KR20190087283A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More specifically, the present invention relates to: a novel compound having excellent light emitting capability; and the organic electroluminescent device having improved characteristics such as high luminous efficiency, low driving voltage, long lifespan and the like by comprising the same in at least one of organic matter layers.

Description

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

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel compound having excellent light-emitting ability and to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, Device.

A study on organic electroluminescent devices that resulted in blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film emission of Bernanose in the 1950s was conducted by Tang in 1987 divided by the functional layer of the hole layer and the light emitting layer An organic electroluminescent device having a laminated structure has been proposed. Since then, in order to make high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form of introducing a 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 anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

The light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting 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. The development of such a phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

NPB, BCP, Alq3 and the like have been widely known as materials used for the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer. Anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host materials. In particular, as a phosphorescent material having a great advantage in terms of efficiency improvement in a light emitting material, a metal complex compound containing Ir such as Firpic, Ir (ppy) 3, (acac) Ir (btp) . So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional luminescent materials are advantageous in terms of luminescence properties, but they are not satisfactory in terms of lifetime in an organic electroluminescent device because the glass transition temperature is low and the thermal stability is not very good. Therefore, development of a luminescent material having excellent performance is required.

Japanese Patent Application Laid-Open No. 2001-160489

SUMMARY OF THE INVENTION The present invention has been conceived to solve the above-mentioned problems, and it is an object of the present invention to provide an organic electroluminescent device which can be applied to an organic electroluminescent device and which has excellent hole injecting ability, hole transporting ability, And to provide a novel organic compound.

It is another object of the present invention to provide an organic electroluminescent device including the above-described novel organic compound, exhibiting a low driving voltage and a high luminous efficiency, and having an improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

In Formula 1,

X ₁ and X ₂ are the same as or different from each other and each independently O or S,

Y ₁ to Y ₁₆ are the same as or different from each other, and each independently CR ₈ or N, provided that when there are a plurality of CR _{8 s} , the plurality of R _{8 s} are the same as or different from each other,

Z ₁ to Z ₃ are the same or different and each independently CR ₅ or N, at least one of them is N,

Ar ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryl group,

Provided that the X ₁ containing ring and the X ₂ containing ring are asymmetrically bonded to each other based on the Z ₁ to Z ₃ containing ring,

m and n are each an integer of 0 to 3, m + n? 1,

A and B are the same or different from each other, and each independently is any one of substituents represented by the following formulas (2) to (4), with the proviso that the carbazole group is excluded;

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,

* Represents a moiety bonded to Formula 1,

X ₃ is selected from the group consisting of or a single bond, or _{O, S, N (Ar 4} ), C (Ar 5) (Ar 6) and _{Si (Ar 7) (Ar 8} ),

L is a single bond or an arylene group having ₆ to ₄₀ carbon atoms,

Ar ₂ to Ar ₈ 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 ₃ to C ₄₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, with or adjacent groups bonded may form a condensed ring,

a, c, and f are each an integer of 0 to 3,

b, d and e are each an integer of 0 to 4, wherein b + m? 4, d + n? 4,

R ₁ to R ₈ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or adjacent groups combine to form a condensed ring And when R ₁ to R ₇ are each plural, they may be the same or different from each other,

An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkyl group of Ar ₁ to Ar ₈ and R ₁ to R ₈ , A halogen atom, a cyano group, a nitro group, a C ₂ to C ₄₀ alkenyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, alkynyl of _{C 2 ~ C 40, C 3} ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ aryl group of C _60, nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ group of the C ₄₀ alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ consisting of an aryl amine of the , And when the substituent is plural, they may be the same or different from each other.

The present invention also provides an organic electroluminescent device comprising a cathode, 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 a compound represented by the general formula An electroluminescent device is provided.

At least one of the organic compound layers including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emission assist layer, a light emitting layer, an electron transport layer, and an electron injection layer, . At this time, the compound represented by Formula 1 may be used as a phosphorescent host of the light emitting layer.

The compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent 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 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer lifetime than conventional host materials can be manufactured. Further, This improved full color display panel can also be manufactured.

Hereinafter, the present invention will be described in detail.

<Organic compounds>

The novel compounds according to the invention are prepared by reacting a nitrogen-containing heteroaromatic ring (for example azine) with two dibenzo-based moieties (for example dibenzofuran or dibenzothiophene) non-symmetrically bonded to both sides thereof ), And a structure in which an electron donating group (EDG) having a typical electron donor group of the art is connected to at least one phenyl group of the two dibenzo series moieties The skeleton. Herein, the electron donating moiety (EDG) excludes a non-fused ring carbazole group.

Specifically, the compound of Chemical Formula 1 has dibenzo-type moieties (eg, dibenzofuran (DBF), dibenzothiophene (DBT)) having both physicochemical properties with respect to holes and electrons, (Such as pyridine, pyrazine, and triazine) which is a kind of azine group, which is a large electron withdrawing group (EWG), in which the dibenzo series moiety includes indolecarbazole, phenoxazine, phenothiazine, An electron donor group such as amine is connected. Since the compound of Formula 1 is a bipolar compound, the recombination of holes and electrons is high, so that the hole injecting / transporting ability, luminous efficiency, driving voltage, lifetime characteristics, durability and the like can be improved. In particular, when the compound of formula (1) is used as a green phosphorescent material, not only excellent luminous efficiency characteristics but also low voltage driving ability can be obtained and lifetime can be increased, and thermal stability, high glass transition temperature characteristics and uniform morphology morphology). Since the organic EL device is also effective in inhibiting crystallization of the organic material layer, the performance and lifetime characteristics of the organic EL device including the compound can be greatly improved.

In the present invention, the planarity and stereoscopic property of the compound can be realized according to the bonding positions of two dibenzofurans or dibenzothiophene moieties bonded to azine groups. As a result, the electron transporting ability is improved, and the driving and efficiency of the device to which these compounds are applied can be expected to be increased. Furthermore, since the dibenzofuran moiety or the dibenzothiophene moiety is more excellent in electron and hole stability than an aryl group, lifetime characteristics of a device to which such a compound is applied can be further improved. In particular, in the present invention, two dibenzo-based moieties bonded to an azine group exhibit an asymmetric structure. This asymmetric structure compound is easier to control the HOMO-LUMO value than a symmetric structure compound. For example, in the case of an asymmetric structural compound having a dibenzo-based moiety, it is relatively easy to control the intermolecular distance as compared with a compound having a symmetric structure. That is, due to the nature of the dibenzo-based moiety capable of bonding at the 1,2,3,4-position, a structural disorder between the hydrogen of triazine and the dibenzo-based moiety occurs at the 1,4-bond, The distance will be farther away, which will also increase the T1 value. By using the above-mentioned characteristics, it is possible to adjust the HOMO-LUMO and T1 and S1 values of the organic material layer through the asymmetry of the chemical structure.

In addition, in the present invention, various types of electron donor groups (EDG) may be introduced, except for carbazole groups in the form of non-fused rings. As the various EDGs are introduced, the HOMO level of the compound can be freely controlled. In addition, the electron-donating group (EDG) of the polycyclic ring and / or fused ring is excellent in thermal stability and electrochemical stability, and has a high glass transition temperature (Tg) and excellent carrier transporting ability. Particularly, the electron and hole transport mobility is very excellent, and the balance of the carriers in the light emitting layer is very excellent.

On the other hand, in the phosphorescent light emitting layer of the organic electroluminescent device, the host material should have a triplet energy gap 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 Formula 1 has a high triplet energy and can be used as a host material because the energy level can be controlled higher than that of the dopant. The compound represented by the formula (1) can prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Accordingly, the luminous efficiency of the device can be improved by increasing the number of the excitons contributing to the light emission in the light emitting layer, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased.

Due to the above-mentioned matters, the compound represented by the above formula (1) can improve the phosphorescence characteristics of the organic electroluminescent device and improve the electron injection / transport ability, luminous efficiency, driving voltage and lifetime characteristics. Therefore, the compound of Chemical Formula (1) according to the present invention can be used as a material of any one of a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer which is an organic material layer of an organic electroluminescent device, , Green and / or red phosphorescent host material). In particular, when the compound represented by formula (1) of the present invention is used as a blue, green and / or red phosphorescent host material, preferably phosphorescent green n-type host and / or phosphor red host, For example, a full color display panel having a low driving voltage, a high efficiency and a long lifetime compared with the organic electroluminescent device can be manufactured, and a high efficiency and a long life can be improved.

Specifically, the compound represented by the general formula (1) according to the present invention is a compound represented by the general formula (1), which comprises an azine group and two dibenzo-based moieties (dibenzofuran or dibenzothiophene moiety) And at least one electron donor (EDG) is coupled to one of the six-member rings in the core.

In the compound represented by the general formula (1), X ₁ and X ₂ are the same as or different from each other and each independently O or S. At this time, when d is 0, dibenzofuran moiety is formed, and in case of S, dibenzothiophene moiety can be formed.

Y ₁ to Y ₁₆ are the same as or different from each other, and each independently CR ₈ or N; In this case, when there are a plurality of CR _{8 s} , the plurality of R _{8 s} may be the same or different. For example, when at least one of Y ₁ to Y ₄ is N, the remaining is CR ₈ ; When at least one of Y ₁₃ to Y ₁₆ is N, the remaining is CR ₈ ; At least one of Y ₁ to Y ₄ is N, and at least one of Y ₉ to Y ₁₂ is N, the remainder is CR ₈ ; At least one of Y ₅ to Y ₈ is N, and at least one of Y ₁₃ to Y ₁₆ is N, the remainder is CR ₈ ; At least one of Y ₁ to Y ₄ is N, and when one of Y ₁₃ to Y ₁₆ is N, the remaining is CR ₈ ; Y ₁ to Y ₁₆ may all be CR ₈ (see the following formulas 9 to 13).

Wherein, R ₈ is hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, an alkynyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C group ₁ ~ C ₄₀ alkyl silyl, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a _{C 6 ~ C 60, C 1} ~ C ₄₀ phosphine groups, C ₁ to C ₄₀ phosphine oxide groups, and C ₆ to C ₆₀ arylamine groups. Specifically, R ₈ is a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of the A cycloalkyl group, and a C ₆ to C ₆₀ aryl group.

Z ₁ to Z ₃ are the same or different and are each independently CR ₅ or N, and at least one of them is N. In one preferred embodiment, from ₁ to ₃ of Z ₁ to Z ₃ may be N, for example, pyridine, pyrimidine, triazine. More preferably, all of Z ₁ to Z ₃ are N and triazine is electron-withdrawing.

Ar ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryl group, and the like. Specifically, Ar ₁ is preferably an aryl group of C ₆ to C ₆₀ , and may be, for example, a phenyl group, a biphenyl group, a naphthyl group, a triphenyl group, an anthryl group, a phenanthryl group and the like.

In one embodiment of the present invention, Ar ₁ can be selected from the group of substituents represented by the following structural formulas.

At this time, although not shown in the above-mentioned structural formula, Ar ₁ may be substituted with at least one substituent group known in the art (for example, the same definition as R ₆ ).

a and c are each an integer of 0 to 3, and b and d are an integer of 0 to 4, respectively. When a to d are 0, hydrogen means not substituted with R ₁ to R ₄ , and when a to d are each an integer of 1 or more, one or more hydrogen atoms are substituted with R ₁ to R ₄ . it means.

R ₁ to R ₅ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or adjacent groups combine to form a condensed ring . Here, when R ₁ to R ₅ each are plural, they are the same as or different from each other. Specifically, R ₁ to R ₅ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ An alkynyl group of C ₄₀ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , and an aryl group of C ₆ to C ₆₀ .

m and n are each an integer of 0 to 3, and m + n? 1. When m or n is 0, it means that hydrogen is not substituted with A or B. When m and n are each an integer of 1 or more, it means that at least one hydrogen is substituted with A and B, respectively. Preferably, m and n may each be an integer of 0 to 2. For example, m = 1, n = 0; m = 0, n = 1; m = 1, n = 1; m = 2, n = 0; m = 0, n = 2. More preferably, m = 1, n = 0 or m = 1 and n = 1. That is, at least one of A and B described later may exist.

And b + m and d + n may be an integer of 0 to 4, respectively. Preferably, when b + m = 1, d + n = 0 or d + n = 1.

In the formula (1) of the present invention, A and B are electron donating substituents each of which serves to provide electrons. In the present invention, an electron donating group (EDG) known in the art, except for a carbazole group in the form of a non-fused ring, can be used without limitation. For example, A and B are each a polycyclic carbazole-based moiety such as a condensed ring or a fused ring (for example, a condensed carbazole, an indolocarbazole, a bicarbazole), a phenoxazine, a phenothiazine, have. Specifically, A and B are the same as or different from each other, and each independently may be any of the substituents represented by the above formulas (2) to (4).

In the substituent represented by the formula 2 and 3, X ₃ is made of either a single bond, or _{O, S, N (Ar 4} ), C (Ar 5) (Ar 6) and _{Si (Ar 7) (Ar 8} ) Can be selected from the group. When X &lt; ₃ &gt; is a single bond, the condensed ring and / or fused ring type polycyclic carbazole-based moiety (e.g., condensed carbazole, indolocarbazole, etc.) Carbazole in the form of a linked bis-carbazole. When X &lt; ₃ &gt; is O or S, phenoxazine or phenothiazine can be formed.

e is an integer of 0 to 4, and f is an integer of 0 to 3. When e and f are each 0, hydrogen means not substituted by R ₆ and R ₇ , and when e and f are each an integer of 1 or more, at least one hydrogen is substituted with R ₆ and R ₇ respectively .

Wherein, R ₆ and R ₇ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ a group of the arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or, or in adjacent groups combine a condensed ring . When R ₆ and R ₇ are plural, they may be the same as or different from each other. , For one preferred embodiment, R ₆ and R ₇ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ A C ₃ to C ₄₀ cycloalkyl group, and a C ₆ to C ₆₀ aryl group, or may be bonded to adjacent groups to form a condensed ring. At this time, adjacent groups may be one R ₆ and one R ₆ , one R ₆ and one Ar ₂ , one R ₇ and another R ₇ , one R _7, and one Ar ₂ .

In the substituent represented by Formula 4, L may be a divalent group linker known in the art. Specifically, L is a single bond or an arylene group having ₆ to ₄₀ carbon atoms. When L is a C ₆ to C ₄₀ arylene group, it may be a phenylene group, a biphenylene group, a naphthylene group, a triphenylene group or the like, preferably a phenylene group or a biphenylene group.

In the substituents represented by the above formulas 2 to 4, Ar ₂ and Ar ₈ 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 alkoxy group, C ₃ ~ C ₄₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, or adjacent groups combined To form a condensed ring. Specifically, said Ar ₂ and Ar ₈ are the same or different from each other, and each independently C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ . &Lt; / RTI &gt;

In an embodiment of the present invention, A and B are the same as or different from each other, and each independently can be any one selected from the group of substituents represented by the following structural formulas.

In the above formulas,

* Represents a moiety bonded to Formula 1,

E is selected from the group consisting of O, S, NR ₁₁ , CR ₁₂ R ₁₃ , and SiR ₁₄ R ₁₅ ,

A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted alkyl group having 5 to 5 nucleus atoms, wherein R ₁₁ to R ₁₅ are the same or different and each independently represents hydrogen, deuterium, Lt; / RTI &gt; to 60, and &lt; RTI ID = 0.0 &gt;

Ar ₁₁ is hydrogen or a C ₆ to C ₆₀ aryl group,

Ar &lt; ₂ &gt; and Ar &lt; ₃ &gt; Although not specifically shown, the above-mentioned structural formula may be substituted with at least one substituent group known in the art (for example, the same definition as R ₆ ).

In the above-described formula (1), a compound represented by formula (1) wherein L is an arylene group, Ar ₁ to Ar ₈ , and R ₁ to R ₈ are an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, , an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently selected from deuterium, halogen, a cyano group, a nitro group, a C ₂ ~ alkenyl of C ₄₀ group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ aryl of C ₄₀ alkyl group, C ₆ ~ C ₆₀ of group, nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and a C ₆ ~ C ₆₀ Ah It may be substituted with one or more substituent species selected from the group consisting of an amine group, and wherein when the substituent is plural, they may be the same or different from each other.

In accordance with the present invention compound represented by the formula (1), the nitrogen-containing heterocycle having an EWG properties (such as, Z ₁ ~ Z ₃ containing ring) 2 dibenzo-based moiety that is bonded to (for example, X ₁ hamyuhwan and X _2- containing rings) according to the positions of the carbon bonds of the asymmetric structure. Specifically, the bonding position of one of Y ₁ to Y ₄ of the X ₁ containing ring connected to the Z ₁ to Z ₃ containing ring and the bonding position of one of Y ₉ to Y ₁₂ of the X ₂ containing ring are asymmetric with each other . In one example, the O rare cases (for example, Z ₁ ~ Z _3-containing ring) is X ₁ containing ring carbon position coupled to Y ₁ il, X ₂ containing ring carbon position which is bonded to the azine is Y ₁₀ to the exception of Y ₉ Y ₁₂ (see Chemical Formula 5 below). The carbon bond positions of two dibenzo-based moieties respectively linked to the nitrogen-containing heterocycle may be represented by any one of the following formulas (5) to (8).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 5 to 8,

The ring containing Z ₁ to Z _{3 in} Formula 5 is bonded to any one of Y ₁₀ to Y ₁₂ (provided that the ring containing Z ₁ to Z ₃ is not bonded to Y ₉ )

The ring containing Z ₁ to Z _{3 in} Formula 6 is bonded to any one of Y ₉ and Y ₁₁ to Y ₁₂ (provided that the ring containing Z ₁ to Z ₃ is not bonded to Y ₁₀ )

The Z ₁ to Z ₃ -containing ring of formula (7) is bonded to any one of Y ₉ , Y ₁₀ and Y ₁₂ (provided that the Z ₁ to Z ₃ containing ring is not bonded to Y ₁₁ )

The ring containing Z ₁ to Z _{3 in} Formula 8 is bonded to any one of Y ₉ to Y ₁₁ (provided that the ring containing Z ₁ to Z ₃ is not bonded to Y ₁₂ )

X ₁ , X ₂ , Y ₁ to Y ₁₆ , Z ₁ to Z ₃ , Ar ₁ , m, n, A, B, a to d and R ₁ to R ₄ are as defined in Formula 1, respectively.

In one embodiment of the present invention, the compound represented by Formula 5 may be further represented by any one of Formulas 5a to 5c.

[Chemical Formula 5a]

[Chemical Formula 5b]

[Chemical Formula 5c]

In another embodiment of the present invention, the compound represented by Formula 6 may be further represented by any one of Formulas 6a to 6c.

[Chemical Formula 6a]

[Formula 6b]

[Chemical Formula 6c]

In another embodiment of the present invention, the compound represented by the above formula (7) may be further represented by any one of formulas (7a) to (7c).

[Formula 7a]

[Formula 7b]

[Formula 7c]

In another embodiment of the present invention, the compound represented by the formula (8) may be further represented by any one of formulas (8a) to (8c).

[Chemical Formula 8a]

[Formula 8b]

[Chemical Formula 8c]

In the compound represented by Formula 1, dibenzo-based moieties such as dibenzofurane or dibenzothiophene moiety may be further represented by any one of the following formulas (9) to (13).

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above formulas (9) to (13)

X ₁ , X ₂ , Z ₁ to Z ₃ , Ar ₁ , n, A and B are as defined in the above formula (1).

More specifically, X ₁ and X ₂ are each independently O or S, and Z ₁ to Z ₃ are each independently CR ₅ or N, both of which are represented by the following formulas Is N, Ar ₁ is a C ₆ to C ₆₀ aryl group, and the carbon position of the X ₁ -containing ring and the carbon position of the X ₂ -containing ring bonded to the azine group (for example, Z ₁ to Z ₃ -containing rings) Structure.

At least one of A and B may be selected from the substituent groups of A and B exemplified above. Provided that A and B are unsubstituted carbazole groups.

The compounds represented by formula (1) according to the present invention described above can be further represented by compounds represented by any of compounds 1 to 222 exemplified below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

"Alkenyl" in the present invention means 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 double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

The term "alkynyl" in the present invention means 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 of such alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.

"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 of the ring, preferably 1 to 3 carbons, Or &lt; RTI ID = 0.0 &gt; Se. &Lt; / RTI &gt; Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

"Aryl" in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having 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 60 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, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, and R 'means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include linear, branched or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

"Alkylsilyl" in the present invention refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "alkyl boron" is boron substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron" means boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms, and "arylphosphine oxide group" means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O do.

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.

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

The compounds represented by formula (1) of the present invention can be prepared without limitation by methods known in the art. For example, various syntheses can be carried out by referring to the synthesis process of the following examples.

&Lt; Organic electroluminescent device &

The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).

More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Specifically, the organic compound layer containing the compound of Formula 1 is preferably a light emitting layer.

The light emitting layer of the organic electroluminescence device of the present invention may include a host material (preferably, a phosphorescent host material). The light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode sequentially stacked Structure. At least one of the hole injecting layer, the hole transporting layer, the light-emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, &Lt; / RTI &gt; compounds. Further, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.

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 used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and 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); A combination of a metal and an oxide such as ZnO: Al or SnO2: 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.

Examples of the negative electrode material 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 LiO2 / 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 ordinary materials known in the art can be used.

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

[Preparation example]

[Preparation Example 1] Synthesis of DF-1

Synthesis of 2- (9-chlorodibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

8-bromo-1-chlorodibenzo [b, d] furan 2.9 g of 4,4,4,4,5,5,5,5-octamethyl-2,2'- -dioxaborolane (2.6 g), Pd (dppf) Cl _{2 (} 0.7 g) and potassium acetate (2.9 g) were added to 100 ml of 1,4-dioxane and stirred at 110 ° C for 8 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated, and purified by column chromatography to obtain the target compound, 2- (9-chlorodibenzo [b, d] furan- 4,5,5-tetramethyl-1,3,2-dioxaborolane (2.5 g, yield 71%).

1 H-NMR:? 7.72 (s, 1H), 7.60 (d, 1H), 7.47-7.42 (m, 2H), 7.28

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 330

<Step 2> Synthesis of DF-1

2- (9-chlorodibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 3.2 g of 2-chloro-4- (dibenzo [b, ] furan-1-yl) -6 -phenyl-1,3,5-triazine 3.5 g, Pd (PPh 3) 4 0.3 g, K 2 CO 3 2.7 g for 100 ml Toluene / Ethanol 25 ml / H ₂ O 25 ml and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 3.5 g , Yield: 67%).

(D, 2H), 7.98 (d, IH), 7.82-7.70 (m, 4H)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 2] Synthesis of DF-2

Synthesis of 2- (8-chlorodibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-bromo-8-chlorodibenzo [b, d] furan 3.0 g of 4,4,4 ', 4,5,5,5,5-octamethyl-2,2'- -dioxaborolane (2.8 g), Pd (dppf) Cl _{2 (} 0.7 g) and potassium acetate (2.9 g) were added to 100 ml of 1,4-dioxane and stirred at 110 ° C for 8 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography to obtain the objective compound, 2- (8-chlorodibenzo [b, d] furan- 4,5,5-tetramethyl-1,3,2-dioxaborolane (2.9 g, yield 72%).

1 H-NMR:? 7.72 (s, 2H), 7.60 (d, 1 H), 7.49-7.40 (m, 3H)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 330

<Step 2> Synthesis of DF-2

A solution of 3.5 g of 2-chloro-4- (dibenzo [b, d (4-fluorophenyl) ] furan-1-yl) -6 -phenyl-1,3,5-triazine 3.8 g, Pd (PPh 3) 4 0.3 g, K 2 CO 3 2.7 g for 100 ml Toluene / Ethanol 25 ml / H ₂ O 25 ml and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 3.7 g , Yield: 66%).

(D, 2H), 7.98 (d, IH), 7.82-7.70 (m, 4H)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 3] Synthesis of DF-3

Synthesis of 2- (7-chlorodibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-bromo-7-chlorodibenzo [b, d] furan 3.0 g of 4,4,4,4,5,5,5,5-octamethyl-2,2'- -dioxaborolane (2.8 g), Pd (dppf) Cl _{2 (} 0.7 g) and potassium acetate (2.9 g) were added to 100 ml of 1,4-dioxane and stirred at 110 ° C for 8 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography to obtain 2- (7-chlorodibenzo [b, d] furan- 4,5,5-tetramethyl-1,3,2-dioxaborolane (2.8 g, yield 70%).

1 H-NMR:? 7.72 (s, 1H), 7.60 (d, 1H), 7.45-7.40 (m, 2H), 7.30

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 330

<Step 2> Synthesis of DF-3

A solution of 3.3 g of 2-chloro-4- (dibenzo [b, d (3-chloro-2- ] furan-1-yl) -6 -phenyl-1,3,5-triazine 3.6 g, Pd (PPh 3) 4 0.3 g, K 2 CO 3 2.8 g for 100 ml Toluene / Ethanol 25 ml / H ₂ O 25 ml and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 3.5 g , Yield: 65%).

(D, 2H), 7.78 (d, IH), 7.78-7.65 (m, 5H), 7.55-7.30

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 4] Synthesis of DF-4

Synthesis of N- (4- (8-chlorodibenzo [b, d] furan-1-yl) phenyl) -N-phenyldibenzo [b,

1-bromo-8-chlorodibenzo [ b, d] furan 5.3 g, (4- (dibenzo [b, d] furan-3-yl (phenyl) amino) phenyl) boronic acid 6.2 g, Pd (PPh 3) 4 0.5 g and 3.2 g of K ₂ CO ₃ were added to 100 ml of Toluene / 25 ml of ethanol / 25 ml of H ₂ O and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain N- (4- Dibenzo [b, d] furan-3-amine (4.6 g, yield 54%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 538

<Step 2> Synthesis of DF-4

Phenyl) -N-phenyldibenzo [b, d] furan-3-amine 3.0 g, 4,4,4 ', 4', 5 ' 2.2 g of 5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane), 0.5 g of Pd (dppf) Cl _{2 and} 2.2 g of potassium acetate were dissolved in 100 ml of 1,4- And the mixture was stirred at 110 ° C for 8 hours. After the completion of the reaction, the reaction mixture was extracted with methylene chloride. The organic layer was dried over magnesium sulfate and concentrated to obtain DF-4 (2.4 g, yield 65%) as a target compound by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 629

[Preparation Example 5] Synthesis of DF-5

5.5 g of 2-chloro-4- (dibenzo [b, d (2-chloro-4- ] furan-1-yl) -6 -phenyl-1,3,5-triazine 5.8 g, Pd (PPh 3) 4 0.5 g, K 2 CO 3 3.7 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O 50 ml and the mixture was stirred at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 5.4 g , Yield: 66%).

2H), 7.85 (d, IH), 7.85 (d, 2H), 7.80-7. 73 (m, 4H)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 6] Synthesis of DF-6

To a solution of 5.8 g of 2-chloro-4- (dibenzo [b, d (3-fluorophenyl) ] furan-1-yl) -6 -phenyl-1,3,5-triazine 6.2 g, Pd (PPh 3) 4 0.5 g, K 2 CO 3 3.7 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O 50 ml, and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 5.6 g , Yield: 65%).

2H), 7.75 (d, 2H), 7.55-7.30 (m, 7H), 7.15 (d, 2H)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 7] Synthesis of DF-7

A solution of 5.3 g of 2-chloro-4- (dibenzo [b, d (4-fluorophenyl) ] furan-1-yl) -6 -phenyl-1,3,5-triazine 5.6 g, Pd (PPh 3) 4 0.5 g, K 2 CO 3 3.9 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O 50 ml, and the mixture was stirred at 100 ° C for 6 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 5.3 g , Yield: 67%).

(D, 2H), 7.95 (d, IH), 7.82-7.66 (m, 5H), 7.58-7.30

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 8] Synthesis of DF-8

5.5 g of 2-chloro-4- (dibenzo [b, d (4-fluorophenyl) ] furan-2-yl) -6 -phenyl-1,3,5-triazine 5.8 g, Pd (PPh 3) 4 0.5 g, K 2 CO 3 3.6 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O 50 ml and the mixture was stirred at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 5.4 g , Yield: 66%).

2H), 7.50-7.30 (m, 8H), 7.15 (d, 2H), 7.80 (d,

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 9] Synthesis of DF-9

A solution of 4.8 g of 2-chloro-4- (dibenzo [b, d (4-fluorophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane ] furan-2-yl) -6 -phenyl-1,3,5-triazine 5.1 g, Pd (PPh 3) 4 0.4 g, K 2 CO 3 3.5 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O 50 ml and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain the desired compound DF-9 (4.9 g, Yield: 68%).

(D, 2H), 7.50-7.30 (m, 9H), 7.15 (d, 2H)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 10] Synthesis of DF-10

To a solution of 5.0 g of 2-chloro-4- (dibenzo [b, d (4-fluorophenyl) -1,2,3,4-tetrahydroisoquinolin- ] furan-2-yl) -6 -phenyl-1,3,5-triazine 5.3 g, Pd (PPh 3) 4 0.5 g, K 2 CO 3 3.5 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O 50 ml and the mixture was stirred at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 4.9 g , Yield: 64%).

2H), 7.60 (s, IH), 7.55-7.35 (m, 9H), 7.15 (d, 2H)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 11] Synthesis of DF-11

5.5 g of 2-chloro-4- (dibenzo [b, d (4-fluorophenyl) ] furan-4-yl) -6- (naphthalen-2-yl) -1,3,5-triazine 5.8 g, Pd (PPh 3) 4 0.5 g, K 2 CO 3 3.7 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O (50 ml), and the mixture was stirred at 100 ° C for 4 hours. After the completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 5.2 g , Yield: 63%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Preparation Example 12] Synthesis of DF-12

A solution of 5.8 g of 2-chloro-4- (dibenzo [b, d (2-chloro-4- ] furan-4-yl) -6- (naphthalen-2-yl) -1,3,5-triazine 6.1 g, Pd (PPh 3) 4 0.6 g, K 2 CO 3 4.1 g for 200 ml Toluene / Ethanol 50 ml / H ₂ O (50 ml), and the mixture was stirred at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was deactivated with a sufficient amount of water. The solution was transferred to a separatory funnel and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and purified by column chromatography to obtain 5.8 g , Yield: 65%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

[Synthesis Example 1] Synthesis of Compound 1

5.2 g of DF-1, 2.5 g of diphenylamine, 0.5 g of Pd ₂ (dba) ₃ , 0.2 g of tri-tert-butylphosphine and 1.9 g of sodium tert-butoxide were added to 100 ml of xylene and the mixture was heated and stirred at 100 ° C for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with methylene chloride, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 1 (4.0 g, yield 60%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 658

[Synthesis Example 2] Synthesis of Compound 2

6.3 g of DF-2, 4.5 g of 10H-phenoxazine, 0.6 g of Pd ₂ (dba) ₃ , 0.3 g of tri-tert-butylphosphine and 2.0 g of sodium tert-butoxide were placed in 100 ml of xylene, Respectively. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the objective compound 2 (4.5 g, yield 58%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 672

[Synthesis Example 3] Synthesis of Compound 3

600 g of DF-3, 4.3 g of 10H-phenothiazine, 0.6 g of Pd ₂ (dba) ₃ , 0.3 g of tri-tert-butylphosphine and 2.0 g of sodium tert-butoxide were placed in 100 ml of xylene, Respectively. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 3 (4.1 g, yield 56%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 668

[Synthesis Example 4] Synthesis of Compound 13

6.2 g of 2-chloro-4- (dibenzo [b, d] thiophen-1-yl) -6-phenyl-1,3,5-triazine and 3.0 g of Cs ₂ CO ₃ were mixed with 5.8 g of DF- , 20 ml of ethanol and 20 ml of water were added, and then 0.1 g of Pd (OAc) ₂ and 0.5 g of Xphos were added thereto, followed by heating and stirring for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with methylene chloride, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 13 (4.0 g, yield 52%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 840

[Synthesis Example 5] Synthesis of Compound 16

A mixture of 3.0 g of DF-5, 2.8 g of 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole and 0.3 g of Pd ₂ (dba) ₃ , 0.1 g of tri-tert-butylphosphine and 1.2 g of sodium tert- And the mixture was heated and stirred at 100 ° C for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with methylene chloride, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 16 (2.6 g, yield 58%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 821

[Synthesis Example 6] Synthesis of Compound 17

3.4 g of 5H-benzofuro [3,2-c] carbazole and 0.4 g of Pd ₂ (dba) ₃ , 0.2 g of tri-tert-butylphosphine and 1.5 g of sodium tert-butoxide were placed in 100 ml of toluene, C &lt; / RTI &gt; for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with methylene chloride, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 17 (3.2 g, yield 65%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 746

[Synthesis Example 7] Synthesis of Compound 18

4.2 g of DF-7, 4.2 g of 12,12-dimethyl-11,12-dihydroindeno [2,1-a] carbazole and 0.5 g of Pd ₂ (dba) ₃ , 0.2 g of Tri-tert-butylphosphine, g was added to 100 ml of xylene, and the mixture was heated and stirred at 100 ° C for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with methylene chloride, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 18 (4.3 g, yield 57%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 772

[Synthesis Example 8] Synthesis of Compound 21

Compound 21 (2.8 g, yield: 58%) was prepared in the same manner as in Synthesis Example 1, except that DF-8 was used instead of DF-1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 658

[Synthesis Example 9] Synthesis of Compound 22

Compound 22 (5.2 g, yield: 61%) was prepared in the same manner as in Synthesis Example 2, except that DF-9 was used instead of DF-2.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 672

[Synthesis Example 10] Synthesis of Compound 23

Compound 23 (3.8 g, yield 55%) was prepared in the same manner as in Synthesis Example 3, except that DF-10 was used instead of DF-3.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 688

[Synthesis Example 11] Synthesis of Compound 155

4.9 g of DF-11, 4.9 g of 10H-phenothiazine, 0.5 g of Pd ₂ (dba) ₃ , 0.2 g of tri-tert-butylphosphine and 1.9 g of sodium tert-butoxide were placed in 100 ml of xylene, Respectively. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with methylene chloride, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 155 (3.4 g, yield 55%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 948

[Synthesis Example 12] Synthesis of Compound 156

Compound 156 (5.2 g, yield: 58%) was prepared in the same manner as in Synthesis Example 5, except that DF-12 was used instead of DF-5.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 871

[Synthesis Example 13] Synthesis of Compound 157

Compound 157 (5.8 g, yield 65%) was prepared in the same manner as in Synthesis Example 6, except that DF-13 was used instead of DF-6.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 796

[Synthesis Example 14] Synthesis of Compound 181

Compound 181 (3.5 g, yield 51%) was prepared in the same manner as in Synthesis Example 1, except that DF-14 was used in place of DF-1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 658

[Synthesis Example 15] Synthesis of Compound 182

Compound 182 (4.8 g, yield 55%) was prepared in the same manner as in Synthesis Example 2, except that DF-15 was used in place of DF-2.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 672

[Synthesis Example 16] Synthesis of Compound 183

Compound 183 (5.1 g, yield 59%) was prepared in the same manner as in Synthesis Example 3, except that DF-16 was used instead of DF-3.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 688

[Synthesis Example 17] Synthesis of Compound 196

Compound 196 (4.8 g, yield 51%) was prepared in the same manner as in Synthesis Example 6, except that DF-17 was used instead of DF-6.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 746

[Synthesis Example 18] Synthesis of Compound 197

Compound 197 (4.8 g, yield 58%) was prepared in the same manner as in Synthesis Example 7, except that DF-18 was used in place of DF-7.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 848

[Synthesis Example 19] Synthesis of Compound 198

4.5 g of Pd ₂ (dba) _{3 and} 0.5 g of tri-n-butyllithium were added to a mixture of 5.3 g of DF-19 and N - ([1,1'-biphenyl] 0.2 g of tert-butylphosphine and 2.0 g of sodium tert-butoxide were placed in 100 ml of xylene, and the mixture was heated and stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 198 (4.6 g, yield 54%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 927

[Synthesis Example 20] Synthesis of Compound 199

Sodium tert-butoxide 2.0 g, 0.6 g of Pd ₂ (dba) ₃ , 0.3 g of tri-tert-butylphosphine, 2.0 g of 10-phenyl-10H, 10'H-9,9'-spirobi [acridine] g was added to 100 ml of xylene, and the mixture was heated and stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate, and dried over MgSO ₄ . The dried organic layer was concentrated under reduced pressure, and the desired compound 199 (5.6 g, yield 62%) was prepared by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 962

[Examples 1 to 20] Fabrication of green organic electroluminescent device

The compounds synthesized in Synthesis Examples 1 to 20 were subjected to high purity sublimation purification by a conventionally known method, and a green 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, 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.

(60 nm) / TCTA (80 nm) / 90% of the above exemplified compound + 10% of 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 electroluminescent device.

[Comparative Example 1] Production of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound 1 as a luminescent host material in forming the light emitting layer.

[Comparative Example 2] Production of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound I was used instead of Compound 1 as a luminescent host material in forming the light emitting layer.

[Comparative Example 3] Production of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound II was used instead of Compound 1 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP, BCP, Compound I and Compound II used in Examples 1 to 20 and Comparative Examples 1 to 3 of the present invention are as follows.

[Evaluation Example 1]

The driving voltage, current efficiency and emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Examples 1 to 3, Respectively.

Sample Host Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 1 One 4.83 515 53.2 Example 2 2 4.96 516 57.1 Example 3 3 5.08 515 55.4 Example 4 13 4.87 517 49.1 Example 5 16 4.97 516 51.7 Example 6 17 4.99 514 53.1 Example 7 18 4.70 515 51.2 Example 8 21 4.76 513 50.6 Example 9 22 4.98 515 51.8 Example 10 23 4.97 516 48.9 Example 11 155 4.67 517 51.0 Example 12 156 4.97 518 50.3 Example 13 157 4.89 519 53.5 Example 14 181 4.55 516 50.3 Example 15 182 5.09 515 48.3 Example 16 183 4.87 516 48.2 Example 17 196 4.98 515 50.1 Example 18 197 4.78 514 51.2 Example 19 198 4.67 517 50.2 Example 20 199 4.98 516 49.8 Comparative Example 1 CBP 6.93 516 38.2 Comparative Example 2 Compound I 5.67 516 42.1 Comparative Example 3 Compound II 5.55 516 41.2

As shown in Table 1, the green organic electroluminescent devices of Examples 1 to 20, in which the compound according to the present invention was applied to the light emitting layer, were prepared in the same manner as the green organic electroluminescent devices of Comparative Examples 1 to 3 in which CBP, It was found that the current efficiency and the driving voltage were superior to those of the electroluminescent device.

Claims (10)

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

In Formula 1,
X ₁ and X ₂ are the same as or different from each other and each independently O or S,
Y ₁ to Y ₁₆ are the same as or different from each other, and each independently CR ₈ or N, provided that when there are a plurality of CR _{8 s} , the plurality of R _{8 s} are the same as or different from each other,
Z ₁ to Z ₃ are the same or different and each independently CR ₅ or N, at least one of them is N,
Ar ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryl group,
Provided that the X ₁ containing ring and the X ₂ containing ring are asymmetrically bonded to each other based on the Z ₁ to Z ₃ containing ring,
m and n are each an integer of 0 to 3, m + n? 1,
A and B are the same or different from each other, and each independently is any one of substituents represented by the following formulas (2) to (4), except that the carbazole group is excluded;
(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,
* Represents a moiety bonded to Formula 1,
X ₃ is selected from the group consisting of or a single bond, or _{O, S, N (Ar 4} ), C (Ar 5) (Ar 6) and _{Si (Ar 7) (Ar 8} ),
L is a single bond or an arylene group having ₆ to ₄₀ carbon atoms,
Ar ₂ to Ar ₈ 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 ₃ to C ₄₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, with or adjacent groups bonded may form a condensed ring,
a, c, and f are each an integer of 0 to 3,
b, d and e are each an integer of 0 to 4, wherein b + m? 4, d + n? 4,
R ₁ to R ₈ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or adjacent groups combine to form a condensed ring And when R ₁ to R ₇ are each plural, they may be the same or different from each other,
An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkyl group of Ar ₁ to Ar ₈ and R ₁ to R ₈ , A halogen atom, a cyano group, a nitro group, a C ₂ to C ₄₀ alkenyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, alkynyl of _{C 2 ~ C 40, C 3} ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ aryl group of C _60, nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ group of the C ₄₀ alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ consisting of an aryl amine of the , And when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
The compound represented by the formula (1) is a compound represented by any one of the following formulas (5) to (8)
[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 5 to 8,
The ring containing Z ₁ to Z _{3 in} Formula 5 is bonded to any one of Y ₁₀ to Y ₁₂ (provided that the ring containing Z ₁ to Z ₃ is not bonded to Y ₉ )
The ring containing Z ₁ to Z _{3 in} Formula 6 is bonded to any one of Y ₉ and Y ₁₁ to Y ₁₂ (provided that the ring containing Z ₁ to Z ₃ is not bonded to Y ₁₀ )
The Z ₁ to Z ₃ -containing ring of formula (7) is bonded to any one of Y ₉ , Y ₁₀ and Y ₁₂ (provided that the Z ₁ to Z ₃ containing ring is not bonded to Y ₁₁ )
The ring containing Z ₁ to Z _{3 in} Formula 8 is bonded to any one of Y ₉ to Y ₁₁ (provided that the ring containing Z ₁ to Z ₃ is not bonded to Y ₁₂ )
X ₁ , X ₂ , Y ₁ to Y ₁₆ , Z ₁ to Z ₃ , Ar ₁ , m, n, A, B, a to d and R ₁ to R ₄ are as defined in claim 1, respectively. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (9) to (13).
[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above formulas (9) to (13)
X ₁ , X ₂ , Z ₁ to Z ₃ , Ar ₁ , n, A and B are as defined in claim 1, respectively. The method according to claim 1,
Wherein Z ₁ to Z ₃ are all N. The method according to claim 1,
Wherein A and B are the same or different from each other, and each independently selected from the group consisting of substituents represented by the following structural formulas.

In the above formulas,
* Represents a moiety bonded to Formula 1,
E is selected from the group consisting of O, S, NR ₁₁ , CR ₁₂ R ₁₃ , and SiR ₁₄ R ₁₅ ,
A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted alkyl group having 5 to 5 nucleus atoms, wherein R ₁₁ to R ₁₅ are the same or different and each independently represents hydrogen, deuterium, Lt; / RTI &gt; to 60, and &lt; RTI ID = 0.0 &gt;
Ar ₁₁ is hydrogen or a C ₆ to C ₆₀ aryl group,
Ar &lt; _{2 &gt;} and Ar &lt; ₃ &gt; are as defined in claim 1, respectively. The method according to claim 1,
Wherein Ar &lt; ₁ &gt; is any one selected from the substituent groups represented by the following structural formulas.

The method according to claim 1,
R ₁ to R ₅ and R ₈ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ An alkynyl group of C ₄₀ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , and an aryl group of C ₆ to C ₆₀ ,
Wherein R ₆ and R ₇ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ A cycloalkyl group having ₃ to ₄₀ carbon atoms, an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 nuclear atoms, or is bonded to an adjacent group to form a condensed ring. 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 according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. 10. The method of claim 9,
Wherein the organic compound layer containing the compound is a phosphorescent light-emitting layer.