KR20150047841A - 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. The compound according to the present invention can be used in an organic substance layer of an organic electroluminescent device, preferably a light emitting layer, thereby increasing light emitting efficiency, driving voltage, lifespan, etc. of the organic electroluminescent device.

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.

Studies on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') by blue electroluminescence using anthracene single crystals in 1965 have been carried out with reference to the observation of organic thin film luminosity 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. In order to produce high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce 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. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies 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. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of light emission characteristics, but their thermal stability is lowered due to a 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 which has a high glass transition temperature and is excellent in thermal stability and can improve the bonding force between holes and electrons.

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,

Ar ₁ is a substituent represented by the following formula (2);

In Formula 2,

L is a single bond, a substituted or unsubstituted C ₆ -C ₄₀ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 40 nucleus atoms;

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

When two or more of X ₁ to X ₅ are C (R ₁₁ ), a plurality of R _{11 s} are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl 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 ~ C ₄₀ aryl the A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkoxy group, unsubstituted C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C with ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, the substituted or unsubstituted C ₆ of ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl groups, or groups or grain to which they are adjacent To which they are attached may form a condensed ring;

R ₁ to R ₃ are the same or different from each other and each independently selected from the group consisting of deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl groups, substituted or unsubstituted C ₂ to C ₄₀ alkenes group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted can be a heteroaryl group of from 5 to 40, a substituted or unsubstituted nucleus of atoms of a C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₃ ~ C _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 ₁ to C ₄₀ alkyl group, , a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ Reel phosphine oxide group, and a substituted or non-substituted aryl group is selected from the group consisting of silyl unsubstituted C ₆ ~ C _40;

When plural R ₁ , R ₂ and R ₃ are present, plural R ₁ , R ₂ and R ₃ are the same or different,

a, b and c are each independently an integer of 0 to 5,

In the above L, R ₁ to R ₃ and R ₁₁ , a C ₆ to C ₁₈ arylene group, a heteroarylene group having 5 to 18 nuclear atoms, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C _A C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, group _{of 6} to arylboronic of C _40, C ₆ to C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl phosphine oxide group, and a C ₆ to an aryl silyl group of C _40, each independently selected from deuterium, halogen, a cyano group , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to 40 of the C ₆ ~ for C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl of Kilgi, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ aryl of C ₄₀ phosphine group may be substituted with one or more substituents selected from aryl phosphine oxide group and an aryl silyl group the group consisting of a C ₆ ~ C ₄₀ of a C ₆ ~ C _40. When a plurality of substituents are introduced at this time, these substituents may be the same as or different from each other.

The organic electroluminescent device according to the present invention includes a cathode, an anode, 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 represented by the general formula A light emitting device is provided.

At least one of the one or more organic layers including the compound of Formula 1 may be selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, and a light emitting layer. In this case, the compound represented by Formula 1 may be a green or red phosphorescent host material.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 according to 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, A full-color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compound according to the present invention has a basic skeleton of a carbozole moiety in which phenyl is bonded at positions 1 and 3, and various substituents are bonded to the basic skeleton. .

When 1,3,5-triphenyl-benzene is used alone, it is not suitable as a material for an organic electroluminescent device. However, in the case of carbazole moieties, materials for organic electroluminescent devices, particularly phosphorescent host materials It is used variously. The carbazole moiety has a triple energy as large as 3.0 eV and a HOMO energy level as low as 6.0 eV and is mainly used for the blue phosphorescent host. Therefore, in the 1,3-diphenyl-9H-carbazole structure represented by Formula 1 of the present invention in which one biphenyl of 1,3,5-triphenyl-benzene is modified with a carbazole, the triplet energy is smaller than 3.0 eV and the HOMO energy The energy band gap becomes suitable for the green / red phosphorescent host.

In particular, the present invention is characterized in that the electron withdrawing group (EWG) represented by the general formula (2) is substituted at the 9-position of the 1,3-diphenyl-9H-carbazole structure. A structure having both an electron withdrawing group (EWG) having a large electron absorbing property and an electron donating group (EDG) having an electron donating property has a bipolar characteristic as a whole molecule, It is advantageous not only as a host in the phosphorescent light-emitting layer but also as a hole transport layer, a hole injection layer, and the like.

In the present invention, the phenyl group substituted at the 1-position of the carbazole moiety and the electron withdrawing group (EWG) of the formula 2 substituted at the carbazole moiety 9 are adjacent to each other to cause steric hinderance. Therefore, compound molecules are distorted to solve the problem of lowering the luminescence property due to pi-pi-stacking, thereby preventing the formation of an excimer (excimer), thereby improving the luminous efficiency do.

In addition, the host material in the phosphorescent light-emitting layer should have a higher triplet energy gap than the dopant in the host, since the lowest excitation state of the host must have a higher energy than the lowest emission state of the dopant to provide effective phosphorescence from the dopant. The novel compound according to the present invention has a lower triplet energy than a compound having a basic carbazole moiety as a basic skeleton by substituting phenyl at positions 1 and 3 of the carbazole moiety, Lt; / RTI &gt;

Meanwhile, the compound represented by the formula (1) of the present invention has an aromatic ring or a heteroaromatic ring substituent introduced into the molecule, and the molecular weight of the compound is significantly increased to improve the glass transition temperature, Of 4,4-dicarbazolylbiphenyl (CBP). Further, the compound represented by the general formula (1) of the present invention is also effective for inhibiting crystallization of the organic material layer.

Generally, a ceramic crucible having a high thermal conductivity is used as a method of forming an organic layer of an organic electroluminescent device through a vacuum deposition method, and a stepwise and continuous evaporation control can be performed and an organic material should not be spattered. The temperature rise of the evaporation source is not properly performed, and the organic material having reached the evaporation temperature in an excessively short time causes a phenomenon of splashing and clogging of the inlet of the evaporation source. As a result, the deposition rate of the organic material becomes unstable, . Also, there is a high possibility that an organic material is discolored or discolored during deposition. Organic materials have the property of being melted or sublimated depending on the material. When they are deposited by the sublimation method, the compound forms an organic layer immediately after the sublimation process in the solid state, whereas in the case of the melting method, And is vaporized to form an organic layer. It is difficult to control the deposition temperature and uniformity because the material undergoes phase change more than the sublimation method. In this case, the 1,3-diphenyl-9H-carbazole structure of the present invention is deposited by the sublimation method, whereas the Ref-1 structure including the unsubstituted carbazole moiety is deposited by the melting method (Table 1), the compound of the present invention can have uniform thin film characteristics, and the luminescence property is improved.

As a result, when the compound of Formula 1 according to the present invention is used as a hole injecting / transporting layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material, compared to a conventional organic material layer material (for example, CBP) The efficiency and lifetime of the organic electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

The novel compound according to the present invention has a structure in which the substituent represented by the general formula (2) is bonded to the carbazole moiety basic skeleton of the general formula (1) in which phenyl is bonded to the positions 1 and 3, respectively.

In the compound represented by the general formula (1), Ar ₁ introduced into the N-position of the carbazole basic skeleton may be formulated as shown in general formula (2).

Wherein L is a divalent group linker known in the art and is a single bond, a substituted or unsubstituted C ₆ -C ₄₀ arylene group, and a substituted or unsubstituted nuclear atom And a heteroarylene group having a number of 5 to 40.

Here, the C ₆ ~ C ₄₀ of the arylene group, for example, the nuclear atoms of 5 to 40 hetero arylene group, phenylene group, biphenylene group, naphthylene group, an anthracenyl group, an indenyl group, a pyran tray carbonyl group , A carbazolyl group, a thiophenylene group, an indolylene group, a prolinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, And the like. In the present invention, it is preferable that L is selected from a single bond, a phenylene group, or a biphenylene group.

In the L, the C ₆ -C ₄₀ arylene group and the heteroarylene group having 5 to 40 nuclear atoms are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl , 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 ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boronic group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ with an aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group substituents of two or more selected from the group consisting of And when the substituent is plural, they may be the same or different.

X ₁ to X ₅ are the same or different and each independently N or C (R ₁₁ ) and include at least one N atom.

When two or more of X ₁ to X ₅ are C (R ₁₁ ), a plurality of R _{11 s} may be the same or different, and each independently represents hydrogen, deuterium (D), halogen, unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms heteroaryl of 5 to 40, a substituted or unsubstituted C ₆ ~ C of _A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group , A substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl phosphine oxide groups and substituted or unsubstituted C ₆ to C ₄₀ arylsilyl groups, May be bonded to adjacent groups to form a condensed ring.

In R ₁₁ , the alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, 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, to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl of the group, 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 may be substituted by one or more substituents selected from the group consisting of arylsilyl _40, wherein when the substituent is plural, they are equal to each other Or it may be different.

According to a preferred embodiment of the present invention, 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 as defined in the above-mentioned formula (1)

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

R ₂₁ represents a hydrogen atom, a heavy hydrogen atom (D), a halogen atom, a cyano group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, A substituted or unsubstituted aryloxy group having 5 to 40 carbon atoms, 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 C ₆ to C ₄₀ aryl An amino 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 arylboron group, An unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, Or they may be bonded to adjacent groups to form a condensed ring,

n is an integer of 0 to 4;

In the above R ₂₁ , an alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, 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, to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl of the group, 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 may be substituted by one or more substituents selected from the group consisting of arylsilyl _40, wherein when the substituent is plural, they are equal to each other Or it may be different.

More specifically, the substituents represented by the above formulas (A-1) to (A-15) are preferably selected from the group of substituents represented by the following structures. However, it is not particularly limited.

In the compounds represented by the general formula (1) according to the present invention, R ₁ to R ₃ Are each independently selected from the group consisting of deuterium (D), 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 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ arylamine group of C _40, C ₃ ~ C ₄₀ the cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a _{C 6 ~ C 40, C 6} ~ C 40 An aryl phosphine group of C ₆ to C _40, an aryl phosphine oxide group of C ₆ to C ₄₀ , and an arylsilyl group of C ₆ to C ₄₀ . Wherein R _1, R ₂ and R ₃ when present is a plurality of, respectively, a plurality of R _1, R ₂ and R ₃ may be the same or different from each other.

In R ₁ to R ₃ , an alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group And arylsilyl groups are each 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 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. When a plurality of substituents are present, they may be the same or different.

In the present invention, R ₁ to R ₃ are each independently preferably a C ₆ to C ₄₀ aryl group, and more preferably a phenyl group.

a, b and c are each independently an integer of 0 to 5;

The compound represented by the formula (1) according to the present invention may be further represented by a compound represented by any one of the following formulas (3) to (7).

(3)

(a=b=c=0)

(a = b = c = 0)

[Chemical Formula 4]

(a=b=0, c=1)

(a = b = 0, c = 1)

[Chemical Formula 5]

(a=b=0, c=2)

(a = b = 0, c = 2)

[Chemical Formula 6]

(a=b=0, c=1)

(a = b = 0, c = 1)

(7)

(a=b=0, c=1)

(a = b = 0, c = 1)

In the above Chemical Formulas 3 to 7,

Ar ₁ is the same as defined in the above formula (2), each Ar ₁ is the same or different,

Z ₁ is selected from O, S, Se, N ( R 4), C (R 5) (R 6) , and _{Si (R 7) (R 8} )

R ₄ to R ₈ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted aryloxy group of nuclear atoms heteroaryl of 5 to 40 groups, substituted or unsubstituted C ₆ ~ C _40, a substituted or unsubstituted C ₁ ~ alkyloxy group of C ₄₀ of , A substituted or unsubstituted C ₆ to C ₄₀ 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 C ₆ ~ 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 phosphine oxide group, and a substituted or unsubstituted C ₆ of To C ₄₀ arylsilyl groups, or they may be bonded to adjacent groups to form a condensed ring. Wherein R ₄ to R ₈ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted five to twenty- Lt; RTI ID = 0.0 &gt; R &lt; / RTI &gt;

In R ₄ to R ₈ , an alkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group And arylsilyl groups are each 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 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. When a plurality of substituents are present, they may be the same or different.

The compounds represented by formula (1) of the present invention described above can be further compounded into compound structures composed of C-1 to C-168 shown below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

"Alkyl" in the present invention 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, but are not limited thereto.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

The term "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, but are not limited thereto.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, 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, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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, but are not limited to, 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 be linear, branched or cyclic . &Lt; / RTI &gt; Examples of such alkyloxy include, but are not limited to, 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, but are not limited to, 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 heterocycloalkyls include, but are not limited to, 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 in various ways 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 &

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds 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. [ Preferably, the organic compound layer containing the compound of Formula 1 may be a light emitting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). 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 compound represented by Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.

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 . Specifically, the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer. 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 layer (for example, a light emitting layer) of the organic material layer includes the compound represented by Formula 1 Other organic material layers and electrodes.

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.

Non-limiting examples of usable cathode materials 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.

Non-limiting examples of usable cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys 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 PCZ-1

<Step 1> Synthesis of 1,3-diphenyl-5- (2-nitrophenyl) benzene

1-bromo-2-nitrobenzene, 6.0 g (150.0 mmol) of NaOH and 250 ml / 120 ml of a mixture of 13.7 g (50.0 mmol) of 1,3-diphenylbenzene-5-boronic acid and 15.2 g Of THF / H ₂ O were added and stirred. 2.89 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C, 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 filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 1,3-diphenyl-5- (2-nitrophenyl) benzene (13.5 g, 38.5 mmol, yield 77%) was obtained by column chromatography.

Mass: [M] &lt; ⁺ & gt ^; = 351 g / mol

Elemental Analysis: C, 82.03; H, 4.88; N, 3.99; O, 9.11

<Step 2> Synthesis of PCZ-1

10.5 g (30.0 mmol) of 1,3-diphenyl-5- (2-nitrophenyl) benzene, 23.6 g (90.0 mmol) of triphenylphosphine and 200 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and the target compound PCZ-1 (6.61 g, 20.7 mmol, yield 69%) was obtained by column chromatography.

Mass: [M] &lt; ⁺ & gt ^; = 319 g / mol

Elemental Analysis: C, 90.25; H, 5.36; N, 4.39

¹ H-NMR:? 7.23 (m, 3H), 7.42 (m, 2H), 7.52 (m, 8H), 7.62 s, 1 H)

[Preparation Example 2] Synthesis of PCZ-2

<Step 1> Synthesis of PCZ-2

To a solution of 4.83 g (10.0 mmol) of 1,3,6,8-tetrabromo-9H-carbazole, 7.32 g (60.0 mmol) of phenylboronic acid, 4.8 g (120.0 mmol) of NaOH and 250 ml / / H ₂ O were added and stirred. 2.32 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C, 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 filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, PCZ-2 (3.06 g, 6.49 mmol, yield 65%) was obtained by column chromatography.

Mass: [M] &lt; ⁺ & gt ^; = 471 g / mol

Elemental Analysis: C, 91.69; H, 5.34; N, 2.97

¹ H-NMR:? 7.22 (d, 4H), 7.45 (m, 4H), 7.57 (m,

[Preparation Example 3] Synthesis of PCZ-3

<Step 1> Synthesis of 1,3-diphenyl-5- (3-chloro-6-nitrophenyl) benzene

The procedure of Step 1 of Preparation Example 1 was repeated except that 2-bromo-4-chloro-1-nitrobenzene (17.7 g, 75.0 mmol) was used in place of 1-bromo-2- , 3-diphenyl-5- (3-chloro-6-nitrophenyl) benzene (13.3 g, 34.5 mmol, yield 69%).

Mass: [M] &lt; ⁺ & gt ^; = 385 g / mol

Elemental Analysis: C, 74.71; H, 4.18; Cl, 9.19; N, 3.63; , 8.29

<Step 2> Synthesis of 6-chloro-1,3-diphenyl-9H-carbazole

Except that 1,3-diphenyl-5- (3-chloro-6-nitrophenyl) benzene (11.6 g, 30.0 mmol) was used instead of 1,3-diphenyl-5- 6-chloro-1,3-diphenyl-9H-carbazole (6.26 g, 17.7 mmol, yield 59%) was obtained in the same manner as in <Step 2> of Example 1.

Mass: [M] &lt; ⁺ & gt ^; = 353 g / mol

Elemental Analysis: C, 81.46; H, 4.56; Cl, 10.02; N, 3.96

<Step 3> Synthesis of PCZ-3

Step 1 of Preparation Example 2 was repeated except that 6-chloro-1,3-diphenyl-9H-carbazole (10.6 g, 30.0 mmol) was used instead of 1,3,6,8-tetrabromo-9H- >, To obtain PCZ-3 (7.49 g, 18.93 mmol, yield 63%).

Mass: [M] &lt; ⁺ & gt ^; = 395 g / mol

Elemental Analysis: C, 91.11; H, 5.35; N, 3.54

¹ H-NMR:? 7.23 (d, 2H), 7.41 (m, 3H), 7.53 (m,

[Preparation Example 4] Synthesis of BCZ-1

<Step 1> Synthesis of 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene

A solution of 13.7 g (50.0 mmol) of 1,3-diphenylbenzene-5-boronic acid and 15.2 g (75.0 mmol) of 2,4-dibromo-1-nitrobenzene in 21.1 g (75.0 mmol) of NaOH and 250 ml / ml of THF / H ₂ O were added and stirred. 2.89 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C, 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 filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene (16.6 g, yield 77%) was obtained by column chromatography.

MS [M + 1] &lt; ⁺ &gt; 430, 432

Elemental Analysis: C, 66.99; H, 3.75; Br, 18.57; N, 3.26; O, 7.44

<Step 2> Synthesis of 6-bromo-1,3-diphenyl-9H-carbazole

12.9 g (30.0 mmol) of 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene, 23.6 g (90.0 mmol) of triphenylphosphine and 200 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours . After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and 6-bromo-1,3-diphenyl-9H-carbazole (8.00 g, yield 67%) was obtained by column chromatography.

MS [M + 1] &lt; ⁺ &gt; 398, 396

Elemental Analysis: C, 72.37; H, 4.05; Br, 20.06; N, 3.52

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

(18.4 g, 46.2 mmol), iodobenzene (14.1 g, 69.3 mmol), Cu powder (0.29 g, 4.62 mmol) and K ₂ CO ₃ (6.38 g, , 46.2 mmol), Na ₂ SO ₄ (6.56 g, 46.2 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C 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 . The solvent was removed from the organic layer from which water had been removed, and the residue was purified by column chromatography to obtain 6-bromo-1,3,9-triphenyl-9H-carbazole (15.6 g, yield 71%).

MS [M + 1] &lt; ⁺ &gt; 476, 474

Elemental Analysis: C, 75.95; H, 4.25; Br, 16.84; N, 2.95

<Step 4> Synthesis of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole

6.08 g (12.8 mmol) of 6-bromo-1,3,9-triphenyl-9H-carbazole was reacted with 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- 4.86 g (19.1 mmol) of Pd (dppf) Cl ₂ , 3.76 g (38.3 mmol) of KOAc and 100 ml of DMF were added and the mixture was stirred at 130 ° C. for 12 h After stirring, the reaction was terminated, extracted with ethyl acetate and the water was removed with MgSO ₄ . After removing the solvent, the reaction product was purified by column chromatography to obtain the objective compound, 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- carbazole (4.74 g, yield 71%).

MS [M + 1] &lt; ⁺ &gt; 522

Elemental Analysis: C, 82.92; H, 6.19; B, 2.07; N, 2.69; O, 6.14

<Step 5> Synthesis of BCZ-1

A solution of 3.89 g (10.0 mmol) of 6-bromo-1,3-diphenyl-9H-carbazole and 7.82 g (15.0 mmol) of 1,3,9-triphenyl- 6- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole, 4.2 g (15.0 mmol) of NaOH and 250 ml / 120 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the Pd (PPh _{3) 4} in 0.6 g (5 mol%) was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene (6.34 g, yield 87%) was obtained by column chromatography.

MS [M + 1] &lt; ⁺ &gt; 713

Elemental Analysis: C, 90.98; H, 5.09; N, 3.93

^{1 H-NMR: δ 7.20 (} m, 4H), 7.42 (m, 5H), 7.52 (m, 18H), 7.75 (m, 5H), 7.88 (d, 1H), 8.00 (d, 1H), 8.19 ( d, 1 H), 10.12 (s, 1 H)

[Preparation Example 5] Synthesis of BCZ-2

<Step 1> Synthesis of BCZ-2

9-phenyl-9H-carbazol-3-ylboronic acid instead of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- (4.71 g, 84% yield) of BCZ-2 was obtained by following the procedure of <Step 5> of Preparation Example 1, except that the title compound (4.30 g, 15.0 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 561

Elemental Analysis: C, 89.97; H, 5.03; N, 5.00

¹ H-NMR:? 7.22 (m, 4H), 7.42 (m, 3H), 7.55 (m, 11H), 7.71 d, 1 H), 10.13 (s, 1 H)

[Preparation Example 6] Synthesis of BCZ-3

<Step 1> Synthesis of BCZ-3

9,9-dimethyl-9H-fluorene-2-carboxylic acid was used in the place of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (4.15 g, yield 81%) was obtained by following the procedure of <Step 5> of Preparation Example 1, except that the title compound was obtained as a white amorphous solid (3.57 g, 15.0 mmol).

MS [M + 1] &lt; ⁺ &gt; 512

Elemental Analysis: C, 91.55; H, 5.71; N, 2.74

^{1 H-NMR: δ 1.72 (} s, 6H), 7.23 (m, 3H), 7.38 (t, 1H), 7.45 (m, 2H), 7.54 (m, 8H), 7.68 (m, 2H), 7.71 ( m, 3H), 7.84 (m, 2H), 7.93 (d, 1H), 10.13

[Preparation Example 7] Synthesis of BCZ-4

<Step 1> Synthesis of BCZ-4

Dibenzo [b, d] furan-2-ylboronic acid instead of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan- (4.13 g, yield 85%) was obtained by carrying out the same procedure as <Step 5> of Preparation Example 1, except that the title compound (3.18 g, 15.0 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 486

Elemental Analysis: C, 89.05; H, 4.77; N, 2.88; , 3.29

^{1 H-NMR: δ 7.20 (} m, 2H), 7.32 (m, 2H), 7.41 (m, 2H), 7.53 (m, 7H), 7.68 (m, 2H), 7.72 (m, 4H), 7.85 ( m, 3 H), 10.13 (s, 1 H)

[Preparation Example 8] Synthesis of BCZ-5

<Step 1> Synthesis of BCZ-5

Dibenzo [b, d] thiophen-4-ylboronic acid instead of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan- (4.36 g, yield 87%) was obtained by carrying out the same procedure as <Step 5> of Preparation Example 1 except that the compound (3.45 g, 15.0 mmol) was used.

MS [M + 1] &lt; ⁺ &gt; 502

Elemental Analysis: C, 86.19; H, 4.62; N, 2.79; S, 6.39

¹ H-NMR:? 7.21 (m, 2H), 7.41 (m, 2H), 7.53 (m, 10H), 7.72 d, 1 H), 8.43 (m, 2H), 10.11 (s, 1 H)

[Synthesis Example 1] Synthesis of C-10

(3.19 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol), NaH (0.24 g, 10.00 mmol) and DMF 50 ml) were mixed and stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into water, the solid compound was filtered, and the residue was purified by column chromatography to obtain the target compound C-10 (5.01 g, yield 91%).

Mass: [M] &lt; ⁺ & gt ^; = 550 g / mol

[Synthesis Example 2] Synthesis of C-12

(3.19 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd ₂ (dba) ₃ 0.46 g, 0.5 mmol), ( t-Bu) 3 P (0.40 g, 2.0 mmol), sodium tert-butoxide (2.88 g, 30.0 mmol) were dissolved in 50 ml toluene was stirred at 110 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C-12 (4.95 g, yield 79%) was obtained by column chromatography.

Mass: [M] &lt; ⁺ & gt ^; = 626 g / mol

[Synthesis Example 3] Synthesis of C-16

3- (3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (5.04 g, 12.00 mmol), the target compound C-16 (4.70 g, yield 67%) was obtained in the same manner as in Synthesis Example 2. [

Mass: [M] &lt; ⁺ & gt ^; = 702 g / mol

[Synthesis Example 4] Synthesis of C-28

2- (3-chlorophenyl) -4,6-di (naphthalen-2-yl) -1,3,5-triazine (5.66 g, yield 78%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that the compound (5.04 g, 12.00 mmol) was used.

Mass: [M] &lt; ⁺ & gt ^; = 726 g / mol

[Synthesis Example 5] Synthesis of C-66

C-66 (5.83 g, yield 83%) was obtained in the same manner as in Synthesis Example 1, except that PCZ-2 (4.71 g, 10.00 mmol) was used instead of PCZ-1.

Mass: [M] &lt; ⁺ & gt ^; = 702 g / mol

[Synthesis Example 6] Synthesis of C-68

C-68 (5.60 g, yield 72%) was obtained in the same manner as in Synthesis Example 2, except that PCZ-2 (4.71 g, 10.00 mmol) was used instead of PCZ-1.

Mass: [M] &lt; ⁺ & gt ^; = 778 g / mol

[Synthesis Example 7] Synthesis of C-94

C-94 (5.38 g, yield 86%) was obtained in the same manner as in Synthesis Example 1, except that PCZ-3 (3.95 g, 10.00 mmol) was used instead of PCZ-1.

Mass: [M] &lt; ⁺ & gt ^; = 626 g / mol

[Synthesis Example 8] Synthesis of C-96

C-96 (4.56 g, yield 65%) was obtained in the same manner as in Synthesis Example 2, except that PCZ-3 (3.95 g, 10.00 mmol) was used instead of PCZ-1.

Mass: [M] &lt; ⁺ & gt ^; = 702 g / mol

[Synthesis Example 9] Synthesis of C-99

3- (3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (5.04 g, 12.00 mmol), the target compound C-99 (5.52 g, yield 71%) was obtained in the same manner as in Synthesis Example 8.

Mass: [M] &lt; ⁺ & gt ^; = 778 g / mol

[Synthesis Example 10] Synthesis of C-25

Except that 2- (3-chlorophenyl) -4-phenylquinazoline (3.79 g, 12.00 mmol) was used instead of 2- (3-chlorophenyl) -4,6- diphenyl- The procedure of Example 2 was repeated to obtain the target compound C-25 (3.65 g, yield 61%).

Mass: [M] &lt; ⁺ & gt ^; = 599 g / mol

[Synthesis Example 11] Synthesis of C-26

Except that 4- (biphenyl-4-yl) -2-chloroquinazoline (3.79 g, 12.00 mmol) was used instead of 2- (3-chlorophenyl) -4,6- diphenyl- The procedure of Synthesis Example 2 was repeated to obtain C-26 (3.29 g, yield 55%) as a target compound.

Mass: [M] &lt; ⁺ & gt ^; = 599 g / mol

[Synthesis Example 12] Synthesis of C-27

2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.39 g, 12.00 mmol) was used instead of 2- (3-chlorophenyl) -4,6- diphenyl- , The target compound C-27 (3.69 g, yield 51%) was obtained by carrying out the same procedure as in Synthesis Example 2.

Mass: [M] &lt; ⁺ & gt ^; = 725 g / mol

[Synthesis Example 13] Synthesis of C-117

(7.13 g, 10.00 mmol), 2-chloro-4,6-diphenylpyridine (3.19 g, 12.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol), (t- Bu) ₃ P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C-117 (7.07 g, yield 75%) of the target compound was obtained by column chromatography.

MS [M + 1] &lt; ⁺ &gt; 942

[Synthesis Example 14] Synthesis of C-120

The procedure of Synthesis Example 13 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.21 g, 12.00 mmol) was used instead of 2-chloro-4,6-diphenylpyridine To obtain the target compound C-120 (7.65 g, yield 81%).

MS [M + 1] &lt; ⁺ &gt; 944

[ Synthetic example  15] Synthesis of C-122

The procedure of Synthetic Example 13 was repeated except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (4.11 g, 12.00 mmol) was used instead of 2-chloro-4,6- -122 (6.27 g, yield 81%).

MS [M + 1] &lt; ⁺ &gt; 1019

[Synthesis Example 16] Synthesis of C-123

The procedure of Synthetic Example 13 was repeated except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.11 g, 12.00 mmol) was used instead of 2-chloro-4,6- -123 (6.22 g, yield 80%).

MS [M + 1] &lt; ⁺ &gt; 1019

[Synthesis Example 17] Synthesis of C-124

Was prepared in the same manner as in Synthesis Example 13 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol) was used in place of 2-chloro-4,6-diphenylpyridine To obtain the target compound C-124 (6.24 g, yield 80%).

MS [M + 1] &lt; ⁺ &gt; 1020

[Synthesis Example 18] Synthesis of C-129

C-129 (5.53 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 13, except that BCZ-2 (5.61 g, 10.00 mmol) was used instead of BCZ-1.

MS [M + 1] &lt; ⁺ &gt; 790

[Synthesis Example 19] Synthesis of C-132

C-132 (5.86 g, yield 74%) was obtained by carrying out the same procedure as in Synthesis Example 14, except that BCZ-2 (5.61 g, 10.00 mmol) was used instead of BCZ-1.

MS [M + 1] &lt; ⁺ &gt; 792

[Synthesis Example 20] Synthesis of C-134

C-134 (6.85 g, yield 79%) was obtained in the same manner as in Synthesis Example 15, except that BCZ-2 (5.61 g, 10.00 mmol) was used instead of BCZ-1.

MS [M + 1] &lt; ⁺ &gt; 867

[Synthesis Example 21] Synthesis of C-135

C-135 (6.80 g, yield 78%) was obtained in the same manner as in Synthesis Example 16, except that BCZ-2 (5.61 g, 10.00 mmol) was used in place of BCZ-1.

MS [M + 1] &lt; ⁺ &gt; 867

[Synthesis Example 22] Synthesis of C-136

C-136 (7.20 g, yield 83%) was obtained in the same manner as in Synthesis Example 17, except that BCZ-2 (5.61 g, 10.00 mmol) was used instead of BCZ-1.

MS [M + 1] &lt; ⁺ &gt; 868

[Synthesis Example 23] Synthesis of C-144

The procedure of Synthesis Example 14 was repeated except that BCZ-3 (5.12 g, 10.00 mmol) was used in place of BCZ-1 to obtain the target compound C-144 (6.46 g, yield 87%).

MS [M + 1] &lt; ⁺ &gt; 743

[Synthesis Example 24] Synthesis of C-148

The procedure of Synthesis Example 17 was repeated except that BCZ-3 (5.12 g, 10.00 mmol) was used instead of BCZ-1 to obtain the target compound C-148 (6.46 g, yield 81%).

MS [M + 1] &lt; ^{+ &} gt ^; 819

[Synthesis Example 25] Synthesis of C-156

C-156 (6.24 g, yield 87%) was obtained in the same manner as in Synthesis Example 14, except that BCZ-4 (4.86 g, 10.00 mmol) was used instead of BCZ-1.

MS [M + 1] &lt; ⁺ &gt; 717

[Synthesis Example 26] Synthesis of C-160

C-160 (6.24 g, yield 87%) was obtained in the same manner as in Synthesis Example 17, except that BCZ-4 (4.86 g, 10.00 mmol) was used in place of BCZ-1.

MS [M + 1] &lt; ⁺ &gt; 793

[Synthesis Example 27] Synthesis of C-164

The procedure of Synthetic Example 14 was repeated except that BCZ-5 (5.02 g, 10.00 mmol) was used instead of BCZ-1 to obtain the target compound C-164 (6.01 g, yield 82%).

MS [M + 1] &lt; ⁺ &gt; 733

[Synthesis Example 28] Synthesis of C-168

The procedure of Synthetic Example 17 was repeated, except that BCZ-5 (5.02 g, 10.00 mmol) was used instead of BCZ-1 to obtain the target compound C-168 (6.47 g, yield 80%).

MS [M + 1] &lt; ⁺ &gt; 809

[Examples 1 to 25] Fabrication of green organic EL device

The compounds synthesized in Synthesis Examples 1 to 9 and 13 to 28 were 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, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

M-MTDATA (60 nm) / TCTA (80 nm) / compound synthesized in Synthesis Examples 1 to 9 and 13-28 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

[ Comparative Example  1 ~ 2] Green organic EL  Device fabrication

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP and Ref-1 were used as luminescent host materials in forming the light emitting layer.

The structure of Ref-1 used is as follows.

[ Evaluation example  One]

Current efficiency and emission peak at the current density (10) mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 1 to 25 and Comparative Examples 1 and 2, Respectively.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 C-10 6.64 517 40.8 Example 2 C-12 6.57 517 40.9 Example 3 C-16 6.46 518 41.9 Example 4 C-28 6.51 518 41.1 Example 5 C-66 6.51 518 41.1 Example 6 C-68 6.59 517 41.7 Example 7 C-94 6.65 518 40.1 Example 8 C-96 6.49 518 41.9 Example 9 C-99 6.59 518 41.5 Example 10 C-117 6.50 519 40.6 Example 11 C-120 6.60 517 41.8 Example 12 C-122 6.55 517 40.9 Example 13 C-123 6.44 516 41.3 Example 14 C-124 6.50 518 41.5 Example 15 C-129 6.45 518 41.5 Example 16 C-132 6.50 519 41.9 Example 17 C-134 6.60 518 40.8 Example 18 C-135 6.45 517 40.5 Example 19 C-136 6.55 518 41.5 Example 20 C-144 6.60 517 41.8 Example 21 C-148 6.60 519 41.5 Example 22 C-156 6.55 517 40.9 Example 23 C-160 6.40 516 41.9 Example 24 C-164 6.50 518 41.8 Example 25 C-168 6.52 518 42.0 Comparative Example 1 CBP 6.93 516 38.2 Comparative Example 2 Ref-1 6.75 517 40.2

As shown in Table 2, the organic EL device of Example 1-25, in which the compound according to the present invention was used as a light emitting layer of a green organic EL device, had a green organic EL of Comparative Examples 1 and 2 using CBP and Ref- Compared with the device, it showed superior performance in terms of efficiency and driving voltage.

[Examples 26 to 28] Preparation of red organic EL device

Compounds (C-25, C-26, C-27) synthesized in Synthesis Examples 10 to 12 were subjected to high purity sublimation purification by a conventionally known method, and red organic electroluminescent devices were fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed using a solvent such as isopropyl alcohol, acetone, and methanol, and the substrate was dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tec). Then, the substrate was cleaned using UV for 5 minutes, The substrate was transferred to an evaporator.

(60 nm) / TCTA (80 nm) / compound of C-25, C-26, C-27 + 10% (piq) ₂ Ir (acac) (30 nm) / BCP 10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[Comparative Example 3] Production of red organic EL device

A red organic electroluminescent device was fabricated in the same manner as in Example 26 except that CBP was used as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 26-28 and Comparative Example 3 are as follows.

[Evaluation Example 2]

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 fabricated in Examples 26 - 28 and Comparative Example 3, and the results are shown in Table 3 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 26 C-81 4.91 13.1 Example 27 C-82 4.95 12.4 Example 28 C-83 4.84 12.6 Comparative Example 3 CBP 5.25 8.2

As shown in Table 3, the organic electroluminescent devices of Examples 26 to 28, in which the compound according to the present invention was used as a material for the light emitting layer of a red organic electroluminescent device, It was found that the organic EL device exhibited excellent performance in terms of efficiency and driving voltage as compared with the organic electroluminescent device.

Claims (9)

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

In Formula 1,
Ar ₁ is a substituent represented by the following formula (2);
(2)

In Formula 2,
L is a single bond, a substituted or unsubstituted C ₆ -C ₄₀ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 40 nucleus atoms;
X ₁ to X ₅ are the same or different and each independently N or C (R ₁₁ ), at least one N,
When two or more of X ₁ to X ₅ are C (R ₁₁ ), a plurality of R _{11 s} are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl 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 ~ C ₄₀ aryl the A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkoxy group, unsubstituted C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C with ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, the substituted or unsubstituted C ₆ of ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl groups, or groups or grain to which they are adjacent To which they are attached may form a condensed ring;
R ₁ to R ₃ are the same or different from each other and each independently selected from the group consisting of deuterium (D), halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl groups, substituted or unsubstituted C ₂ to C ₄₀ alkenes group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted can be a heteroaryl group of from 5 to 40, a substituted or unsubstituted nucleus of atoms of a C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₃ ~ C _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 ₁ to C ₄₀ alkyl group, , a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ Reel phosphine oxide group, and a substituted or non-substituted aryl group is selected from the group consisting of silyl unsubstituted C ₆ ~ C _40;
When plural R ₁ , R ₂ and R ₃ are present, plural R ₁ , R ₂ and R ₃ are the same or different,
a, b and c are each independently an integer of 0 to 5,
In the above L, R ₁ to R ₃ and R ₁₁ , a C ₆ to C ₁₈ arylene group, a heteroarylene group having 5 to 18 nuclear atoms, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C _A C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, C ₆ ~ aryl silyl group of C _40, each independently selected from deuterium, halogen, a cyano group , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to 40 of the C ₆ ~ aryloxy group of C _40, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl of Al Group, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ aryl of C ₄₀ phosphine group may be substituted with one or more substituents selected from aryl phosphine oxide group and an aryl silyl group the group consisting of a C ₆ ~ C ₄₀ of a C ₆ ~ C _40. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (7)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 3 to 7,
Ar ₁ is the same as defined in the above formula (2), each Ar ₁ is the same or different,
Z ₁ is selected from O, S, Se, N ( R 4), C (R 5) (R 6) , and _{Si (R 7) (R 8} )
R ₄ to R ₈ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted aryloxy group of nuclear atoms heteroaryl of 5 to 40 groups, substituted or unsubstituted C ₆ ~ C _40, a substituted or unsubstituted C ₁ ~ alkyloxy group of C ₄₀ of , A substituted or unsubstituted C ₆ to C ₄₀ 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 C ₆ ~ 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 phosphine oxide group, and a substituted or unsubstituted C ₆ of Or an arylsilyl group having a carbon number of from 1 to ₄₀ , or they are bonded to adjacent groups to form a condensed ring Is a compound. 2. The compound according to claim 1, wherein the substituent represented by the formula (2) is selected from the group consisting of substituents represented by the following formulas (A-1) to (A-15).

In the above formulas A-1 to A-15,
L and R &lt; ₁₁ &gt; are as defined in formula (1)
When there are a plurality of R &lt; ₁₁ &gt; s, they are the same as or different from each other,
R ₂₁ represents a hydrogen atom, a heavy hydrogen atom (D), a halogen atom, a cyano group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, A substituted or unsubstituted aryloxy group having 5 to 40 carbon atoms, 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 C ₆ to C ₄₀ aryl An amino 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 arylboron group, An unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, Or they may be bonded to adjacent groups to form a condensed ring,
n is an integer of 0 to 4; 4. The compound according to claim 3, wherein the formulas (A-1) to (A-15) are selected from the group consisting of substituents consisting of the following substituents.

The compound according to claim 1, wherein L is a single bond, a phenylene group or a biphenylene group. The compound according to claim 1, wherein R ₁ to R ₃ are the same or different and each independently represents a C ₆ to C ₄₀ aryl group,
Wherein a plurality of R ₁ to R ₃ are present are the same or different from each other. The compound according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following Formulas C-1 to C-168.

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 according to any one of claims 1 to 7. The organic electroluminescent device according to claim 8, wherein at least one of the one or more organic layers including the compound is a phosphorescent light-emitting layer.