KR20170136832A - 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, wherein 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,

Z ₁ to Z ₃ are each independently N or C (R ₂ ), or at least two of Z ₁ to Z ₃ are N;

m is an integer from 0 to 4;

R ₁ 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, 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, an aryloxy group of a C ₆ ~ C ₆₀ of, C _A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphonyl group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of, when the plurality of R ₁ individual, a plurality of R ₁ are the same or different from each other;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

R ₂ 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 ₃ to C ₄₀ cycloalkyl, 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 aryloxy group , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

Arylene group and a heteroarylene group, an alkyl group of said R ₁ and R ₂ of the L, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl 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, ~ 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 boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ aryl silyl group And when they are substituted with a plurality of substituents, they are the same as or different from each other;

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

n is an integer of 1 or 2, and when n is 2, two D's are the same as or different from each other;

(2)

In Formula 2,

* Denotes the part where the bond is made;

Ar ₁ and Ar ₂ 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 ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl groups of the Ar ₁ and Ar _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl 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, an arylthio 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, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same as or different from each other.

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

"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. 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 phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / 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.

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

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,

Z ₁ to Z ₃ are each independently N or C (R ₂ ), or at least two of Z ₁ to Z ₃ are N;

m is an integer of 0 to 4, preferably 1 or 2;

R ₁ 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, 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, an aryloxy group of a C ₆ ~ C ₆₀ of, C _A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphonyl group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of, when the plurality of R ₁ individual, a plurality of R ₁ are the same or different from each other;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;

R ₂ 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 ₃ to C ₄₀ cycloalkyl, 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 aryloxy group , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

Arylene group and a heteroarylene group, an alkyl group of said R ₁ and R ₂ of the L, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl 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, ~ 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 boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ aryl silyl group And when they are substituted with a plurality of substituents, they are the same as or different from each other;

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

n is an integer of 1 or 2, and when n is 2, two D's are the same as or different from each other;

(2)

In Formula 2,

* Denotes the part where the bond is made;

Ar ₁ and Ar ₂ 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 ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl groups of the Ar ₁ and Ar _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl 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, an arylthio 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, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same as or different from each other.

The condensed compounds having excellent EWG (electronwithdrawing group) characteristics represented by the formula (1) of the present invention are electrochemically stable and have excellent electron mobility as well as high glass transition temperature and thermal stability Is excellent. Therefore, the compound represented by the general formula (1) of the present invention is excellent in electron transporting ability and luminescent property, and can be used as a material for a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, . Preferably used as a material of any one of the light-emitting layer, the electron transporting layer and the electron transporting layer which is further laminated on the electron transporting layer, more preferably the material of the electron transporting layer or the electron transporting layer.

Accordingly, when the compound represented by the formula (1) of the present invention is used for an organic electroluminescent device, not only excellent thermal stability and carrier transport ability (in particular, electron transporting ability and light emitting ability) can be expected, Life and the like can be improved and high triplet energy can exhibit excellent efficiency increase due to the triplet-triplet fusion (TTF) effect as the latest ETL material.

In addition, the compound represented by Chemical Formula (1) of the present invention is highly advantageous for electron injection, and the long-lasting life span of the indium derivative containing nitrogen (N) and the materials having the phosphine-oxide functional group (phosphinyl group) Properties. The excellent electron transporting ability can have high efficiency and fast mobility in organic electroluminescent devices.

In addition, the compound represented by the general formula (1) of the present invention has a broad bandgap value in general, and a material comprising a bond of an indene derivative containing nitrogen (N) and a phosphine-oxide functional group (phosphine group) It is easy to adjust HOMO and LUMO energy levels according to direction and position. The organic electroluminescent device using such a compound can exhibit a high electron transporting property.

According to a preferred embodiment of the present invention, the compound of Formula 1 may be a compound represented by Formula 3:

(3)

In Formula 3,

R ₃ and R ₄ are each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and an arylamine group having a C ₆ to C ₆₀ Wherein R < ₃ > and R < ₄ > are not all hydrogen;

The alkyl, aryl, heteroaryl and arylamine groups of R ₃ and R ₄ 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 ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ substituted by one substituent at least one selected from the aryl group consisting of an amine group in the C ₆₀ or beach And when they are substituted with a plurality of substituents, they may be the same or different,

Each of Z ₁ to Z ₃ , L, D and n is as defined in the above formula (1).

According to one preferred embodiment of the present invention, the compound of Formula 1 may be a compound represented by Formula 4:

[Chemical Formula 4]

In Formula 4,

Each of R ₁ , L, D, m and n is as defined in the above formula (1).

According to a preferred embodiment of the present invention, R ₁ may be selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a phenanthrenyl group and a triphenylenyl group.

According to a preferred embodiment of the present invention, at least one of R ₃ and R ₄ may be selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a phenanthrenyl group and a triphenylenyl group.

According to a preferred embodiment of the present invention, L may be a linker represented by the following formula (5)

[Chemical Formula 5]

In Formula 5,

* Denotes the part where the bond is made;

L ₁ to L ₃ each independently may be selected from the group consisting of a single bond, a phenylene group, a pyridinyl group, and a naphthalenyl group.

According to a preferred embodiment of the present invention, when n is 1, L may be a linker selected from the group consisting of the following groups A1 to A5, and when n is 2, L is a group selected from the group consisting of the following B1 to B4 The linker may be selected, but is not limited to:

In the above-mentioned A1 to A5 and B1 to B4, * denotes a portion where bonding is performed. In A1 to A5, any one of the two bond lines (*) may be bonded to an N-containing indene derivative and the other bond to D. In B 1 to B 4, any one of the three bonding lines (- *) may be bonded to an N-containing indene derivative, and the other two bonding lines may be bonded to two Ds, which are the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ and Ar ₂ are each independently selected from the group consisting of 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.

According to a preferred embodiment of the present invention, Ar ₁ and Ar ₂ may each independently be represented by a substituent represented by the following formula (5):

[Chemical Formula 5]

In Formula 5,

* Denotes the part where the bond is made;

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

R ₅ is hydrogen, C ₁ ~ C ₄₀ alkyl group, are selected from the group consisting of C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group for, when the R ₅ a plurality individual, a plurality of R ₅ Are the same or different from each other;

The alkyl, aryl and heteroaryl groups of R ₅ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, A heteroaryl group having 5 to 60 nuclear atoms and an arylamine group having ₆ to ₆₀ carbon atoms, 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 and Ar ₂ may each independently be a substituent represented by any one of the following C1 to C58:

In the above C1 to C58, * denotes a portion where bonding is performed.

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

In the present invention, the compound represented by Formula 1 may be synthesized by the synthesis method shown in the following Reaction Scheme 1, but it is not limited thereto and may be synthesized by a general synthetic method (Chem. Rev., 60: 313 1960), J. Chem. SOC., 4482 (1955), Chem. Rev. 95: 2457 (1995), etc.). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

[Reaction Scheme 1]

In the above Reaction Scheme 1,

Y ₁ , Y ₂ and Y ₃ are each independently selected from the group consisting of hydrogen, Cl and Br,

R ₃ , R ₄ , L, n, Ar ₁ and Ar ₂ are each as defined in the above formulas (1) and (2).

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, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI >

In the present invention, the compound represented by the general formula (1) has excellent electrochemical stability, high glass transition temperature and excellent carrier transporting ability, and excellent electron mobility. The materials represented by Formula 1 are structurally characteristic to be bonded with core core and EWG (electron withdrawing group), and have excellent electron mobility and excellent high glass transition temperature and thermal stability. Therefore, it is preferable that the organic material layer containing the compound represented by Formula 1 is a light emitting layer, an electron transporting layer, or an electron transporting supporting layer.

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 auxiliary layer, and the electron injecting layer may include the compound represented by the above Formula 1, And the transporting auxiliary layer may include the compound represented by the above formula (1).

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 can be formed by using a material known in the art (for example, an electron transport layer or an electron transporting auxiliary layer) such that at least one or more of the organic material layers And forming other organic layers and electrodes using the method.

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] 2- Bromo - [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

≪ Step 1 > [(2- Pyridinylamino ) Thioxomethyl ] -, Ethyl ester (9CI)  synthesis

To 100 g (1.06 mol) of 2-aminopyridine was added 500 mL of dichloromethane. Cooled to 0 < 0 > C and 139.3 g (1.06 mol) of ethoxycarbonyl isocyanate was slowly added dropwise over 15 minutes. The reaction solution was warmed to room temperature and stirred for 20 hours. The solvent was appropriately removed by distillation under reduced pressure and the mixture was filtered. After drying with warm air, 215 g of the objective compound (yield: 90%) was obtained.

<Step 2> [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

A mixed solvent of EtOH / MeOH (1: 1, 2.15 L) was added to 298 g (4.29 mol) of hydroxylamine hydrochloride. 399 mL (2.86 mol) of triethylamine was added to the reaction solution, which was stirred for 1 hour. 215 g (0.95 mol) of [(2-pyridinylamino) thioxomethyl] -, ethyl ester (9CI) was added and the temperature was gradually raised, and the mixture was refluxed for 3 hours. The temperature was cooled to room temperature and the resulting solid was filtered. The obtained solid products were combined, washed with purified water, an EtOH / MeOH mixed solvent and n-hexane, and dried under a humid atmosphere to obtain 115 g of the title compound (yield 90%).

^{1 H-NMR (in DMSO)} : δ 8.50 (dd, 1H), 7.39 (t, 1H), 7.29 (dd, 1H), 6.81 (t, 1H), 5.97 (s, 2H)

[LCMS]: 134

<Step 3> 2- Bromo - [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

57.5 g (0.26 mol) of CuBr ₂ and 1.2 L of THF were added to 115 g (0.86 mol) of [1,2,4] triazolo [1,5-a] pyridin- The reaction solution was cooled to 0 ° C, 1.2 L of HBr was added slowly, and 177 g (2.57 mol) of NaNO ₂ was dissolved in 600 mL of purified water and slowly added dropwise. The reaction solution was stirred at room temperature for 12 hours. 500 mL of an aqueous solution of sodium hydroxide was added to the reaction solution, and the mixture was stirred for 1 hour. Then, the mixture was extracted with 2 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 102 g of the target compound (yield: 60%).

^{1 H-NMR (in DMSO)} : δ 8.92 (dd, 1H), 7.78 (dd, 1H), 7.72 (td, 1H), 7.23 (td, 1H)

[LCMS]: 198

[ Preparation Example  2] 2- Bromo -8-phenyl- [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

<Step 1> Synthesis of N - [[(3- Bromo -2- Pyridinyl ) Amino] Thioxomethyl ] -, Ethyl ester  synthesis

The procedure of Step 1 of [Preparation Example 1] was repeated except for using 2-amino-3-bromopyridine as a reactant to obtain 32 g (yield: 88%) of the desired compound.

<Step 2> 8- Bromo - [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

The procedure of Step 2 of Preparation Example 1 was repeated except that N - [[(3-bromo-2-pyridinyl) amino] thioxomethyl] - ethyl ester was used as a reactant, g (yield: 90%).

^{1 H-NMR (300Mz, CDCl} 3): δ 8.54 (d, 1H), 7.69 (d, 1H), 6.77 (t, 1H), 6.22 (s, 2H)

[LCMS]: 213

<Step 3> 2- Bromo - [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

To 20 g (93.9 mmol) of 8-bromo- [1,2,4] triazolo [1,5-a] pyridin- 2-amine and 13.7 g (113 mmol) of phenylboronic acid were added 300 mL of dioxane, ₂ O 100 mL was added. 5.4 g (4.7 mmol) of Pd (PPh ₃ ) _{4 and} 38.9 g (282 mmol) of K ₂ CO ₃ were added, and the mixture was refluxed at 120 ° C. for 3 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (16.8 g, yield 85%).

[LCMS]: 210

<Step 4> Synthesis of 2- Bromo -8-phenyl- [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

The procedure of Step 3 of [Preparation Example 1] was repeated except for using 2-bromo- [1,2,4] triazolo [1,5-a] pyridine as a reactant to obtain the title compound (14.2 g, 65%).

^{1 H-NMR (in DMSO)} : δ 8.92 (dd, 1H), 8.02 (m, 2H), 7.96 (dd, 1H), 7.52 (t, 2H), 7.46 (d, 1H), 7.33 (t, 1H )

[LCMS]: 274

[ Preparation Example  3] 2- Bromo -6-phenyl- [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

The procedure of Steps 1 to 4 in [Preparation Example 2] was repeated except that 2-amino-5-bromopyridine was used as a reactant, to obtain 10.5 g (yield 38%) of the desired compound.

[LCMS]: 274

[ Preparation Example  4] 2- Bromo -6,8-diphenyl- [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

<Step 1> [ [(3,5- Dichloro -2- Pyridinyl ) Amino] Thioxomethyl ] -, Ethyl ester  (9CI) Synthesis of

The procedure of Step 1 of [Preparation Example 1] was repeated except for using 2-amino-3,5-dichloropyridine as a reactant to obtain 48 g of the title compound (yield 92%).

&Lt; Step 2 > 6,8- Dichloro - [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

The same procedure as in Step 2 of [Preparation Example 1] was carried out except that [(3,5-dichloro-2-pyridinyl) amino] thioxomethyl] -, ethyl ester (9CI) 29.8 g (yield 90%) of the compound was obtained.

^{1 H-NMR (300Mz, DMSO} ): δ 8.88 (s, 1H), 7.77 (s, 1H), 6.36 (s, 2H)

[LCMS]: 203

&Lt; Step 3 > 6,8-Diphenyl- [1,2,4] triazolo [1,5-a] pyridine -2- Amine  synthesis

To 400 mL of dioxane and 41.8 g (0.34 mol) of phenylboronic acid were added 29 g (0.14 mol) of 6,8-dichloro- [1,2,4] triazolo [1,5- 150 mL of H ₂ O was added. After adding 3.2 g (0.014 mol) of Pd (OAc) ₂ , 13.6 g (0.0.09 mol) of XPhos and 140 g (0.43 mol) of Cs ₂ CO ₃ , the mixture was refluxed at 120 ° C for 3 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of purified water. The mixture was extracted with 1 L of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4, distilled under reduced pressure, and purified by silica gel column chromatography to obtain the title compound (35.6 g, yield 87%).

^{1 H-NMR (300Mz, CDCl} 3): δ 8.49 (d, 1H), 7.95 (d, 2H), 7.76 (d, 1H), 7.59 (d, 2H), 7.49 (m, 4H), 7.42 (t , &Lt; / RTI &gt; 2H), 4.60 (s, 2H)

[LCMS]: 286

<Step 4> Synthesis of 2- Bromo -6,8-diphenyl- [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

The same procedure as in Step 3 of [Preparation Example 1] was carried out except that 6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridin- 22.3 g (yield 52%) of the desired compound was obtained.

^{1 H-NMR (300Mz, CDCl} 3): δ 8.66 (d, 1H), 8.00 (dd, 2H), 7.92 (d, 1H), 7.60 (d, 2H), 7.52 (m, 4H), 7.46 (d , 2H)

[LCMS]: 350

[ Preparation Example  5] 2- Bromo -6,8-di (naphthalen-1-yl) - [1,2,4] triazolo [1,5- a] pyridine

The same procedure as in steps 1 to 4 of [Preparation example 4] was carried out except that 2-amino-3,5-dichloropyridine and [1,1'-biphenyl] -4-ylboronic acid were used as reactants 9.5 g (yield: 28%) of the desired compound was obtained.

[LCMS]: 502

[ Preparation Example  6] 2- Bromo -6,8-di (naphthalen-2-yl) - [1,2,4] triazolo [1,5- a] pyridine

The procedure of Steps 1 to 4 of [Preparation Example 4] was repeated except for using 2-amino-3,5-dichloropyridine and naphthalene-2-ylboronic acid as a reactant to obtain 16.4 g (yield: 28% ).

^{1 H-NMR (in DMSO)} : δ 9.07 (s, 1H), 8.79 (s, 1H), 8.44 (s, 1H), 8.33 (dd, 1H), 8.27 (s, 1H), 8.00 (m, 5H ), 7.94 (m, 2H), 7.54 (m, 4H)

[LCMS]: 450

[ Preparation Example  7] 2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) phenyl) - [1, 2,4] triazolo [1,5-a] pyridine

<Step 1> 2 -(4- Chlorophenyl ) - [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

The procedure of Preparation Example 2 was repeated except that 2-bromo- [1,2,4] triazolo [1,5-a] pyridine and (4-chlorophenyl) boronic acid of Preparation Example 1 were used as a reactant. 3, 9.6 g (yield 82%) of the desired compound was obtained.

[LCMS]: 229

<Step 2> Synthesis of 2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) phenyl) - [L, 2,4] triazolo [l, 5-a] pyridine  synthesis

A solution of 9.6 g (41.8 mmol) of 2- (4-chlorophenyl) - [1,2,4] triazolo [1,5- a] pyridine synthesized above, 4,4,4 ' , Dioxane (200 mL) was added to 12.7 g (50.2 mmol) of 5 ', 5'-octamethyl-2,2' -bis (1,3,2-dioxaborolane). 1.7 g (2.1 mmol) of Pd (dppf) Cl ₂ and 12.3 g (125 mmol) of KOAc were added to the reaction solution. The mixture was heated to 130 DEG C for 6 hours under reflux. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of ammonium chloride aqueous solution. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (11.1 g, yield 83%).

[LCMS]: 321

[ Preparation Example  8] 2- (3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) phenyl) - [1, 2,4] triazolo [1,5-a] pyridine

The procedure of Preparation Example 7 was repeated except that 2-bromo- [1,2,4] triazolo [1,5-a] pyridine and (3-chlorophenyl) boronic acid of Preparation Example 1 were used as a reactant. 1 and 2, 7.2 g (yield: 40%) of the target compound was obtained.

[LCMS]: 321

[ Preparation Example  9] 8-phenyl-2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) phenyl) - [1, 2,4] triazolo [1,5-a] pyridine

Except that 2-bromo-8-phenyl- [1,2,4] triazolo [1,5-a] pyridine and (4-chlorophenyl) boronic acid of Preparation Example 2 were used as the reactants 7], 10.5 g (yield 58%) of the desired compound was obtained.

[LCMS]: 397

[ Preparation Example  10] diphenyl (6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-2-yl) phosphine oxide

<Step 1> Synthesis of (6-bromonaphthalene-2-yl) diphenylphosphine oxide  synthesis

500 mL of toluene was added to 25 g (0.124 mol) of diphenylphosphine oxide and 82.3 g (0.247 mol) of 2-bromo-6-iodonaphthalene. Pd (PPh ₃₎ after the addition of _{4 7.1 g (6.2 mmol),} TEA 51.7 mL (0.371 mol) was heated to reflux at 120 ℃ 6 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain 24.2 g (yield: 48%) of the target compound.

[LCMS]: 407

Step 2 Synthesis of diphenyl (6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-2-yl) phosphine oxide

The procedure of Step 2 of [Preparation Example 7] was repeated except for using 24 g of (6-bromonaphthalene-2-yl) diphenylphosphine oxide synthesized in the above, to obtain the title compound (14.2 g, %).

[LCMS]: 454

[ Preparation Example  11] diphenyl (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) phosphine oxide

The procedure of Steps 1 and 2 of [Preparation Example 10] was repeated except for using diphenylphosphine oxide and 1-bromo-4-iodonaphthalene as a reactant to obtain the desired compound (9.4 g, yield 55%) .

[LCMS]: 454

[ Preparation Example  12] 6-phenyl-2- (3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) phenyl) - [1, 2,4] triazolo [1,5-a] pyridine

Except that 2-bromo-6-phenyl- [1,2,4] triazolo [1,5-a] pyridine and (3-chlorophenyl) boronic acid of Preparation Example 3 were used as reaction materials 7], the target compound (8.8 g, yield 48%) was obtained.

[LCMS]: 397

[ Preparation Example  13] 6,8-Diphenyl-2- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) phenyl) - [1, 2,4] triazolo [1,5-a] pyridine

Except that 2-bromo-6,8-diphenyl- [1,2,4] triazolo [1,5-a] pyridine and (4-chlorophenyl) boronic acid of Preparation Example 4 were used as a reactant The procedure of Steps 1 and 2 of [Preparation Example 7] was repeated to obtain 6.2 g of the desired compound (yield: 49%).

^{1 H-NMR (300Mz, CDCl} 3): δ 8.76 (s, 1H), 8.34 (d, 2H), 8.18 (d, 2H), 7.92 (d, 2H), 7.90 (s, 1H), 7.64 (d , &Lt; / RTI &gt; 2H), 7.52 (m, 6H)

[LCMS]: 473

[ Preparation Example  14] 6,8-di ([1,1'-biphenyl] -4-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborato Yl) phenyl) - [1, 2,4] triazolo [1,5-a] pyridine

To a reaction mixture were added 6,8-di ([1,1'-biphenyl] -4-yl) -2-bromo- [1,2,4] triazolo [ (Yield: 49%) was obtained by carrying out the same processes as in [1] to [2] of [Preparation Example 7], except that 4- (4-chlorophenyl) boronic acid was used.

[LCMS]: 625

[ Preparation Example  15] 6,8-di (naphthalen-2-yl) -2- (4- (4,4,5,5-tetramethyl- 1,3,2-dioxabororan- - [l, 2,4] triazolo [l, 5-a] pyridine

To a reaction mixture were added 2-bromo-6,8-di (naphthalen-2-yl) - [1,2,4] triazolo [1,5- a] pyridine prepared in Preparation Example 6 and (4-chlorophenyl) boronic acid , The procedure of Steps 1 and 2 of [Preparation Example 7] was repeated to obtain 11.4 g (yield: 56%) of the desired compound.

[LCMS]: 573

[ Synthetic example  1] Synthesis of Compound 2

Except that 2-bromo- [1,2,4] triazolo [1,5-a] pyridine and (4-bromophenyl) diphenylphosphine oxide of Preparation Example 1 were used as the reactants 2] to obtain the title compound (5.5 g, yield 38%).

[LCMS]: 395

[ Synthetic example  2] Synthesis of Compound 3

To the reaction mixture was added a solution of 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ The procedure of Step 3 of [Preparation Example 2] was repeated except for using [1,5-a] pyridine and (4-bromophenyl) diphenylphosphine oxide to obtain 3.7 g of the title compound (yield: 44% ).

[LCMS]: 471

[ Synthetic example  3] Synthesis of Compound 6

To the reaction mixture was added a solution of 2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) - [ (39% yield) of the desired compound was obtained by carrying out the same processes as in [Step 3] of [Preparation Example 2], except that [l, 5-a] pyridine and (3-bromophenyl) diphenylphosphine oxide were used, ).

[LCMS]: 471

[ Synthetic example  4] Synthesis of Compound 10

To the reaction mixture was added a solution of 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ The same procedure as in the step 3 of [Preparation Example 2] was carried out except that [5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) To obtain 5.4 g (yield 47%) of the desired compound.

[LCMS]: 671

[ Synthetic example  5] Synthesis of Compound 15

To a solution of 8-phenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ , 4] The procedure of Step 3 of [Preparation Example 2] was repeated except that triazolo [1,5-a] pyridine and (3-bromophenyl) diphenylphosphine oxide were used, (Yield: 58%).

[LCMS]: 547

[ Synthetic example  6] Synthesis of Compound 19

Bromo-8-phenyl- [1,2,4] triazolo [1,5-a] pyridine prepared in Preparation Example 2 and diphenyl (6- (4,4,5,5 -Tetramethyl-1,3,2-dioxabororane-2-yl) naphthalen-2-yl) phosphine oxide was used in place of [ 6.2 g (yield 55%) of the compound was obtained.

[LCMS]: 521

[ Synthetic example  7] Synthesis of Compound 21

To a solution of 8-phenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ , 4] triazolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) The same procedure was carried out to obtain 2.9 g (yield: 60%) of the desired compound.

[LCMS]: 747

[ Synthetic example  8] Synthesis of Compound 29

Bromo-6-phenyl- [1,2,4] triazolo [1,5-a] pyridine prepared in Preparation Example 3 and diphenyl (4- (4,4,5,5 -Tetramethyl-1,3,2-dioxabororane-2-yl) naphthalen-1-yl) phosphine oxide was used in place of [ 4.3 g (yield 37%) of the compound was obtained.

[LCMS]: 521

[ Synthetic example  9] Synthesis of Compound 33

Phenyl-2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ , 4] triazolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) The same procedure was followed to obtain 2.5 g of the desired compound (yield: 60%).

[LCMS]: 747

[ Synthetic example  10] Synthesis of Compound 36

To a solution of 6,8-diphenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ 1,2,4] triazolo [l, 5-a] pyridine and (4-bromophenyl) diphenylphosphine oxide were used in the same manner as in [Step 3 of Preparation Example 2] 5.7 g (yield 52%) of the compound was obtained.

^{1 H-NMR (300Mz, CDCl} 3): δ 8.77 (d, 1H), 8.43 (d, 2H), 8.20 (d, 2H), 7.91 (d, 1H), 7.76 (m, 8H), 7.68 (dd 2H), 7.64 (dd, 2H), 7.55 (m, 6H), 7.46 (m, 6H)

[LCMS]: 623

[ Synthetic example  11] Synthesis of Compound 37

To a solution of 6,8-diphenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ 1,2,3] triazolo [1,5-a] pyridine and (3-bromophenyl) phenylphosphine oxide was used in place of [ 3.4 g (yield 54%) of the compound was obtained.

^{1 H-NMR (300Mz, CDCl} 3): δ 8.78 (d, 1H), 8.39 (d, 2H), 8.19 (d, 2H), 8.03 (d, 1H), 7.91 (d, 1H), 7.84 (d 7H), 7.46 (m, 7H), 7.72 (m, 2H)

[LCMS]: 623

[ Synthetic example  12] Synthesis of Compound 43

To a solution of 6,8-diphenyl-2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ 1,2,3] triazolo [1,5-a] pyridine and (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) The procedure of Step 3 was repeated to obtain the desired compound (7.3 g, yield 45%).

[LCMS]: 823

[ Synthetic example  13] Synthesis of Compound 47

([1,1'-biphenyl] -4-yl) -2- (4- (4,4,5,5,5-tetramethyl-1,3,2- Yl] phenyl) - [1,2,4] triazolo [1,5-a] pyridine and (4-bromophenyl) diphenylphosphine oxide were used instead of [ The procedure of Step 3 of Preparation Example 2] was repeated to obtain the desired compound (3.3 g, yield 40%).

[LCMS]: 775

[ Synthetic example  14] Synthesis of Compound 51

To a reaction mixture were added 6,8-di ([1,1'-biphenyl] -4-yl) -2-bromo- [1,2,4] triazolo [ Except that the diphenyl (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-1-yl) phosphine oxide of Preparation Example 11 was used The procedure of Step 3 of [Preparation Example 2] was repeated to obtain 5.3 g of the desired compound (yield: 41%).

[LCMS]: 749

[ Synthetic example  15] Synthesis of Compound 59

As the reactant, 6,8-di (naphthalen-2-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (3-bromophenyl) phenylphenyl) - [1,2,4] triazolo [1,5-a] pyridine and The same procedure was followed to obtain 2.5 g of the desired compound (yield: 40%).

[LCMS]: 723

[ Synthetic example  16] Synthesis of Compound 62

A mixture of 2-bromo-6,8-di (naphthalen-2-yl) - [1,2,4] triazolo [1,5- a] pyridine prepared in Preparation Example 6 and diphenyl - (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) naphthalen-1-yl) phosphine oxide was used instead of [ The procedure of Step 3 was followed to obtain the desired compound (5.5 g, yield 35%).

[LCMS]: 697

[ Synthetic example  17] Synthesis of Compound 64

As the reactant, 6,8-di (naphthalen-2-yl) -2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (5-bromo-1,3-phenylene) bis (diphenylphosphine oxide) was used in place of The procedure of Step 3 of [Preparation Example 2] was repeated to yield the desired compound (4.0 g, yield 49%).

[LCMS]: 923

[ Example  1 to 13] blue organic Field  Fabrication of light emitting device

Compounds 2, 3, 10, 19, 21, 29, 36, 37, 43, 47, 51, 62 and 64 synthesized in Synthesis Example were subjected to high purity sublimation purification by a conventionally known method, A light emitting device was fabricated.

first. Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed 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.

NPN (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound 2, 3, 10 and 19 (30 nm) / LiF (1 nm) / Al (200 nm) in the order of 21, 29, 36, 37, 43, 47, 51, 62 and 64 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 Alq ₃ was used instead of Compound 2 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 Compound 2 was not used as the electron transport layer material.

The structures of NPB, AND and Alq3 used in Examples 1 to 13 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example  One]

The driving voltage, current efficiency and emission wavelength at the current density of 10 mA / cm 2 were measured for the blue organic electroluminescent devices fabricated in Examples 1 to 13 and Comparative Examples 1 and 2, Respectively.

Sample Electron transport layer The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 Compound 2 3.8 452 7.5 Example 2 Compound 3 4.2 452 8.0 Example 3 Compound 10 3.6 453 7.8 Example 4 Compound 19 3.3 452 8.2 Example 5 Compound 21 3.8 453 8.0 Example 6 Compound 29 4.1 452 7.8 Example 7 Compound 36 3.9 455 8.4 Example 8 Compound 37 3.6 450 8.5 Example 9 Compound 43 3.3 452 7.7 Example 10 Compound 47 3.6 453 7.9 Example 11 Compound 51 3.9 450 8.3 Example 12 Compound 62 4.0 454 7.9 Example 13 Compound 64 3.9 452 8.1 Comparative Example 1 Alq ₃ 5.4 458 5.5 Comparative Example 2 - 4.9 460 5.8

As shown in Table 1 above, the blue organic electroluminescent devices (Examples 1 to 13) using the compound of the present invention as the electron transporting layer (Comparative Examples 1 and 2) using conventional Alq ₃ as the electron transporting layer and the blue organic electroluminescent devices Emitting layer and the blue organic electroluminescent device without the electron transport layer (Comparative Example 2).

[ Example  14-23] Blue organic Field  Fabrication of light emitting device

Compounds 3, 6, 15, 21, 33, 37, 51, 59, 62 and 64 synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method and then blue organic electroluminescent devices Respectively.

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

NPN (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound 20, 25, 83, 95 Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

A blue organic electroluminescent device was fabricated in the same manner as in Example 12 except that Compound 3 was not used as an electron transporting auxiliary layer material and Alq ₃ , which is an electron transporting layer material, was deposited at 30 nm instead of 25 nm .

[ Evaluation example  2]

The driving voltage, light emission wavelength and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 14 to 23 and Comparative Example 3, respectively, and the results are shown in Table 2 below.

Sample Electron transporting auxiliary layer The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 14 Compound 3 4.4 456 8.7 Example 15 Compound 6 3.3 450 8.5 Example 16 Compound 15 3.7 452 9.0 Example 17 Compound 21 3.8 455 8.2 Example 18 Compound 33 3.6 458 7.9 Example 19 Compound 37 3.9 458 8.5 Example 20 Compound 51 3.5 450 8.8 Example 21 Compound 59 4.1 452 8.5 Example 22 Compound 62 3.7 455 7.5 Example 23 Compound 64 3.8 456 8.4 Comparative Example 3 - 4.8 458 6.0

As shown in Table 2, the blue organic electroluminescent devices (Examples 14 to 23) using the compound of the present invention as the electron transporting auxiliary layer (Examples 14 to 23) were superior to the blue organic electroluminescent devices Current efficiency, emission peak, and driving voltage.

Claims (13)

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

In Formula 1,
Z ₁ to Z ₃ are each independently N or C (R ₂ ), or at least two of Z ₁ to Z ₃ are N;
m is an integer from 0 to 4;
R ₁ 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, 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, an aryloxy group of a C ₆ ~ C ₆₀ of, C _A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphonyl group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl group of an amine of, when the plurality of R ₁ individual, a plurality of R ₁ are the same or different from each other;
L is selected from the group consisting of a single bond, an arylene group having ₆ to ₃₀ carbon atoms and a heteroarylene group having 5 to 30 nuclear atoms;
R ₂ 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 ₃ to C ₄₀ cycloalkyl, 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 aryloxy group , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;
Arylene group and a heteroarylene group, an alkyl group of said R ₁ and R ₂ of the L, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl 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, ~ 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 boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ aryl silyl group And when they are substituted with a plurality of substituents, they are the same as or different from each other;
D is a substituent represented by the following formula (2);
n is an integer of 1 or 2, and when n is 2, two D's are the same as or different from each other;
(2)

In Formula 2,
* Denotes the part where the bond is made;
Ar ₁ and Ar ₂ 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 ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
Alkyl groups of the Ar ₁ and Ar _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl 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, an arylthio 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, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same as or different from each other. The method according to claim 1,
The compound is a compound represented by the following formula (3): &lt; EMI ID =
(3)

In Formula 3,
R ₃ and R ₄ are each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and an arylamine group having a C ₆ to C ₆₀ Wherein R &lt; ₃ &gt; and R &lt; ₄ &gt; are not all hydrogen;
The alkyl, aryl, heteroaryl and arylamine groups of R ₃ and R ₄ 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 ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ substituted by one substituent at least one selected from the aryl group consisting of an amine group in the C ₆₀ or beach And when they are substituted with a plurality of substituents, they may be the same or different,
Each of Z ₁ to Z ₃ , L, D and n is as defined in claim 1. The method according to claim 1,
The compound is a compound represented by the following formula 4:
[Chemical Formula 4]

In Formula 4,
R ₁ , L, D, m and n are each as defined in claim 1. The method according to claim 1,
Wherein R &lt; ₁ &gt; is selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a phenanthrenyl group and a triphenylenyl group. 3. The method of claim 2,
Wherein at least one of R ₃ and R ₄ is selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a phenanthrenyl group and a triphenylenyl group. The method according to claim 1,
Wherein L is a linker represented by the following formula 5:
[Chemical Formula 5]

In Formula 5,
* Denotes the part where the bond is made;
L ₁ to L ₃ each independently may be selected from the group consisting of a single bond, a phenylene group, a pyridinyl group, and a naphthalenyl group. The method according to claim 1,
Wherein when n is 1, L is a linker selected from the group consisting of the following groups A1 to A5:

In the above-mentioned A1 to A5,
* Means the part where the bond is made. The method according to claim 1,
When n is 2, L is a linker selected from the group consisting of the following B1 to B4: Compound:

In the above B1 to B4,
* Means the part where the bond is made. The method according to claim 1,
Wherein Ar ₁ and Ar ₂ are each independently a substituent represented by the following formula (5):
[Chemical Formula 5]

In Formula 5,
* Denotes the part where the bond is made;
X ₁ to X ₅ are each independently N or C (R ₅ );
R ₅ is hydrogen, C ₁ ~ C ₄₀ alkyl group, are selected from the group consisting of C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group for, when the R ₅ a plurality individual, a plurality of R ₅ Are the same or different from each other;
The alkyl, aryl and heteroaryl groups of R ₅ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, A heteroaryl group having 5 to 60 nuclear atoms and an arylamine group having ₆ to ₆₀ carbon atoms, and when they are substituted with a plurality of substituents, they may be the same or different from each other . The method according to claim 1,
Wherein Ar ₁ and Ar ₂ are each independently a substituent represented by any one of the following C1 to C58:

In the above C1 to C58,
* Means the part where the combination is made. 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). 13. The method of claim 12,
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.