KR101585297B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device including the same, and the compound according to the present invention is used for an organic compound layer, preferably a light emitting layer, of an organic electroluminescent device, And the like can be improved.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound that can be used as a material of an organic electroluminescent device, and an organic electroluminescent device including the same and having improved luminous efficiency, driving voltage, and life span of the device.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film emission of Bernanose in the 1950s In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to make a high efficiency and high number of organic EL devices, each organic EL device has been developed in a manner of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

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.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

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, researches on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. In particular, the phosphor has a great advantage in improving the efficiency aspects of the light-emitting material materials _{Firpic, Ir (ppy) 3,} (acac) Ir (btp) 2 Ir metal complex compound is blue (blue), which includes the same as the green ( green and red dopant materials, and CBP is a phosphorescent host material.

However, existing materials have an advantage in terms of luminescence properties, but their thermal stability is not very good due to their low glass transition temperature, so that they are not satisfactory in terms of lifetime in OLED devices. Therefore, development of materials with higher performance is required.

An object of the present invention is to provide a novel organic compound capable of improving the bonding force between holes and electrons while having excellent thermal stability due to a high glass transition temperature.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and having improved driving voltage, luminous efficiency, and the like.

The present invention provides a compound represented by the following formula (1): < EMI ID =

In Formula 1,

A is O or S,

Y ₁ and a, and Y ₂ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ Selected,

Provided that at least one of Y ₁ and Y ₂ is N (Ar ₁ ), and when a plurality of N (Ar ₁ ) s are the same or different,

At least one Ar ₁ and Ar ₂ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ - a heteroaryl group of C ₄₀ aryl group, the number of nuclear atoms of 5 to 40, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _40, C ₆ ~ C ₄₀ is selected from the aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl,

Provided that at least one of the at least one Ar ₁ is a substituent represented by the following formula (2)

In Formula 2,

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

X ₁ to X ₅ are the same or different and are each independently N or C (R ₁₁ )

Provided that at least one of X ₁ to X ₅ is N,

Wherein when C (R < ₁₁ >) is plural, they are the same or different;

Z ₁ to Z ₈ are the same or different from each other and each independently N or CR _1, wherein when CR ₁ is plural, they are the same as or different from each other,

L ₁ and L ₂ are each independently a single bond or a group selected from the group consisting of a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nuclear atoms,

R ₁₁ and R ₁ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ An arylamine 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 ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ of is selected from the aryl phosphine oxide group, and the group consisting arylsilyl of C ₆ ~ C _40, or that the condensation tile adjacent fused ring Lt; / RTI >

In R ₁ , R ₁₁ and Ar ₁ to Ar ₅ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a nucleus A heteroaryl group having 5 to 40 atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nucleus A heterocyclic alkyl group having 3 to 40 atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, A C ₆ to C ₄₀ arylphosphine oxide group and a C ₆ to C ₄₀ arylsilyl group, and the L, L ₁ and L ₂ to C ₆ to C ₁₈ arylene groups and a heteroarylene group having 5 to 18 nucleus atoms Each of which is independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, A C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ cyano group, Reels of an amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ substituted by one substituent at least one selected from an aryl silyl group consisting of C ₄₀ or unsubstituted be ring And when there are plural substituents, they may be the same as or different from each other.

Also, the present invention is an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound of the above formula And an organic electroluminescent device.

At least one of the one or more organic layers may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer, and is preferably a light emitting layer. At this time, the compound represented by Formula 1 is a blue, green or red phosphorescent host material.

The compound represented by the general formula (1) of the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, it is possible to produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, and long life time as compared with conventional host materials, And a full color display panel in which the lifetime is greatly improved can also be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compound according to the present invention is characterized in that a carbazole moiety is introduced (bonded) to one side of thiophene or furan and carbazole, dibenzo [b dibenzo [b, d] furan, dibenzo [b, d] silole, dibenzo [b, d] selenophene, fluorine ) Moiety is introduced (bonded), preferably a carbazole moiety is introduced (bonded) on both sides, and a structure in which various substituents are bonded to the basic skeleton , And represented by the above formula (1).

Generally, in the phosphorescent light emitting layer of the organic electroluminescent device, the host material should have a triplet energy gap of higher than the dopant of the host. That is, in order to effectively provide phosphorescent emission from the dopant, the lowest excitation state of the host must be higher energy than the lowest emission state of the dopant. The compound represented by the formula (1) has a triazole energy of 2.30 eV or more and a triplet energy suitable for blue, green or red phosphorescence emission by introducing (bonding) carbazole moiety to at least one side of thiophene or furan In addition, by including thiophene or furan moieties, they are excellent in electrical characteristics and electron transporting ability, and have high thermal stability.

In the case of the compound of Formula 1, the substituent represented by Formula 2 is introduced (bonded) to N of the carbazole moiety. The substituent represented by the general formula (2) is an electron withdrawing group (EWG) having a high electron absorbing property such as pyridine, pyrimidine, triazine, quinoline, quinoxaline and quinazoline. Since the substituent of Formula 2 has a structure bound to the carbazole moiety, the compound of the present invention can increase the binding force between holes and electrons because the molecule has bipolar characteristics as a whole. Accordingly, the compound of Formula 1 can improve the phosphorescence characteristics of the organic EL device, and improve the hole injecting ability, transporting ability, or light emitting efficiency.

In addition, the compound of formula (1) has a remarkable increase in the molecular weight of the compound due to various aromatic ring substituents introduced into the carbazole moiety, and as a result, the glass transition temperature is improved, 4,4-dicarbazolylbiphenyl). &Lt; / RTI &gt; In addition, since the organic EL device is effective in inhibiting crystallization of the organic material layer, the organic EL device including the compound of Formula 1 according to the present invention can greatly improve the durability and lifetime characteristics.

When the compound represented by Formula 1 according to the present invention is used as a blue, green and / or red phosphorescent host material as a hole injection / transport layer material of an organic EL device, Excellent effect can be exhibited. Therefore, the compound represented by the general formula (1) of the present invention can greatly improve the performance and lifetime of the organic EL device, and the performance and lifetime of the organic EL device can maximize the performance of the full color organic light emitting panel.

In the compound represented by the formula (1) according to the present invention, A is O or S.

Further, Y ₁ and Y ₂ are the same or different, and each independently consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) With the proviso that at least one of Y ₁ and Y ₂ is N (Ar ₁ ), preferably both Y ₁ and Y ₂ may be N (Ar ₁ ). When a plurality of N (Ar ₁ ) s are present, they are the same or different from each other.

Wherein at least one of Ar ₁ and Ar ₂ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to ₄₀ C ₆ ~ C 40 aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C _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 ₄₀ arylboron group, a C ₆ ~ C ₄₀ aryl phosphine group, and is selected from the group consisting of C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group in the silyl.

Preferably, the one or more Ar ₁ and Ar ₂ to Ar ₅ are the same or different and each independently represents a C ₆ to C ₄₀ aryl group, Or a heteroaryl group having 6 to 40 carbon atoms.

Wherein at least one of Ar ₁ and Ar ₂ to Ar ₅ is a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a nucleus A heteroaryl group having 5 to 40 atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nucleus A heterocyclic alkyl group having 3 to 40 atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, C ₆ to C ₄₀ arylphosphine oxide groups and C ₆ to C ₄₀ arylsilyl groups are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms heterocycloalkyl of , C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine An aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, and an arylsilyl group of C ₆ to C ₄₀ , provided that when the substituent is plural, they may be the same as or different from each other.

Provided that at least one of the at least one Ar ₁ is a substituent represented by the general formula (2).

In Formula 2, L is either a single bond or a C ₆ ~ be an arylene group, and the nucleus of atoms of C ₁₈ is selected from the group consisting of a hetero arylene of 5 to 18, and preferably is a single bond or phenylene group, Or a biphenylene group.

In the L, the C ₆ -C ₁₈ arylene group, the heteroarylene group having 5 to 18 nucleus atoms, the phenylene group and the biphenylene group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group , A C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C _A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group of the And may be substituted or unsubstituted with at least one substituent selected from the group consisting of However, when there are a plurality of substituents, they may be the same or different.

X ₁ to X ₅ are the same or different and are each independently N or C (R ₁₁ ), provided that at least one of X ₁ to X ₅ is N, and when C (R ₁₁ ) is plural, They are the same or different.

Wherein R ₁₁ is selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ -C ₄₀ alkyl, substituted or unsubstituted C ₂ -C ₄₀ alkenyl, substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted aryl 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 C ₆ to C ₄₀ alkylsulfonyl group, C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group and a substituted or a non-phosphine oxide Hwandoen to C ₆ ~ C ₄₀ selected from the group consisting of aryl or silyl, or adjacent groups fused to may form a condensed ring.

In R ₁₁ , R ₁₁ is a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a hetero atom having 5 to 40 nuclear atoms An aryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ aryl The phosphine oxide group and the C ₆ to C ₄₀ arylsilyl groups are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl , C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and aryl of C ₆ ~ C ₄₀ And a silyl group, and when the substituent is plural, they may be the same as or different from each other.

Preferably, the substituent represented by the formula (2) may be a substituent represented by any one of the following formulas (A-1) to (A-15).

In the above formulas A-1 to A-15,

L and R &lt; ₁₁ &gt; are the same as defined in the above formula (1)

When there are a plurality of R &lt; ₁₁ &gt; s, they are the same as or different from each other,

n is an integer of 0 to 4, and when n is 0, hydrogen is not substituted by substituent R ₂₁ ; when n is an integer of 1 to 4, R ₂₁ is deuterium (D), halogen, cyano, A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, A substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted aryloxy group, a C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 heterocycloalkyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ of An aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups condensed to a condensed ring Lt; / RTI &gt;

In the formula, R _{21 represents} a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms An aryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ aryl The phosphine oxide group and the C ₆ to C ₄₀ arylsilyl groups are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl , C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and aryl of C ₆ ~ C ₄₀ And a silyl group, and when the substituent is plural, they may be the same as or different from each other.

Specific examples of the substituent represented by the formula (2) include a substituent represented by the following formula (s1) to substituent represented by the formula (s66), but are not limited thereto.

In the compound represented by the general formula (1), Z ₁ to Z ₈ Is the same or different and are each independently N or CR ₁ with each other, wherein when the plurality of CR _1, which are the same or different from each other. Preferably, all of Z ₁ to Z ₈ may be CR ₁ , and when CR ₁ is plural, they are the same as or different from each other.

Wherein R ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C ₂ -C ₄₀ alkynyl, C ₆ -C ₄₀ aryl , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine 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 ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine pingi, it is possible to C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl group, or of, or adjacent groups of the condensation to form a condensed ring.

In the formula, R _{1 represents} a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroatom having 5 to 40 nuclear atoms An aryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ aryl The phosphine oxide group and the C ₆ to C ₄₀ arylsilyl groups are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group , C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and aryl of C ₆ ~ C ₄₀ And a silyl group, and when the substituent is plural, they may be the same as or different from each other.

L ₁ and L ₂ are each independently a single bond or a group selected from the group consisting of a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nucleus atoms and is preferably a single bond, Or a phenylene group.

At this time, in the L ₁ and L ₂ aryl group, a heteroaryl group, a phenylene group each independently selected from deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ alkenyl group of C _40, C ₂ ~ C _A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ alkoxy group, A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl 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 ₄₀ the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ substituted with at least one selected from an aryl silyl group consisting of C ₄₀ or unsubstituted be ring And when there are plural substituents, they may be the same as or different from each other.

Examples of the compound represented by the formula (1) of the present invention include compounds represented by the following formulas (3) to (10), but are not limited thereto.

In the above formulas 3 to 10,

A plurality of Ar &lt; _{1 &gt;} may be the same or different from each other,

Ar ₁ is as defined in the above formula (1).

Specific examples of the compound represented by Formula 1 include the following compounds Inv 1 to Inv 96, but are not 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, , Hexyl, and the like.

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

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

In the present invention, "aryl" 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.

"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, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form 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" means 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 term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may have 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.

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

"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, preferably 1 to 3 carbons, of the ring is replaced by N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyl include morpholine, piperazine and the like.

"Alkylsilyl" in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 ), Etc.), for example, with reference to the following Synthesis Examples. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

&Lt; Organic electroluminescent device &

Meanwhile, the present invention provides an organic electroluminescent device including the compound represented by Formula 1.

Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, A compound represented by the formula (1), preferably a compound represented by any one of the formulas (3) to (10). At this time, the compound of formula (1) may be used alone or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of the organic layers may include a compound represented by Formula 1. [ At this time, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer.

Specifically, the light emitting layer of the organic electroluminescent device according to the present invention may include a host material, and may include the compound of Formula 1 as a host material. When the compound of Formula 1 is included in the light emitting layer material of the organic electroluminescent device, preferably blue, green, and red phosphorescent host materials, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. 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 a compound represented by Formula 1, and preferably, the emitting layer includes a compound represented by Formula 1 . At this time, the compound represented by the general formula (1) of the present invention can be used as a phosphorescent host material in the light emitting layer. 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 anode, one or more organic layers and an anode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one of the organic material layers (for example, the light emitting layer) An organic material layer and an electrode.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode material 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 or 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 or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Compound Core1

<Step 1> Synthesis of 3- (5-bromothiophen-2-yl) -9-phenyl-9H-carbazole

9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (20 g, 54.16 mmol), 2,5-dibromothiophene 10.91 g, 45.13 mmol), K2CO3 (18.7 g, 135.8 mmol) and THF / H ₂ O (200 ml / 50 ml) were mixed and stirred. Then, at 40 ℃ here insert the _{Pd (PPh 3) 4 (1.57} g, 1.358 mmol) , then stirred under reflux at 80 ℃ for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 3- (5-bromothiophen-2-yl) -9-phenyl-9H-carbazole (9.8 g, yield: 81%) was obtained by column chromatography.

¹ H-NMR:? 7.25 (m, 3H), 7.55 (m, 6H), 7.87

<Step 2> Synthesis of Compound Core1

3- (5-bromothiophen-2-yl) -9-phenyl-9H-carbazole (9.8 g, 24.23 mmol) obtained in Step 1 of Preparation Example 1, 3- (10.05 g, 72.71 mmol) and THF / H ₂ O (120 ml / 30 ml) were mixed in a nitrogen atmosphere and the mixture was stirred at room temperature for 2 hours. Followed by stirring. Then, at 40 ℃ here into the _{Pd (PPh 3) 4 (0.84} g, 0.727mmol), it was stirred under reflux at 80 ℃ for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and then subjected to column chromatography to obtain Compound Core1 (7.8 g, yield: 66%).

¹ H-NMR:? 7.28 (m, 3H), 7.58 (m, 7H), 7.82 (m, 8H), 8.33

[Preparation Example 2] Synthesis of Compound Core2

<Step 1> Synthesis of 3- (4-bromothiophen-3-yl) -9-phenyl-9H-carbazole

The same procedure as in <Step 1> of Preparation Example 1 was carried out except that 3,4-dibromothiophene (10.91 g, 45.13 mmol) was used instead of 2,5-dibromothiophene used in <Step 1> of Preparation Example 1 (9.4 g, yield: 71%) of 3- (4-bromothiophen-3-yl) -9-phenyl-9H-carbazole.

^{1 H-NMR: δ 7.22 (} m, 2H), 7.58 (m, 5H), 7.82 (m, 5H), 8.57 (m, 2H)

<Step 2> Synthesis of Compound Core2

(4-bromothiophen-3-yl) -9-phenyl-9H-carbazole obtained in Step 1 of Preparation Example 2 was used instead of 3- (5-bromothiophen- (8.5 g, yield: 74%) was obtained by carrying out the same processes as in [Step 2] of Preparation Example 1, except that 9-phenyl-9-phenyl-9H-carbazole (8.18 g, 27.92 mmol) ).

¹ H-NMR:? 7.25 (m, 3H), 7.55 (m, 7H), 7.80 (m, 8H)

[Preparation Example 3] Synthesis of Compound Core3

<Step 1> Synthesis of 3- (5-bromofuran-2-yl) -9-phenyl-9H-carbazole

The same procedure as in <Step 1> of Preparation Example 1 was carried out except that 2,5-dibromofuran (10.19 g, 45.13 mmol) was used instead of 2,5-dibromothiophene used in <Step 1> in Preparation Example 1 To obtain 3- (5-bromofuran-2-yl) -9-phenyl-9H-carbazole (11.9 g, yield: 68%).

^{1 H-NMR: δ 6.42 (} d, 1H), 7.20 (m, 3H), 7.56 (m, 6H), 7.88 (m, 3H), 8.55 (d, 1H)

<Step 2> Synthesis of Compound Core3

(5-bromothiophen-2-yl) -9-phenyl-9H-carbazole used in <Step 2> of Preparation Example 1 was used instead of 3- (9.8 g, yield: 67%) was obtained by carrying out the same processes as in [Step 2] of Preparation Example 1, except that 9-phenyl-9-phenyl-9H-carbazole (10.78 g, 36.77 mmol) ).

¹ H-NMR:? 7.02 (m, 2H), 7.25 (m, 3H), 7.58 (m, 6H)

[Preparation Example 4] Synthesis of Compound Core 4

<Step 1> Synthesis of 3- (4-bromofuran-3-yl) -9-phenyl-9H-carbazole

The same procedure as in <Step 1> of Preparation Example 3 was carried out except that 3,4-dibromofuran (10.19 g, 45.13 mmol) was used instead of 2,5-dibromofuran used in <Step 1> of Preparation Example 3 To obtain 3- (4-bromofuran-3-yl) -9-phenyl-9H-carbazole (12.3 g, yield: 70%).

¹ H-NMR:? 7.25 (m, 2H), 7.57 (m, 5H), 7.78

<Step 2> Synthesis of Compound Core4

(4-bromofuran-3-yl) -9-phenyl-9H-carbazole obtained in Step 1 of Preparation Example 4 was used instead of 3- (5-bromofuran- (10.3 g, yield: 68%) was obtained by carrying out the same procedure as <Step 2> of Preparation Example 3, except that the compound Core4 (11.14 g, 38.01 mmol) .

¹ H-NMR:? 7.25 (m, 3H), 7.58 (m, 6H), 7.83 (m, 8H), 8.34

[Synthesis Example 1] Synthesis of Compound Inv 2

(3.0 g, 6.11 mmol), 2- (3-bromophenyl) pyridine (1.17 g, 7.33 mmol), Cu powder (0.19 g, 3.05 mmol), K ₂ CO ₃ g, 9.17 mmol), Na ₂ SO ₄ (1.73 g, 12.22 mmol) and nitrobenzene (80 ml) were mixed and then stirred at 190 ° C for 12 hours.

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the compound Inv 2 (2.4 g, yield 61%).

GC-Mass (calculated: 643.8 g / mol, measured: 643 g / mol)

[Synthesis Example 2] Synthesis of Compound Inv 8

The procedure of Synthesis Example 1 was repeated except that 2-bromo-4-phenylpyrimidine (1.72 g, 7.33 mmol) was used instead of 2- (3-bromophenyl) 2.2 g, yield 56%).

GC-Mass (calculated: 644.78 g / mol, measured: 644 g / mol)

[Synthesis Example 3] Synthesis of Compound Inv 12

The procedure of Synthesis Example 1 was repeated except that 4-bromo-2,6-diphenylpyrimidine (2.28 g, 7.33 mmol) was used instead of 2- (3-bromophenyl) pyridine used in Synthesis Example 1, Inv 12 (2.7 g, yield 61%).

GC-Mass (calculated: 720.88 g / mol, measured: 720 g / mol)

[Synthesis Example 4] Synthesis of compound Inv 17

(3.0 g, 6.11 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.96 g, 7.33 mmol) and NaH (0.03 g, 1.22 mmol) in a nitrogen stream. ) And DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After completion of the reaction, water was added thereto, and the solid product was filtered and purified by column chromatography to obtain a compound Inv 17 (2.6 g, yield 59%).

GC-Mass (calculated: 721.87 g / mol, measured: 721 g / mol)

[Synthesis Example 5] Synthesis of Inv 19

(3.0 g, 6.11 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.69 g, 7.33 mmol) prepared in Preparation Example 1, Pd ) ₂ (0.04 g, 0.18 mmol), NaO (t-bu) (1.76 g, 18.34 mmol), P (t-bu) ₃ (0.12 g, 0.61 mmol) and Toluene Lt; 0 &gt; C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and then water was removed with MgSO _{4. The} residue was purified by column chromatography to obtain Compound Inv 19 (2.8 g, yield 58%).

GC-Mass (theory: 797.96 g / mol, measured: 797 g / mol)

[Synthesis Example 6] Synthesis of compound Inv 22

Except that 2-chloro-4-phenylquinazoline (1.76 g, 7.33 mmol) was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 5, The same procedure as in Synthesis Example 5 was carried out to obtain a compound Inv 22 (2.5 g, yield 59%)

GC-Mass (calculated: 694.84 g / mol, measured: 694 g / mol)

[Synthesis Example 7] Synthesis of Compound Inv 38

The compound Core2 (3 g, 6.11 mmol) obtained in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 5 and 4 (4-chlorophenyl) -4,6-diphenyl-1,3,5- Compound Inv 38 (2.6 g, yield 53%) was obtained by following the same procedure as in Synthesis Example 5, except that 3- (3-chlorophenyl) -2,6-diphenylpyrimidine (2.29 g, 7.33 mmol) was used.

GC-Mass (calculated: 796.98 g / mol, measured: 796 g / mol)

[Synthesis Example 8] Synthesis of compound Inv 43

(2.7 g, yield 55%) was obtained by following the same procedure as in Synthesis Example 5, except that the compound Core2 (2.52 g, 7.33 mmol) obtained in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 5, ).

GC-Mass (theory: 797.96 g / mol, measured: 797 g / mol)

[Synthesis Example 9] Synthesis of compound Inv 44

2- (biphenyl-4-yl) -4-chloro-1,3,5-triazine (1.96 g, 7.33 mmol) was used instead of 4- (3-chlorophenyl) -2,6-diphenylpyrimidine used in Synthesis Example 7 , The same procedure as in Synthesis Example 7 was carried out to obtain a compound Inv 44 (2.4 g, yield 54%).

GC-Mass (calculated: 721.87 g / mol, measured: 721 g / mol)

[Synthesis Example 10] Synthesis of compound Inv 57

2-bromo-4,6-diphenylpyridine (2.27 g, 7.33 mmol) was used instead of the compound Core1 used in Synthesis Example 1, instead of the compound Core3 (3 g, 6.11 mmol) mmol), the same procedure as in Synthesis Example 1 was carried out to obtain a compound Inv 57 (2.5 g, yield: 58%).

GC-Mass (703.83 g / mol, measured: 703 g / mol)

[Synthesis Example 11] Synthesis of Compound Inv 64

Except that 2- (3-bromophenyl) -4,6-diphenylpyrimidine (2.51 g, 7.33 mmol) was used instead of 2-bromo-4,6-diphenylpyridine used in Synthesis Example 10, To obtain the compound Inv 64 (2.8 g, yield 58%).

GC-Mass (theoretical value: 780.91 g / mol, measured: 780 g / mol)

[Synthesis Example 12] Synthesis of compound Inv 72

(3 g, 6.11 mmol) obtained in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 5, and 2 (3-chlorophenyl) -4,6-diphenyl-1,3,5- Compound Inv 72 (2.8 g, yield 57%) was obtained by following the same procedure as in Synthesis Example 5, except that 2-chloro-4- (4- (naphthalen-1yl) phenyl) quinazoline (2.68 g, 7.33 mmol) ).

GC-Mass (theory: 804.93 g / mol, measurement: 804 g / mol)

[Synthesis Example 13] Synthesis of Compound Inv 76

6-bromo-2,2'-bipyridine (1.72 g, 6.11 mmol) was used instead of the compound Core1 used in Synthesis Example 1, and Core4 (3.0 g, 6.11 mmol) 7.33 mmol), the procedure of Synthesis Example 1 was repeated to obtain the compound Inv 76 (2.5 g, yield 65%).

GC-Mass (calculated: 628.72 g / mol, measured: 628 g / mol)

[Synthesis Example 14] Synthesis of compound Inv 83

The procedure of Synthesis Example 13 was repeated except that 2-bromo-4,6-diphenylpyrimidine (2.28 g, 7.33 mmol) was used instead of 6-bromo-2,2'- Compound Inv 83 (2.6 g, yield 60%) was obtained.

GC-Mass (calculated: 704.82 g / mol, measured: 704 g / mol)

[Synthesis Example 15] Synthesis of compound Inv 93

Instead of Compound Core1 used in Synthesis Example 5, Compound Core4 (3.0 g, 6.11 mmol) obtained in Preparation Example 4 was used and 2 (3-chlorophenyl) -4,6-diphenyl-1,3,5- 3-yl) -4-chloro-1,3,5-triazine (1.96 g, 7.33 mmol) was used in place of 3- , Yield: 53%).

GC-Mass (theory: 705.80 g / mol, measurement: 705 g / mol)

[Example 1] Production of green organic EL device

The compound synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

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

(60 nm) / TCTA (80 nm) / compound Inv 2 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq prepared in Synthesis Example 1 on the ITO transparent electrode thus prepared ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in that order.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP used are as follows.

[Example 2] - [Example 13] - Preparation of green organic EL device

Inv 12, Inv 17, Inv 19, Inv 38, and Inv 38, which were synthesized in Synthesis Examples 2 to 5, 7 to 11, and 13 to 15, respectively, instead of Compound Inv 2 used as a luminescent host material in the formation of the light- Inv 43, Inv 44, Inv 57, Inv 64, Inv 76, Inv 83, and Inv 93 were used in place of the organic EL device.

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound Inv 2 as a luminescent host material in forming the light emitting layer in Example 1. The structure of CBP used is as follows.

[Evaluation Example 1]

The green organic EL devices prepared in Examples 1 to 13 and Comparative Example 1 were measured for driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2, and the results are shown in Table 1 below.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Inv2 6.70 515 42.1 Example 2 Inv8 6.50 518 39.9 Example 3 Inv12 6.64 515 40.1 Example 4 Inv17 6.70 517 41.1 Example 5 Inv19 6.65 515 40.6 Example 6 Inv38 6.50 517 40.9 Example 7 Inv43 6.55 520 40.7 Example 8 Inv44 6.60 515 39.2 Example 9 Inv57 6.45 518 39.1 Example 10 Inv64 6.60 517 39.7 Example 11 Inv76 6.70 515 40.1 Example 12 Inv83 6.61 518 41.9 Example 13 Inv93 6.70 516 41.1 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound according to the present invention was used as a light emitting layer of a green organic EL device (Examples 1 to 13), compared with the green organic EL device using Comparative Example 1 (Comparative Example 1) And the driving voltage.

[Example 14] - Preparation of red organic EL device

The compound synthesized in Synthesis Example 6 was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

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

On the prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / compound Inv 22 + 10% (piq) ₂ Ir (acac) (300 nm) / BCP (10 nm) / Alq ₃ ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structure of (piq) ₂ Ir (acac) used is as follows, and the structures of m-MTDATA, TCTA and BCP are as described in Example 1. [

[Example 15] - Preparation of red organic EL device

A red organic EL device was prepared in the same manner as in Example 14, except that the compound Inv 72 synthesized in Synthesis Example 12 was used instead of the compound Inv 22 used as a light emitting host material in the light emitting layer formation in Example 14.

[Comparative Example 2] - Production of red organic EL device

A red organic electroluminescent device was fabricated in the same manner as in Example 14, except that CBP was used in place of the compound Inv 22 used as a luminescent host material in forming the light emitting layer in Example 14. The structure of CBP used is as described in Comparative Example 1.

[ Evaluation example  2]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 14 and 15 and Comparative Example 2, respectively, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 14 Inv22 4.70 10.9 Example 15 Inv72 4.75 11.2 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used as the material of the light emitting layer of the red organic electroluminescent device (Examples 14 and 15), the red organic electroluminescent device using conventional CBP as the material of the light emitting layer The current efficiency and the driving voltage are superior to those of Example 2).

Claims (6)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
A is O or S,
Y ₁ and Y ₂ are each independently N (Ar ₁ )
In this case, and a plurality of N (Ar ₁₎ are the same or different from each other, and one or more Ar ₁ is selected from the group consisting of each independently C ₆ ~ C ₄₀ aryl group, and the number of nuclear atoms group heteroaryl of 5 to 40,
Provided that at least one of the at least one Ar ₁ is a substituent represented by any one of the following formulas A-1 to A-15;

L is a single bond or a group selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
Wherein the plurality of R &lt; ₁₁ &gt; are the same or different;
n is an integer from 0 to 4, and R &lt; ₂₁ &gt; are each independently hydrogen,
Z ₁ to Z ₈ are the same or different from each other and each independently N or CR _1, wherein when CR ₁ is plural, they are the same as or different from each other,
L ₁ and L ₂ are each independently a single bond or a group selected from the group consisting of a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nuclear atoms,
R ₁₁ and R ₁ are the same or different and are each independently selected from the group consisting of hydrogen, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms,
In R ₁ , R ₁₁ and Ar ₁ , a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, and an arylene group and a heteroarylene group in L, L ₁ and L ₂ are each independently A C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms, and when the substituent is plural, they may be the same or different from each other can do. delete The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (10):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above formulas 3 to 10,
A plurality of Ar &lt; _{1 &gt;} may be the same or different from each other,
Ar &_lt; 1 &gt; is as defined in claim ₁ ; delete A cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic compound layers comprises a compound according to any one of claims 1 to 3. 6. The method of claim 5,
Wherein at least one organic compound layer containing the compound is a light emitting layer.