KR101998435B1 - Organic electro luminescence device - Google Patents

Abstract

The present invention relates to a positive electrode; cathode; And one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a first host and a second host.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescence device,

The present invention relates to an organic electroluminescent device including at least one organic material layer.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

In order to increase the luminous efficiency of the organic electroluminescent device, it is necessary to increase the color purity and to transfer energy. For this purpose, a luminescent material mixed with a host material and a dopant material can be used. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted. As a phosphorescent dopant material of the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like are known and CBP is known as a phosphorescent host material.

However, since conventional materials have low glass transition temperature and poor thermal stability, they are not satisfactory in terms of lifetime in an organic electroluminescent device. Therefore, development of an organic electroluminescent device including a luminescent material having excellent performance is required.

In order to solve the above problems, it is an object of the present invention to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and life span.

In order to achieve the above object, cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the one or more organic material layers includes a first host and a second host, And the second host is a compound represented by the following general formula (2).

In Formula 1,

R _a to R _d are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, and a substituted or unsubstituted C ₆ to C ₆₀ aryl group Selected,

In Formula 2,

X ₁ is selected from the group consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ),

Y ₁ to Y ₄ are the same or different and each independently N or C (R ₁ ), wherein when there are plural C (R ₁ ) s, plural R _{1 s} are the same or different, To form a condensed ring;

X ₂ and X ₃ are the same as or different from each other and each independently N or C (R ₂ ), wherein when there are a plurality of C (R ₂ ) s, the plurality of R _{2 s} are the same or different, May form a ring;

R ₁ to R ₂ and Ar ₁ to Ar ₅ are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C ₁ to C ₄₀ An alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atoms, 3 to 40 heterocycloalkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted number of 5 to 60 heteroaryl unsubstituted nucleus atoms an aryl group, a substituted or unsubstituted C ₁ ~ C ₄₀ of A substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, A substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C Is selected from ₁ ~ C ₄₀ of the phosphine group, a substituted or unsubstituted C ₁ ~ C ₄₀ phosphine oxide group, and the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine,

In the above R _a to R _d , R ₁ to R ₂ and Ar ₁ to Ar ₅ , an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, A halogen group, a cyano group, a nitro group, an amino group, a C _{1 to} C ₆ alkyl group, an aryl group, an aryloxy group, an aryloxy group, an aryloxy group, a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ C ₄₀ of the An aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl silyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, a C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₆₀ of the An arylamine group And may be substituted with one or more selected from the group consisting of lauric acid.

Here, the organic material layer including the first host and the second host is preferably a phosphorescent light-emitting layer.

The light emitting layer preferably includes a metal complex compound dopant.

The organic electroluminescent device of the present invention includes an organic material layer including a first host and a second host, wherein the first host and the second host are used in combination of the compound represented by Formula 1 and the compound represented by Formula 2, , The driving voltage of the device, the luminous efficiency and the life can be improved. Accordingly, when a display panel is manufactured using the organic electroluminescent device of the present invention, a display panel having improved performance and lifetime can be provided.

Hereinafter, the present invention will be described.

The organic electroluminescent device of the present invention includes a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes one or more of a first host and a second host , The first host is a compound represented by Formula 1, and the second host is a compound represented by Formula 2 below.

The compound represented by Formula 1, which is used as a first host in the present invention, is a compound in which hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, or a C ₆ to C ₆₀ aryl group is substituted in the 3,3'-biscarbazole basic skeleton .

In general, the carbazole skeleton has electron donating group characteristics, which are electron donating and hole transporting properties. Therefore, when two carbazole skeletons are included in the molecule as shown in Formula 1, they have a high hole transporting property, and the molecular weight of the carbazole skeleton is significantly higher than that of a single carbazole skeleton, resulting in high thermal stability. In particular, the basic skeleton in the form of 3,3'-bonded biscarbazole is the main binding site of carbazole, which can firmly link two carbazoles to enhance the thermal and electrical stability of the molecule itself.

According to the present invention, in the compound represented by the general formula (1), R _a to R _d are the same or different and each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group and a C ₆ to C ₆₀ aryl group It is selected from the group. More specifically, R _a to R _d may be the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl, . The above-described alkyl and aryl groups as substituents have electron donating and hole transporting properties, thereby enhancing the electron donating group characteristic in the molecule. In the present invention, it is preferable that each of R _a to R _d is independently a phenyl group, and the bonding position of the phenyl group is not particularly limited and is not limited.

The compound represented by the formula (1) according to the present invention may be further compounded into a group of compounds represented by the following formulas. However, it is not particularly limited.

The compound represented by the general formula (2) used as the second host in the present invention is a compound in which a condensed carbon ring or a condensed heterocyclic moiety, preferably a condensed heterocyclic moiety, is connected to an indole based basic skeleton, The level is adjusted to have a broad energy band gap (sky blue ~ red). Accordingly, when the compound represented by the general formula (2) is used as the second host of the organic compound layer of the organic electroluminescence device, the light emission (phosphorescence) characteristics of the organic electroluminescence device are improved and the electron and / .

More specifically, the compound represented by Formula 2 has various aromatic rings bonded to the indole-based basic skeleton as a substituent, so that the molecular weight of the compound is significantly increased. Therefore, the glass transition temperature (Tg) can be improved and therefore, can have higher thermal stability than conventional CBP. In addition, since the molecule has a bipolar nature due to various aromatic ring substituents bonded to the indole based basic skeleton and can increase the bonding force between holes and electrons, it has superior properties as a phosphorescent host material in the light emitting layer .

In the compound represented by the formula (2) in accordance with the present invention, X ₁ is O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ Is selected.

And Y ₁ to Y ₄ are the same or different and are each independently N or C (R ₁ ). In this case, when there are a plurality of C (R ₁ ) s, a plurality of R _{1 s} may be the same or different, and they may each form a condensed ring with adjacent groups.

X ₂ and X ₃ are the same or different and are each independently N or C (R ₂ ). When there are a plurality of C (R ₂ ) s, the plurality of R _{2 s} may be the same or different, and they may form a condensed ring with adjacent groups.

In the present invention, "forming an adjacent group and a condensed ring" means that two or more substituents adjacent to each other are bonded to each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, Quot; means forming a heteroaromatic ring.

The compound represented by the formula (2) may be further illustrated by the following A-1 to A-24, but is not limited thereto.

In the above A-1 to A-24,

R ₂ , Y ₁ to Y _4, and Ar ₁ to Ar ₅ are the same as defined in the above-described formula (2). Considering the physical and chemical characteristics of the compound, the case of A-1 to A-6 is preferable.

The compound represented by the general formula (2) of the present invention may be used alone in the structure of the general formula (2), or the compound of the general formula (2) may be combined with the following general formula (3) or (4) to form a condensation structure.

More specifically, when Y ₁ to Y ₄ are plural C (R ₁ ) in Formula 2, _{one of} Y ₁ and Y ₂ , Y ₂ and Y _3, or Y ₃ and Y ₄ may be a condensed ring Can be formed. The plurality of R < ₁ > s may be the same or different from each other. For example, Y ₁ to Y ₄ in formula (2) may be bonded to X ₉ and X ₁₀ in formula (3).

When X ₂ and X ₃ are both C (R ₂ ) in the general formula ( ₂ ), the plurality of R ₂ may bond with the general formula (3) or (4) to form a condensed ring. And may be bonded to the formula (4) to form a condensed ring. For example, X ₂ and X ₃ in the general formula (2) may combine with Y ₁₁ to Y ₁₄ in the general formula (4) to form a condensed ring.

In the above formulas (3) and (4)

Y ₅ to Y ₁₄ are the same as or different from each other and each independently N or C (R ₃ ), wherein when there are a plurality of C (R ₃ ) s, the plurality of R _{3 s} are the same or different, To form a condensed ring (ring)

X ₄ is the same as X ₁ described above, wherein a plurality of Ar ₁ to Ar ₅ are the same or different.

R _{3, which} is non-forming the condensation ring of Formula 2, is, independently, hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C ₁ to C ₄₀ alkyl, the unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ - C ₄₀ alkynyl group, a substituted or unsubstituted number of C ₃ to a cycloalkyl group, a substituted or unsubstituted of C ₄₀ unsubstituted nucleus atom 3 to the A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group , A substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₁ ~ C ₄₀ of the phosphine , Is selected from substituted or unsubstituted C ₁ ~ phosphine oxide of a C ₄₀ group, and a substituted or unsubstituted group consisting of a ring with an aryl amine of the C ₆ ~ C _60, or they may combine adjacent groups may form a condensed ring .

In R ₃ , an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, A halogen atom, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₆ to C ₄₀ alkenyl group, ₂ or an alkynyl group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, a number of the aryl group, the nucleus of atoms of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ of from 5 to 40 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ a group - C ₆₀ aryl boron, C ₁ ~ C ₄₀ of the phosphine group, at least one selected from the group consisting of C ₁ ~ C ₄₀ of the phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amines Hwandoel can.

In the present invention, the compounds formed by condensation of the above-mentioned formulas (2) and (3) may be further represented by the following formulas (2a) to (2f).

(2a)

(2b)

[Chemical Formula 2c]

(2d)

[Formula 2e]

(2f)

In the above general formulas (2a) to (2f)

X ₁ to X ₄ and Y ₁ to Y ₈ are as defined in formulas (2) and (3), respectively.

More particularly, Y ₁ to Y ₄ to form a condensed ring ratio (非) is N or C (R _1), wherein if the Y ₁ to Y ₄ are both C (R ₁₎ is preferred.

And Y ₅ to Y ₈ are N or C (R ₃ ), wherein Y ₅ to Y ₈ are both C (R ₃ ). Wherein a plurality of R ₁ and R ₃ are the same or different from each other.

The compounds of the present invention in which the above-mentioned formulas (2) and (3) are condensed can be further compounded as a group of compounds represented by the following formulas (B-1) to (B-30). However, it is not particularly limited.

In Formulas B-1 to B-30, Ar ₁ and R ₁ to R ₃ are the same as defined in Formula 2 and Formula 3 described above.

More specifically, Ar ₁ is a substituted or unsubstituted C ₆ -C ₄₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms,

R ₁ to R ₃ are each independently hydrogen, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, or a substituted or unsubstituted 5 to 40 Gt; is preferably a heteroaryl group of < RTI ID = 0.0 >

Herein, the formulas B-1 to B-30 having a structure formed by condensing the above-mentioned formulas (2) and (3) include at least one condensed indole or condensed carbazole moiety.

In the present invention, the compounds formed by condensation of the above-mentioned formulas (2) and (4) may be further represented by compounds represented by the following formulas (2g) to (2n).

[Chemical Formula 2g]

[Chemical Formula 2h]

(2i)

(2j)

[Chemical Formula 2k]

≪ EMI ID =

[Formula 2m]

(2n)

In the general formulas (2g) to (2n), X ₁ , X ₄ and Y ₁ to Y ₁₄ are the same as defined in the above-mentioned formulas (2) and (4), respectively.

More preferably, X ₁ and X ₄ are each independently O, S or N (Ar ₁ ), more preferably both X ₁ and X ₄ are N (Ar ₁ ), wherein a plurality of Ar ₁ Are the same or different.

Y ₁ to Y ₄ are each independently N or C (R ₁ ), and it is preferable that Y ₁ to Y ₄ are all C (R ₁ ), wherein plural R _{1 s} are the same or different.

Y ₅ to Y ₁₄ are each independently N or C (R ₃ ), and it is preferable that Y ₅ to Y ₁₄ are both C (R ₃ ), wherein the plurality of R ₃ are the same or different.

Here, Ar ₁ and R ₁ to R ₃ are the same as those defined in the above-mentioned formulas (2) and (4).

In the present invention, in consideration of characteristics such as luminous efficiency, driving voltage and lifetime of the organic electroluminescent device, the compound represented by any one of formulas (2a) to (2n) used as the second host is a compound wherein X ₁ and X ₄ are each independently N (Ar &_lt; ₁ >) or S. That is, it is preferable that X ₁ is N (Ar ₁ ), X ₄ is S, X ₁ is S, X ₄ is N (Ar ₁ ), or X ₁ and X ₄ are both N (Ar ₁ ).

In the compounds represented by the above formulas (2a) to (2n), Ar ₁ is preferably a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, Ar ₂ to Ar ₅ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group (specifically, a methyl group) or a substituted or unsubstituted C ₆ to C ₆₀ aryl group Is preferably a phenyl group).

In particular, Ar ₁ is preferably a substituent represented by the following formula (5) or a phenyl group.

In Formula 5,

L is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms,

Z ₁ to Z ₅ are the same or different and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N,

R ₁₁ represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, hwandoen C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group of nuclear atoms of 5 to 60, a substituted or unsubstituted C ₆ ~ C _A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocyclic alkyl group having 3 to 40 nucleus atoms , A substituted or unsubstituted C ₆ to C ₆₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted arylamine group, a C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the aryl phosphine oxazol Deugi, and a substituted or unsubstituted aryl group is selected from the group consisting of silyl unsubstituted C ₆ ~ C _60, or by combining groups to which they are contiguous and may form a condensed ring,

In the above L and R ₁₁ , an aryl group, a heteroarylene group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkoxy group, an aryloxy group, an aryloxy group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₆ ~ C _{40 60} aryloxy, alkyl of C ₁ ~ C ₄₀ oxy group, C of ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ alkyl a boron group, the group consisting of C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group in the silyl May be substituted or unsubstituted with one or more substituents selected from the above-mentioned substituents, provided that when there are a plurality of substituents, they may be the same or different.

In the substituent represented by Formula 5, L is preferably a single bond, a phenylene group or a biphenylene group.

* Represents a moiety bonded to Formula 2, and when two or more of Z ₁ to Z ₅ are C (R ₁₁ ), a plurality of R _{11 s} may be the same as or different from each other.

More specifically, it is preferable that the substituent represented by the above-mentioned formula (5) is selected from the substituent group having the structure represented by the following C-1 to C-15.

In the above C-1 to C-15,

L and R < ₁₁ > are the same as defined in the above formula (5)

R ₁₂ represents hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C ₁ -C ₄₀ alkyl, substituted or unsubstituted C ₂ -C ₄₀ alkenyl, substituted or unsubstituted C _2- an aryl group of C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom to C40 heterocycloalkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ of, A substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted aryloxy group, a C ₆ ~ C ₆₀ aryl amine group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ group of an alkyl boron, substituted or unsubstituted C ₆ ~ C ₆₀ of the arylboronic group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl ring of the phosphine oxide group, and a substituted or Is selected from the group consisting of aryl silyl unsubstituted C ₆ ~ C _60, or by combining groups to which they are contiguous and may form a condensed ring,

n is an integer of 1 to 4;

In R ₁₂ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryl of C ₆₀ An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of C ₆₀ aryl silyl Alternatively, if the beach may be unsubstituted, wherein the substituent is clear up a plurality, they may be the same or different from each other.

In the compounds represented by formulas (2a) to (2n) of the present invention, Ar ₁ to Ar ₅ and R ₁ to R ₃ are each independently selected from the group of substituents (S1-S206) consisting of hydrogen or the following substituents (functional groups) , And is not particularly limited thereto.

In the present invention, alkyl is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like.

The alkenyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, allyl, Isopropenyl, 2-butenyl, and the like.

Alkynyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2- 2-propynyl, and the like.

The aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl and the like.

The heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, the ring may be pendant or condensed with each other, or may be condensed with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2- isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

In the present invention, aryloxy is a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

The alkyloxy in the present invention is a monovalent substituent group represented by R'O-, wherein R 'is an alkyl having 1 to 40 carbon atoms and includes a linear, branched or cyclic structure . Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

The arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

The cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon of the ring, preferably 1 to 3 carbons, is N, O, S or Se. ≪ / RTI > Examples of such heterocycloalkyl include morpholine, piperazine and the like.

The alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms.

The condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the organic electroluminescent device of the present invention configured as described above, at least one of the plurality of organic layers includes the first host and the second host to balance the holes and electrons injected into the device, have. Here, the mixing ratio of the first host and the second host is not particularly limited in the production of the organic material layer. For example, the first host and the second host may be mixed at a weight ratio of 1:99 to 99: 1. At this time, it is preferable that the usage rate of the first host is higher.

In the organic electroluminescent device of the present invention, the light emitting layer may be a single light emitting layer or may have a plurality of light emitting layers to realize a mixed color thereof. More specifically, in the present invention, a plurality of light emitting layers may be sequentially stacked between a hole transporting layer and an electron transporting layer to realize a mixed color thereof when voltage and current are applied.

As described above, the stacked organic electroluminescent device of the present invention including a plurality of light emitting layers or a plurality of light emitting layers including a plurality of different materials between the hole transporting layer and the electron transporting layer can be realized by implementing a mixed color upon application of voltage and current, The light emitting efficiency can be increased by the number of the light emitting layers.

Meanwhile, the organic compound layer of the present invention including the first host and the second host is preferably a light emitting layer, and the light emitting layer of the present invention may include a dopant together with the first host and the second host.

Here, the dopant included in the light emitting layer may be a dopant that is known in the art without limitation. For example, it is preferable to use a metal complex compound containing iridium (Ir).

The method for producing the light emitting layer including the first host, the second host and the dopant described above can be manufactured without specific limitation according to a method known in the art. Hereinafter, two preferred embodiments for manufacturing the light emitting layer will be described below, but the present invention is not limited thereto.

The first method among the above two embodiments is a co-deposition method in which a first host and a second host are placed in a first heat source and a second heat source, respectively, and a dopant is placed in a third heat source and heat is applied to form a light emitting layer .

More specifically, a second host having a high hole mobility and a high hole injection efficiency is placed in a first heat source at a vacuum degree of 1 x 10 ^-06 torr or less, and electron mobility ) Is high and a second host having a good electron injection efficiency is positioned and the dopant and the evaporation rate per second of the third heat source are adjusted to co-deposit at a proper ratio. At this time, the number of co-deposited hosts may be two or more depending on the characteristics of the light emitting layer.

The amount of the first host, the second host and the dopant is not particularly limited. For example, the first host and the second host may be used in an amount of 70 to 99% by weight and the dopant may be used in an amount of 1 to 30% by weight. Specifically, it is preferable to use 80 to 95% by weight of the first host and the second host and 5 to 20% by weight of the dopant.

In the second method of the above two embodiments, in order to reduce the number of heat sources used and simplify the formation process, the first host and the second host used for forming the light emitting layer are mixed at a proper ratio, Emitting layer is formed.

More specifically, the host (first host + second host) mixed in the first heat source is placed at a degree of vacuum of 1 x 10 ^-06 or less, the dopant is placed in the second heat source, . This second method has the advantage of reducing the error in the mixing ratio that occurs when one or more hosts are used and forming a light emitting layer with a small number of heat sources.

The amount of the first host, the second host and the dopant is not particularly limited. For example, the first host and the second host may be used in an amount of 70 to 99% by weight and the dopant may be used in an amount of 1 to 30% by weight. Specifically, it is preferable to use 80 to 95% by weight of the first host and the second host and 5 to 20% by weight of the dopant.

The material usable as the anode included in the organic electroluminescent device of the present invention is not particularly limited, but examples thereof include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al, SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; And carbon black.

Examples of materials usable as an anode included in the organic electroluminescent device of the present invention include, but are not limited to, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, , Alloys thereof, and multi-layered materials such as LiF / Al and LiO ₂ / Al.

The structure of the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include, but are not limited to, a structure in which a substrate, a cathode, an organic material layer (a hole injecting layer -> hole transporting layer -> light emitting layer -> electron transporting layer) . At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1 as a first host.

On the other hand, an electron injection layer may be further stacked on the electron transport layer. In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the anode and the cathode and the organic layer.

The organic electroluminescent device of the present invention can be formed using conventional materials and methods known in the art, except that at least one layer (for example, a light emitting layer) of the organic material layer includes the first host and the second host Another organic material layer can be formed.

Meanwhile, the substrate used in the production of the organic electroluminescent device of the present invention is not particularly limited, but examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

Hereinafter, the present invention will be described in detail with reference to Examples. However, the present invention is not limited by the following Examples.

[Preparation Example 1] Synthesis of IC-1

<Step 1> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

(25 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3 , 2-dioxaborolane) (48.58 g , 0.191 mol), mixed with _{Pd (dppf) Cl 2 (5.2} g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) and 130 ℃ Lt; / RTI &gt; for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 5- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-indole (22.32 g, yield 72%).

¹ H-NMR:? 1.24 (s, 12H), 6.45 (d, IH), 7.27 (d, IH), 7.42 s, 1 H)

<Step 2> Synthesis of 5- (2-nitrophenyl) -1H-indole

1-bromo-2-nitrobenzene (15.23 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22 g, 90.49 mmol), NaOH (9.05 g, 226.24 mmol) and THF / H ₂ O, and then, Pd (PPh ₃₎ in 40 ℃ ₄ (4.36 g mixture of (400 ml / 200 ml) , 5 mol%) were added, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1H-indole (11.32 g, yield 63%).

^{1 H-NMR: δ 6.47 (} d, 1H), 7.25 (d, 1H), 7.44 (d, 1H), 7.53 (d, 1H), 7.65 (t, 1H), 7.86 (t, 1H), 7.95 ( (s, 1 H), 8.00 (d, 1 H), 8.09 (t,

<Step 3> Synthesis of 5- (2-nitrophenyl) -1-phenyl-1H-indole

Indole (11 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol), K ₂ mixing the _{CO 3 (6.38 g, 46.17 mmol} ), Na 2 SO 4 (6.56 g, 46.17 mmol), nitrobenzene (200 ml) and stirred at 190 ℃ for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1- 71%).

^{1 H-NMR: δ 6.48 (} d, 1H), 7.26 (d, 1H), 7.45 (m, 3H), 7.55 (m, 4H), 7.63 (t, 1H), 7.84 (t, 1H), 7.93 ( s, 1 H), 8.01 (d, 1 H), 8.11 (t, 1 H)

<Step 4> Synthesis of IC-1

Phenyl-1H-indole (5 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) and 1,2-dichlorobenzene (50 ml ) Were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-1 (2.38 g, yield 53%).

^{1 H-NMR: δ 6.99 (} d, 1H), 7.12 (t, 1H), 7.27 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.50 (d, 1H), 7.60 ( (d, IH), 8.05 (d, IH)

[Preparation Example 2] Synthesis of IC-2

<Step 1> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole

Was synthesized in the same manner as in the step 1 of Preparation Example 1 except that 5-bromo-1H-indazole (25.22 g, 0.128 mol) was used instead of 5-bromo-1H- 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.49 g, yield 72%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.60 (d, 1H), 8.15 (m, 2H), 8.34 (d, 1H), 12.34 (s, 1H)

<Step 2> Synthesis of 5- (2-nitrophenyl) -1H-indazole

Instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole, 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl) -1H-indazole (22.09 g, 90.49 mmol) was used in place of 5- (2-nitrophenyl) -1H- g, yield: 63%).

¹ H-NMR: 8 7.64 (m, 2H), 7.90 (m, IH), 8.05 (m, 3H), 8.21

<Step 3> Synthesis of 5- (2-nitrophenyl) -1-phenyl-1H-indazole

Was synthesized in the same manner as in the step 3 of Preparation Example 1 except that 5- (2-nitrophenyl) -1H-indazole (11.04 g, 46.17 mmol) was used instead of 5- (2-nitrophenyl) , 5- (2-nitrophenyl) -1-phenyl-1H-indazole (10.34 g, yield 71%).

^{1 H-NMR: δ 7.48 (} t, 1H), 7.62 (m, 6H), 7.90 (m, 1H), 8.05 (m, 3H), 8.37 (m, 2H)

<Step 4> Synthesis of IC-2

Except that 5- (2-nitrophenyl) -1-phenyl-1H-indazole (5.01 g, 15.91 mmol) was used in place of 5- (2-nitrophenyl) -1- Was synthesized in the same manner as in Step 4 to obtain IC-2 (2.39 g, yield 53%).

¹ H-NMR:? 7.29 (t, 1 H), 7.45 (m, 3H), 7.60 (m, 5H), 8.12

[Preparation Example 3] Synthesis of IC-3

<Step 1> N - (2,4-Dibromophenyl) benzamide

2,4-dibromoaniline (25.09 g, 0.1 mol) was added to the reactor, and methylene chloride (100 ml) was added thereto, followed by stirring. Benzoyl chloride (11.6 mL, 0.1 mol) and pyridine (1.62 mL, 0.02 mol) were added dropwise to the reactor, followed by stirring at room temperature for 2 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, then the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain N- (2,4- dibromophenyl) 25.1 g, yield: 71%).

^{1 H-NMR: δ 7.52 (} d, 1H), 7.59 (d, 1H), 7.63 (dd, 2H), 7.70 (t, 1H), 7.98 (s, 1H), 8.03 (d, 2H), 9.15 ( b, 1H)

&Lt; Step 2 > 6-Bromo-2-phenylbenzo [ d ] oxazole

N- (2,4-dibromophenyl) benzamide (25.1 g, 71.0 mmol), K ₂ CO ₃ (19.6 g, 142 mmol) and DMSO (710 ml) were mixed under a nitrogen stream and stirred at 140 ° C for 1.5 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 9: 1 (v / v)) to obtain 6-bromo-2-phenylbenzo [ 14.8 g, yield 76%).

^{1 H-NMR: δ 7.41 (} t, 1H) 7.43 (s, 1H), 7.51 (m, 3H), 7.60 (d, 1H), 8.05 (d, 2H)

<Step 3> Synthesis of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole

(14.8 g, 54.0 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi Dioxane (15.1 g, 59.4 mmol), Pd (dppf) Cl ₂ (6.24 g, 5.40 mmol), KOAc (15.25 g, 0.162 mol) and 1,4- And the mixture was stirred at 130 DEG C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to obtain 2-phenyl- , 5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (13.35 g, yield 77%).

^{1 H-NMR: δ 1.24 (} s, 12H) 7.41 (d, 1H), 7.44 (s, 1H), 7.51 (dd, 2H), 7.62 (d, 1H), 7.75 (s, 1H), 8.05 (d , 2H)

<Step 4> Synthesis of 6- (2-nitrophenyl) -2-phenylbenzo [d] oxazole

2-yl) benzo [d] oxazole (13.35 g, 41.58 mmol), 1-bromo-2 (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -nitrobenzene (9.24 g, 45.74 mmol) , Pd (PPh 3) 4 (2.4 g, 2.08 mmol), K 2 CO 3 (14.37 g, 0.104 mol), 1,4-dioxane / H 2 O (40 ml / 10 ml) were mixed and stirred at 120 ° C for 4 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to obtain 6- (2-nitrophenyl) -2- phenylbenzo [d] oxazole (11.05 g, &Lt; / RTI &gt;

¹ H-NMR:? 7.41-7.51 (m, 4H), 7.67-7.68 (m, 2H), 7.79 (d,

<Step 5> Synthesis of IC-3

(11.05 g, 34.9 mmol), triphenylphosphine (27.46 g, 104.7 mmol) and 1,2-dichlorobenzene (150 ml) were added thereto under nitrogen atmosphere and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain IC-3 (5.56 g, yield 56%) as a target compound.

^{1 H-NMR: δ 7.23-7.29 (} m, 2H), 7.41-7.51 (m, 4H), 7.63 (d, 1H), 8.05-8.12 (m, 4H), 10.1 (b, 1H)

 [Preparation Example 4] Synthesis of IC-4

<Step 1> N- (2,4-dibromophenyl) benzothioamide Synthesis of

N - (2,4-dibromophenyl) benzamide (26.62 g, 0.075 mol) obtained in Step 1 of Preparation Example 3 was added to the reactor, and toluene (300 ml) was added thereto and stirred. Lawesson's reagent (22.92 g, 0.053 mol) was added dropwise to the reactor, followed by mixing and stirring at 110 ° C for 4 hours.

Extracted with methylene chloride and then the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to give the N - (2,4-dibromophenyl) benzothioamide ( 26.35 g, yield 95%).

^{1 H-NMR: δ 6.41 (} d, 1H), 7.29 (d, 1H), 7.44-7.45 (m, 3H), 7.75 (s, 1H), 7.98 (d, 2H), 8.59 (b, 1H)

<Step 2> Synthesis of 6-bromo-2-phenylbenzo [d] thiazole

A (2,4-dibromophenyl) benzothioamide (26.35 g, 71.0 mmol), K 2 CO 3 (19.63 g, 142 mmol) and DMSO (710 ml) - <Step 1> of the preparation obtained in Example 8 N in a nitrogen atmosphere And the mixture was stirred at 140 DEG C for 1.5 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 6-bromo-2-phenylbenzo [d] thiazole 15.66 g, yield 76%).

^{1 H-NMR: δ 7.41 (} t, 1H) 7.51 (dd, 2H), 7.64 (d, 1H), 7.72 (d, 1H), 8.03 (d, 2H), 8.83 (s, 1H)

Synthesis of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole

Was synthesized in the same manner as in Step 3 of Preparation Example 3 except that 6-bromo-2-phenylbenzo [d] thiazole (15.66 g, 54.0 mmol) was used instead of 6-bromo-2- , 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole (14.02 g, yield 77%).

^{1 H-NMR: δ 1.24 (} s, 12H) 7.38 (d, 1H), 7.41 (t, 1H), 7.51 (dd, 2H), 7.75 (d, 1H), 7.95 (s, 1H), 8.03 (d , 2H)

<Step 4> Synthesis of 6- (2-nitrophenyl) -2-phenylbenzo [d] thiazole

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [ 2-yl) benzo [d] thiazole (14.02 g, 41.57 mmol) was used in place of 4- (tert-butyldimethylsilyloxy) 2-nitrophenyl) -2-phenylbenzo [d] thiazole (11.61 g, yield 84%).

^{1 H-NMR: δ 7.41-7.51 (} m, 3H), 7.67 (dd, 1H), 7.77-7.90 (m, 3H), 8.00-8.05 (m, 4H), 8.34 (s, 1H)

<Step 5> Synthesis of Compound IC-4

Except that 6- (2-nitrophenyl) -2-phenylbenzo [d] thiazole (11.61 g, 34.9 mmol) was used in place of 6- (2-nitrophenyl) -2-phenylbenzo [ The compound IC-4 (5.56 g, yield 53%) was obtained by the same method as in the step 5.

^{1 H-NMR: δ 7.29 (} dd, 1H), 7.41-7.63 (m, 6H), 7.75 (d, 1H), 8.03-8.12 (m, 3H), 10.1 (b, 1H)

[Preparation Example 5] Synthesis of IC-5.

<Step 1> Synthesis of 5- (2-nitrophenyl) -1H-benzo [d] imidazole.

A solution of 6.5 g (32.98 mmol) of 5-bromo-1H-benzo [d] imidazole, 6.6 g (39.58 mmol) of 2-nitrophenylboronic acid and 3.9 g (98.96 mmol) of NaOH in 150 ml / / H ₂ O were added and stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 1.14 g (0.98mmol) was stirred under reflux at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 5.2 g (yield: 66%) of 5- (2-nitrophenyl) -1H-benzo [d] imidazole was obtained by column chromatography.

¹ H-NMR: 8 7.68 (m, 2H), 8.02 (m, 5H)

<Step 2> Synthesis of 5- (2-nitrophenyl) -1-phenyl-1H-indole

Except that 5- (2-nitrophenyl) -1H-benzo [d] imidazole (5.2 g, 21.75 mmol) was used in place of 5- (2-nitrophenyl) To obtain 5- (2-nitrophenyl) -1-phenyl-1H-benzo [d] imidazole (6.84 g, yield 71%).

¹ H-NMR:? 7.55 (m, 6H), 7.98 (m, 2H), 8.05 (m, 4H), 8.32

<Step 3> Synthesis of IC-5

Except that 5- (2-nitrophenyl) -1-phenyl-1H-benzo [d] imidazole (6.84 g, 21.73 mmol) was used instead of 5- (2-nitrophenyl) Was synthesized in the same manner as in the step 4 of Preparation Example 1 to obtain IC-5 (1.8 g, yield 40%).

¹ H-NMR:? 7.31 (t, IH), 7.55 (m, 3H), 7.87 (d, IH), 8.15 (m, 2H), 8.43

[Preparation Example 6] Synthesis of IC-6

<Step 1> Synthesis of 5- (5-bromo-2-nitrophenyl) -1H-indole

The procedure of Step 2 of Preparation Example 1 was repeated except that 2,4-dibromo-1-nitrobenzene was used instead of 1-bromo-2-nitrobenzene to obtain 5- (5-bromo- ) -1H-indole.

^{1 H NMR: δ 6.45 (d} , 1H), 7.26 (d, 1H), 7.45 (d, 1H), 7.55 (d, 1H), 7.64 (d, 1H), 7.85 (d, 1H), 7.96 (s , &Lt; / RTI &gt; 1H), 8.13 (s, 1H), 8.21

<Step 2> Synthesis of 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole

Step 3 of Preparation Example 1 was repeated except that 5- (5-bromo-2-nitrophenyl) -1H-indole obtained in the above Step 1 was used instead of 5- (2-nitrophenyl) To obtain 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole.

^{1 H NMR: δ 6.44 (d} , 1H), 7.25 (d, 1H), 7.46 (m, 3H), 7.56 (m, 4H), 7.65 (d, 1H), 7.86 (d, 1H), 7.95 (s , &Lt; / RTI &gt; 1H), 8.11 (s, 1H)

<Step 3> Synthesis of 7-bromo-3-phenyl-3,10-dihydropyrrolo [3,2-a]

Except that 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole obtained in the above Step 2 was used instead of 5- (2-nitrophenyl) Bromo-3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole was obtained in the same manner as in <Step 4> of Preparation Example 1 above.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.26 (d, 1H), 7.38 (m, 2H), 7.45 (d, 1H), 7.51 (d, 1H), 7.57 (m, 3H), 7.64 ( (d, IH), 7.85 (d, IH), 8.10 (s, IH), 8.23

<Step 4> Synthesis of IC-6

Except that the 7-bromo-3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole obtained in the above Step 3 was used instead of 5- (2-nitrophenyl) IC-6 was obtained in the same manner as in Step 3 of Preparation 1.

^{1 H NMR: δ 6.52 (d} , 1H), 7.25 (d, 1H), 7.54 (m, 11H), 7.72 (s, 1H), 7.88 (d, 1H), 7.95 (m, 2H)

[Preparation Example 7] Synthesis of IC-7

<Step 1> Synthesis of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

The procedure of Step 1 of Preparation Example 1 was repeated except that 6-bromo-1H-indole was used instead of 5-bromo-1H-indole to obtain 6- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-indole.

¹ H-NMR:? 1.25 (s, 12H), 6.52 (d, IH), 7.16 (d, IH), 7.21 s, 1 H)

<Step 2> Synthesis of 6- (2-nitrophenyl) -1H-indole

Instead of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole, -2-yl) -1H-indole, the procedure of Step 2 of Preparation Example 1 was repeated to obtain 6- (2-nitrophenyl) -1H-indole.

^{1 H-NMR: δ 6.57 (} d, 1H), 7.07 (d, 1H), 7.24 (d, 1H), 7.35 (s, 1H), 7.43 (t, 1H), 7.50 (d, 1H), 7.58 ( t, 1 H), 7.66 (d, 1 H), 7.78 (d,

<Step 3> Synthesis of 6- (2-nitrophenyl) -1-phenyl-1H-indole

The procedure of Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1H-indole was used instead of 5- (2-nitrophenyl) -1H- -nitrophenyl) -1-phenyl-1H-indole.

^{1 H-NMR: δ 6.81 (} d, 1H), 7.12 (t, 1H), 7.22 (t, 1H), 7.35 (s, 1H), 7.43 (d, 1H), 7.51 (m, 3H), 7.56 ( (m, 2H), 7.62 (m, 2H), 7.85 (d,

<Step 4> Synthesis of IC-7

Step 4 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1-phenyl-1H-indole was used in place of 5- (2-nitrophenyl) And PC-2 was obtained.

^{1 H-NMR: δ 6.80 (} d, 1H), 7.11 (t, 1H), 7.23 (t, 1H), 7.42 (d, 1H), 7.50 (m, 3H), 7.57 (m, 2H), 7.63 ( (m, 2H), 7.86 (d, 1H), 8.03 (d,

[Preparation Example 8] Synthesis of compound IC-8

<Step 1> Synthesis of 5-phenyl-5H-dibenzo [b, f] azepine

Iodobenzene (12.67 g, 62.10 mmol), Cu (1.64 g, 25.87 mmol), K ₂ CO ₃ (14.30 g, 103.5 mmol) and 5-dibenzo [b, f] azepine (10 g, 51.75 mmol) nitrobenzene (100 ml) were mixed and stirred at 210 캜 for 12 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate, and then concentrated and recrystallized from ethanol to obtain 5-phenyl-5H-dibenzo [b, f] azepine (10.04 g, yield 72%).

^{1 H-NMR: δ 6.63-6.81 (} m, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.20 (d, 2H), 7.26-7.45 (m, 8H)

Step 2 Synthesis of 6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine

5-phenyl-5H-dibenzo [b, f] azepine (10.04 g, 37.26 mmol), meta- chloroperoxybenzoic acid (7.72 g, 44.71 mmol) obtained in Step 1 of Preparation Example 2, silica ), NaOCl (20.07 g) and acetonitrile (100 ml) were mixed and stirred at 80 ° C for 2 hours.

After the reaction was completed, the organic layer was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and recrystallized from ethanol to obtain 6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxireno [2,3- d] azepine (8.40 g, yield 79%).

¹ H-NMR:? 4.31 (s, 2H), 6.63-6.81 (m, 3H), 7.24-7.53 (m,

<Step 3> Synthesis of 5-phenyl-5H-dibenzo [b, f] azepin-10 (11H)

Dihydro-1aH-dibenzo [b, f] oxireno [2,3-d] azepine (8.40 g, 29.43 mmol) obtained in Step 2 of Preparation Example 2, lithium iodide (4.73 g, 35.32 mmol) and chloroform (84 ml) were mixed and stirred at 60 ° C for 1 hour.

After the reaction was completed, the organic layer was extracted with ethyl acetate, the water was removed with MgSO ₄ and recrystallized in ethanol to obtain 5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) 81%).

^{1 H-NMR: δ 3.42 (} d, 1H), 4.21 (d, 1H), 6.62-6.74 (m, 3H), 7.25-7.40 (m, 7H), 7.51-7.59 (m, 2H), 8.10 (d , 1H)

<Step 4> Synthesis of Compound IC-8

5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) -one (6.80 g, 23.84 mmol) obtained in Step 3 of Preparation Example 2 and phenylhydrazine (2.84 g, 26.23 mmol) and acetic acid (70 ml) were mixed, followed by stirring at 120 ° C for 12 hours.

After completion of the reaction, the organic layer was extracted with dichloromethane, and then MgSO ₄ was added thereto. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain compound IC-8 (6.07 g, yield 71%).

IC-9 ¹ H-NMR of: δ 6.63-6.69 (m, 4H) , 6.81-6.87 (m, 3H), 7.08-7.20 (m, 6H), 7.44-7.56 (m, 3H), 8.83 (d, 1H), 11.36 (b, 1 H)

[Preparation Example 9] Synthesis of IIC-1

<Step 1> Synthesis of IIC-1

(27.8 g, 113 mmol), (9H-carbazol-3-yl) boronic acid (23.8 g, 113 mmol), K ₂ CO ₃ (46.8 g, 339 mmol) and THF / H ₂ O were mixed (400 ml / 100 ml) into the _{following, Pd (PPh 3) 4 (} 6.53 g, 5.65 mmol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-1 (30 g, yield 80%).

¹ H-NMR of IIC-1:? 7.29-7.50 (m, 5H), 7.94 (d,

[Preparation Example 10] Synthesis of IIC-2

<Step 1> Synthesis of IIC-2

(24.9 g, 77.4 mmol), (6-phenyl-9H-carbazol-3-yl) boronic acid (22.2 g, 77.4 mmol), K ₂ CO ₃ 32.0 g, 232 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.47 g, 3.86 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-2 (30 g, yield 80%).

¹ H-NMR of IIC-2:? 7.29-7.50 (m, 10H), 7.92 (s,

[Preparation Example 11] Synthesis of IIC-3

<Step 1> Synthesis of 3-bromo-6,9-diphenyl-9H-carbazole

(35.9 g, 111 mmol), iodobenzene (22.7 g, 111 mmol), Pd (OAc) ₂ (1.25 g, 5.57 mmol), NaO (t-Bu) (21.4 g, 223 mmol), P (t-Bu) ₃ (50 wt%) (4.51 g, 11.1 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO _{4. The} objective compound 3-bromo-6,9-diphenyl-9H-carbazole (31.7 g, 60%) was obtained.

^{1 H-NMR: δ 7.07-7.35 (} m, 14H), 7.92 (s, 1H), 7.98 (s, 1H)

<Step 2> Synthesis of IIC-3

(26.2 g, 66.9 mmol), 6-phenyl-9H-carbazol-3-yl) boronic acid (19.2 g, 66.9 mmol), K ₂ CO ₃ (27.7 g, 200 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed and Pd (PPh ₃ ) ₄ (3.86 g, 3.34 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-3 (30 g, yield 80%).

¹ H-NMR:? 7.05-7.33 (m, 15H), 7.38-7.42 (m, 8H), 7.92 (s, ), 10.3 (s, 1 H)

[Preparation Example 12] Synthesis of IIC-4

<Step 1> Synthesis of IIC-4

(24.9 g, 77.4 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid (22.2 g, 77.4 mmol), K ₂ CO ₃ 32.1 g, 232 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.47 g, 3.87 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-4 (30 g, yield 80%).

^{1 H-NMR: δ 7.03-7.29 (} m, 10H), 7.38-7.42 (m, 9H), 7.94 (s, 1H), 7.96 (s, 1H), 7.98 (s, 1H), 8.01 (s, 1H ), 10.2 (s, 1 H)

[Preparation Example 13] Synthesis of IIC-5

<Step 1> Synthesis of 9- (biphenyl-3-yl) -3-bromo-9H-carbazole

3-iodobiphenyl (39.7 g, 111 mmol), 3-bromo-9H-carbazole (27.4 g, 111 mmol), Pd (OAc) ₂ (1.25 g, 5.57 mmol), NaO g, 223 mmol), P (t-Bu) ₃ (50 wt%) (4.51 g, 11.1 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO _{4. The} desired compound 9- (biphenyl-3-yl) -3-bromo-9H- ).

^{1 H-NMR: δ 7.25-7.52 (} m, 12H), 7.94 (d, 1H), 8.07 (m, 2H), 8.55 (d, 1H)

<Step 2> Synthesis of IIC-5

(26.9 g, 67.7 mmol), (9H-carbazol-3-yl) boronic acid (14.1 g, 66.9 mmol), K ₂ CO ₃ (27.7 g, 200 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed and Pd (PPh ₃ ) ₄ (3.86 g, 3.34 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-5 (24.6 g, yield 75%).

^{1 H-NMR: δ 7.29 (} t, 2H), 7.46-7.69 (m, 13H), 7.77 (s, 2H), 7.87-8.18 (m, 6H), 10.1 (s, 1H)

[Synthesis Example 1] Synthesis of C-1

(5 g, 15.0 mmol), 4-bromo-1,1'-biphenyl (7.01 g, 30.1 mmol), Pd (OAc) ₂ (338 mg, 1.50 mmol), NaO ) (5.78 g, 60.2 mmol), P (t-Bu) ₃ (50 wt%) (1.22 g, 3.01 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove water with MgSO ₄ to obtain the desired compound C-1 (6.70 g, 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 2] Synthesis of C-2

The procedure of Synthetic Example 1 was repeated except that 3-bromo-1,1'-biphenyl (7.02 g, 30.1 mmol) was used instead of 4-bromo-1,1'- -2 (6.70 g, yield 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 3] Synthesis of C-3

Iodobenzene (4.21 g, 20.6 mmol), Pd (OAc) ₂ (232 mg, 1.03 mmol), NaO (t-Bu) (3.96 g, 41.2 mmol), IIC- P (t-Bu) ₃ (50 wt%) (836 mg, 2.06 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove the water with MgSO ₄ to obtain the desired compound C-3 (4.60 g, 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 4] Synthesis of C-4

Was obtained in the same manner as in Synthesis Example 1, except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (9.30 g, 30.1 mmol) was used in place of 4-bromo-1,1'- To obtain the target compound C-4 (8.31 g, yield 70%).

Mass (theory: 788.97 g / mol, measurement: 788 g / mol)

[Synthesis Example 5] Synthesis of C-5

(2.0 g, 8.92 mmol), Pd (OAc) ₂ (100 mg, 0.446 mmol), NaO (t-Bu ) (1.71 g, 17.8 mmol), P (t-Bu) ₃ (50 wt%) (361 mg, 0.892 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography using MgSO ₄ to remove the desired compound C-5 (4.45 g, 70%).

Mass (theory: 712.88 g / mol, measurement: 712 g / mol)

[Synthesis Example 6] Synthesis of C-6

4-bromo-1,1'-biphenyl (2.08 g, 8.92 mmol), Pd (OAc) ₂ (100 mg, 0.446 mmol), NaO (t-Bu ) (1.71 g, 17.8 mmol), P (t-Bu) ₃ (50 wt%) (361 mg, 0.892 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO ₄ to obtain the desired compound C-6 (4.60 g, yield 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 7] Synthesis of C-7

(2.0 g, 8.92 mmol), Pd (OAc) ₂ (100 mg, 0.446 mmol), NaO (t-Bu ) (1.71 g, 17.8 mmol), P (t-Bu) ₃ (50 wt%) (361 mg, 0.892 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove water with MgSO ₄ to obtain the desired compound C-7 (3.68 g, yield 65%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 8] Synthesis of Com-1

(3 g, 10.63 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.38 g, 12.75 mmol), Pd (OAc) ₂ (2.01 g, 21.25 mmol), P (t-bu) ₃ (0.21 g, 1.06 mmol) and Toluene (100 ml) were mixed and heated at 110 ° C for 12 hours Lt; / RTI &gt;

Extracted with ethyl acetate. After the reaction was terminated, and then remove the water with MgSO ₄ and purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to give the desired compound of Com-1 (4.89 g, yield: 78 to %).

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[Synthesis Example 9] Synthesis of Com-2

Except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (4.36 g, 12.75 mmol) was used instead of 2- (3-chlorophenyl) -4,6-diphenyl- The procedure of Synthetic Example 8 was repeated to obtain the desired compound Com-2 (4.68 g, yield 75%).

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[Synthesis Example 10] Synthesis of Com-3

Except that 2- (3-chlorophenyl) -4,6-diphenylpyridine (4.34 g, 12.75 mmol) was used instead of 2- (3-chlorophenyl) -4,6-diphenyl- The procedure of Synthesis Example 8 was repeated to yield the desired compound Com-3 (4.36 g, yield 70%).

GC-Mass (calculated: 587.23 g / mol, measured: 587 g / mol)

[Synthesis Example 11] Synthesis of Com-4

2- (3-chloro-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3-chlorophenyl) -4,6-diphenyl- , 12.75 mmol) was used in place of the compound obtained in Preparation Example 1 to obtain the desired compound Com-4 (4.81 g, yield 75%).

GC-Mass (theory: 603.24 g / mol, measured: 603 g / mol)

[Synthesis Example 12] Synthesis of Com-5

(4.81 g, yield 75%) was obtained in the same manner as in Synthesis Example 8, except that IC-7 (3 g, 10.63 mmol) was used instead of IC-1.

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[Synthesis Example 13] Synthesis of Com-6

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.40 g, 12.75 mmol) was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- , The target compound, Com-6 (3.98 g, yield 73%) was obtained in the same manner as in Synthesis Example 8.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

[Synthesis Example 14] Synthesis of Com-7

Except that 2-chloro-4,6-diphenylpyrimidine (3.40 g, 12.75 mmol) was used in place of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- The same procedure was followed to obtain the target compound Com-7 (3.81 g, yield 70%).

GC-Mass (calculated: 512.20 g / mol, measured: 512 g / mol)

[Synthesis Example 15] Synthesis of Com-8

Except that 2-chloro-4,6-diphenylpyridine (3.38 g, 12.75 mmol) was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- The same procedure was followed to obtain the target compound Com-8 (4.07 g, yield 75%).

GC-Mass (calculated: 511.20 g / mol, measured: 511 g / mol)

[Synthesis Example 16] Synthesis of Com-9

Except that IC-7 (3 g, 10.63 mmol) was used in place of IC-1 and 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2- (3-chlorophenyl) (3.92 g, yield 72%) was obtained in the same manner as in Synthesis Example 8, except that 1,3,5-triazine (3.38 g, 12.75 mmol) was used.

GC-Mass (theory: 513.20 g / mol, measured: 513 g / mol)

[Synthesis Example 17] Synthesis of Com-10

The procedure of Synthetic Example 8 was repeated except that IC-2 (3 g, 10.63 mmol) was used instead of IC-1 to obtain the desired compound Com-10 (4.39 g, yield 70%).

GC-Mass (calculated: 590.22 g / mol, measured: 590 g / mol)

[Synthesis Example 18] Synthesis of Com-11

(4.39 g, yield 70%) was obtained in the same manner as in Synthesis Example 8, except that IC-3 (3.02 g, 10.63 mmol) was used instead of IC-1.

GC-Mass (calculated: 591.21 g / mol, measured: 591 g / mol)

[Synthesis Example 19] Synthesis of Com-12

(4.39 g, yield 68%) was obtained in the same manner as in Synthesis Example 8, except that IC-4 (3.18 g, 10.63 mmol) was used instead of IC-1.

GC-Mass (theory: 607.18 g / mol, measurement: 607 g / mol)

[Synthesis Example 20] Synthesis of Com-13

Instead of IC-5 (3 g, 10.63 mmol) and 2-chloro-4,6-diphenyltriazine (3.40 g, 12.75 mmol) was used in place of the compound obtained in Synthesis Example 8 to obtain the desired compound Com-13 (3.87 g, yield 71%).

GC-Mass (calculated: 514.19 g / mol, measured: 514 g / mol)

[Synthesis Example 21] Synthesis of Com-14

IC-6 (3.20 g, 7.31 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl) phenyl) -1,3,5-triazine (3.81 g, 8.77 mmol), NaOH (0.87 g, 21.93 mmol), Pd (PPh 3) 4 (0.25 g, 0.21 mmol) and 1,4 -dioxane, H 2 O (30 ml, 8 ml) were mixed and stirred at 100 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, Com-14 (2.67 g, yield 55%) was obtained by column chromatography.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[Synthesis Example 22] Synthesis of Com-15

(2.4 g, 6.7 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) synthesized in Preparation Example 8, Pd (OAc) ₂ (0.08 g, 0.34 mmol), P ( t- Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t- Bu) (1.29 g, 13.4 mmol) and toluene , And the mixture was stirred at 110 DEG C for 5 hours. After completion of the reaction, toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain Compound Com-15 (3.3 g, yield 73%).

Mass (theory: 665.26, found: 665 g / mol)

[Synthesis Example 23] Synthesis of Com-16

Instead of 2- (3'-chlorobiphenyl-3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, IC- 16 (4.89 g, 12.75 mmol) was obtained by following the same procedure as in Synthesis Example 8, except that 4-methyl-4,6-diphenyl-1,3,5- Yield: 69%).

GC-Mass (theory: 667.24 g / mol, measured: 667 g / mol)

[Examples 1 to 78] Preparation of Organic Electroluminescent Device

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was ultrasonically cleaned with distilled water. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and then the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) was formed on the ITO transparent substrate prepared above using C-1 to C-7 as the first host and the compounds represented by Com-1 to Com-16 as the second host, / TCTA (80 nm) / 90% first host and second host + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF 200 nm) were stacked in this order to fabricate an organic electroluminescent device.

At this time, the structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP used were as follows, and the mixing ratio of the first host and the second host was 7: 3.

[Examples 79 to 81] Preparation of organic electroluminescent device

Example 1 MTDATA (60 nm) / TCTA (80 nm) / 90% of the ITO transparent substrate prepared above, using the above C-3 as the first host and the compound represented by Com-1 as the second host The first host and the second host were laminated in the order of 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al The device was fabricated.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP used were the same as those of Example 1, and the mixing ratios of the first host and the second host were adjusted as shown in Table 1 below.

[Comparative Example 1] Production of organic electroluminescent device

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that 90% of CBP + 10% Ir (ppy) ₃ was used in forming the light emitting layer. At this time, the structure of CBP used is as follows.

[Comparative Example 2] Production of organic electroluminescent device

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that 90% of the second host (Com-1) + 10% Ir (ppy) ₃ was used for forming the light emitting layer.

[Comparative Example 3] Production of organic electroluminescent device

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that 90% of the first host (C-3) + 10% Ir (ppy) ₃ was used for forming the light emitting layer.

[Experimental Example]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 81 and Comparative Examples 1 to 3, and the results are shown in Table 1 below.

Sample Host usage rate The driving voltage (V) Current efficiency (cd / A) Example 1 70% C-1 + 30% Com-1 6.10 42.9 Example 2 70% C-1 + 30% Com-2 6.15 42.8 Example 3 70% C-1 + 30% Com-3 6.15 42.8 Example 4 70% C-1 + 30% Com-4 6.10 42.9 Example 5 70% C-1 + 30% Com-5 6.10 42.5 Example 6 70% C-1 + 30% Com-6 6.25 42.6 Example 7 70% C-1 + 30% Com-7 6.15 42.5 Example 8 70% C-1 + 30% Com-8 6.20 42.9 Example 9 70% C-1 + 30% Com-9 6.25 43.0 Example 10 70% C-1 + 30% Com-10 6.20 42.7 Example 11 70% C-1 + 30% Com-11 6.25 42.9 Example 12 70% C-1 + 30% Com-12 6.35 42.5 Example 13 70% C-1 + 30% Com-13 6.30 43.2 Example 14 70% C-1 + 30% Com-14 6.10 43.0 Example 15 70% C-1 + 30% Com-15 6.25 42.9 Example 16 70% C-2 + 30% Com-1 6.25 43.1 Example 17 70% C-2 + 30% Com-2 6.20 42.9 Example 18 70% C-2 + 30% Com-3 6.25 42.8 Example 19 70% C-2 + 30% Com-4 6.25 42.8 Example 20 70% C-2 + 30% Com-5 6.40 42.9 Example 21 70% C-2 + 30% Com-6 6.50 42.5 Example 22 70% C-2 + 30% Com-7 6.55 42.6 Example 23 70% C-2 + 30% Com-8 6.55 42.5 Example 24 70% C-2 + 30% Com-9 6.40 42.9 Example 25 70% C-2 + 30% Com-10 6.45 43.0 Example 26 70% C-2 + 30% Com-11 6.90 42.7 Example 27 70% C-2 + 30% Com-12 6.95 42.9 Example 28 70% C-2 + 30% Com-13 6.95 42.5 Example 29 70% C-2 + 30% Com-14 6.90 43.2 Example 30 70% C-2 + 30% Com-15 6.90 43.0 Example 31 70% C-3 + 30% Com-1 6.95 42.9 Example 32 70% C-3 + 30% Com-2 6.00 43.3 Example 33 70% C-3 + 30% Com-3 6.05 43.0 Example 34 70% C-3 + 30% Com-4 6.15 42.8 Example 35 70% C-3 + 30% Com-5 6.10 42.9 Example 36 70% C-3 + 30% Com-6 6.00 43.0 Example 37 70% C-3 + 30% Com-7 6.20 43.2 Example 38 70% C-3 + 30% Com-8 6.10 43.0 Example 39 70% C-3 + 30% Com-9 6.15 42.7 Example 40 70% C-3 + 30% Com-10 6.25 42.5 Example 41 70% C-3 + 30% Com-11 6.20 42.3 Example 42 70% C-3 + 30% Com-12 6.25 42.4 Example 43 70% C-3 + 30% Com-13 6.30 43.0 Example 44 70% C-3 + 30% Com-14 6.30 43.8 Example 45 70% C-3 + 30% Com-15 6.40 43.7 Example 46 70% C-4 + 30% Com-1 6.95 43.1 Example 47 70% C-4 + 30% Com-2 6.50 42.0 Example 48 70% C-4 + 30% Com-3 6.45 42.8 Example 49 70% C-4 + 30% Com-4 6.45 42.8 Example 50 70% C-4 + 30% Com-5 6.40 42.0 Example 51 70% C-4 + 30% Com-6 6.50 42.5 Example 52 70% C-4 + 30% Com-7 6.55 42.3 Example 53 70% C-4 + 30% Com-8 6.55 42.5 Example 54 70% C-4 + 30% Com-9 6.40 42.9 Example 55 70% C-4 + 30% Com-10 6.45 43.0 Example 56 70% C-4 + 30% Com-11 6.30 42.7 Example 57 70% C-4 + 30% Com-12 6.35 42.6 Example 58 70% C-4 + 30% Com-13 6.35 42.5 Example 59 70% C-4 + 30% Com-14 6.30 42.8 Example 60 70% C-4 + 30% Com-15 6.30 43.0 Example 61 70% C-5 + 30% Com-1 6.50 42.5 Example 62 70% C-6 + 30% Com-1 6.45 42.8 Example 63 70% C-7 + 30% Com-1 6.05 43.9 Example 64 70% C-7 + 30% Com-2 6.10 42.9 Example 65 70% C-7 + 30% Com-3 6.20 42.5 Example 66 70% C-7 + 30% Com-4 6.15 42.6 Example 67 70% C-7 + 30% Com-5 6.15 42.5 Example 68 70% C-7 + 30% Com-6 6.20 42.9 Example 69 70% C-7 + 30% Com-7 6.25 43.0 Example 70 70% C-7 + 30% Com-8 6.20 42.7 Example 71 70% C-7 + 30% Com-9 6.25 42.9 Example 72 70% C-7 + 30% Com-10 6.35 42.5 Example 73 70% C-7 + 30% Com-11 6.20 43.2 Example 74 70% C-7 + 30% Com-12 6.30 43.0 Example 75 70% C-7 + 30% Com-13 6.35 42.9 Example 76 70% C-7 + 30% Com-14 6.20 42.0 Example 77 70% C-7 + 30% Com-15 6.15 42.1 Example 78 70% C-3 + 30% Com-16 6.20 42.9 Example 79 80% C-3 + 20% Com-1 6.45 41.1 Example 80 60% C-3 + 40% Com-1 6.20 42.9 Example 81 50% C-3 + 50% Com-1 6.35 42.7 Comparative Example 1 CBP 6.93 38.2 Comparative Example 2 Com-1 6.55 41.0 Comparative Example 3 C-3 6.40 35.2

Referring to Table 1, the organic electroluminescent devices of Examples 1 to 81 using the light emitting layer including the first host and the second host were compared with Comparative Example 1 using conventional CBP. Or the organic electroluminescent device of Comparative Example 2 and Comparative Example 3 using a light-emitting layer containing Com-1 and C-3 as a single host material, respectively, exhibited better performance in terms of current efficiency and driving voltage .

Claims (11)

anode; cathode; And at least one organic material layer interposed between the anode and the cathode,
At least one of the one or more organic layers is a light emitting layer including a first host and a second host,
Wherein the first host is a compound represented by the following general formula (1)
Wherein the second host is a compound represented by the following formula (2)
Wherein a mixing ratio of the first host to the second host is 70 to 80: 30 to 20:
[Chemical Formula 1]

In Formula 1,
R _a to R _d are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, and a substituted or unsubstituted C ₆ to C ₆₀ aryl group Lt; / RTI &gt;
(2)

In Formula 2,
X ₁ is selected from the group consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ),
Y ₁ to Y ₄ are each independently C (R ₁ ), wherein the plurality of R _{1 s} are the same or different and each is capable of forming a condensed ring with adjacent groups;
X ₂ and X ₃ are each independently C (R ₂ ), wherein the plurality of R ₂ may combine with each other to form a condensed ring;
R ₁ to R ₂ and Ar ₁ to Ar ₅ are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C ₁ to C ₄₀ An alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atoms, 3 to 40 heterocycloalkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted number of 5 to 60 heteroaryl unsubstituted nucleus atoms an aryl group, a substituted or unsubstituted C ₁ ~ C ₄₀ of A substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, A substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C Is selected from ₁ ~ C ₄₀ of the phosphine group, a substituted or unsubstituted C ₁ ~ C ₄₀ phosphine oxide group, and the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine,
(3)

[Chemical Formula 4]

In the above formulas (3) and (4)
X ₄ is selected from the group consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ),
Y ₅ to Y ₈ in Formula 3 are each independently C (R ₃ ), wherein the plurality of R _{3 s} are the same or different and are capable of forming a condensed ring with Formula 2,
Y ₉ to Y ₁₀ in Formula 3 are each independently N or C (R ₃ ), provided that one of Y ₉ to Y ₁₀ includes N, and the X ₄ -containing ring includes two heteroatoms which are the same as or different from each other ;
Y ₅ to Y ₁₄ in Formula 4 are each independently C (R ₃ ), wherein the plurality of R _{3 s} are the same or different and are capable of forming a condensed ring with Formula 2,
R ₃ in the formulas (3) and (4) forming the condensation ring of formula (2) are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C ₁ -C ₄₀ A substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₆ heteroaryl group, _40-alkyloxy group, the substituted or unsubstituted C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₆ ~ aryl of C ₆₀ silyl group , substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group of boron, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted Phosphine oxide group, and a substituted or unsubstituted selected from the group consisting of an aryl amine of the unsubstituted C ₆ ~ C _60, or they are adjacent tile combination of C ₁ ~ C ₄₀ of a phosphine group, a substituted or unsubstituted C ₁ ~ C ₄₀ To form a condensed ring,
Wherein R _a to R _d, R ₁ to R ₃ and Ar ₁ to from Ar _5, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, A halogen group, a cyano group, a nitro group, an amino group, a C _{1 to} C ₆ alkyl group, an aryl group, an aryloxy group, an aryloxy group, an aryloxy group, a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ C ₄₀ of the An aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl silyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, a C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₆₀ of the An arylamine group And may be substituted with one or more selected from the group consisting of lauric acid. The method according to claim 1,
Wherein R _a to R _d are the same or different and each independently selected from the group consisting of hydrogen, deuterium, methyl, t-butyl, and phenyl. The method according to claim 1,
Wherein the first host is selected from the group consisting of the following compounds:

delete delete delete The method according to claim 1,
X ₁ and X ₄ are the same or different and are each independently N (Ar ₁ ) or S,
Ar ₁ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,
A halogen atom, a cyano group, a nitro group, an amino group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C ₆ ~ of the C ₄₀ of the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₁ ~ C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ An organic boron phosphide, an arylboron group, a phosphine group of C ₁ to C ₄₀ , a phosphine oxide group of C ₁ to C ₄₀ , and an arylamine group of C ₆ to C ₆₀ . device. delete The method according to claim 1,
Wherein the light emitting layer including the first host and the second host is a phosphorescent light emitting layer. The method according to claim 1,
Wherein the light emitting layer comprises a dopant, and the dopant is a metal complex compound. The method according to claim 1,
Wherein the second host has a moiety represented by the following formula (5): &lt; EMI ID =
[Chemical Formula 5]

In Formula 5,
L is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms,
Z ₁ to Z ₅ are the same or different and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N,
R ₁₁ represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, hwandoen C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group of nuclear atoms of 5 to 60, a substituted or unsubstituted C ₆ ~ C _A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocyclic alkyl group having 3 to 40 nucleus atoms , A substituted or unsubstituted C ₆ to C ₆₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted arylamine group, a C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the aryl phosphine oxazol Deugi, and a substituted or unsubstituted aryl group is selected from the group consisting of silyl unsubstituted C ₆ ~ C _60, or by combining groups to which they are contiguous and may form a condensed ring,
* Denotes a portion coupled to the second host,
In the above L and R ₁₁ , an aryl group, a heteroarylene group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkoxy group, an aryloxy group, an aryloxy group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₆ ~ C _{40 60} aryloxy, alkyl of C ₁ ~ C ₄₀ oxy group, C of ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ alkyl a boron group, the group consisting of C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group in the silyl Lt; / RTI &gt; may be substituted or unsubstituted.