KR20170075524A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

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

Description

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

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, Tang The organic light emitting device having a laminated structure in which the hole layer and the functional layer of the light emitting layer are divided. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into 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 to realize better natural colors. 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. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP and Alq ₃ are widely known as electron transporting layer materials and anthracene derivatives as light emitting layer materials. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.

However, conventional organic material layers are advantageous from the viewpoint of light emitting properties, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of the organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

The present invention has been made to solve the above problems and it is an object of the present invention to provide a novel compound capable of improving the efficiency, lifetime and stability of the organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ is an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms;

The aryl and heteroaryl groups of Ar ₁ and the arylene and heteroarylene groups of L ₁ to L ₄ are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl A boron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group When they are substituted or unsubstituted with one or more substituents and when they are substituted with a plurality of substituents, they may be the same or different;

Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group consisting of the groups represented by the following formulas A-1 to A-24, wherein Ar ₂ and Ar ₃ are different from each other;

In the above Formulas A-1 to A-24,

* Denotes the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₇ );

Y ₁ and Y ₂ are each independently selected from the group consisting of a single bond, C (R ₈ ) (R ₉ ), N (R ₁₀ ), O and S, but not both Y ₁ and Y ₂ are single bonds;

m and n are each independently an integer of 0 to 4;

l is an integer from 0 to 3;

R ₁ and R ₂ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ 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 arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, and groups binding to selected or adjacent from the group consisting of C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ with an aryl amine of the C ₆₀ to which they are attached may form a fused ring, wherein R ₁ and When there are a plurality of R < ₂ > s, they are the same as or different from each other;

R ₃ to R ₁₀ are each independently 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 alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C group ₆₀ arylamine of the combined groups is selected or adjacent from the group consisting they are attached may form a fused ring, wherein R ₇ to R < ₁₀ > each are the same or different from each other;

Alkyl group of the R ₁ to R _10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .

"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.

As used herein, the term "alkenyl" is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, 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 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, 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, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl (carbazol yl) A polycyclic 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 . ≪ / RTI > 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 of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

"Alkylsilyl" in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 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.

Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel compounds of the present invention can be represented by the following formula

[Chemical Formula 1]

In Formula 1,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ is an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms;

The aryl and heteroaryl groups of Ar ₁ and the arylene and heteroarylene groups of L ₁ to L ₄ are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl A boron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group When they are substituted or unsubstituted with one or more substituents and when they are substituted with a plurality of substituents, they may be the same or different;

Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group consisting of the groups represented by the following formulas A-1 to A-24, wherein Ar ₂ and Ar ₃ are different from each other;

In the above Formulas A-1 to A-24,

* Denotes the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₇ );

Y ₁ and Y ₂ are each independently selected from the group consisting of a single bond, C (R ₈ ) (R ₉ ), N (R ₁₀ ), O and S, but not both Y ₁ and Y ₂ are single bonds;

m and n are each independently an integer of 0 to 4;

l is an integer from 0 to 3;

R ₁ and R ₂ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ 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 arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, and groups binding to selected or adjacent from the group consisting of C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ with an aryl amine of the C ₆₀ to which they are attached may form a fused ring, wherein R ₁ and When there are a plurality of R < ₂ > s, they are the same as or different from each other;

R ₃ to R ₁₀ are each independently 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 alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C group ₆₀ arylamine of the combined groups is selected or adjacent from the group consisting they are attached may form a fused ring, wherein R ₇ to R < ₁₀ > each are the same or different from each other;

Alkyl group of the R ₁ to R _10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, the compound may be a compound represented by the following formula (2): < EMI ID =

(2)

In Formula 2,

Each of L ₁ to L ₄ and Ar ₁ to Ar ₃ is as defined in the above formula (1).

The novel compound according to the present invention is a structure that binds various asymmetric substituents at positions 3 and 6 of the carbazole moiety and has a larger molecular weight than that of conventional materials for organic electroluminescence devices such as CBP, And the bonding force between holes and electrons can be increased. Therefore, when the compound of Formula 1 is used in an organic electroluminescent device, driving voltage, efficiency (luminous efficiency, power efficiency), lifetime and brightness of the device can be improved.

In addition, the compound of the present invention is relatively easy to control due to the asymmetric substituent bonded to the basic skeleton. For example, the triphenylene group has a relatively small difference (singlet energy - triplet energy) as compared with biphenyl having a triplet energy, and the triphenylene group and the benzo - When the fused thiophenyl groups are compared, both are used as EDG. However, the triphenylene group is superior to hole transport in electron transport, but in the case of benzo-fused thiophenyl group, the properties are opposite, .

Therefore, when the compound of the present invention is applied to an organic electroluminescent device, excellent characteristics as a host material of a light emitting layer can be exhibited as compared with conventional CBP, so that the phosphorescent characteristics of the device are improved and the hole injecting ability and / The light emitting efficiency, the driving voltage, the lifetime characteristics, and the like can be improved. The energy level can be controlled according to the substituents and thus has a wide band gap (sky blue to red). Therefore, it can be applied not only to a light emitting layer but also to an electron transporting auxiliary layer, an electron transporting layer, a hole transporting layer, .

In addition, since the molecular weight of the compound of the present invention is significantly increased, the glass transition temperature can be improved, and thereby, it can have higher thermal stability than conventional CBP. Further, not only the thermal stability of the compound can be improved but also the effect of inhibiting the crystallization of the organic layer containing the compound of the formula (1). Therefore, the device including the compound of Formula 1 according to the present invention can greatly improve durability and lifetime characteristics.

In addition, when the compound of Formula 1 according to the present invention is used as a hole injection / transport layer material, an electron injection / transport layer material, and a blue, green and / or red phosphorescent host material of an organic electroluminescent device, It is possible to exert a remarkably excellent effect on the surface. Therefore, the compound according to the present invention can greatly contribute to the improvement of the performance and lifetime of the organic electroluminescent device, and in particular, the lifetime improvement of the device has a great effect on maximizing the performance of the full-color organic electroluminescent panel.

Different from the one implemented embodiment of the present invention, wherein Ar ₂ and Ar ₃ is a substituent and the Ar ₂ and Ar ₃ is selected from the group consisting of each independently hydrogen or the formula A-5 and A-10 to A-24 Are different from each other.

According to a preferred embodiment of the present invention, when any one of Ar ₂ and Ar ₃ is hydrogen, the remainder is a substituent selected from the group represented by the above formulas A-5 and A-10 to A-24 .

According to a preferred embodiment of the present invention, each of L ₁ to L ₄ is independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group, May be selected from the group consisting of a single bond, a phenylene group, a biphenylene group, and a naphthalenyl group.

According to a preferred embodiment of the present invention, each of R ₁ to R ₃ is independently selected from the group consisting of a C ₁ to C ₁₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms Can be selected.

According to a preferred embodiment of the present invention, R ₁ to R ₃ are each independently selected from the group consisting of methyl, ethyl, propanyl, butyl, phenyl, biphenyl and naphthalenyl,

The methyl, ethyl, propyl, butyl, phenyl, biphenyl and naphthalenyl groups of R ₁ to R ₃ are each independently selected from the group consisting of deuterium, a halogen, a C ₁ to C ₁₀ alkyl group and a C ₆ to C ₆₀ aryl group And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁ to R ₃ are each independently selected from the group consisting of methyl, ethyl, propanyl, butyl, phenyl, biphenyl and naphthalenyl,

The methyl, ethyl, propyl, butyl, phenyl, biphenyl and naphthalenyl groups of R ₁ to R ₃ are each independently substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, , When they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, each of R ₄ to R ₆ is independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms Can be selected from the group.

According to a preferred embodiment of the present invention, each of R ₄ to R ₆ may be independently selected from the group consisting of hydrogen, phenyl, biphenyl, fluorenyl, and naphthalenyl.

According to a preferred embodiment of the present invention, Ar ₁ is a substituent selected from the group consisting of the following formulas B-1 to B-9 in terms of luminous efficiency, but is not limited thereto:

In the above Formulas B-1 to B-9,

* Denotes the part where the bond is made;

X ₁ to X ₈ are each independently N or C (R ₁₆ );

In formula (B-2), any of X ₁ to X ₄ connected to L ₂ is C (R ₁₆ ), wherein R ₁₆ is a member;

T ₁ is O, S, N (R ₁₇ ), C (R ₁₈ ) (R ₁₉ ) or SO ₂ ;

R ₁₁ and R ₁₄ to R ₁₉ are each independently 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 ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, A C ₆ to C ₆₀ aryloxy group, a C ₃ 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 arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ groups of the aryl amine group selected from the group consisting of or adjacent (e. g., a plurality of R ₁₆ adjacent Are bonded to each other to form a condensed ring, and when a plurality of R < ₁₆ > s are present, they are the same as or different from each other;

q and r are each independently an integer of 0 to 4;

p is an integer from 0 to 3;

R ₁₂ and R ₁₃ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ 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 arylboron group, a C ₆ to C ₆₀ (For example, adjacent R ₁₂ or R _13, etc.) selected from the group consisting of an arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, To form a condensed ring, and when a plurality of each of R ₁₂ and R ₁₃ is plural, they are the same or different from each other;

Alkyl group of said R ₁₁ to R _19, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, a halogen C ₁ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group of the When substituted with luer binary 1 or more substituents selected from the group Beach and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a substituent selected from the group consisting of Formulas B-2 to B-5 and B-9.

According to a preferred embodiment of the present invention, each of R ₁₁ to R ₁₆ may be independently selected from the group consisting of C ₆ to C ₆₀ aryl groups and 5 to 60 heteroaryl groups.

According to a preferred embodiment of the present invention, each of R ₁₁ to R ₁₆ is independently selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group and a naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group and naphthalenyl group of R ₁₁ to R ₁₆ are each independently selected from the group consisting of halogen, cyano group, C ₁ to C ₁₀ alkyl group, halogen C ₁ to C ₄ alkyl group and C ₆ to C ₆₀ And aryl groups, and when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, each of R ₁₁ to R ₁₆ is independently selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group and a naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group and naphthalenyl group of R ₁₁ to R ₁₆ are each independently a group selected from the group consisting of a cyano group, a fluorine group, a methyl group, an ethyl group, a butyl group, a cyano group, a trifluoroethanyl group and a naphthalenyl group And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a substituent selected from the group represented by the following formulas (F-1) to (F-26), but is not limited thereto:

In Formulas F-1 to F-26,

* Denotes the part where the bond is made;

t and x are each independently an integer of 0 to 5;

u, q and r are each independently an integer of 0 to 4;

v is an integer from 0 to 3;

w is an integer from 0 to 2;

R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl , C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, the cycloalkyl group of C ₃ ~ C _40, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ arylboronic of C ₆₀ group , the group bonded to C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of aryl silyl, or of, or adjacent to form a condensed ring And when there are a plurality of R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ each, they are the same as or different from each other;

R _{11 and} R ₁₆ to R ₁₉ are each independently 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, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a nucleus A C ₆ to C ₆₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, mono or diaryl phosphine of C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of, or combine tile adjacent to form a condensed ring ;

Alkyl group of said R ₁₁ to R ₁₃ and R ₁₆ to R _21, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine group consisting of blood, and C ₆ ~ C ₆₀ aryl silyl group of the When in or substituted with one or more substituents selected is unsubstituted, substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ is preferably a substituent selected from the group consisting of the above-mentioned formulas F-1 to F-15, F-21, F-22 and F-26 from the viewpoint of luminous efficiency .

The compounds represented by Formula 1 of the present invention may be represented by the following compounds, but are not limited thereto:

In the present invention, the compound represented by Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960), J. Chem. SOC. 4482 (1955) 2457 (1995)). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic Field  Light emitting element

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used singly or in combination of two or more.

The at least one organic material layer may be at least one of a hole injection layer, a hole transporting layer, a light emitting layer, a light emission assisting layer, a life improving layer, an electron transporting layer, an electron transporting assisting layer and an electron injecting layer, 1, and preferably a light emitting layer may be included.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, which may include a compound represented by the above formula (1) as a host material. Thus, when the compound represented by Formula 1 is incorporated as a light emitting layer material of an organic electroluminescent device, preferably a green phosphorescent host, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency and power efficiency), lifetime, luminance and driving voltage, etc., can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked. At this time, an electron transporting auxiliary layer may be further laminated between the light emitting layer and the electron transporting layer, and an electron injection layer may further be laminated on the electron transporting layer. In the present invention, at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron transporting supporting layer and the electron injecting layer may include the compound represented by the above formula (1) (1). ≪ / RTI >

In addition, the structure of the organic electroluminescent device of the present invention may be a structure in which not only an anode, one or more organic compound layers and a cathode are sequentially laminated but also an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic compound layer.

The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, a light emitting layer or an electron transporting layer) To form another organic material layer and an electrode.

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

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

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

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

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 A-1

< Step 1 > Synthesis of A-1

Carbazole (3.22 g, 10 mmol), [1,1'-biphenyl] -3-ylboronic acid (1.98 g, 10 mmol), K ₂ CO ₃ (2.76 g, 20 mmol), Pd (PPh ₃ ) 4 (0.58 g, 0.5 mmol) and THF (60 mL) and purified water (15 mL) were mixed and stirred at 110 ° C for 12 hours. After cooling to room temperature, H2O was added and extracted with brine. After removing water with Na ₂ SO 4, the organic layer was concentrated and subjected to column chromatography to obtain the target compound A-1 (2.77 g, 70%).

¹ H-NMR :? 7.45 (m, 6H), 7.61 (d, 2H), 7.75 (m, 7H)

[ Preparation Example  2] Synthesis of A-2

< Step 1 > Synthesis of A-2

[1,1'-biphenyl] -4-ylboronic acid (1.98 g, 10 mmol) was used instead of [1,1'-biphenyl] -3-ylboronic acid used in <Step 1> A-2 was obtained by carrying out the same procedure as < Step 1 > of Preparation Example 1 except for using.

^{1 H-NMR: δ 7.25 (} m, 4H), 7.45 (m, 6H), 7.76 (m, 6H), 7.89 (m, 2H), 7.99 (m, 2H), 11.66 (s, 1H)

[ Preparation Example  3] Synthesis of A-3

< Step 1 > Synthesis of A-3

Bromo-9H-carbazole instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, Dibenzo [b, d] furan-4-ylboronic acid (2.12 g, 10 mmol) instead of [1,1'-biphenyl] -3-ylboronic acid was obtained by using carbazole (3.98 g, The procedure of <Step 1> of Preparation Example 1 was repeated to obtain A-3.

¹ H-NMR :? 7.50 (m, 9H), 7.70 (m, 5H), 8.00 (m, 8H)

[ Preparation Example  4] Synthesis of A-4

< Step 1 > Synthesis of A-4

Instead of 3-bromo-6-phenyl-9H-carbazole used in Step 1 of Preparation Example 1, 3,3 - ([1,1'-biphenyl] Dibenzo [b, d] thiophen-2-ylboronic acid (2.28 g, 10 mmol) instead of [1,1'- biphenyl] -3-ylboronic acid ) Was used to obtain A-4 in the same manner as in &lt; Step 1 &gt; of Preparation Example 1 above.

^{1 H-NMR: δ 7.25 (} m, 4H), 7.49 (m, 5H), 7.75 (m, 4H), 7.99 (m, 6H), 8.12 (m, 2H), 8.45 (d, 1H), 11.65 ( s, 1 H)

[ Preparation Example  5] Synthesis of A-5

< Step 1 > 3- Chloro -6- ( Triphenylene Yl) -9H- Carbazole  Synthesis of

6-chloro-9H-carbazole (2.80 g, 10 mmol) was used instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> , Step 1 of Preparation Example 1 was repeated except that triphenylene-2-ylboronic acid (2.72 g, 10 mmol) was used instead of 1'-biphenyl] -3-ylboronic acid To obtain 3-chloro-6- (triphenylene-2-yl) -9H-carbazole.

^{1 H-NMR: δ 7.09 (} d, 1H), 7.60 (m, 9H), 7.89 (s, 1H), 7.99 (d, 1H), 8.35 (m, 3H), 9.26 (s, 1H), 9.60 ( d, 1 H), 11.63 (s, 1 H)

< Step 2 > Synthesis of A-5

(Triphenylen-2-yl) -9H-carbazole (4.27 g, 10.0 mmol) and (9,9-dimethyl-9H- fluoren-2-yl) boronic acid 2.38 g, 10.0 mmol), Cs 2 CO 3 (6.51 g, 20.0 mmol), Pd (OAc) ₂ (0.11 g, 5 mol%) and X-Phos (0.47 g, 1.00 mmol) were placed in 120 ml / 40 ml of THF / H ₂ O and stirred at 90 ° 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, the desired compound A-5 (3.51 g, yield 60%) was obtained by column chromatography.

^{1 H-NMR: δ 1.69 (} s, 6H), 7.33 (m, 2H), 7.70 (m, 10H), 7.89 (m, 4H), 7.99 (m, 2H), 8.09 (d, 1H), 8.33 ( m, 3H), 9.26 (s, IH), 9.60 (d, IH), 11.63

[ Preparation Example  6] Synthesis of A-6

< Step 1 > 3- Chloro -6- (3- (phenanthren-9-yl) phenyl) -9H- Carbazole  Synthesis of

Except that (3- (phenanthrene-9-yl) phenyl) boronic acid (2.98 g, 10 mmol) was used in place of triphenylene-2-ylboronic acid used in Step 1 of Preparation Example 5 (3-chloro-6- (3- (phenanthren-9-yl) phenyl) -9H-carbazole was obtained in the same manner as in <Step 1> of Preparation Example 5 above.

^{1 H-NMR: δ 7.09 (} d, 1H), 7.66 (m, 10H), 7.95 (m, 5H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 ( s, 1 H)

< Step 2 > Synthesis of A-6

The title compound was obtained in the same manner as in Step 2 of Preparation Example 5, except that 3-chloro-6- (triphenylene-2-yl) -9H- (9,9-dimethyl-9H-fluoren-2-yl) boronic acid was used instead of naphthalene-2- The same procedure as in <Step 2> of Preparation Example 5 was carried out except that acetic acid (1.71 g, 10.0 mmol) was used to obtain A-6.

^{1 H-NMR: δ 7.38 (} d, 1H), 7.66 (m, 12H), 7.94 (m, 10H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 ( s, 1 H)

[ Preparation Example  7] Synthesis of A-7

< Step 1 > 3 - ([1,1 ': 3', 1 "'- Terphenyl ] -5'-yl) -6- Chloro -9H- Carbazole  Synthesis of

1'-terphenyl] -5'-ylboronic acid (2.74 g, 10 mmol) instead of triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 1 '' - terphenyl] -5'-yl) -6 (4'-fluorophenyl) -acetic acid was prepared by following the procedure of <Step 1> of Preparation Example 5, -Chloro-9H-carbazole.

^{1 H-NMR: δ 7.09 (} d, 1H), 7.52 (m, 8H), 7.76 (m, 5H), 7.89 (s, 1H), 8.00 (m, 4H), 11.66 (s, 1H)

< Step 2 > Synthesis of A-7

(3-chloro-6- (triphenylen-2-yl) -9H-carbazole obtained in Step 1 of Preparation Example 7 was used in place of 3-chloro-6- Yl) -6-chloro-9H-carbazole (4.29 g, 10 mmol) and (9,9-dimethyl-9H- fluoren-2 Step 2 of Preparation Example 5 was repeated except that 9,9'-spiro [fluorene] -4-ylboronic acid (3.60 g, 10.0 mmol) was used instead of 3- A-7 was obtained.

^{1 H-NMR: δ 7.47 (} m, 16H), 7.65 (d, 1H), 7.77 (m, 7H), 7.89 (m, 10H), 11.66 (s, 1H)

[ Preparation Example  8] Synthesis of A-8

< Step 1 > 3- Chloro -6- ( Fluoranthene Yl) -9H- Carbazole  synthesis

Except that fluoranthene-3-ylboronic acid (2.46 g, 10 mmol) was used in place of triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5, Step 1] to obtain 3-chloro-6- (fluoranthen-3-yl) -9H-carbazole.

^{1 H-NMR: δ 7.09 (} d, 1H), 7.37 (d, 1H), 7.50 (m, 3H), 7.66 (m, 4H), 7.89 (s, 1H), 8.00 (m, 3H), 8.42 ( d, 2 H), 11.65 (s, 1 H)

< Step 2 > Synthesis of A-8

The title compound was obtained in the same manner as in PREPARATION 5, except that 3-chloro-6- (triphenylene-2-yl) (Triphenylsilyl) -9H-carbazole (4.01 g, 10 mmol) was used instead of (9,9-dimethyl-9H-fluoren- Phenyl) boronic acid (3.80 g, 10.0 mmol) was used in place of the compound obtained in Step 5 of Preparation Example 5 to obtain A-8.

^{1 H-NMR: δ 7.37 (} m, 17H), 7.65 (m, 4H), 7.77 (m, 3H), 7.89 (m, 4H), 7.99 (m, 2H), 8.10 (d, 2H), 8.42 ( d, 2 H), 11.66 (s, 1 H)

[ Preparation Example  9] Synthesis of A-9

< Step 1 > 4- (6- Chloro -9H- Carbazole -3 days)- N, N - Of diphenyl aniline  synthesis

Except that (4- (diphenylamino) phenyl) boronic acid (2.89 g, 10 mmol) was used in place of triphenylene-2-ylboronic acid used in Step 1 of Preparation Example 5 (6-chloro-9H-carbazol-3-yl) -N, N-diphenyl aniline was obtained in the same manner as in <

¹ H-NMR :? 7.00 (m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 4H), 7.77 d, 1 H), 11.65 (s, 1 H)

< Step 2 > Synthesis of A-9

(6-Chloro-pyridin-2-yl) -9H-carbazole obtained in Step 1 of Preparation Example 9 was used in place of 3-chloro-6- (triphenylene- Instead of (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (7.7 g, 10 mmol) A-9 was obtained by carrying out the same procedure as <Step 2> of Preparation Example 5 except that 3-chloro-7H-benzo [c] carbazol-10-yl) boronic acid (3.37 g, 10.0 mmol) .

^{1 H-NMR: δ 7.00 (} m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 11H), 7.77 (d, 2H), 7.90 (m, 6H), 8.13 ( (d, IH), 8.30 (d, IH), 8.54 (d, IH), 11.65

[ Preparation Example  10] Synthesis of A-10

< Step 1 > N - ([1,1'-biphenyl] -4-yl) -N- (4- (6- Chloro -9H- Carbazole Yl) phenyl) -9,9-dimethyl-9H-fluoren-2-amine

(9, 9-dimethyl-9H-fluorene-2-yl) propionic acid was used in place of triphenylene-2-ylboronic acid used in <Step 1> (1, 1'-biphenyl (2-amino) phenyl) boronic acid (4.81 g, 10 mmol) was used in place of N- ] -4-yl) -N- (4- (6-chloro-9H-carbazol-3-yl) phenyl) -9,9-dimethyl-9H-fluoren-2-amine.

^{1 H-NMR: δ 1.69 (} s, 6H), 7.11 (m, 2H), 7.55 (m, 17H), 7.77 (m, 3H), 7.89 (m, 3H), 7.99 (d, 1H), 11.67 ( s, 1 H)

< Step 2 > Synthesis of A-10

N - ([1,1] dioxolan-2-yl) -carbamic acid obtained in Step 1 of Preparation Example 10 was used in place of 3-chloro-6- (triphenylene- -9,9-dimethyl-9H-fluoren-2-amine (6.37 g, < RTI ID = 0.0 & , 10 mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol) instead of (9,9- The procedure of Step 2 of Preparation Example 5 was repeated to obtain A-10.

¹ H-NMR :? 1.69 (s, 6H), 7.16 (m, 2H), 7.50 (m, 20H), 7.87

[ Preparation Example  11] Synthesis of A-11

< Step 1 > A- Eleven  synthesis

(3.22 g, 10 mmol) and 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole (3.32 g, 10 mmol) were added to a solution of 3-bromo- Pd (OAc) ₂ (0.22 g, 1 mmol), P ( t- Bu) ₃ (0.47 ml, 2 mmol), NaO ( t- Bu) (1.92 g, 20 mmol) and toluene Were mixed and stirred at 110 ° C for 2 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound A-11 (2.86 g, yield 50%).

^{1 H-NMR: δ 7.16 (} m, 2H), 7.50 (m, 17H), 7.90 (m, 4H), 8.12 (d, 1H), 8.55 (d, 2H), 11.66 (s, 1H)

[ Preparation Example  12] Synthesis of A-12

< Step 1 > Synthesis of A-12

(Phenyl-d5) -9H-carbazole (3.27 g, 10 mmol) instead of 3-bromo-6-phenyl-9H-carbazole used in Step 1 of Preparation Example 11 Benzo [c] benzo [4,5] thieno [2,3-a] carbazole instead of 11-phenyl-11,12-dihydroindolo [2,3- a] , 10 mmol) was used in place of A-12, to thereby obtain A-12.

^{1 H-NMR: δ 7.16 (} t, 1H), 7.35 (m, 2H), 7.66 (m, 7H), 7.90 (m, 4H), 8.50 (m, 4H), 11.66 (s, 1H)

[ Preparation Example  13] Synthesis of A-13

< Step 1 > Synthesis of A-13

Bromo-9H-carbazole (2.46 g, 10 mmol) instead of 3-bromo-6-phenyl-9H-carbazole used in Preparation 1, Step 1, (Dibenzo [b, d] thiophen-4-yl) phenyl) boronic acid (3.04 g, 10 mmol) was used in place of biphenyl] -3-ylboronic acid. Was obtained in the same manner as in < Step 1 >.

¹ H-NMR :? 7.22 (m, 5H), 7.66 (m, 6H), 7.93 (m, 3H), 8.19 (d, 1H), 8.32 d, 1 H), 11.66 (s, 1 H)

[ Preparation Example  14] Synthesis of A-14

< Step 1 > Synthesis of A-14

Bromo-9H-carbazole (2.46 g, 10 mmol) instead of 3-bromo-6-phenyl-9H-carbazole used in Preparation 1, Step 1, (Dibenzo [b, d] furan-2-yl) phenyl) boronic acid (2.88 g, 10 mmol) was used in place of biphenyl] -3-ylboronic acid. The same procedure as in < Step 1 > was carried out to obtain A-14.

¹ H-NMR :? 7.40 (m, 9H), 7.63 (d, IH), 7.77 (m, 5H)

[ Preparation Example  15] Synthesis of A-15

< Step 1 > Synthesis of A-15

Bromo-9H-carbazole (2.46 g, 10 mmol) instead of 3-bromo-6-phenyl-9H-carbazole used in Preparation 1, Step 1, Yl) phenyl) boronic acid (3.14 g, 10 mmol) was used in place of (3-fluoro-3- Step 1 of < RTI ID = 0.0 > 1 &lt; / RTI &gt;

¹ H-NMR :? 1.69 (s, 6H), 7.28 (m, 3H), 7.55 (m, 5H), 7.77 d, 1 H), 11.66 (s, 1 H)

[ Preparation Example  16] Synthesis of A-16

< Step 1 > Synthesis of A-16

Bromo-9H-carbazole (2.46 g, 10 mmol) instead of 3-bromo-6-phenyl-9H-carbazole used in Preparation 1, Step 1, Step 1> of Preparation Example 1 was repeated except that (3- (triphenylene-2-yl) phenyl) boronic acid (3.48 g, 10 mmol) was used instead of 3- The same procedure was followed to obtain A-16.

^{1 H-NMR: δ 7.20 (} t, 1H), 7.50 (m, 12H), 7.90 (m, 3H), 8.19 (d, 1H), 8.33 (d, 1H), 8.46 (m, 2H), 9.11 ( d, 1 H), 9.60 (d, 1 H), 11.66 (s, 1 H)

[ Synthetic example  1] Synthesis of J-1

(3.88 g, 10 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.88 g, 10 mmol), Pd ) ₂ (0.22 g, 1 mmol), P ( t- Bu) ₃ (0.47 ml, 2 mmol), NaO ( t- Bu) (1.92 g, 20 mmol) and toluene And stirred for 2 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound J-1 (3.51 g, yield 50%).

[Mass]: 702

[ Synthetic example  2] Synthesis of J-2

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine using A-2 (3.95 g, 10.0 mmol) instead of A- -Biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine (4.64 g, 10.0 mmol) The target compound J-2 (3.97 g, yield 51%) was obtained.

[Mass]: 778

[ Synthetic example  3] Synthesis of J-3

Instead of 2- (3'-bromo) -4,6-diphenyl-1,3,5-triazine in place of A-1 (4.85 g, 10.0 mmol) Synthesis Example 1 and Synthesis Example 1 were repeated except for using [[1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.64 g, 10.0 mmol) The same procedure was followed to obtain the objective compound J-3 (4.51 g, yield 52%).

[Mass]: 869.04

[ Synthetic example  4] Synthesis of J-4

A solution of 4 - ([1,1,1] -thiophene-3-yl) -1,6- (4.63 g, 10.0 mmol) was used in place of 4- (3-bromo-phenyl) -biphenyl] -4- Compound J-4 (4.68 g, yield 53%).

[Mass]: 884.11

[ Synthetic example  5] Synthesis of J-5

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, A-5 (5.85 g, 10.0 mmol) The procedure of Synthesis Example 1 was repeated except that 6-bis (3,5-dimethylphenyl) -1,3,5-triazine (3.68 g, 10.0 mmol) 4.71 g, yield 54%).

[Mass]: 873.12

[ Synthetic example  6] Synthesis of J-6

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, A-6 (5.45 g, 10.0 mmol) Phenyl) -4,6-diphenyl-1,3,5-triazine (3.88 g, 10.0 mmol) was used in place of the target compound J-6 , Yield: 55%).

[Mass]: 853.04

[ Synthetic example  7] Synthesis of J-7

(4-bromo-phenyl) -4,6-diphenyl-1,3,5-triazine was used instead of A-7 instead of A- The same procedure as in Synthesis Example 1 was carried out except that 4,4'-di-tert-butyl-2,2 ': 6', 2 "-terpyridine (5.00 g, 10.0 mmol) To obtain the objective compound J-7 (6.32 g, yield 56%).

[Mass]: 1129.46

[ Synthetic example  8] Synthesis of J-8

A-8 (7.01 g, 10.0 mmol) was used in place of A-1, and 5-bromoisophthalonitrile (4.71 g, yield 57%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound (2.07 g, 10.0 mmol) was used.

[Mass]: 828.06

[ Synthetic example  9] Synthesis of J-9

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, A-9 (7.01 g, 10.0 mmol) The procedure of Synthesis Example 1 was repeated except that 6-bis (4- (trifluoromethyl) phenyl) -1,3,5-triazine (4.48 g, 10.0 mmol) -9 (6.20 g, yield 58%).

[Mass]: 1069.13

[ Synthetic example  10] Synthesis of J-10

Instead of A- 1 (8.44 g, 10.0 mmol) was used instead of A-1 and 5,5 '- (6 (trifluoromethyl) - (3-bromophenyl) -1,3,5-triazine-2,4-diyl) diquinoline (4.90 g, 10.0 mmol) To obtain compound J-10 (7.39 g, yield 59%).

[Mass]: 1253.53

[ Synthetic example  11] Synthesis of J-11

Instead of A-11 (5.73 g, 10.0 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- J-11 (4.54 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 1, except using fluorodibenzo [b, d] furan (2.65 g, 10.0 mmol).

[Mass]: 757.87

[ Synthetic example  12] Synthesis of J-12

(4-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of A-1 instead of A-12 (5.69 g, 10.0 mmol) The procedure of Synthesis Example 1 was repeated except that diphenylphosphine oxide (3.57 g, 10.0 mmol) was used to obtain the target compound J-12 (4.99 g, yield 59%).

[Mass]: 846.01

[ Synthetic example  13] Synthesis of J-13

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine using A-13 instead of A-1 (4.25 g, 10.0 mmol) -Biphenyl] -4-yl) -4- (4-bromophenyl) -6- (4-fluorophenyl) pyrimidine (4.81 g, 10.0 mmol) The same procedure was followed to obtain the target compound J-13 (4.79 g, yield 58%).

[Mass]: 826.01

[ Synthetic example  14] Synthesis of J-14

Instead of A-14 (4.25 g, 10.0 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- J-14 (3.49 g, yield 57%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that phenyl quinazoline (2.85 g, 10.0 mmol) was used.

[Mass]: 613.72

[ Synthetic example  15] Synthesis of J-15

(4.35 g, 10.0 mmol) was used instead of A-1 and 2-bromo-4- (4-fluorophenyl) (4.28 g, yield 56%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 4- (naphthalen-1-yl) phenyl) quinazoline (4.11 g, 10.0 mmol) ).

[Mass]: 765.96

[ Synthetic example  16] Synthesis of J-16

A-16 was used instead of A-1 (4.69 g, 10.0 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- J-16 (3.85 g, yield 55%) was obtained in the same manner as in Synthesis Example 1, except that 6-diphenyl-1,3,5-triazine (3.12 g, 10.0 mmol) .

[Mass]: 700.85

[ Synthetic example  17] Synthesis of J-17

Phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- (4.64 g, 10.0 mmol) instead of (3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine Was subjected to the same procedure as in Synthesis Example 1 to obtain J-17 (3.38 g, yield 54%) as a target compound.

[Mass]: 626.76

[ Synthetic example  18] Synthesis of J-18

Phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- 3-yl) -4,6-diphenyl-1,3,5-triazine (5.40 g, 10.0 &lt; RTI ID = 0.0 &gt; mmol), the target compound J-18 (3.72 g, yield 53%) was obtained by carrying out the same procedure as in Synthesis Example 1.

[Mass]: 702.86

[ Synthetic example  19] Synthesis of J-19

Phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- Biphenyl] -3-yl) -2-phenylpyrimidine (5.39 g, 10.0 &lt; RTI ID = 0.0 & mmol), the target compound J-19 (3.64 g, yield 52%) was obtained by carrying out the same procedure as in Synthesis Example 1.

[Mass]: 701.87

[ Synthetic example  20] Synthesis of J-20

3-yl) -9H-carbazole (3.19 g, 10.0 mmol) was used instead of A-1 to give 2- (3-bromophenyl) Instead of 2- (4 &quot; -bromo- [1,1 ': 3', 1 &quot; -terphenyl] -4-yl) -4,6-diphenyl- -1,3,5-triazine (5.40 g, 10.0 mmol) was used in place of the compound obtained in Example 1 to obtain the target compound J-20 (3.97 g, yield 51%).

[Mass]: 778.96

[ Synthetic example  21] Synthesis of J-21

Carbazole (3.19 g, 10.0 mmol) was used instead of A- 1 and 3 - ([1,1'-biphenyl] -4-yl) The procedure of Synthesis Example 1 was repeated except that 2-bromo-4-phenylquinazoline (2.85 g, 10.0 mmol) was used instead of diphenyl-1,3,5- 21 (2.61 g, yield 50%).

[Mass]: 523.64

[ Example  1 ~ 18] Organic Field  Fabrication of light emitting device

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

First, the glass substrate coated with ITO (In tin oxide) thin film with thickness of 1500 Å 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.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent electrode + host compound + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ 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] Organic Field  Fabrication of light emitting device

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

[ Evaluation example ]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 18 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 1 J-1 6.81 518 39.7 Example 2 J-2 6.68 518 38.9 Example 3 J-3 6.66 518 41.3 Example 4 J-4 6.7 517 41.3 Example 5 J-5 6.7 515 43.1 Example 6 J-6 6.51 518 43.5 Example 7 J-8 6.77 518 41.4 Example 8 J-11 6.46 518 42.2 Example 9 J-12 6.81 517 42 Example 10 J-13 6.68 515 41.8 Example 11 J-14 6.66 518 41.3 Example 12 J-15 6.48 518 41.2 Example 13 J-16 6.86 517 41.2 Example 14 J-17 6.77 515 41.4 Example 15 J-18 6.66 518 42.2 Example 16 J-19 6.81 518 39.7 Example 17 J-20 6.68 518 38.9 Example 18 J-21 6.66 518 41.3 Comparative Example 1 CBP 6.93 516 38.2

When the compounds (J-1 to J-6, J-8, J-11 to J-21) according to the present invention were used as a light emitting layer of a green organic electroluminescent device as shown in Table 1 To 18). It can be seen that the organic electroluminescent device of the present invention exhibits excellent performance in terms of efficiency and driving voltage as compared with the conventional green organic electroluminescent device using CBP (Comparative Example 1).

Claims (12)

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

In Formula 1,
L ₁ to L ₄ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Ar ₁ is an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms;
The aryl and heteroaryl groups of Ar ₁ and the arylene and heteroarylene groups of L ₁ to L ₄ are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl A boron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group When they are substituted or unsubstituted with one or more substituents and when they are substituted with a plurality of substituents, they may be the same or different;
Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group consisting of the groups represented by the following formulas A-1 to A-24, wherein Ar ₂ and Ar ₃ are different from each other;

In the above Formulas A-1 to A-24,
* Denotes the part where the bond is made;
Z ₁ to Z ₅ are each independently N or C (R ₇ );
Y ₁ and Y ₂ are each independently selected from the group consisting of a single bond, C (R ₈ ) (R ₉ ), N (R ₁₀ ), O and S, but not both Y ₁ and Y ₂ are single bonds;
m and n are each independently an integer of 0 to 4;
l is an integer from 0 to 3;
R ₁ and R ₂ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ 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 arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, and groups binding to selected or adjacent from the group consisting of C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ with an aryl amine of the C ₆₀ to which they are attached may form a fused ring, wherein R ₁ and When there are a plurality of R &lt; ₂ &gt; s, they are the same as or different from each other;
R ₃ to R ₁₀ are each independently 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 alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C group ₆₀ arylamine of the combined groups is selected or adjacent from the group consisting they are attached may form a fused ring, wherein R ₇ to R &lt; ₁₀ &gt; each are the same or different from each other;
Alkyl group of the R ₁ to R _10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other. The method according to claim 1,
The compound is a compound represented by the following formula 2:
(2)

In Formula 2,
Each of L ₁ to L ₄ and Ar ₁ to Ar ₃ is as defined in claim 1. The method according to claim 1,
Each of L ₁ to L ₄ is independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group. The method according to claim 1,
Wherein Ar ₁ is a substituent selected from the group of the formula B-1 to B-9 The following compounds:

In the above Formulas B-1 to B-9,
* Denotes the part where the bond is made;
X ₁ to X ₈ are each independently N or C (R ₁₆ );
In formula (B-2), any of X ₁ to X ₄ connected to L ₂ is C (R ₁₆ ), wherein R ₁₆ is a member;
T ₁ is O, S, N (R ₁₇ ), C (R ₁₈ ) (R ₁₉ ) or SO ₂ ;
R ₁₁ and R ₁₄ to R ₁₉ are each independently 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 ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, A C ₆ to C ₆₀ aryloxy group, a C ₃ 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 arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ tile to selected or adjacent from the group consisting of an aryl amine of the C ₆₀ combined to form a condensed ring, and , When a plurality of R &lt; ₁₆ &gt; s are present, they are the same as or different from each other;
q and r are each independently an integer of 0 to 4;
p is an integer from 0 to 3;
R ₁₂ and R ₁₃ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ 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 arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, and groups binding to selected or adjacent from the group consisting of C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ with an aryl amine of the C ₆₀ to which they are attached may form a fused ring, wherein R ₁₂ and R &lt; ₁₃ &gt; each are the same or different from each other;
Alkyl group of said R ₁₁ to R _19, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, a halogen C ₁ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group of the When substituted with luer binary 1 or more substituents selected from the group Beach and ring, which is substituted with plural substituents, they may be the same or different from each other. The method according to claim 1,
Wherein Ar ₁ is The compound substituents selected from the group represented by the formula F-1 to F-26 to:

In Formulas F-1 to F-26,
* Denotes the part where the bond is made;
t and x are each independently an integer of 0 to 5;
u, q and r are each independently an integer of 0 to 4;
v is an integer from 0 to 3;
w is an integer from 0 to 2;
R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl , C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, the cycloalkyl group of C ₃ ~ C _40, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ arylboronic of C ₆₀ group , the group bonded to C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of aryl silyl, or of, or adjacent to form a condensed ring And when there are a plurality of R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ each, they are the same as or different from each other;
R _{11 and} R ₁₆ to R ₁₉ are each independently 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, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a nucleus A C ₆ to C ₆₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, mono or diaryl phosphine of C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of, or combine tile adjacent to form a condensed ring ;
Alkyl group of said R ₁₁ to R ₁₃ and R ₁₆ to R _21, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine group consisting of blood, and C ₆ ~ C ₆₀ aryl silyl group of the When in or substituted with one or more substituents selected is unsubstituted, substituted with a plurality of substituents, they may be the same or different from each other. 5. The method of claim 4,
Wherein each of R ₁₁ to R ₁₆ is independently selected from the group consisting of a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms. The method according to claim 1,
Wherein Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group represented by the above formulas A-5 and A-10 to A-24, and Ar ₂ and Ar ₃ are different from each other. The method according to claim 1,
Each of R ₁ to R ₃ is independently selected from the group consisting of a C ₁ to C ₁₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. The method according to claim 1,
Each of R ₄ to R ₆ is independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound represented by the general formula (1). 12. The method of claim 11,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron transporting auxiliary layer, an electron injecting layer, a lifetime improving layer, a light emitting layer and a light emitting auxiliary layer.