KR20140074857A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an electroluminescent compound and an electroluminescent device including the same. The electroluminescent compound according to the present invention has improved thermal stability, hole and electron transporting performance, power efficiency, and driving voltage characteristics and prevents the problem of concentration quenching due to steric hindrance and molecular association.

Description

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

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

Recently, an organic electroluminescent device which can be driven by a self-luminous type and can be driven at a low voltage has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, requires no backlight, It is attracting attention as a next-generation display device because it is advantageous from the viewpoints of power and wide range of color reproduction.

In organic light emitting diodes (OLEDs), when electrons are injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), electrons and holes are paired, to be.

An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, . When a voltage is applied between the two electrodes in the structure of the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out.

Organic electroluminescent devices can be formed on flexible transparent substrates such as plastic, and can be driven at voltages as low as 10 V compared to plasma display panels (PDP) and inorganic electroluminescent displays Has a relatively low power consumption, and is excellent in 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.

In order for the organic electroluminescent device to fully 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 light emitting material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not yet been sufficiently developed. Therefore, there is a continuing need in the art for the development of new materials having low-voltage driving, high efficiency and long life.

In order to solve the above problems, the present invention has been made to solve the above-described problems, and has an object of providing an organic electroluminescent device which is excellent in thermal stability, high in hole and electron transporting ability, excellent in power efficiency and driving voltage characteristics, An organic electroluminescent compound in which no problem of defects occurs at all.

In addition, the problem of crystal nitriding does not occur at all, and uniformity of light emission at high temperature can be ensured. In addition, the solubility can be increased to 3% or more with respect to the solvent without using any additional thickener, An organic electroluminescent compound capable of forming an organic electroluminescent compound.

Also, an organic thin film layer for an organic electroluminescent device including the organic electroluminescent compound and an organic electroluminescent device including the same are provided.

The present invention provides an organic electroluminescent compound represented by the following general formula (1) or (2) to solve the above problems.

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

[Chemical Formula 1]

(2)

The present invention also provides an organic thin film layer for an organic electroluminescent device comprising at least one organic electroluminescent compound represented by the above formula (1) or (2) and an organic electroluminescent device comprising the same.

The organic electroluminescent compound according to various embodiments of the present invention is excellent in thermal stability, high in hole and electron transporting ability, and excellent in power efficiency and driving voltage characteristics. Therefore, when an electric field is applied for a long time (for example, It is confirmed that there is no problem of pixel defects caused by the defects.

In addition, the organic electroluminescent compound according to some embodiments of the present invention does not cause any problem of crystal nitriding and can secure uniformity of light emission at a high temperature. In addition, the organic electroluminescent compound has a solubility of 3 %, And it was confirmed that the film formation by the solution coating method is possible.

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

One aspect of the present invention relates to an organic electroluminescent compound represented by the following Chemical Formula 1 or Chemical Formula 2.

[Chemical Formula 1]

(2)

In the above Chemical Formulas 1 to 2,

R ₁ to R ₆ are the same or different and each represents a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms , A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 A substituted or unsubstituted C1 to C20 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, a substituted or unsubstituted C1 to C50 arylalkylamino group, A substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a hydroxyl group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfone 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 aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, , A cyano group, a halogen group, a medium-small water, and hydrogen, and R ₁ to R ₆ Lt; / RTI > is a heteroaryl group containing nitrogen.

The substituents of R ₁ to R ₆ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, A salt thereof, a phosphoric acid or its salt, an alkyl group having 1 to 60 carbon atoms, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, An aryloxy group having 6 to 60 carbon atoms, an arylthio group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, -SiRRR or -NRR (wherein R may be the same as or different from each other, Independently, hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms.

L is a single bond or a substituted or unsubstituted alkylene having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene having 2 to 60 carbon atoms, a substituted or unsubstituted A cycloalkylene having 3 to 60 carbon atoms, a heterocycloalkylene having 2 to 6 carbon atoms and at least one selected from N, O and S, a substituted or unsubstituted arylene having 6 to 50 carbon atoms and a substituted or unsubstituted carbon number And 3 to 50 heteroarylene.

m or n is an integer of 0 to 4, and when m or n is 2 or more, plural Ls may be the same or different.

X ₁ and X ₂ are CRR and the two Rs are the same or different and each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms to be.

In (CR ₂ ) _n of the above formula ( ₂ ), n is an integer of 3 to 6, and each of R ₂ is independently hydrogen, deuterium or an alkyl group of 1 to 10 carbon atoms.

In the case of Y, n is an integer of 0 to 1, and when n is 1, Y is selected from CRR, O and S, each R is independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, An aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.

According to a preferred embodiment of the present invention, L 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 of the ring in each structural formula, and R is the same as defined for R ₁ to R ₆ in the formula (1) or (2).

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.

Meanwhile, the heteroaryl group contained in the organic light emitting 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,

More preferably, [Structural formulas 1] to [Structural formula 10] may be any one selected from the following structural formula [11].

[Structural Formula 11]

In the above structural formula 11,

X is 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, an unsubstituted or substituted 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 or more 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, m is an integer from 1 to 11, is a plurality of X are the same or different when m is 2 or more.

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.

The organic electroluminescent compound represented by the formula (1) or (2) according to the present invention is not limited in the range of the following specific compounds, but more specifically, among the compounds represented by the following formulas (3) to It can be selected.

The organic electroluminescent compound represented by the formula (1) or (2) according to the present invention is not limited in the range of the following specific compounds, but more specifically, among the compounds represented by the following formulas (3) to It can be selected.

[Chemical Formula 3] < EMI ID =

[Chemical Formula 8] < EMI ID =

[Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14]

[Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 18]

[Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]

[Chemical Formula 25] [Chemical Formula 25]

[Chemical Formula 30] [Chemical Formula 30]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42]

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

[Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50]

[Chemical Formula 51]

[Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62]

[Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 70] [Chemical Formula 70]

[Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74]

[Formula 75] < EMI ID = 78.1 >

[Formula 80] [Formula 81] [Formula 82]

[Formula 83] [Formula 85] [Formula 86]

[Formula 90] [Formula 90] [Formula 90]

[Chemical Formula 91] [Chemical Formula 93] [Chemical Formula 94]

[Chemical Formula 97] [Chemical Formula 97] [Chemical Formula 98]

[Chemical Formula 100] [Chemical Formula 101] [Chemical Formula 101]

[Formula 103] [Formula 105] [Formula 106]

[Formula 110] [Formula 110] [Formula 110]

[Formula 111] [Formula 113] [Formula 114]

[Chemical Formula 116] [Chemical Formula 117] [Chemical Formula 118]

[화학식 119] [화학식 120] [화학식 121] [화학식 122]

[Chemical Formula 120]

[Formula 124] [Formula 125] [Formula 126]

[Formula 127] < EMI ID = 129.0 >

[Formula 131] [Formula 133] [Formula 134]

[Chemical Formula 135] [Chemical Formula 135]

[Formula 140] [Formula 141] [Formula 142]

[Chemical Formula 144] [Chemical Formula 145] [Chemical Formula 146]

[Formula 150] [Formula 149] [Formula 150]

[Formula 154] [Formula 154] [Formula 154]

[Formula 157] < EMI ID = 158.1 >

[Formula 161] [Formula 161] [Formula 161]

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

[Formula 16] [Formula 16]

[Formula 173] [Formula 174] [Formula 174]

[Formula 177] [Formula 177] [Formula 178]

[Formula 181] [Formula 181] [Formula 182]

[Formula 184] [Formula 184] [Formula 186] [Formula 186]

[Formula 188] [Chemical Formula 189] [Chemical Formula 190]

[193] [193] [193] [194]

[197] [198] [198] [198] [198]

[Chemical Formula 200] [Chemical Formula 201] [Chemical Formula 202]

[Chemical Formula 203]

[Chemical Formula 20] [Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 212] [Chemical Formula 213] [Chemical Formula 214]

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

[Formula 21] < EMI ID =

[화학식 223] [화학식 224] [화학식 225] [화학식 226]

[Formula 226] [Formula 226] [Formula 226]

[228] [230] [229]

[233] [233] [233]

[238] [237] [237]

[240] [248]

[화학식 243] [화학식 244] [화학식 245]

[245] [243]

Another aspect of the present invention relates to an organic thin film layer for an organic electroluminescence device, which comprises at least one compound represented by the following formulas (1) to (2) according to various embodiments 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.

According to another aspect of the present invention, there is provided an organic electroluminescent device including a first electrode, a second electrode, and at least one organic thin film layer interposed between the first electrode and the second electrode, ] To [Formula 2].

The organic thin film layer containing the organic light emitting compound of the present invention may further include at least one selected from the group consisting of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, can do.

At this time, the organic thin film layer interposed between the first electrode and the second electrode may include a light emitting layer, and the light emitting layer may comprise a host and a dopant, and the organic electroluminescent compound according to the present invention may be used as a host.

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.

According to an 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 device for monochromatic or white illumination.

In the organic electroluminescent device of the present invention, a further known organic electroluminescent device material may be added as required. For example, a compound capable of transporting a hole having a bisarylamino structure or an N-arylcarbazolyl structure or a compound capable of transporting an electron having a benzimidazolyl structure may be added. Specifically, a material for forming a hole injection and hole transport layer described below and an electron injection material can be used.

In the organic electroluminescent device of the present invention, at least one organic thin film layer including at least a light emitting layer is sandwiched between a cathode and an anode. At least one layer of the organic thin film layer contains the organic electroluminescent compound according to the present invention either alone or as a component of the mixture.

The organic electroluminescent compound according to the present invention may be used for a hole injecting layer, a hole transporting layer, an electron injecting layer, and an electron transporting layer in addition to the light emitting layer. The organic electroluminescent device according to the present invention is an organic electroluminescent device in which an organic thin film layer is formed in a plurality of layers, specifically (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injecting layer / cathode) (Anode / hole injecting layer / hole transporting layer / light emitting layer / electron injecting layer / cathode) and the like can be cited as examples of the light emitting layer / the hole injection layer / the light emitting layer /

In the organic electroluminescent device according to the present invention, by making the organic thin film layer have a multiple layer structure, it is possible to prevent the luminance and the life of the organic electroluminescent device from deteriorating due to etching. Further, a light emitting material, a doping material, a hole injecting material, and an electron injecting material may be used in combination if necessary. Further, the light emission luminance and the light emitting efficiency may be improved by the doping material. The hole injection layer, the light emitting layer, and the electron injection layer may each be formed by two or more layers. At that time, in the case of the hole injection layer, the layer for injecting holes from the electrode is called a hole injection layer, and the layer for injecting holes from the hole injection layer to the light emitting layer is called a hole transport layer. Similarly, in the case of the electron injecting layer, a layer for injecting electrons from the electrode is called an electron injecting layer, and a layer for receiving electrons from the electron injecting layer to transport electrons to the light emitting layer is called an electron transporting layer. Each of these layers is selected and used according to various factors such as the energy level of the material, heat resistance, adhesion to the organic layer or the metal electrode, and the like.

As the hole injecting material, a compound having a hole transporting ability, a hole injecting effect from the anode, an excellent hole injecting effect to the light emitting layer or the light emitting material, and excellent film forming ability is preferable. Specific examples thereof include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, benzidine type triphenylamine, diamine type triphenylamine, hexacyanohexaazatriphenylene, derivatives thereof, and polyvinylcarbazole, polysilane, , But are not limited thereto.

Among the hole injecting materials usable in the organic electroluminescent device of the present invention, a more effective hole injecting material is a phthalocyanine derivative. (HO) GaPc, VOPc, TiOPc, ClO2Pc, Cl2Pc, ClSnPc, Cl2SiPc, (HO) AlPc, (HO) GaPc, VOPc, TiOPc, Phthalocyanine derivatives such as MoOPc and GaPc-O-GaPc, and naphthalocyanine derivatives, but the present invention is not limited thereto.

The carrier may be increased or decreased by adding an electron accepting material such as a TCNQ derivative to the hole injecting material. A preferable hole transporting material that can be used in the organic EL device of the present invention is an aromatic tertiary amine derivative. Examples of aromatic tertiary amine derivatives include N, N'-diphenyl-N, N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N, -Tetrabiphenyl-1,1'-biphenyl-4,4'-diamine, or oligomers or polymers having these aromatic tertiary amine skeletons, but are not limited thereto.

As the electron injecting material, a compound having an ability to transport electrons, an electron injecting effect from a cathode, an electron injecting effect to a light emitting layer or a light emitting material, and an excellent thin film forming ability is preferable. In the organic EL device of the present invention, a more effective electron injecting material is a metal complex compound and a nitrogen-containing heterocyclic derivative.

Examples of the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinate) zinc, tris (8-hydroxyquinolinate) aluminum, tris (8- (10-hydroxybenzo [h] quinolinate) beryllium, bis (10-hydroxybenzo [h] quinolinate) zinc, and the like.

Examples of the nitrogen-containing heterocyclic derivative include oxazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzimidazole and imidazopyridine Among them, benzimidazole derivatives, phenanthroline derivatives and imidazopyridine derivatives are preferable.

In a preferred embodiment, a dopant represented by an alkali metal is doped in the vicinity of the cathode interface of the second organic layer so as to further contain a dopant in these electron injecting materials and to facilitate the reception of electrons from the cathode. As the dopant, an electron-donor metal, an electron-donor metal compound and an electron-donor metal complex can be exemplified, and these reductive dopants can be used singly or in combination of two or more.

In the organic electroluminescent device of the present invention, at least one of the light emitting material, the doping material, the hole injecting material, the hole transporting material, and the electron injecting material is contained in the same layer in addition to at least one selected from the organic electroluminescent compound It is possible. In order to improve the stability of the organic electroluminescent device obtained by the present invention with respect to temperature, humidity, atmosphere, etc., it is also possible to provide a protective layer on the surface of the device, or to protect the entire device with a silicone oil or a resin.

The conductive material used for the anode of the organic electroluminescent device of the present invention is preferably a material having a work function larger than 4 eV and is preferably a material having a work function such as carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, And alloys thereof, ITO substrates, metal oxides such as tin oxide and indium oxide used for NESA substrates, and further organic conductive resins such as polythiophene and polypyrrole. As the conductive material used for the cathode, those having a work function smaller than 4 eV are suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, , But is not limited thereto. Examples of the alloys include magnesium / silver, magnesium / indium, lithium / aluminum and the like, but the present invention is not limited thereto. The proportion of the alloy is controlled in accordance with the temperature, atmosphere, vacuum degree, etc. of the evaporation source and is selected in an appropriate ratio. The positive electrode and the negative electrode may be formed by two or more layer structures, if necessary.

In order to efficiently emit light in the organic electroluminescent device of the present invention, it is preferable that at least one surface is made sufficiently transparent in the light emitting wavelength region of the device. It is also preferable that the substrate is also transparent. The transparent electrode is set so as to ensure a predetermined light transmittance by a method such as vapor deposition or sputtering using the above-described conductive material. It is preferable that the electrode of the light emitting surface has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, but there is a glass substrate and a transparent resin film.

The formation of each layer of the organic electroluminescent device of the present invention may be performed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film formation method such as spin coating, dipping or flow coating . The film thickness is not particularly limited, but it is necessary to set the film thickness to an appropriate value. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, which leads to poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance can not be obtained even when an electric field is applied. A typical film thickness is suitably in the range of 5 nm to 10 mu m, more preferably in the range of 10 nm to 0.2 mu m.

In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., and any solvent may be used. As a solution suitable for such a wet film formation method, a solution containing an organic electroluminescent material containing an aromatic amine derivative of the present invention and a solvent as an organic electroluminescent material can be used.

The organic electroluminescent device of the present invention can be used as a planar light emitting device such as a flat panel display of a wall-hanging television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or a meter, The compounds of the present invention can be used not only in organic electroluminescent devices but also in fields of electrophotographic photosensitive members, photoelectric conversion devices, solar cells, image sensors and the like.

In addition, those skilled in the art can easily make the compounds described in the claims of the present invention without undue experimentation or high experimentation based on common sense at the time of filing and disclosure of the present invention It is obvious that it can be utilized.

That is, although not described in all of the following examples, according to the results of experiments conducted by the present inventors, it has been found that the size, the orientation, the possibility of steric hindrance, the polarity difference, etc., between the compounds described in the following examples and those not described in the following examples The specific manufacturing process described in the following examples is not so complicated, and complicated side reactions are not accompanied. Thus, it will be apparent to those skilled in the art of the present invention that, based on the technical knowledge at the time of filing, It is apparent that the compounds described in the claims of the present invention can be produced without adding any special knowledge only by describing the specific production method of the examples.

Hereinafter, the present invention will be described in more detail with reference to examples. The following examples are given by way of illustration only and the present invention is not limited thereto.

Synthetic example  1. Synthesis of Formula 3

Synthetic example  1-1. Synthesis of <1-a>

<1-a> was synthesized according to Reaction Scheme 1 below.

[Reaction Scheme 1]

<1-a>

100 g (0.598 mol) of carbazole was added to a 2000 mL round bottom flask under nitrogen, and 250 mL of N, N-diethylformamide was added to the flask, and the temperature of the reaction was cooled to 0 ° C. 106.44 g (0.598 mol) of N-bromosuccinimide was dissolved in 530 mL of N, N-dimethylamide and added dropwise. After the dropwise addition, the mixture was stirred at room temperature. When the reaction was completed, the reaction product was poured into water, stirred, filtered, and washed with water and methanol to obtain 76.4 g (51.9%) of <1-a>.

Synthetic example  1-2. Synthesis of <1-b>

<1-b> was synthesized according to Reaction Scheme 2 below.

[Reaction Scheme 2]

<1-b>

39.5 g (1.7 mol) of magnesium, 10 g of iodine and 100 mL of tetrahydrofuran were placed in a 2 L round bottom flask and refluxed under nitrogen for 2 hours. After cooling to room temperature, 212.8 g (1.4 mol) of bromobenzene was dissolved in 200 mL of tetrahydrofuran and slowly added dropwise. The mixture was refluxed for 2 hours and cooled to room temperature. In another 2 L round bottom flask, 100 g (0.54 mol) of cyanuric chloride is dissolved in 200 mL of tetrahydrofuran, and the reaction solution is cooled to 0 ° C. The above reaction solution is slowly added dropwise while maintaining the temperature at 0 ° C. After completion of the reaction, the reaction was terminated with 4 M hydrochloric acid aqueous solution and extraction. The organic layer was concentrated under reduced pressure, recrystallized with hexane, and dried to obtain 100 g (68.9%) of the compound represented by the formula 1-b.

Synthetic example  1-3. Synthesis of <1-c>

&Lt; 1-c > was synthesized by the following Reaction Scheme 3.

[Reaction Scheme 3]

<1-c>

Add sodium hydride (60% mineral oil) (NaH), 0.94 g (0.024 mol) and 100.0 mL of N, N-dimethylformamide in a 500 mL round bottom flask under nitrogen atmosphere and cool the reaction solution to 0 ° C. A solution obtained by dissolving 10 g (0.019 mol) of the compound represented by the formula 1-a synthesized in Scheme 3 in 100 mL of N, N-dimethylformamide was slowly added dropwise at 0 ° C, and the mixture was stirred at 0 ° C for 1 hour . After 1 hour, a solution of 6.5 g (0.024 mol) of the compound represented by the formula 1-b synthesized in the reaction formula 2 in 100 mL of N, N-dimethylformamide is slowly added dropwise. When the dropwise addition is complete, the reaction solution is warmed to room temperature and stirred. When the reaction is completed, the reaction solution is poured into 1 L of water to precipitate a solid, which is then filtered. The solid was recrystallized using toluene to obtain 5.9 g (41.1%) of the compound represented by the formula (2).

Synthetic example  1-4. Synthesis of <1-d>

<1-d> was synthesized according to Reaction Scheme 4 below.

[Reaction Scheme 4]

<1-d>

40 g (0.3699 mol) of phenylhydrazine, 41.5 g (0.3699 mol) of 2-methylcyclohexanone and 240 mL of acetic acid are placed in a 500 mL round bottom flask and refluxed for 6 hours. After completion of the reaction, the reaction solution is basified with sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography using hexane and methylene chloride as eluent to obtain 57.5 g (84%) of <1-d> ).

Synthetic example  1-5. Synthesis of <1-e>

<1-e> was synthesized by the following Reaction Scheme 5.

[Reaction Scheme 5]

<1-e>

In a 500 mL round-bottomed flask under nitrogen atmosphere, 50 g (0.2699 mol) of <1-d> obtained from the formula (1) is dissolved in 150 mL of toluene, and the temperature is lowered to -20 ° C. 260 mL (0.1753 mol) of 1.6 M methyl lithium is slowly added dropwise to the above solution and reacted at -20 ° C for 3 hours. After the reaction is completed, slowly pour 200 mL of a 1: 1 solution of toluene and water into the reaction solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 47.3 g (87%) of <1-e> obtained by column chromatography using hexane and methylene chloride as eluent were prepared.

Synthetic example  1-6. Synthesis of <1-f>

<1-f> was synthesized by the following Reaction Scheme 6.

[Reaction Scheme 6]

<1-f>

To a 1 L round bottom flask was added 40.0 g (0.199 mol) of <1-b>, 37.44 g (0.238 mol) of bromobenzene, 3.6 g (0.004 mol) of Pd ₂ (dba) ₃ , 38.19 g mol) and 2.47 g (0.004 mol) of BINAP are dissolved in toluene. Reflux for 8 hours. The completion of the reaction is confirmed by TLC. When the reaction is completed, the organic layer is concentrated after filtration. The product is separated by column chromatography (developing solvent MC: Hex = 1: 3). &Lt; 1-f > 40.4g (73.3%).

Synthetic example  1-7. Synthesis of <1-g>

<1-g> was synthesized according to the following Reaction Scheme 7.

[Reaction Scheme 7]

<1-g>

Add 1-f> 40.0 g (0.144 mol) to a 1 L reaction vessel, dissolve in 400 mL of chloroform, and lower the temperature of the reactor to 0 ° C. 23.0 g (0.144 mol) of bromine is diluted in 120 mL of chloroform and then slowly added dropwise to the reaction vessel. After the dropwise addition, the temperature is slowly raised to room temperature and stirred for 8 hours. The completion of the reaction is confirmed by TLC. When the reaction is complete, add 100 mL of water and remove bromine with sodium thiosulfate. Extract with chloroform and water. The organic layer is concentrated and recrystallized from ethanol. Repeat the recrystallization with methylene chloride and ethanol to increase the purity. 37.1 g (72.2%) of &lt; 1-g &gt;

Synthetic example  1-8. Synthesis of <1-h>

<1-h> was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

<1-h>

(0.098 mol) of <1-g>, 37.4 g (0.147 mol) of bis (pinacolato) diboron, 1.6 g (0.002 mol) of PdCl 2 (dppf) and 28.90 g ), Add 525 mL of toluene, and reflux at 110 ° C for 12 hours. When the reaction is completed, the reaction is filtered under reduced pressure in a hot state. After drying the solution, 27.7 g (69.9%) of <1-h> was prepared by column chromatography using methylene chloride and n-hexane as eluent.

Synthetic example  1-9. < Compound 3 > Synthesis of

<Compound 3> was synthesized by the following Reaction Scheme 9.

[Reaction Scheme 9]

<Compound 3>

(0.071 mol), <1-h> 21.2 g (0.086 mol), tetrakis triphenylphosphine palladium (0) 1.7 g (0.001 mol), potassium carbonate 19.7 g, and 100 mL of 1,4-dioxane, 100 mL of toluene and 40 mL of water, and the mixture is stirred at 80 ° C for 6 hours. Upon completion of the reaction, the reaction mixture was extracted and the organic layer was dried, and 18.4 g (63.9%) of <Compound 3> was prepared by column chromatography.

MS [M] ^&lt; ⁺ & gt ^; 673

Synthetic example  2. Synthesis of Compound (17)

Synthetic example  2-1. Synthesis of <2-a>

&Lt; 2-a > was synthesized by the following Reaction Scheme 10.

[Reaction Scheme 10]

<2-a>

<2-a> was synthesized by the same method except that 2-bromonaphthalene was used instead of bromobenzene used in Scheme 6.

Synthetic example  2-2. Synthesis of <2-b>

<2-b> was synthesized according to the following Reaction Scheme 11.

[Reaction Scheme 11]

<2-b>

<2-b> was synthesized by the same method except that <2-a> was used instead of <1-e> used in Scheme 7.

Synthetic example  2-3. Synthesis of <2-c>

&Lt; 2-c > was synthesized according to Reaction Scheme 12 below.

[Reaction Scheme 12]

<2-c>

<2-c> was synthesized by the same method except that <2-b> was used in place of <1-g> used in Scheme 8.

Synthetic example  2-4. Synthesis of <2-d>

<2-d> was synthesized by the following Reaction Scheme 13.

[Reaction Scheme 13]

<2-d>

<2-d> was synthesized in the same way except that 3-bromocarbazole and <2-c> were used instead of <1-h> in place of <1-c> used in Scheme 9.

Synthetic example  2-5. Synthesis of <2-e>

<2-e> was synthesized by the following Reaction Scheme 14.

[Reaction Scheme 14]

<2-e>

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 (80%) of the compound represented by 2-e.

Synthetic example  2-6. Synthesis of Compound (17)

<Compound 17> was synthesized by the following Reaction Scheme 15.

[Reaction Scheme 15]

<Compound 17>

<Compound 17> was synthesized in the same manner except that <2-e> was used instead of bromobenzene used in Reaction Scheme 6, and <2-d> was used in place of <1-b>.

MS [M] ^&lt; ⁺ & gt ^; 800

Synthetic example  3. Synthesis of Formula 33

Synthetic example  3-1. Synthesis of <3-a>

&Lt; 3-a > was synthesized by the following Reaction Scheme 16.

[Reaction Scheme 16]

<3-a>

(0.318 mol) of tribromobenzene, 89.1 g (0.731 mol) of phenylboronic acid, 18.4 g (0.016 mol) of tetrakis triphenylphosphine palladium (0), 219.5 g mol), add 500 mL of 1,4-dioxane, 500 mL of toluene and 2000 mL of water, and stir at 80 ° C for 6 hours. Upon completion of the reaction, the reaction mixture was extracted and the organic layer was dried, and 54.3 g (42.9%) of <3-a> was prepared by column chromatography.

Synthetic example  3-2. Synthesis of <3-b>

<3-b> was synthesized by the following Reaction Scheme 17.

[Reaction Scheme 17]

<3-b>

<3-b> was synthesized by the same method except that <3-a> was used instead of bromobenzene used in Scheme 6.

Synthetic example  3-3. Synthesis of <3-c>

<3-c> was synthesized by the following Reaction Scheme 18.

[Reaction Scheme 18]

<3-c>

<3-c> was synthesized in the same manner except that <3-b> was used instead of <1-f> used in Scheme 7.

Synthetic example  3-4. Synthesis of <3-d>

&Lt; 3-d > was synthesized according to the following Reaction Scheme 19.

[Reaction Scheme 19]

<3-d>

<3-d> was synthesized by the same method except that <3-c> was used instead of <1-g> used in Scheme 8.

Synthetic example  3-5. Synthesis of <3-e>

<3-e> was synthesized by the following Reaction Scheme 20.

[Reaction Scheme 20]

<3-e>

<3-e> was synthesized in the same manner except that 3-bromocarbazole was used instead of <1-c> used in Scheme 9, and <3-d> was used in place of <1-g>.

Synthetic example  3-6. Synthesis of <3-f>

<3-f> was synthesized by the following Reaction Scheme 21.

[Reaction Scheme 21]

<3-f>

<3-f> was synthesized in the same way except that 3-bromophenylboronic acid was used instead of 4-bromophenylboronic acid used in Scheme 14.

Synthetic example  3-7. Synthesis of Compound 33

<Compound 33> was synthesized according to the following Reaction Formula 22.

[Reaction Scheme 22]

<Compound 33>

<Compound 33> was synthesized in the same manner except that <3-f> was used instead of bromobenzene used in Reaction Scheme 6 and <3-e> was used in place of <1-b>.

MS [M] ^&lt; ⁺ & gt ^; 902

Synthetic example  4. Synthesis of Formula 86

Synthetic example  4-1. Synthesis of <4-a>

&Lt; 4-a > was synthesized by the following Reaction Formula 23.

[Reaction Scheme 23]

<4-a>

In a 1000 mL round bottom flask, 25 g (0.128 mol) of 4-bromoindole and 500 mL of acetic acid were added under nitrogen and stirred, and the temperature of the reaction was cooled to 0 ° C. 24.5 g (0.390 mol) of sodium cyanoborohydride was slowly added. And the mixture was stirred at room temperature. After the reaction was completed, the reaction product was poured into water, stirred, and basified with sodium hydroxide. The organic layer was concentrated under reduced pressure and then purified by column chromatography using hexane to obtain 17.2 g (51.9%) of the formula <4-a> .

Synthetic example  4-2. Synthesis of <4-b>

<4-b> was synthesized by the following Reaction Scheme 24.

[Reaction Scheme 24]

<4-b>

<4-b> was synthesized in the same way except that <1-b> was used instead of <4-a> used in Scheme 6 and 1-iodonaphthalene was used in place of bromobenzene.

Synthetic example  4-3. Synthesis of <4-c>

<4-c> was synthesized according to Reaction Scheme 25 below.

[Reaction Scheme 25]

<4-c>

<4-c> was synthesized by the same method except that <4-b> was used instead of <1-g> used in Scheme 8.

Synthetic example  4-4. Synthesis of Compound 86

<Compound 86> was synthesized by the following Reaction Formula 26.

[Reaction Scheme 26]

<Compound 86>

<Compound 86> was synthesized by the same method except that <4-c> was used in place of <1-h> used in Scheme 9.

MS [M] ^&lt; ⁺ & gt ^; 641

Synthetic example  5. Synthesis of Formula 107

Synthetic example  5-1. Synthesis of <5-a>

&Lt; 5-a > was synthesized according to the following Reaction Formula 27.

[Reaction Scheme 27]

<5-a>

<5-a> was synthesized by the same method except that 1,2,3,4-tetrahydroquinoline was used instead of <1-f> used in Scheme 7.

Synthetic example  5-2. Synthesis of <5-b>

&Lt; 5-b > was synthesized according to Reaction Scheme 28 below.

[Reaction Scheme 28]

<5-b>

<5-b> was prepared by the same method except that <5-a> was used instead of <1-b> used in Scheme 6 and iodobenzene was used in place of bromobenzene.

Synthetic example  5-3. Synthesis of <5-c>

&Lt; 5-c > was synthesized according to Reaction Scheme 29 below.

[Reaction Scheme 29]

<5-c>

<5-c> was synthesized by the same method except that <5-b> was used instead of <1-g> used in Scheme 9.

Synthetic example  5-4. Synthesis of <5-d>

<5-d> was synthesized according to Reaction Scheme 30 below.

[Reaction Scheme 30]

<5-d>

<5-d> was synthesized in the same manner except that 3-bromocarbazole and <5-c> were used in place of <1-h> instead of <1-c> used in Scheme 9.

Synthetic example  5-5. Synthesis of Compound 107

<Compound 107> was synthesized according to Reaction Scheme 31 below.

[Reaction Scheme 31]

<Compound 107>

Compound <107> was synthesized in the same way except that bromobenzene used in Scheme 6 was used instead of <2-e> and <5-d> instead of <1-b>.

MS [M] ^&lt; ⁺ & gt ^; 681

Synthetic example  6. Synthesis of Formula 115

Synthetic example  6-1. Synthesis of <6-a>

&Lt; 6-a > was synthesized according to Reaction Scheme 32 below.

[Reaction Scheme 32]

<6-a>

<5-a> was synthesized in the same way except that dihydrobenzoazine was used instead of <1-b> used in Scheme 6, and iodobenzene was used in place of bromobenzene.

Synthetic example  6-2. Synthesis of <6-b>

&Lt; 6-b > was synthesized by the following Reaction Formula 33.

[Reaction Scheme 33]

<6-b>

<6-b> was synthesized by the same method except that <6-a> was used instead of <1-g> used in Scheme 7.

Synthetic example  6-3. Synthesis of <6-c>

&Lt; 6-c > was synthesized by the following Reaction Formula 34.

[Reaction Scheme 34]

<6-c>

<6-c> was synthesized by the same method except that <6-b> was used in place of <1-g> used in Scheme 8.

Synthetic example  6-4. Synthesis of Compound 115

<Compound 115> was synthesized by the following Reaction Scheme 35.

[Reaction Scheme 35]

<Compound 115>

Compound <115> was synthesized by the same method except that <6-c> was used in place of <1-h> used in Scheme 9.

MS [M] ^&lt; ⁺ & gt ^; 607

Synthetic example  7. Synthesis of Formula 146

Synthetic example  7-1. Synthesis of <7-a>

<7-a> was synthesized by the following Reaction Formula 36.

[Reaction Scheme 36]

<7-a>

5 L round bottom flask, 4-bromo-benzene Yo de 200g (0.707mol), 1- naphthyl boronic acid 121.6 g (0.707mol), Pd ( PPh 3) 4 16.4g (0.014mol), potassium carbonate 195.4g (1.414 mol), 1000 mL of tetrahydrofuran, 1000 mL of toluene and 400 mL of water are added, and the mixture is refluxed for 12 hours. The completion of the reaction is confirmed by TLC. When the reaction is completed, the organic layer is extracted and dried. <Column 7-a> 120.1 g (60.0%) was prepared by column chromatography.

Synthetic example  7-2. Synthesis of <7-b>

<7-b> was synthesized by the following Reaction Scheme 37.

[Reaction Scheme 37]

<7-b>

<7-b> was synthesized in the same way except that 3-bromocarbazole and <7-a> were used instead of bromobenzene instead of <1-e> used in Scheme 6.

Synthetic example  7-3. Synthesis of <7-c>

&Lt; 7-c > was synthesized by the following Reaction Formula 38.

[Reaction Scheme 38]

<7-c>

<7-c> was synthesized in the same manner except that <7-b> was used instead of <1-g> used in Scheme 8.

Synthetic example  7-4. Synthesis of <7-d>

<7-d> was synthesized by the following Reaction Scheme 39.

[Reaction Scheme 39]

<7-d>

<7-d> was synthesized in the same manner except that <7-c> was used instead of <1-e> and <1-h> in place of <1-c> used in Scheme 9.

Synthetic example  7-5. Synthesis of Compound 146

<Compound 146> was synthesized by the following Reaction Formula 40.

[Reaction Scheme 40]

<Compound 146>

<Compound 146> was synthesized in the same manner except that <3-f> was used instead of bromobenzene used in Scheme 6, and <7-d> was used in place of <1-b>.

MS [M] ^&lt; ⁺ & gt ^; 876

Synthetic example  8. Synthesis of Formula 196

Synthetic example  8-1. Synthesis of <8-a>

<8-a> was synthesized by the following Reaction Scheme 41.

[Reaction Scheme 41]

<8-a>

<8-a> was synthesized by the same method except that D5-bromobenzene was used instead of bromobenzene used in Reaction Scheme 6.

Synthetic example  8-2. Synthesis of <8-b>

<8-b> was synthesized by the following reaction scheme.

[Reaction Scheme 42]

<8-b>

<8-b> was synthesized by the same method except that <8-a> was used instead of <1-f> used in Scheme 7.

Synthetic example  8-3. Synthesis of <8-c>

<8-c> was synthesized by the following reaction scheme 43.

[Reaction Scheme 43]

<8-c>

<8-c> was prepared by the same method except that bromobenzene used in Reaction Scheme 6 was replaced with iodobenzene.

Synthetic example  8-4. Synthesis of <8-d>

<8-d> was synthesized by the following reaction scheme 44.

[Reaction Scheme 44]

<8-d>

<8-d> was synthesized by the same method except that <8-c> was used instead of <1-g> used in Scheme 8.

Synthetic example  8-5. <Compound 196> Synthesis of

<Compound 196> was synthesized by the following Reaction Scheme 45.

[Reaction Scheme 45]

<Compound 196>

Compound 196> was synthesized in the same way except that <8-b> was used instead of <8-b> and <8-d> was used in place of <1-c> used in Scheme 9.

MS [M] ^&lt; ⁺ & gt ^; 523

Synthetic example  9. Synthesis of Formula 235

Synthetic example  9-1. Synthesis of <9-a>

<9-a> was synthesized by the following reaction scheme 46.

[Reaction Scheme 46]

<9-a>

<9-a> was synthesized in the same manner except that bromobutanol was used instead of bromobenzene used in Reaction Scheme 6.

Synthetic example  9-2. Synthesis of <9-b>

<9-b> was synthesized by the following Reaction Scheme 47.

[Reaction Scheme 47]

<9-b>

<2-b> was synthesized by the same method except that <2-a> was used instead of <1-f> used in Scheme 7.

Synthetic example  9-3. Synthesis of <9-c>

&Lt; 9-c > was synthesized according to the following Reaction Formula 48.

[Reaction Scheme 48]

<9-c>

<9-c> was synthesized by the same method except that 2-bromocarbazole was used instead of <1-g> used in Scheme 8.

Synthetic example  9-4. Synthesis of <9-d>

<9-d> was synthesized by the following Reaction Formula 49.

[Reaction Scheme 49]

<9-d>

9-d> was synthesized in the same way except that <9-c> was used instead of <9-b> and <1-h> in place of <1-c> used in Scheme 9.

Synthetic example  9-5. Synthesis of Compound 235

<Compound 235> was synthesized by the following Reaction Formula 50.

[Reaction Scheme 50]

<Compound 235>

<Compound 235> was synthesized in the same way except that bromobenzene used in Scheme 6 was used instead of <2-e> and <9-d> instead of <1-b>.

MS [M] ^&lt; ⁺ & gt ^; 826

Example : Manufacture of Organic Light Emitting Diodes

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, and then an organic material was deposited on the ITO using DNTPD (700 Å), NPD (300 Å), the compound prepared by the present invention + (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å) and Al (1,000 Å) in this order.

Comparative Example

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.

<CBP>

division Host Dopant Doping concentration% V Cd / ㎡ CIEx CIEy Comparative Example 1 CBP (piq) 2Ir (acac) 10 7.50 1000 0.671 0.329 Example 1 3 (piq) 2Ir (acac) 10 4.00 1611 0.673 0.327 Example 2 15 (piq) 2Ir (acac) 10 3.06 1562 0.671 0.328 Example 3 17 (piq) 2Ir (acac) 10 3.57 1594 0.672 0.327 Example 4 27 (piq) 2Ir (acac) 10 3.24 1579 0.670 0.329 Example 5 33 (piq) 2Ir (acac) 10 3.37 1678 0.672 0.326 Example 6 54 (piq) 2Ir (acac) 10 4.02 1478 0.671 0.327 Example 7 68 (piq) 2Ir (acac) 10 3.84 1542 0.673 0.327 Example 8 83 (piq) 2Ir (acac) 10 3.98 1524 0.671 0.326 Example 9 86 (piq) 2Ir (acac) 10 3.47 1631 0.671 0.326 Example 10 99 (piq) 2Ir (acac) 10 4.13 1597 0.672 0.325 Example 11 106 (piq) 2Ir (acac) 10 3.71 1538 0.673 0.326 Example 12 107 (piq) 2Ir (acac) 10 3.86 1473 0.672 0.326 Example 13 115 (piq) 2Ir (acac) 10 3.46 1582 0.672 0.325 Example 14 122 (piq) 2Ir (acac) 10 3.99 1486 0.673 0.325 Example 15 127 (piq) 2Ir (acac) 10 3.06 1543 0.672 0.326 Example 16 141 (piq) 2Ir (acac) 10 3.91 1527 0.673 0.326 Example 17 146 (piq) 2Ir (acac) 10 4.03 1671 0.671 0.327 Example 18 176 (piq) 2Ir (acac) 10 3.87 1472 0.672 0.326 Example 19 190 (piq) 2Ir (acac) 10 4.16 1549 0.672 0.327 Example 20 196 (piq) 2Ir (acac) 10 3.94 1574 0.673 0.327 Example 21 228 (piq) 2Ir (acac) 10 3.74 1592 0.673 0.326 Example 22 231 (piq) 2Ir (acac) 10 3.54 1608 0.673 0.326

In addition, even in the case of compounds included in the scope of the present invention or a combination thereof, some compounds may not have uniform emission uniformity at high temperature, whereas compounds of the above formulas (3) to (245) The compounds of the above formulas (3) to (245) are excellent in the uniformity of light emission at a high temperature (for example, 100 hours or more) since the uniformity of light emission is not deteriorated on the basis of area and time after application of an electric field for a long time And the uniformity of light emission based on area and time is ensured even after a long operation time of 100 hours or more.

In addition, even if a combination of compounds included in the scope of the present invention (for example, the formula (VW)) can not exhibit a viscosity of 7 cP or more without using a separate thickener, film formation by the solution coating method is almost impossible, One or more selected from among the above-mentioned chemical formulas 3, 15, 17, 27, 33, 54, 68, 83, 86, 99, 106, 107, 115, 122, 127, 141, 146, 176, 190, 196, In the case of using the mixture of these, viscosity of 7 cP or more can be expressed without using any additional thickener, and it is confirmed that the film formation by the solution coating method is possible.

Claims (11)

An organic electroluminescent compound represented by the following Chemical Formula 1 or Chemical Formula 2:
[Chemical Formula 1]

(2)

In the above Chemical Formulas 1 to 2,
R ₁ to R ₆ are the same or different and each represents a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms , A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C6-C30 A substituted or unsubstituted C1 to C20 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, a substituted or unsubstituted C1 to C50 arylalkylamino group, A substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a hydroxyl group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfone 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 aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, , A cyano group, a halogen group, a medium-small water, hydrogen,
R ₁ to R ₆ Is a heteroaryl group containing nitrogen,
L is a single bond or a substituted or unsubstituted alkylene having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene having 2 to 60 carbon atoms, a substituted or unsubstituted Cycloalkylene having 3 to 60 carbon atoms, heterocycloalkylene having 2 to 6 carbon atoms and at least one selected from N, O and S, substituted or unsubstituted arylene having 6 to 50 carbon atoms and substituted or unsubstituted carbon number Lt; / RTI &gt; is a divalent linking group selected from the group consisting of &lt; RTI ID = 0.0 &gt;
m or n is an integer of 0 to 4, and when m or n is 2 or more, plural Ls may be the same or different,
X ₁ and X ₂ are CRR and the two Rs are the same or different and each independently represents hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms ego,
Y is selected from the group consisting of CRR, O and S (wherein ( _n ) is an integer of 0 to 1 in (Y) _n ), R is independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, Or a heteroaryl group having 2 to 60 carbon atoms,
In (CR ₂ ) _n of the above formula ( ₂ ), n is an integer of 3 to 6, and each of R ₂ is independently hydrogen, deuterium or an alkyl group of 1 to 10 carbon atoms. The method according to claim 1,
The above R, R ₁ to R ₆ And L each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano 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, An alkyl group having 1 to 60 carbon atoms, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, An arylthio group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, -SiRRR, and -NRR (wherein R may be the same or different and each independently represents hydrogen, deuterium, An aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms), wherein the substituent is at least one substituent selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms. The method according to claim 1,
Wherein L is any one selected from the following Structural Formula C1 to Structural Formula 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 the same as defined for R ₁ to R ₆ in the formula (1) or (2). The method according to claim 1,
R ₁ connected to L And R &lt; ₂ &gt; are each independently any one selected from the following Structural Formulas 1 to 10:
[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7]

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

In the above Structural Formulas 1 to 10,
T ₁ to T ₁₂ are the same or different and each independently selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ )
R ₄₁ to R ₄₄ 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 cycloalkyl group having 3 to 30 carbon atoms, An aryl group having 5 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. [ 5. The method of claim 4,
The organic electroluminescent compound according to any one of [Structural Formulas 1] to [Structural Formula 10] is one selected from the following [Structural Formula 11]:
[Structural Formula 11]

In the above structural formula 11,
X is 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, an unsubstituted or substituted 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 or more 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, It is selected from,
m is an integer of 1 to 11, and when m is 2 or more, plural Xs are the same or different from each other. The method according to claim 1,
The organic electroluminescent compound represented by Formula 1 or Formula 2 is any one selected from the following Formulas 3 to 245:

[Chemical Formula 3] &lt; EMI ID =

[Chemical Formula 8] &lt; EMI ID =

[Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14]

[Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 18]

[Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]

[Chemical Formula 25] [Chemical Formula 25]

[Chemical Formula 30] [Chemical Formula 30]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42]

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

[Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50]

[Chemical Formula 51]

[Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62]

[Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 70] [Chemical Formula 70]

[Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74]

[Formula 75] &lt; EMI ID = 78.1 &gt;

[Formula 80] [Formula 81] [Formula 82]

[Formula 83] [Formula 85] [Formula 86]

[Formula 90] [Formula 90] [Formula 90]

[Chemical Formula 91] [Chemical Formula 93] [Chemical Formula 94]

[Chemical Formula 97] [Chemical Formula 97] [Chemical Formula 98]

[Chemical Formula 100] [Chemical Formula 101] [Chemical Formula 101]

[Formula 103] [Formula 105] [Formula 106]

[Formula 110] [Formula 110] [Formula 110]

[Formula 111] [Formula 113] [Formula 114]

[Chemical Formula 116] [Chemical Formula 117] [Chemical Formula 118]

[Chemical Formula 120]

[Formula 124] [Formula 125] [Formula 126]

[Formula 127] &lt; EMI ID = 129.0 &gt;

[Formula 131] [Formula 133] [Formula 134]

[Chemical Formula 135] [Chemical Formula 135]

[Formula 140] [Formula 141] [Formula 142]

[Chemical Formula 144] [Chemical Formula 145] [Chemical Formula 146]

[Formula 150] [Formula 149] [Formula 150]

[Formula 154] [Formula 154] [Formula 154]

[Formula 157] &lt; EMI ID = 158.1 &gt;

[Formula 161] [Formula 161] [Formula 161]

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

[Formula 16] [Formula 16]

[Formula 173] [Formula 174] [Formula 174]

[Formula 177] [Formula 177] [Formula 178]

[Formula 181] [Formula 181] [Formula 182]

[Formula 184] [Formula 184] [Formula 186] [Formula 186]

[Formula 188] [Chemical Formula 189] [Chemical Formula 190]

[193] [193] [193] [194]

[197] [198] [198] [198] [198]

[Chemical Formula 200] [Chemical Formula 201] [Chemical Formula 202]

[Chemical Formula 203]

[Chemical Formula 20] [Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 212] [Chemical Formula 213] [Chemical Formula 214]

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

[Formula 21] &lt; EMI ID =

[Formula 226] [Formula 226] [Formula 226]

[228] [230] [229]

[233] [233] [233]

[238] [237] [237]

[240] [248]

[245] [243] An organic thin film layer for an organic electroluminescence device, comprising at least one compound according to any one of claims 1 to 6. 8. The method of claim 7,
Wherein the organic thin film layer comprises an organic light emitting compound represented by Formula 1 or Formula 2 as a host and further contains at least one dopant compound. A first electrode; A second electrode; And an organic thin film layer interposed between the first electrode and the second electrode. 10. The method of claim 9,
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 first electrode and the second electrode ,
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 6. 10. The method of claim 9,
Wherein the organic electroluminescent device comprises one or more organic electroluminescent layers emitting blue, red or green light to emit white light.