.76 mmol) is slowly added dropwise, and the mixture is stirred for 1 hour while maintaining the temperature at -78 ° C. Thereafter, 18.2 g (71.76 mmol) of iodine was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. When the reaction is completed, 200 mL of sodium thiosulfate aqueous solution is added dropwise and stirred for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 23.2 g of a compound represented by the formula (4-b). (Yield: 89%)

(3) Synthesis of Compound Represented by Formula 34

A compound represented by the formula (34) was synthesized by the following reaction scheme [11].

[Reaction Scheme 11]

[Chemical Formula 1-c] [Chemical Formula 4-b] [Chemical Formula 34]

20.0 g (55.80 mmol) of the compound represented by the formula (1-c) obtained from the above scheme 3, 36.43 g (88.7 mmol) of the compound represented by the formula 4-b obtained from the above scheme 10, 7.09 g (111.6 mmol) of 18-crown-6, 2.95 g (11.16 mmol) of potassium carbonate and 123.14 g (167.4 mmol) of potassium carbonate were added in this order. 200 mL of 1,2-dichlorobenzene was added thereto, Reflux and stir. After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 27.3 g of a compound represented by the formula (34). (Yield: 73%)

MS [M] &lt; ⁺ & gt ^; 665.26

Example 5 Synthesis of Compound Represented by Formula 35

(1) Synthesis of a compound represented by the formula (5-a)

A compound represented by the formula (5-a) was synthesized by the following reaction scheme (12).

[Reaction Scheme 12]

[Formula 5-a]

250.0 g (1.35 mol) of 3-bromobenzaldehyde, 162.35 g (1.35 mol) of acetophenone, 1000 mL of 3 M KOH and 2500 mL of ethanol were charged and refluxed and stirred for 24 hours. After the reaction was completed, the temperature was adjusted to room temperature, followed by filtration and washing with 1000 mL of ethanol to obtain 330 g of a compound represented by the formula 5-a. (Yield: 85%)

(2) Synthesis of Compound Represented by Formula 5-b

[Chemical Formula 5-b] was synthesized by the following Reaction Scheme [13].

[Reaction Scheme 13]

[Formula 5-a] [Formula 5-b]

330 g (1.15 mol) of the compound represented by the above formula [5-a], 179.98 g (1.15 mol) of benzamidine hydrochloride and 91.94 g (2.3 mol) of NaOH were placed in 4500 mL of ethanol, And the mixture was refluxed and stirred. When the reaction is complete, wash with 1000 mL of hexane . Recrystallization from hexane and methylene chloride gave 175 g of a compound represented by the formula (5-b) was obtained. (Yield: 39%)

(3) Synthesis of Compound Represented by Formula 5-c

[Chemical Formula 5-c] was synthesized by the following Reaction Scheme 14.

[Reaction Scheme 14]

[Chemical Formula 5-b] [Chemical Formula 5-c]

23.2 g (59.9 mmol) of the compound represented by the above formula [5-b] obtained from the above Reaction Scheme 13 was dissolved in 230 mL of tetrahydrofuran in a nitrogen stream, and thereto was added dropwise a solution of 1.6 M n-butyllithium 71.76 mmol) is slowly added dropwise, and the mixture is stirred for 1 hour while maintaining the temperature at -78 ° C. Thereafter, 18.2 g (71.76 mmol) of iodine was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. When the reaction is completed, 200 mL of sodium thiosulfate aqueous solution is added dropwise and stirred for 30 minutes. The mixture was extracted with ethyl acetate and water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 23.2 g of a compound represented by the formula 5-c. (Yield: 89%)

(4) Synthesis of Compound Represented by Formula 35

A compound represented by the following formula (35) was synthesized by the following scheme (15).

[Reaction Scheme 15]

[Chemical Formula 1-c] [Chemical Formula 5-c] [Chemical Formula 35]

20.0 g (55.80 mmol) of the compound represented by the formula 1-c obtained from the above reaction scheme 3, 36.43 g (88.8 mmol) of the formula 5-c obtained from the above scheme 14, 7.09 g , 2.95 g (11.16 mmol) of 18-crown-6 and 123.14 g (167.4 mmol) of potassium carbonate were added in this order. 200 ml of 1,2-dichlorobenzene was added thereto and the mixture was refluxed and stirred for 1 day at 180 ° C . After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 31 g of a compound represented by the formula (35). (Yield: 83%)

MS [M] &lt; ⁺ & gt ^; 664.26

Example 6 Synthesis of Compound Represented by Formula 66

(1) Synthesis of Compound Represented by Formula (6-a)

A compound represented by the formula [6-a] was synthesized by the following reaction scheme [16].

[Reaction Scheme 16]

[Chemical Formula 6-a]

18.0 g (89.7 mmol) of 4-bromophenylboronic acid, 1.7 g (1.5 mmol) of tetrakis (triphenylphosphine) palladium and 20.7 g (149.4 mmol ), 100 mL of 1,4-dioxane, 100 mL of toluene, and 50 mL of distilled water, and the mixture is stirred at 100 ° C for 12 hours. When the reaction is complete, extract using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 23.2 g of a compound represented by the formula 6-a. (Yield: 80%)

(2) Synthesis of Compound Represented by Formula 6-b

[Chemical Formula 6-b] was synthesized by the following Reaction Scheme 17.

[Reaction Scheme 17]

[Formula 6-a] [Formula 6-b]

23.2 g (59.8 mmol) of the compound represented by the above formula [6-a] obtained from the above-mentioned scheme 16 was dissolved in 230 mL of tetrahydrofuran in a nitrogen stream and 45 mL of 1.6 M normal- 71.76 mmol) is slowly added dropwise, and the mixture is stirred for 1 hour while maintaining the temperature at -78 ° C. Thereafter, 18.2 g (71.76 mmol) of iodine was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. When the reaction is completed, 200 mL of sodium thiosulfate aqueous solution is added dropwise, and the mixture is stirred for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 23.2 g of a compound represented by the formula (6-b). (Yield: 89%)

(3) Synthesis of Compound Represented by Formula 66

A compound represented by the formula (66) was synthesized by the following scheme (18).

[Reaction Scheme 18]

[Chemical Formula 1-c] [Chemical Formula 6-b] [Chemical Formula 66]

20.0 g (55.80 mmol) of the compound represented by the formula (1-c) obtained from the above scheme 3, 36.43 g (88.7 mmol) of the compound represented by the formula 6-b obtained from the above scheme 17, 7.09 g (111.6 mmol) of 18-crown-6, 2.95 g (11.16 mmol) of potassium carbonate and 123.14 g (167.4 mmol) of potassium carbonate were added in this order. 200 mL of 1,2-dichlorobenzene was added thereto, Reflux and stir. After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 27.3 g of a compound represented by the following formula (66). (Yield: 73%)

MS [M] &lt; ⁺ & gt ^; 665.26

Example 7 Synthesis of Compound Represented by Formula 67

(1) Synthesis of Compound Represented by Formula 7-a

[Chemical Formula 7-a] was synthesized by the following Reaction Scheme (19).

[Reaction Scheme 19]

[Formula 7-a]

250.0 g (1.35 mol) of 4-bromobenzaldehyde, 162.35 g (1.35 mol) of acetophenone, 1000 mL of 3 M KOH and 2500 mL of ethanol were charged and refluxed and stirred for 24 hours. After the reaction was completed, the temperature was adjusted to room temperature, followed by filtration and washing with 1000 mL of ethanol to obtain 298 g of a compound represented by the formula 7-a. (Yield: 77%)

(2) Synthesis of Compound Represented by Formula 7-b

[Chemical Formula 7-b] was synthesized by the following Reaction Formula (20).

[Reaction Scheme 20]

[Formula 7-a] [Formula 7-b]

(1.04 mol), 162.53 g (1.04 mol) of benzamidine hydrochloride and 83.02 g (2.08 mol) of sodium hydroxide obtained in the above Reaction Scheme 19 were placed in 4500 mL of ethanol and reacted for 24 hours And the mixture was refluxed and stirred. When the reaction is complete, wash with 1000 mL of hexane . Recrystallization from hexane and methylene chloride gave 160 g of a compound represented by the general formula [7-b] was obtained. (Yield: 40%)

(3) Synthesis of Compound Represented by Formula 7-c

[Chemical Formula 7-c] was synthesized by the following Reaction Scheme (21).

[Reaction Scheme 21]

[Formula 7-b] [Formula 7-c]

23.2 g (59.9 mmol) of the compound represented by the formula [7-b] obtained from the above-mentioned reaction scheme 20 was dissolved in 230 mL of tetrahydrofuran under a nitrogen stream, and 45 mL of 1.6 M normal- 71.76 mmol) is slowly added dropwise, and the mixture is stirred for 1 hour while maintaining the temperature at -78 ° C. Thereafter, 18.2 g (71.76 mmol) of iodine was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. When the reaction is completed, 200 mL of sodium thiosulfate aqueous solution is added dropwise, and the mixture is stirred for 30 minutes. The mixture was extracted with ethyl acetate and water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 23.2 g of a compound represented by the formula 7-c. (Yield: 89%)

(4) Synthesis of Compound Represented by Formula 67

A compound represented by the formula (67) was synthesized by the following reaction scheme (22).

[Reaction Scheme 22]

[Chemical Formula 1-c] [Chemical Formula 7-c] [Chemical Formula 67]

20.0 g (55.80 mmol) of the compound represented by the formula 1-c obtained from the above scheme 3, 38.5 g (88.8 mmol) of the compound represented by the formula 7-c obtained from the above scheme 21, 7.09 g (111.6 mmol) of 18-crown-6, 2.95 g (11.16 mmol) of potassium carbonate and 123.14 g (167.4 mmol) of potassium carbonate were added in this order. 200 mL of 1,2-dichlorobenzene was added thereto, Reflux and stir. After the completion of the reaction, the solution was concentrated under reduced pressure, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 31.5 g of a compound represented by the formula (34). (Yield: 85%)

MS [M] &lt; ⁺ & gt ^; 664.26

Example 8 Synthesis of Compound Represented by Formula 94

(1) Synthesis of Compound Represented by Formula (8-a)

A compound represented by the following formula (8-a) was synthesized by the following Reaction Scheme (23).

[Reaction Scheme 23]

[Formula 8-a]

20.0 g (81.26 mmol) of 3-bromocarbazole and 8.1 g (121.9 mmol) of 60% sodium hydride were placed in 300 ml of dimethylformamide and stirred at room temperature for 30 minutes. 26.11 g (97.52 mmol) of chlorodiphenyltriazine was dissolved in 200 ml of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 200 ml of distilled water was added, followed by filtration and recrystallization to obtain 32.30 g of a compound represented by the formula (8-a). (Yield: 83%)

(2) Synthesis of Compound Represented by Formula 94

A compound represented by the formula (94) was synthesized by the following reaction scheme.

[Reaction Scheme 24]

[Formula 8-a] [Formula 94]

10.0 g (21 mmol) of the compound represented by the formula 8-a, 2.95 g (25 mmol) of indole and 0.38 g (0.4 mmol) of tris (dibenzylideneacetone) dipalladium obtained from the above- 0.6 g (2.09 mmol) of silicalbutylphosphonium tetrafluoroborate 5.79 g (41.90 mmol) of sodium tertiary butoxide is added to a mixed solvent of 100 mL of xylene, and the mixture is stirred and refluxed for 12 hours. After completion of the reaction, the organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and the residue was recrystallized from methylene chloride and a nucleic acid to obtain 7.1 g of a compound represented by the formula (94). (Yield 66%)

MS [M] &lt; ⁺ & gt ^; 513.20

Example 9 Synthesis of Compound Represented by Formula 154

(1) Synthesis of Compound Represented by Formula 9-a

A compound represented by the following formula (9-a) was synthesized by the following reaction scheme (25).

[Reaction Scheme 25]

[Chemical Formula 9-a]

A mixture of 187.1 g (661 mmol) of 1-bromo 4-iodobenzene, 100 g (661 mmol) of 2-amino-benzoic acid methyl ester, 15.31 g (26 mmol) of zincphosphate, 306.15 g (926 mmol) of cesium carbonate, 2.97 g (13 mmol) of triethylamine and 1500 mL of toluene were charged, and the mixture was refluxed for 24 hours and stirred. When the reaction was completed, the reaction mixture was filtered, concentrated under reduced pressure, and then separated by column chromatography to obtain 140 g of a compound represented by the following formula (9-a). (Yield 69%)

(2) Synthesis of Compound Represented by Formula 9-b

[Chemical Formula 9-b] was synthesized by the following Reaction Formula 26.

[Reaction Scheme 26]

[Formula 9-a] [Formula 9-b]

70 g (228.6 mmol) of the compound represented by the formula [9-a] obtained from the above-mentioned scheme [25] is dissolved in 550 mL of tetrahydrofuran, and then dissolved. 228 mL (685.8 mmol) of 3.0 M methylmagnesium bromide is slowly added dropwise, and when the dropwise addition is completed, the temperature is raised to room temperature and stirred for 12 hours. After completion of the reaction, 300 mL of a 2 M aqueous hydrochloric acid solution is added dropwise at room temperature, and the mixture is stirred for 30 minutes. Thereafter, the mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and then recrystallized from methylene chloride and a nucleic acid to obtain 60.3 g of a compound represented by the formula (9-b). (Yield: 91%)

(3) Synthesis of Compound Represented by Formula 9-c

A compound represented by the following formula (9-c) was synthesized by the following scheme (27).

[Reaction Scheme 27]

[Chemical Formula 9-b] [Chemical Formula 9-c]

60 g (196.8 mmol) of the compound represented by the formula 9-b obtained from the above-mentioned scheme 26 is added to 1200 mL of phosphoric acid and stirred for 24 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 then separated by column chromatography to obtain 48.3 g of a compound represented by the following formula 9-c. (Yield: 88%)

(3) Synthesis of Compound Represented by Formula 9-d

[Chemical Formula 9-d] was synthesized by the following Reaction Formula 28.

[Reaction Scheme 28]

[Chemical Formula 9-c] [Chemical Formula 9-d]

20.0 g (69.40 mmol) of the compound represented by the formula 9-c obtained from the above-mentioned scheme 27 and 6.9 g (104.1 mmol) of 60% sodium hydride were added to 300 mL of dimethylformamide and stirred at room temperature for 30 minutes . Then, 22.3 g (83.28 mmol) of chlorodiphenyltriazine was dissolved in 200 mL of dimethylformamide, and the mixture was slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 29.5 g of a compound represented by the formula 9-d. (Yield: 90%)

(4) Synthesis of Compound Represented by Formula 154

A compound represented by the formula (154) was synthesized by the following Reaction Scheme (29).

[Reaction Scheme 29]

[Chemical Formula 1-b] [Chemical Formula 9-c]

, 6.85 g (28.88 mmol) of the compound represented by the formula (1-b) obtained from the above reaction scheme 2, 10 g (19.25 mmol) of the compound represented by the formula 9-c obtained from the above scheme 28, (Triphenylphosphine) palladium (414 mg, 0.39 mmol), potassium carbonate (5.32 g, 38.5 mmol), 1,4-dioxane (50 mL), toluene (50 mL) and distilled water (20 mL). After the reaction is completed, the temperature is adjusted to room temperature and the crystals are filtered. The crystals were recrystallized from methylene chloride and acetone to obtain 8.2 g of a compound represented by the formula (154). (Yield 67%)

MS [M] &lt; ⁺ & gt ^; 631.27

Example 10 Synthesis of Compound Represented by Formula 194

(1) Synthesis of Compound Represented by Formula 10-a

[Chemical Formula 10-a] was synthesized by the following Reaction Formula 30.

[Reaction Scheme 30]

[Chemical Formula 10-a]

20.0 g (119.61 mmol) of carbazole and 11.97 g (179.42 mmol) of 60% sodium hydride are placed in 300 mL of dimethylformamide and stirred at room temperature for 30 minutes. 38.42 g (143.53 mmol) of chlorodiphenyltriazine is dissolved in 200 mL of dimethylformamide, and the mixture is slowly added dropwise, followed by stirring for 1 hour. After completion of the reaction, 200 mL of distilled water was added, followed by filtration and recrystallization to obtain 40 g of a compound represented by Formula 10-a. (Yield: 84%)

(2) Synthesis of Compound Represented by Formula 10-b

[Chemical Formula 10-b] was synthesized by the following Reaction Formula 31.

[Reaction Scheme 31]

[Chemical Formula 10-a] [Chemical Formula 10-b]

40 g (100.39 mmol) of the compound represented by the above formula [10-a] obtained from the above-mentioned Reaction formula 30 was dissolved in 1.0 L of dimethylformamide and stirred at 0 ° C. Then, 23.69 g (200.77 mmol) of N-bromosuccinimide was dissolved in 0.5 L of dimethylformamide and slowly dropped for 1 hour while maintaining the temperature at 0 占 폚. After dropwise addition, the mixture is warmed to room temperature and stirred for 12 hours. When the reaction was completed, distilled water was added dropwise at room temperature. When brown crystals were formed, the crystals were filtered and recrystallized from toluene and methanol to obtain 47 g of a compound represented by the formula 10-b. (Yield: 84%)

(3) Synthesis of a compound represented by the formula (194)

A compound represented by the formula (194) was synthesized by the following reaction scheme [32].

[Reaction Scheme 32]

[Chemical Formula 10-b] [Chemical Formula 194]

47 g (84.49 mmol) of the compound represented by the formula 10-b obtained from the above-mentioned Reaction Scheme 31, 24.7 g (211.23 mmol) of indole and 1.5 g (1.69 mmol) of tris (dibenzylideneacetone) dipalladium, 2.45 g (8.44 mmol) of silylbutylphosphonium tetrafluoroborate and 58.38 g (422.47 mmol) of sodium tertiarybutoxide are placed in a mixed solvent of 500 mL of xylene, and the mixture is stirred and refluxed for 12 hours. After completion of the reaction, the organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and the residue was recrystallized from methylene chloride and a nucleic acid to obtain 46 g of a compound represented by the formula (194). (Yield: 87%)

MS [M] &lt; ⁺ & gt ^; 628.24

Example 11 Synthesis of Compound Represented by Formula 218

(1) Synthesis of Compound Represented by Formula (11-a)

A compound represented by the formula (11-a) was synthesized by the following reaction scheme (33).

[Reaction Scheme 33]

[Formula 11-a]

The dried 2 L reactor was purged with nitrogen, and 45.0 g (381 mmol) of 2-aminobenzonitrile and 405 mL of tetrahydrofuran were added thereto. 279 mL (838 mmol) of 3 M phenylmagnesium bromide was slowly added dropwise thereto at 0 ° C., The mixture is stirred at reflux. After lowering to a low temperature, 62 g (0.571 mmol) of ethyl chloroformate was dissolved in 200 mL of tetrahydrofuran, and the mixture was slowly added dropwise, followed by stirring under reflux for 2 hours. The residue was purified by column chromatography to obtain 50 g of a compound represented by the formula (11-a). (Yield: 58%)

(2) Synthesis of Compound Represented by Formula (11-b)

[Chemical Formula 11-b] was synthesized by the following Reaction Scheme [34].

[Reaction Scheme 34]

[Formula 11-b]

50 g (225 mmol) of [Formula 11-a] obtained from the above-mentioned Reaction Formula 33 and 500 mL of phosphorus oxychloride are added and stirred under reflux for 5 hours. When the reaction is complete, slowly drop it in warm water. After the dropwise addition was completed, the solution was filtered, followed by extraction with methylene chloride and water, followed by separation by column chromatography to obtain 41 g of a compound represented by the formula (11-b). (Yield: 75%)

(3) Synthesis of Compound Represented by Formula 11-c

[Chemical Formula 11-c] was synthesized by the following Reaction Scheme 35.

[Reaction Scheme 35]

[Formula 11-b] [Formula 11-c]

To 60 g of sodium hydride (2.1 g, 53 mmol) was added 50 mL of dimethylformamide, and the mixture was stirred at room temperature for about 30 minutes. 10.0 g (41 mmol) of 4-bromo-9H-carbazole and 100 mL of dimethylformamide were added dropwise thereto, followed by stirring for about 1 hour. 12.9 g (53 mmol) of [Formula 11-b] obtained from the above-mentioned Reaction Scheme 34 and 100 mL of dimethylformamide were added thereto and stirred overnight. 600 mL of distilled water was added to the flask, and the resulting solid was filtered. And recrystallized from toluene to obtain 16.2 g of a compound represented by the formula (11-c). (Yield: 79%)

(4) Synthesis of a compound represented by the formula (218)

A compound represented by the formula (218) was synthesized according to the following scheme (36).

[Reaction Scheme 36]

[Chemical Formula 11-c] [Chemical Formula 218]

12.7 g (28.16 mmol) of the compound represented by the formula 11-c, 2.19 g (25.01 mmol) of indole and 1.5 g (1.69 mmol) of tris (dibenzylideneacetone) dipalladium obtained from the above- 2.45 g (8.44 mmol) of silylbutylphosphonium tetrafluoroborate and 9.73 g (70.41 mmol) of sodium tertiary butoxide are placed in a mixed solvent of 500 mL of xylene and the mixture is refluxed for 12 hours. After completion of the reaction, the organic layer is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure and then recrystallized from methylene chloride and a nucleic acid to obtain 10 g of a compound represented by the formula (218). (Yield: 82%)

MS [M] ^&lt; ⁺ & gt ^; : 486.18

Example 12 Synthesis of Compound Represented by Formula 223

(1) Synthesis of Compound Represented by Formula 12-a

A compound represented by the formula (12-a) was synthesized by the following reaction scheme [37].

[Reaction Scheme 37]

[Chemical Formula 12-a]

97 g (0.56 mol) of 1-nitronaphthalene, 166.5 g (1.68 mol) of methyl cyanoacetate, 40.1 g (0.62 mol) of potassium cyanide and 62.9 g (1.12 mol) of potassium hydroxide were added and stirred. Dimethylformamide (970 mL) was added and the mixture was stirred at 60 ° C overnight. The solvent was removed by concentrating under reduced pressure at room temperature, 500 mL of a 10% sodium hydroxide aqueous solution was added, and the mixture was refluxed for about 1 hour. After extraction with ethyl acetate, the reaction mixture was separated by column chromatography, and recrystallized from toluene and heptane to obtain 50.8 g of a compound represented by the formula (12-a). (Yield: 54%)

(2) Synthesis of Compound Represented by Formula 12-b

[Chemical Formula 12-b] was synthesized by the following Reaction Scheme [38].

[Reaction Scheme 38]

[Chemical Formula 12-a] [Chemical Formula 12-b]

25.0 g (149 mmol) of [Formula 12-a] obtained from the above-mentioned Reaction Formula 37 was added to 200 mL of tetrahydrofuran and stirred. 87.4 mL (297 mmol) of phenylmagnesium bromide (3.0 M in Et ₂ O) was added dropwise and refluxed at 0 ° C for about 1 hour. 19.4 g (179 mmol) of ethyl chloroformate was added dropwise, and the mixture was refluxed for about 1 hour. Ammonium chloride aqueous solution was added until it became slightly acidic and washed with water and heptane to obtain 32.4 g of a compound represented by the formula (12-b). (Yield: 80%)

(3) Synthesis of Compound Represented by Formula 12-c

[Chemical Formula 12-c] was synthesized by the following Reaction Formula 39.

[Reaction Scheme 39]

[Chemical Formula 12-b] [Chemical Formula 12-c]

30 g (110 mmol) of [Formula 12-b] obtained from the above-mentioned Reaction Scheme 38 was placed in about 80 mL of phosphorus oxychloride and refluxed overnight. After cooling to -20 ° C, approximately 400 mL of distilled water was slowly added. Washed with water, methanol and heptane, and recrystallized from toluene and heptane to obtain 14.1 g (yield: 44%) of a compound represented by [Intermediate 1-c].

(4) Synthesis of Compound Represented by Formula 12-d

A compound represented by the formula [12-d] was synthesized by the following reaction scheme [40].

[Reaction Scheme 40]

[Chemical Formula 12-c] [Chemical Formula 12-d]

To 60 g of sodium hydride (2.1 g, 53 mmol) was added 50 mL of dimethylformamide, and the mixture was stirred at room temperature for about 30 minutes. 11.4 g (41 mmol) of 10H-phenoxazinol and 100 mL of dimethylformamide were added dropwise thereto, followed by stirring for about 1 hour. 12.9 g (53 mmol) of [Formula 12-c] obtained from the above-mentioned Reaction Scheme 39 and 100 mL of dimethylformamide were added and stirred overnight. 600 mL of distilled water was added to the flask, and the resulting solid was filtered. And recrystallized from toluene to obtain 15.3 g of a compound represented by the formula [12-d]. (70% yield)

(5) Synthesis of Compound Represented by Formula 12-e

[Chemical Formula 12-e] was synthesized by the following Reaction Formula 41.

[Reaction Scheme 41]

[Formula 12-e]

40.3 g (162.5 mmol) of 4-iodophenylboronic acid, 10.3 g (162.5 mmol) of copper powder, 4.3 g (16.3 mmol) of 18-crown-6 and 33.7 g ) Was added 200 mL of 1,2-dichlorobenzene, and the mixture was refluxed at 180 DEG C for 1 day. After high-temperature filtration, the product was separated by column chromatography to obtain 16.9 g of a compound represented by the formula (12-e). (Yield: 88%)

(6) Synthesis of Compound Represented by Formula 223

A compound represented by the formula (223) was synthesized by the following scheme (42).

[Reaction Scheme 42]

[Chemical Formula 12-d] [Chemical Formula 12-e] [Chemical Formula 223]

15 g (28 mmol) of the compound of the formula 12-d obtained from the above-mentioned scheme 40, 8.1 g (34 mmol) of the compound 12-e obtained from the above reaction scheme 41, tetrakis (triphenylphosphine) palladium 80 g of 1,4-dioxane, 80 mL of toluene and 30 mL of distilled water were added to 0.7 g (0.64 mmol) of potassium carbonate and 8.9 g (64 mmol) of potassium carbonate, and the mixture was refluxed overnight. Extracted with ethyl acetate, and recrystallized from dichloromethane and acetone to obtain 13.2 g of a compound represented by [Compound 223]. (Yield: 73%)

MS [M] ^&lt; ⁺ & gt ^; : 644.20

Example 13 Synthesis of Compound Represented by Formula 228

(1) Synthesis of Compound Represented by Formula (13-a)

A compound represented by the formula (13-a) was synthesized by the following reaction scheme [43].

[Reaction Scheme 43]

[Chemical Formula 13-a]

Was synthesized in the same manner as in [Reaction scheme 37] to [Reaction scheme 39] using 5-nitroisoquinoline instead of 1-nitronaphthalene used in the above scheme [Reaction formula 37] to obtain a compound represented by formula 13-a. (Yield: 42%)

(2) Synthesis of Compound Represented by Formula (13-b)

A compound represented by the formula (13-b) was synthesized by the following scheme (Scheme 44).

[Reaction Scheme 44]

[Chemical Formula 13-b]

Was synthesized by the same method using 1-amino-4-bromonaphthalene instead of [Formula 12-d] used in [Reaction Scheme 42] above to give the compound represented by Formula 13-b. (70% yield)

(3) Synthesis of Compound Represented by Formula 13-c

A compound represented by the following formula [13-c] was synthesized by the following reaction scheme [45].

[Reaction Scheme 45]

[Chemical Formula 13-b] [Chemical Formula 13-c]

26.7 g (0.08 mol) of the compound represented by the above formula [13-b], 22.6 g (0.08 mol) of 2-bromoiodobenzene, 1.1 g (0.1 mmol) of tris (dibenzylideneacetone) dipalladium, , 0.7 g (0.1 mmol) of 1'-bis (diphenylphosphino) ferrocene and 15.3 g (0.16 mol) of sodium tertiary butoxide were placed in 250 mL of toluene and refluxed for 24 hours. The residue was purified by column chromatography to obtain 17.2 g of a compound represented by the formula (13-c) (yield: 44%).

(4) Synthesis of a compound represented by the formula (13-d)

[Chemical Formula 13-d] was synthesized by the following Reaction Formula 46.

[Reaction Scheme 46]

[Chemical Formula 13-c] [Chemical Formula 13-d]

14.7 g (0.03 mol) of the compound [13-c] obtained from the above-mentioned scheme 45, 4.0 g (0.04 mol) of potassium acetate and 0.8 g (0.001 mol) of tetrakistriphenylphosphine palladium were placed in 125 ml of dimethylformamide Stir at 150 &lt; 0 &gt; C for 24 hours. The reaction mixture was separated by column chromatography and recrystallized with hexane to obtain 4.0 g of a compound represented by the formula (13-d). (Yield: 33%)

(5) Synthesis of Compound Represented by Formula 228

A compound represented by the formula (228) was synthesized by the following reaction scheme [47].

[Reaction Scheme 47]

[Chemical Formula 13-a] [Chemical Formula 13-d] [Chemical Formula 228]

13-a] obtained from the above scheme [43] instead of the above-mentioned scheme [12-c] used in the above scheme [40] To obtain the compound represented by the formula (228). (Yield 64%)

MS [M] ^&lt; ⁺ & gt ^; : 663.24

Example  1 to 24: 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 base pressure was adjusted to 1 x 10 &lt; ^-6 &gt; torr. Then, organic substances were injected onto the ITO using DNTPD (700 ANGSTROM), NPD (300 ANGSTROM) deposition was in the order of _{3 (10%) (300 Å} ), Alq 3 (350 Å), LiF (5 Å), Al (1,000 Å), were measured at 0.4 mA.

Comparative Example  One

The organic light emitting diode device for the comparative example was fabricated in the same manner except that CBP, which is generally used as a phosphorescent host material, was used in place of the compound prepared by the invention in the device structure of the embodiment, and the structure of the CBP is as follows.

division Host Dopant Doping concentration% V CD / ㎡ C IEx C IEy T ₈₀ ( Hr ) Comparative Example 1 CBP Ir (ppy) ₃ 10 7.9 3800 0.297 0.624 68 Example 1 4 Ir (ppy) ₃ 10 4.2 4980 0.315 0.620 180 Example 2 5 Ir (ppy) ₃ 10 4.0 5110 0.311 0.619 224 Example 3 9 Ir (ppy) ₃ 10 4.6 5890 0.303 0.627 125 Example 4 11 Ir (ppy) ₃ 10 3.7 5160 0.309 0.640 187 Example 5 73 Ir (ppy) ₃ 10 3.9 5240 0.317 0.621 216 Example 6 76 Ir (ppy) ₃ 10 3.7 5250 0.310 0.639 191 Example 7 94 Ir (ppy) ₃ 10 4.5 5250 0.310 0.625 190 Example 8 98 Ir (ppy) ₃ 10 4.3 4990 0.306 0.628 213 Example 9 12 Ir (ppy) ₃ 10 4.7 5050 0.314 0.621 174 Example 10 13 Ir (ppy) ₃ 10 4.4 5190 0.312 0.619 179 Example 11 24 Ir (ppy) ₃ 10 3.6 5190 0.304 0.628 186 Example 12 25 Ir (ppy) ₃ 10 4.1 4960 0.310 0.625 197 Example 13 59 Ir (ppy) ₃ 10 3.6 5230 0.316 0.627 203 Example 14 60 Ir (ppy) ₃ 10 4.1 5110 0.312 0.624 184 Example 15 70 Ir (ppy) ₃ 10 4.1 5240 0.321 0.624 198 Example 16 75 Ir (ppy) ₃ 10 4.7 5270 0.306 0.625 211 Example 17 77 Ir (ppy) ₃ 10 3.8 5010 0.321 0.629 130 Example 18 82 Ir (ppy) ₃ 10 4.3 5120 0.315 0.619 188 Example 19 83 Ir (ppy) ₃ 10 4.0 5250 0.307 0.621 200 Example 20 85 Ir (ppy) ₃ 10 3.8 5140 0.309 0.621 183 Example 21 90 Ir (ppy) ₃ 10 4.4 5090 0.318 0.614 189 Example 22 99 Ir (ppy) ₃ 10 4.2 5250 0.301 0.611 147 Example 23 114 Ir (ppy) ₃ 10 4.9 5130 0.323 0.614 171 Example 24 127 Ir (ppy) ₃ 10 4.5 4890 0.315 0.624 197

Example  25 to 28: 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), α-NPB (300 Å) ) ₂ Ir (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å) and Al (1,000 Å) were deposited in this order and measured at 0.4 mA.

Comparative Example  2

The organic light emitting diode device for Comparative Example 2 used CBP, which is generally used as a phosphorescent host material instead of the compound prepared by the invention in the device structures of Examples 25 to 28.

division Host Dopant Voltage (V) Cd / ㎡ CIEx CIEy T ₉₀ (Hr) Comparative Example 2 CBP (piq) &lt; / RTI &gt; ₂ Ir (acac) 7.5 410 0.667 0.328 410 Example 25 218 (piq) &lt; / RTI &gt; ₂ Ir (acac) 4.2 4980 0.671 0.328 1105 Example 26 219 (piq) &lt; / RTI &gt; ₂ Ir (acac) 4.0 5110 0.670 0.327 1125 Example 27 223 (piq) &lt; / RTI &gt; ₂ Ir (acac) 4.1 5890 0.671 0.327 1020 Example 28 228 (piq) &lt; / RTI &gt; ₂ Ir (acac) 4.2 5160 0.671 0.329 1077

In Table 1 and Table 2, T ₈₀ represents the time required for the luminance to be reduced to 80% of the initial luminance.

As shown in [Table 1] and [Table 2], when the organic electroluminescent compound to be embodied according to the present invention is employed as a host compound for a light emitting layer of an organic electroluminescent device, life characteristics are remarkably improved, In addition, by lowering the driving voltage, it is possible to increase the power efficiency and improve the power consumption.

10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims (13)

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

In the above formula (1)
L is selected from a substituted or unsubstituted aryl group having 6 to 60 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
Y ₁ and Y ₂ represent a single bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 30 carbon atoms, A substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, p and q are each a An integer of 0 to 5, and when p and q are 2 or more, a plurality of Y ₁ and Y ₂ are the same or different from each other,
Z is a single bond or CR ₁ R ₂ , O, S, SiR ₃ R ₄ And NR ₅ , R ₁ to R _{5 each} represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms An aryl group, and may combine with each other or adjacent substituents to form a saturated or unsaturated ring,
X ₁ to X ₁₄ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, an amidino group, a hydrazine, a hard lone, a carboxyl group or a salt thereof, Substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C3- A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C1- A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, An arylalkylamino group having 1 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Each of X ₁ to X ₁₄ may be bonded to adjacent substituents to form a saturated or unsaturated ring,
m is an integer of 0 to 8; The method according to claim 1,
An alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 50 carbon atoms, an aryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 3 to 30 carbon atoms, when L, Y ₁ , Y ₂ , R ₁ to R ₅ and X ₁ to X ₁₄ are further substituted. An alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted C1 to C20 A substituted or unsubstituted arylalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 5 to 60 carbon atoms, an aryl group having 2 to 50 carbon atoms, a hydroxyl group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, Sai Oi, City An amino group, an amino group, an amino group, an amino group, an amino group, an amino group, an amino group, an amino group, an amino group, an anion group, a halogen group and a medium or small water. The method according to claim 1,
Wherein Y ₁ and Y ₂ are any one selected from the following Structural Formulas C1 to C14:

[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]
In the above Structural Formula C1 to Structural Formula C14,
Hydrogen or deuterium may be bonded to the carbon of the ring in each structural formula, and R is a group represented by X ₁ To X &lt; _{14 &} gt ;. The method according to claim 1,
Wherein L connected to Y &lt; ₂ &gt; is 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 the different and are each independently of one _{another, C (R 41), C} (R 42) (R 43), N, N (R 44), O , and is selected from S, wherein R ₄₁ To R &lt; ₄₄ &gt; 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 cycloalkyl group having 3 to 30 carbon atoms, And a heteroaryl group having 2 to 30 carbon atoms having a substituted or unsubstituted hetero atom, O, N, S or P, The method according to claim 1,
Wherein L is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing at least one nitrogen atom. 5. The method of claim 4,
The organic electroluminescent compound according to any one of [1] to [10] is any one selected from the following structural formulas:
[Structural Formula 11]

In the above structural formula 11,
X is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms An amino group, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S, or P as a hetero atom, a cyano group, Is selected from a, m is an integer from 1 to 11, is a plurality of X are the same or different when m is 2 or more. The method according to claim 1,
The organic luminescent compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from compounds represented by Formula 2 to Formula 228:

[Chemical Formula 2] &lt; EMI ID =

[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]

[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]

[Formula 79] [Formula 80] [Formula 81]

[Chemical Formula 82]

[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]

[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 100] [Chemical Formula 100]

[Formula 103] [Formula 103]

[Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Chemical Formula 115]

[Chemical Formula 120] [Chemical Formula 120] [Chemical Formula 120]

[Formula 124] [Formula 124] [Formula 125]

[Formula 126] &lt; EMI ID = 129.1 &gt;

[Formula 130] &lt; EMI ID = 131.0 &gt;

[Formula 135] [Formula 135] [Formula 137]

[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]

[Chemical Formula 144] [Chemical Formula 144] [Chemical Formula 145]

[Chemical Formula 146] [Chemical Formula 148] [Chemical Formula 149]

[Formula 15] [Formula 15] [Formula 15] [Formula 15]

[Chemical Formula 155] [Chemical Formula 156] [Chemical Formula 157]

[Formula 15] [Formula 15] [Formula 15] [Formula 15] [Formula 15]

[166] [165] [165]

[Formula 166] [Formula 169] [Formula 169]

[173] [173] [173]

[Formula 177] [Formula 177] [Formula 177]

[Formula 181] [Formula 181] [Formula 181] [Formula 181]

[Formula 182] [Formula 184] [Formula 184]

[Formula 188] [Formula 188] [Formula 189]

[Formula 19] [Formula 19] [Formula 193] [Formula 193]

[Formula 19] [Formula 19] [Formula 19] [Formula 19] [Formula 19]

[201] [201] [201]

[Chemical Formula 203]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 210] [Chemical Formula 212] [Chemical Formula 213]

[Formula 21] [Formula 21] [Formula 21] [Formula 21]

[Formula 21] &lt; EMI ID =

[Formula 22] &lt; EMI ID =

[228] [228] An organic thin film layer for an organic electroluminescence device, comprising at least one organic luminescent compound according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein the organic thin film layer comprises an organic light emitting compound represented by Formula 1 as a host and further includes at least one dopant compound. Anode; A cathode facing the anode; And an organic thin film layer according to claim 8 interposed between the anode and the cathode. 11. The method of claim 10,
The organic electroluminescent device further includes at least one layer selected from the group consisting of a light emitting layer, a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer and an electron blocking layer between the anode and the cathode,
Wherein one of the light emitting layer, the hole injecting layer, the hole transporting layer, the hole blocking layer, the electron transporting layer, the electron injecting layer and the electron blocking layer is the organic thin film layer according to claim 8. 12. The method of claim 11,
Wherein the light emitting layer is the organic thin film layer according to claim 8. 12. The method of claim 11,
Wherein the organic electroluminescent device comprises one or more organic electroluminescent layers emitting blue, red or green light to emit white light.

Images