KR101801003B1 - 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 comprising the same. The compound according to the present invention is used in an organic compound layer of an organic electroluminescent device, preferably a light emitting layer, an electron transporting layer, or an electron transporting supporting layer, thereby improving the luminous efficiency, driving voltage and lifetime of the organic electroluminescent device.

Description

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

The present invention relates to a novel organic compound that can be used as a material 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,

A is represented by the following formula (2) or (3);

(2)

(3)

The dotted line means the part where condensation occurs;

a is an integer from 0 to 3;

b is an integer from 0 to 4;

R ₁ and R ₂ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₃₀ alkyl, C ₂ to C ₃₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl , A heterocycloalkyl group having 5 to 7 nuclear atoms, a C ₆ to C ₃₀ aryl group, a heteroaryl group having 5 to 30 nuclear atoms, a C ₁ to C ₃₀ alkyloxy group, a C ₆ to C ₃₀ aryloxy group, C group ₁ ~ C ₃₀ alkyl silyl, C ₅ ~ C aryl silyl group of _30, C ₁ ~ C ₃₀ group of an alkyl boron, C ₆ ~ C group ₃₀ arylboronic of, C ₆ ~ aryl phosphine of C ₃₀ and the wave group, C ₆ ~ C ₃₀ mono or is selected from diaryl phosphine blood group and the group consisting of an aryl amine of the C ₆ ~ C ₃₀ of, in the case where the R ₁ and the individual R ₂ each are a plurality these same as or different from each other,

Alkyl group of the R ₁ and R _2, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ 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 ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, 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 a plurality of substituents, they are the same as or different from each other;

Ar ₁ is a substituent represented by the following formula (4);

[Chemical Formula 4]

In Formula 4,

* Denotes the part where the bond is made;

Each of Z ₁ to Z ₅ is independently N or C (R ₃ ), or at least one of Z ₁ to Z ₅ is N;

R ₃ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₆₀ aryl, nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphospha 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 as in the combination group and adjacent, may form a condensed ring, a plurality of individual said R ₃ They are the same or different from each other;

Alkyl group of the R _3, 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, 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 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _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 ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, 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.

&Quot; 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. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, 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 one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity). 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, Click 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.

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

&Quot; 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.

&Quot; 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.

&Quot; 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.

The compound represented by the formula (1) according to the present invention has excellent thermal stability, hole transportability, hole injection performance, electron transport and electron injection performance, and excellent phosphorescence property as a light emitting layer. .

In addition, when the novel compound represented by the general formula (1) of the present invention is used as a material of an electron transport layer or an electron transporting auxiliary layer, an organic electroluminescent device having an excellent light emitting performance, a low driving voltage, And further, a full color display panel in which performance and lifetime are greatly improved can be also manufactured.

1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

One. New organic compounds

The novel organic compound according to the present invention is characterized in that an electron attracting agent (EWG) having a high electron absorbing property such as a nitrogen-containing heterocycle (e.g., pyridine, pyrimidine and triazine) is added to a naphthyl condensed benzofuran moiety through an m- To form a basic skeleton. The compound represented by the above formula (1).

 [Chemical Formula 1]

In Formula 1,

A is represented by the following formula (2) or (3);

(2)

(3)

The dotted line means the part where condensation occurs;

a is an integer from 0 to 3;

b is an integer from 0 to 4;

R ₁ and R ₂ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₃₀ alkyl, C ₂ to C ₃₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl , A heterocycloalkyl group having 5 to 7 nuclear atoms, a C ₆ to C ₃₀ aryl group, a heteroaryl group having 5 to 30 nuclear atoms, a C ₁ to C ₃₀ alkyloxy group, a C ₆ to C ₃₀ aryloxy group, C group ₁ ~ C ₃₀ alkyl silyl, C ₅ ~ C aryl silyl group of _30, C ₁ ~ C ₃₀ group of an alkyl boron, C ₆ ~ C group ₃₀ arylboronic of, C ₆ ~ aryl phosphine of C ₃₀ and the wave group, C ₆ ~ C ₃₀ mono or is selected from diaryl phosphine blood group and the group consisting of an aryl amine of the C ₆ ~ C ₃₀ of, in the case where the R ₁ and the individual R ₂ each are a plurality these same as or different from each other,

Alkyl group of the R ₁ and R _2, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ 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 ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, 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 a plurality of substituents, they are the same as or different from each other;

Ar ₁ is a substituent represented by the following formula (4);

[Chemical Formula 4]

In Formula 4,

* Denotes the part where the bond is made;

Each of Z ₁ to Z ₅ is independently N or C (R ₃ ), or at least one of Z ₁ to Z ₅ is N;

R ₃ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₆₀ aryl, nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphospha 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 as in the combination group and adjacent, may form a condensed ring, a plurality of individual said R ₃ They are the same or different from each other;

Alkyl group of the R _3, 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, 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 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _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 ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

In the present invention, the compound represented by the above formula (1) is characterized in that an electron-withdrawing group (EWG) is bonded to a naphthyl condensed benzofuran moiety via an m-terphenyl linker, The transition temperature and thermal stability are excellent.

The naphthyl condensed benzofuran moiety is an amphoteric substance having an electron attracting group (EWG) characteristic in which an electron donor has a large electron donating group (EDG) property and a high electron attracting property. When such a moiety is bonded to a triazine group, such as an electron-withdrawing group (EWG) having a high electron attractive property by an m-terphenyl linker group, the whole molecule has a bipolar characteristic or a stronger property of electron attracting property . Therefore, the bonding force between holes and electrons can be enhanced, and the present invention can be applied to an electron-friendly organic electroluminescent device. The m-terphenyl used as the linker group of the compound represented by the formula (1) minimizes the interaction between the electron donor group and the electron attracting group. Therefore, the compound of the present invention into which the m-terphenyl linking group is introduced has a wide band gap and a high triple And has a negative energy. Therefore, when the compound of the present invention is applied to an organic material layer, it is minimized that the exciton is diffused to another adjacent organic material layer. The organic electroluminescent device including such an organic material layer is a compound not having a linker group introduced therein, The light emitting efficiency and lifetime can be improved as compared with an organic electroluminescent device including a monophenyl having a phenyl structure or less and an organic material layer having a biphenyl linker group applied thereto. In addition, the compound of the present invention has an increased molecular weight as compared with a compound having no linker group as a linker group is introduced, thereby improving thermal stability.

The effect is maximized when the effect is designed with m-terphenyl, which is a phosphorus structure proposed in the present invention, rather than substitution positions such as o-terphenyl and p-terphenyl.

In addition, since the compound represented by Formula 1 of the present invention has a high triplet energy, it can exhibit excellent efficiency due to a triplet-triplet fusion (TTF) effect, and most preferably, Can be used. In detail, the compound represented by 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 number of the excitons contributing to light emission in the light emitting layer can be increased to improve the light emitting efficiency of the device, durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that can be driven at low voltage, thereby improving lifetime.

According to a preferred embodiment of the present invention, the compound may be a compound represented by any one of the following formulas (5) to (7)

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 5 to 7,

Each of R ₁ , R ₂ , a, b and Ar ₁ is as defined in the above formula (1).

In the compounds represented by the above formulas (5) to (7) of the present invention, the substituent is connected to the 2-position corresponding to the active site of the naphthyl-condensed benzofuran-type core, The chemical properties are stabilized, high current efficiency and low driving voltage can be secured

In the present invention, m-terphenyl linker has a steric hindrance effect. Therefore, when a compound including m-terphenyl linker is used as a material for an electron transporting layer or the like, the increase of the triplet energy value of the material The triplet-triplet fusion (TTF) effect according to the present invention can prevent the excitons from crossing into the light emitting layer, and thus a synergistic effect of additional efficiency can be expected.

According to a preferred embodiment of the present invention, Ar ₁ is a substituent represented by any of the following formulas A-1 to A-9 in terms of current efficiency and driving voltage, but is not limited thereto:

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

* Denotes the part where the bond is made;

p is an integer from 0 to 4;

q is an integer from 0 to 3;

r is an integer of 0 to 2

R ₄ is 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 ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryloxy 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 _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, a C ₆ to C ₆₀ arylphosphonyl group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent, may form a condensed ring, when individual said R ₄ is a plurality, they Are the same or different from each other;

Alkyl groups of the R _4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, 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 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _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 ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, 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 represented by any one of formulas A-4, A-6 and A-9, more preferably Ar ₁ is a substituent represented by the above formula A- Lt; / RTI >

According to a preferred embodiment of the present invention, each of p, q and r is independently an integer of 0 to 2, preferably 1 or 2.

According to a preferred embodiment of the present invention, R ₄ is selected from the group consisting of halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group and 5 to 60 nuclear heteroaryl groups And the alkyl, aryl and heteroaryl groups of R ₄ are each independently substituted with one or more substituents selected from the group consisting of halogen, cyano, C ₁ to C ₄₀ alkyl and C ₆ to C ₆₀ aryl, 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 ₄ is a C ₆ to C ₂₀ aryl group, and the aryl group of R ₄ is at least one selected from the group consisting of halogen, cyano group and C ₆ to C ₂₀ aryl group When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, R ₄ may be a phenyl group, a biphenyl group or a naphthalenyl group, and each of the phenyl group, biphenyl group and naphthalenyl group of R ₄ may be substituted with one kind of a fluorine group, And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a more preferred embodiment of the present invention, the compound represented by the formula (1) is the compound represented by the formula (5), and Ar ₁ is a triazinyl group substituted with at least one phenyl group in the material of the organic layer, If used, enables high current efficiency and low voltage driving, but is not limited thereto.

According to one preferred embodiment of the invention, the compound is selected from the group consisting of 2- (3 "- (naphtho [2,1-b] benzofuran-10-yl) - [1,1 ' (3, < RTI ID = 0.0 > 1'-biphenyl-4-yl) -4- - (1,1 ': 3', 1 "-terphenyl] -3-yl) -6-phenyl-1,3,5 - (3, < / RTI > < RTI ID = 0.0 & - [1,1 ': 3', 1 "-terphenyl] -3-yl) -1,3,5-triazine or 2,4- - [1,1 ': 3', 1 " -terphenyl] -6- (3 "-( naphtho [2,1- b] benzofuran-10- Yl) -1,3,5-triazine. ≪ / RTI >

The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (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 injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer. ≪ / RTI > compounds.

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, referring to FIG. 1, an anode 10 and a cathode 20 facing each other, 20). ≪ / RTI > Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. A hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32. An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.

2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).

In the present invention, the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO. The layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.

The electron injecting layer 36 is a layer which is stacked on the electron transporting layer to facilitate injection of electrons from the cathode to ultimately improve the power efficiency. For example, LiF, Liq, NaCl, CsF, Li ₂ O, BaO, or the like can be used.

In addition, although not shown in the drawings, the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.

In addition, although not shown in the drawings, the electron transport layer 35 may further include an electron transporting layer between the electron transport layer 35 and the emission layer 32. Holes migrating to the ionization potential level in the organic light emitting element by the light emitting layer 32 are blocked by the high energy barrier of the electron transporting layer and can not diffuse or move to the electron transporting layer and consequently have the function of limiting the holes to the light emitting layer do. The function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .

In the present invention, the naphthyl condensed benzofuran moiety of the compound represented by the formula (1) is basically excellent in electrochemical stability, high in glass transition temperature and carrier transporting ability, and excellent in electron mobility, ≪ / RTI > In addition, the materials represented by the above formula (1) are characterized in that core core and EWG (electron withdrawing group) are bonded to each other through m-terphenyl, and they have a high electron mobility and a high glass transition temperature and thermal stability Is excellent. Therefore, the organic material layer containing the compound represented by Formula 1 is preferably a light emitting layer, an electron transporting layer, or an electron transporting layer, and more preferably an electron transporting layer or an electron transporting layer.

In the present invention, since the compound represented by Formula 1 has a high triplet energy, it can exhibit an excellent efficiency due to a triplet-triplet fusion (TTF) effect, and more preferably, Can be used. More specifically, in the present invention, the compound represented by 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 number of the excitons contributing to light emission in the light emitting layer can be increased to improve the light emitting efficiency of the device, durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that can be driven at low voltage, thereby improving lifetime.

In addition, the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.

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, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 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.

The anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, 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 made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal 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.

[ Synthetic example  1] Synthesis of Compound 1

≪ Step 1 > 4,4,5,5- Tetramethyl -2-( Naphtho [2,1-b] benzofuran -10-yl) -1,3,2- Dioxaborolane synthesis

Bromomapto [2,1-b] benzofuran (50.0 g, 168.3 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- (13.3 g, 201.9 mmol) and Pd (dppf) Cl ₂ (4.1 g, 5.1 mmol), KOAc (33.0 g, 336.5 mmol) were placed in dioxane Lt; / RTI > for one hour. 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 4,4,5,5-tetramethyl-2- (naphtho [2,1-b] benzofuran-10-yl) To obtain 3,2-dioxaborolane (46.3 g, yield 80%).

[LCMS]: 345

<Step 2> Synthesis of Compound 1

The title compound (5 g, 14.5 mmol) obtained in step 1 and 2- (3 '' - chloro- [1,1 ': 3', 1 "-terphenyl] -3- -diphenyl-1,3,5-triazine (7.2 g, 14.5 mmol) and _{Pd (OAc) 2 (0.3 g} , 1.4 mmol), Xphos (1.4 g, 2.9 mmol), Cs 2 CO 3 (9.5 g, 29.5 mmol) was added to 100 ml of toluene, 20 ml of EtOH and 20 ml of H ₂ O, and the mixture was refluxed 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, Compound 1 (6.9 g, yield 70%) was obtained by column chromatography.

[LCMS]: 678

[ Synthetic example  2] Synthesis of Compound 2

(3 &quot; -chloro- [1,1 ': 3', 1 &quot; -terphenyl] -3-yl) -4,6-diphenyl-1-ol used in Step 2 of Synthesis Example 1 , 3'-chloro-l, l ': 3', 1 &quot; -terphenyl ] -3-yl) -6-phenyl-1,3,5-triazine (8.3 g, 14.5 mmol) was used in place of the target compound, Compound 2 7.8 g, yield 61%).

[LCMS]: 754

[ Synthetic example  3] Synthesis of Compound 3

(3 &quot; -chloro- [1,1 ': 3', 1 &quot; -terphenyl] -3-yl) -4,6-diphenyl-1-ol used in Step 2 of Synthesis Example 1 (3 '' - biphenyl-3-yl) -4 - ([1,1'-biphenyl] -4-yl) -6- (9.4 g, 14.5 mmol) was used as the starting material instead of 2-chloro- [1,1 ': 3', 1 "-terphenyl] -3- The procedure of Example 1 was repeated to obtain Compound 3 (7.8 g, yield 55%) as a target compound.

[LCMS]: 831

[ Synthetic example  4] Synthesis of Compound 4

(3 &quot; -chloro- [1,1 ': 3', 1 &quot; -terphenyl] -3-yl) -4,6-diphenyl-1-ol used in Step 2 of Synthesis Example 1 , 3, 4-di (naphthalen-1-yl) -1,3-di ) -1,3,5-triazine (8.6 g, 14.5 mmol) was used in place of the compound 4 (7.4 g, yield 51%) as a target compound .

[LCMS]: 778

[ Synthetic example  5] Synthesis of Compound 5

Except that 2-bromonaphtho [2,3-b] benzofuran (50.0 g, 168.3 mmol) was used instead of 10-bromonaphtho [2,1-b] benzofuran used in Step 1 of Synthesis Example 1 The procedure of Synthesis Example 1 was repeated to obtain Compound 5 (6.1 g, yield 53%) as a target compound.

[LCMS]: 678

[ Synthetic example  6] Synthesis of Compound 9

Except that 8-bromonaphtho [1,2-b] benzofuran (50.0 g, 168.3 mmol) was used instead of 10-bromonaphtho [2,1- b] benzofuran used in Step 1 of Synthesis Example 1 The procedure of Synthesis Example 1 was repeated to obtain Compound 9 (6.0 g, yield 52%) as a target compound.

[LCMS]: 678

[ Example  1 to 6] blue 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 blue organic electroluminescent device was prepared as follows.

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, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

 (DS-205) (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Synthesis Examples 1 to 6 on a prepared ITO transparent electrode Each compound (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  1] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq3 was used instead of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

[ Comparative Example  2] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following compound A was used in place of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

[ Comparative Example  3] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following compound B was used in place of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

[ Comparative Example  4] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following compound C was used in place of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

[ Comparative Example  5] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that the following compound D was used instead of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

[ Comparative Example  6] blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following compound E was used instead of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

[ Comparative Example  7] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following compound F was used in place of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

[ Comparative Example  8] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following compound G was used instead of the compound synthesized in Synthesis Example 1 as the electron transport layer material.

The structures of NPB, ADN and Alq3 used in Examples 1 to 6 and Comparative Examples 1 to 8 are as follows.

[ Evaluation example  One]

Current efficiency and emission peak at current density (10) mA / cm &lt; 2 &gt; were measured for each of the blue organic electroluminescent devices prepared in Examples 1 to 6 and Comparative Examples 1 to 8, Table 1 shows the results.

Transportation material The driving voltage (V) Current efficiency (cd / A) Emission peak (nm) Example 1 Compound 1 3.9 7.3 458 Example 2 Compound 2 4.2 6.9 459 Example 3 Compound 3 4.2 7.0 458 Example 4 Compound 4 4.3 7.0 458 Example 5 Compound 5 4.2 6.8 457 Example 6 Compound 9 4.4 6.9 458 Comparative Example 1 Alq3 4.7 5.9 459 Comparative Example 2 Compound A 4.7 6.1 458 Comparative Example 3 Compound B 4.6 6.1 458 Comparative Example 4 Compound C 4.6 6.4 458 Comparative Example 5 Compound D 4.8 6.2 458 Comparative Example 6 Compound E 4.7 6.2 457 Comparative Example 7 Compound F 4.7 5.9 458 Comparative Example 8 Compound G 4.8 6.0 458

As shown in Table 1 above, the compound of the present invention was used in the electron transport layer

The blue organic electroluminescent devices (Examples 1 to 6) exhibited superior performance in terms of driving voltage, luminescent peak, and current efficiency as compared with the blue organic electroluminescent device using the conventional Alq3 as the electron transport layer (Comparative Example 1) there was. In addition, it was confirmed that the compounds having a terphenyl linker showed improved driving voltage and efficiency characteristics than the compounds F and G having a monophenyl or biphenyl linker. Especially, Compounds A to E having different linker substitution positions among the terphenyl linkers have higher driving voltage and less efficiency than compounds having a specific substitution position according to the present invention.

[ Example  7-12] Blue organic Field  Fabrication of light emitting device

Each of the compounds synthesized in Synthesis Examples 1 to 6 was subjected to high purity sublimation refining as conventionally known, and blue organic EL devices as shown in Table 2 below were prepared.

Hole injection layer Hole transport layer The light- Electron transporting auxiliary layer Electron transport layer Electron injection layer cathode compound DS-205 (Doosan) NPB ADN + 5% DS-405
(Doosan Corporation) Each of the compounds synthesized in Synthesis Examples 1 to 6 Alq ₃ LiF Al thickness 80 nm 15 nm 30 nm 5 nm 25 nm 1 nm 200 nm

In Table 2, the structures of NPB, ADN and Alq ₃ are as follows.

[ Comparative Example  9] Blue organic Field  Fabrication of light emitting device

The device was fabricated in the same manner as in Comparative Example 1.

[ Comparative Example  10] Blue organic Field  Fabrication of light emitting device

A device was prepared in the same manner as in Example 7, except that BCP having the following structure was used instead of Compound 1 as an electron transporting auxiliary layer material.

[ Comparative Example  11] Blue organic Field  Fabrication of light emitting device

A device was fabricated in the same manner as in Example 7 except that Compound A was used instead of Compound 1 as an electron transporting auxiliary layer material.

[ Comparative Example  12] Blue organic Field  Fabrication of light emitting device

A device was fabricated in the same manner as in Example 7 except that Compound B was used instead of Compound 1 as an electron transporting auxiliary layer material.

[ Comparative Example  13] Blue organic Field  Fabrication of light emitting device

A device was fabricated in the same manner as in Example 7, except that Compound C was used instead of Compound 1 as an electron transporting auxiliary layer material.

[ Comparative Example  14] Blue organic Field  Fabrication of light emitting device

A device was fabricated in the same manner as in Example 7 except that Compound D was used instead of Compound 1 as an electron transporting auxiliary layer material.

[ Comparative Example  15] blue organic Field  Fabrication of light emitting device

A device was fabricated in the same manner as in Example 7 except that Compound E was used in place of Compound 1 as an electron transporting auxiliary layer material.

[ Comparative Example  16] Blue organic Field  Fabrication of light emitting device

The device was fabricated in the same manner as in Example 7 except that Compound F was used instead of Compound 1 as an electron transporting auxiliary layer material.

[ Comparative Example  17] Blue organic Field  Fabrication of light emitting device

A device was fabricated in the same manner as in Example 7 except that Compound G was used instead of Compound 1 as an electron transporting auxiliary layer material.

[ Evaluation example  2]

Current efficiency and emission peak at current density (10) mA / cm &lt; 2 &gt; were measured for each of the blue organic electroluminescent devices prepared in Examples 7 to 12 and Comparative Examples 9 to 17, Table 3 shows the results.

Auxiliary layer material The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 7 Compound 1 3.2 459 8.1 Example 8 Compound 2 3.4 459 7.7 Example 9 Compound 3 3.4 458 7.6 Example 10 Compound 4 3.5 459 7.6 Example 11 Compound 5 3.4 458 7.4 Example 12 Compound 9 3.6 459 7.5 Comparative Example 9 - 4.7 459 5.9 Comparative Example 10 BCP 4.6 457 6.2 Comparative Example 11 Compound A 4.1 456 7.2 Comparative Example 12 Compound B 3.9 458 7.0 Comparative Example 13 Compound C 3.9 460 7.3 Comparative Example 14 Compound D 3.8 456 7.3 Comparative Example 15 Compound E 4.0 460 7.2 Comparative Example 16 Compound F 4.5 457 6.6 Comparative Example 17 Compound G 4.4 452 6.8

As shown in Table 3, it was confirmed that the organic electroluminescent devices of Examples 7 to 12 including the electron transporting layer of the present invention had higher current efficiency and better driving voltage than the organic electroluminescent devices of Comparative Examples 9 to 17. In addition, it was confirmed that the compounds having a terphenyl linker showed improved driving voltage and efficiency characteristics than the compounds F and G having a monophenyl or biphenyl linker. In particular, compounds having specific substitution positions according to the present invention as compared to Compounds A to E having different linker substitution positions in the terphenyl linker significantly improve the characteristics of the device in the use of the electron transporting layer as well as the electron transporting layer .

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transporting auxiliary layer
34: Electron transport layer 35: Electron transport layer
36: electron injection layer 37: hole injection layer

Claims (11)

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

In Formula 1,
A is represented by the following formula (2) or (3);
(2)

(3)

The dotted line means the part where condensation occurs;
a is an integer from 0 to 3;
b is an integer from 0 to 4;
R ₁ and R ₂ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₃₀ alkyl, C ₂ to C ₃₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl , A heterocycloalkyl group having 5 to 7 nuclear atoms, a C ₆ to C ₃₀ aryl group, a heteroaryl group having 5 to 30 nuclear atoms, a C ₁ to C ₃₀ alkyloxy group, a C ₆ to C ₃₀ aryloxy group, C group ₁ ~ C ₃₀ alkyl silyl, C ₅ ~ C aryl silyl group of _30, C ₁ ~ C ₃₀ group of an alkyl boron, C ₆ ~ C group ₃₀ arylboronic of, C ₆ ~ aryl phosphine of C ₃₀ and the wave group, C ₆ ~ C ₃₀ mono or is selected from diaryl phosphine blood group and the group consisting of an aryl amine of the C ₆ ~ C ₃₀ of, in the case where the R ₁ and the individual R ₂ each are a plurality these same as or different from each other,
Alkyl group of the R ₁ and R _2, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ 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 ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, 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 a plurality of substituents, they are the same as or different from each other;
Ar ₁ is a substituent represented by the following formula (4);
[Chemical Formula 4]

In Formula 4,
* Denotes the part where the bond is made;
Z ₁ , Z ₃ and Z ₅ are each independently N or C (R ₃ ), or at least one of Z ₁ , Z ₃ and Z ₅ is N;
Z ₂ and Z ₄ are each independently C (R ₃ );
R ₃ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₆₀ aryl, nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphospha 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 as in the combination group and adjacent, may form a condensed ring, a plurality of individual said R ₃ They are the same or different from each other;
Alkyl group of the R _3, 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, 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 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _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 ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. The method according to claim 1,
Wherein said compound is represented by any one of the following formulas (5) to (7):
[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 5 to 7,
R ₁ , R ₂ , a, b and Ar ₁ are each as defined in claim ₁ . The method according to claim 1,
Wherein Ar ₁ is a substituent represented by any one of the following formulas A-1, A-3, A-4, A-6 and A-

In Formulas A-1, A-3, A-4, A-6 and A-9,
* Denotes the part where the bond is made;
p is an integer from 0 to 4;
q is an integer from 0 to 3;
r is an integer of 0 to 2
R ₄ is 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 ₃ to C ₄₀ cycloalkyl, A C ₆ to C ₆₀ aryloxy 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 _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, a C ₆ to C ₆₀ arylphosphonyl group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent, may form a condensed ring, when individual said R ₄ is a plurality, they Are the same or different from each other;
Alkyl groups of the R _4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, 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 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _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 ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. The method of claim 3,
Wherein R ₄ is selected from the group consisting of halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group and 5 to 60 nuclear heteroaryl groups, and the R ₄ alkyl group, aryl group And heteroaryl groups are each independently substituted or unsubstituted with at least one substituent selected from the group consisting of halogen, cyano group, C ₁ to C ₄₀ alkyl group and C ₆ to C ₆₀ aryl group, and when substituted with a plurality of substituent groups , Which are the same or different from each other. The method of claim 3,
Wherein R ₄ is a C ₆ to C ₂₀ aryl group, and the aryl group of R ₄ is substituted or unsubstituted with at least one substituent selected from the group consisting of halogen, cyano group and C ₆ to C ₂₀ aryl group, When they are substituted with a substituent, they are the same as or different from each other. The method according to claim 1,
Wherein said compound is an electron transporting layer of an organic electroluminescent device. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds:

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). 9. The method of claim 8,
Wherein the organic material layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transporting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and a light emitting layer. 10. The method of claim 9,
Wherein the organic compound layer containing the compound is selected from the group consisting of a light emitting layer, an electron transport layer, and an electron transporting auxiliary layer. 10. The method of claim 9,
Wherein the organic compound layer containing the compound is an electron transporting auxiliary layer.

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