KR20160079415A - 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. More specifically, the present invention relates to a novel carbazole-based compound having excellent thermal stability, phosphorescent properties, and the like, and relates to an organic electroluminescent device comprising the same in at least one organic matter layer, which has a low driving voltage, the high light-emitting efficiency, and the improved durability. The compound is represented by chemical formula 1.

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 luminescent compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel carbazole compound having excellent thermal stability and phosphorescence characteristics, Efficiency and lifetime characteristics of an organic electroluminescent device.

The electroluminescent (EL) device (hereinafter, simply referred to as 'organic EL device') was fabricated by blue electroluminescence using anthracene single crystal in 1965, starting from the observation of the organic thin film emission of Bernanose in the 1950s. Research has continued. In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to make a high efficiency and high number of organic EL devices, each organic EL device has been developed in a manner of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

In the organic EL 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 light emitting layer forming material of the organic EL device can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing better natural colors according to luminescent 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 phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, researches on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolylbiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of light emission characteristics, but their thermal stability is lowered due to a low glass transition temperature, so that they are not satisfactory in terms of lifetime in OLED devices. Therefore, development of materials with higher performance is required.

An object of the present invention is to provide a novel organic compound which has a high glass transition temperature and is excellent in thermal stability and can improve the bonding force between holes and electrons.

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

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

[Chemical Formula 1]

In Formula 1,

X ₁ and X ₂ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ With the proviso that at least one of X ₁ and X ₂ is N (Ar ₁ );

L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nucleus atoms;

Ar ₁ to Ar ₅ and R ₁ to R ₆ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ alkynyl group of C _40, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C of ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the A phosphinyl group, and an arylsilyl group of C ₆ to C ₆₀ , or may combine with adjacent groups to form a condensed ring;

a, b, c and d are each independently an integer of 0 to 4;

e is an integer from 0 to 3;

f is an integer from 0 to 2;

Arylene group and a heteroarylene group and Ar ₁ to Ar ₅ and R ₁ to the alkyl group of R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group of the L _1, an arylamine group, An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkylboron group, an arylboron group, an alkylphosphine group, , A cyano group, 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 40 nuclear atoms, An aryloxy group of C ₆ to C ₆₀ , an alkyloxy group of C ₁ to C ₄₀ , an arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, group C ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic Blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C substituted with one or more substituents selected from the ₆₀ arylsilyl group the group consisting of or being unsubstituted , When they are substituted with a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of Chemical Formulas 2 to 7.

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 2 to 7,

Each of L ₁ , X ₁ to X ₂ , R ₁ to R ₆ , Ar ₁ to Ar ₅ and a to f is as defined in the above formula (1).

According to a preferred embodiment of the present invention, X ₁ and X ₂ in the general formula ( ₁ ) are all N (Ar ₁ ), and a plurality of Ar _{1 s} may be the same as or different from each other.

According to a preferred embodiment of the present invention, L ₁ in the general formula ( ₁₎ may be a single bond, a phenylene group or a biphenylene group.

According to a preferred embodiment of the present invention, Ar ₁ to Ar ₅ and R ₁ to R ₄ in Formula 1 are each independently hydrogen, deuterium (D), C ₆ to C ₆₀ aryl, To 40 heteroaryl groups, and R < ₅ > and R < ₆ > may all be hydrogen.

According to a preferred embodiment of the present invention, at least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ in Formula 1 may be a substituent represented by Formula 8 below.

[Chemical Formula 8]

In Formula 8,

* Represents a moiety bonded to Formula 1;

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nucleus atoms;

Z ₁ to Z ₅ are the same or different from each other and each independently N or C (R ₁₁ ), at least one of Z ₁ to Z ₅ is N;

When the R ₁₁ multiple individuals, all of which are the same or different, wherein R ₁₁ is 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 of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, an aryloxy group of C ₆ ~ C ₆₀ C ₁ ~ alkyloxy group of C _40, C C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C group _{of 6} to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphine group, C ₆ to C ₆₀ mono or diaryl phosphine blood group and a C ₆ - or selected from the group consisting arylsilyl of C ₆₀ of the adjacent To form a condensed ring;

Alkyl group of the R _11, 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 alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 40 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of 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, the substituent represented by the formula (8) may be a substituent represented by any one of the following formulas (A-1) to (A-15).

In the above formulas A-1 to A-15,

* Denotes the part where the bond is made;

n is an integer of 0 to 4, and when n is 0, hydrogen means not substituted by substituent R ₂₁ , and when n is an integer of 1 to 4, R ₂₁ is each independently selected from the group consisting of deuterium, 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 alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms , C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C of aryloxy ₆₀ C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryl amine 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 arylphosphine group, a C ₆ to C ₆₀ mono or diaryl A phosphinyl group and an arylsilyl group having ₆ to ₆₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring;

Alkyl group of the R _21, 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 alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 40 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of And when they are substituted with a plurality of substituents, they are the same as or different from each other;

L < ₂ > and R < ₁₁ > are the same as defined in the above formula (8).

According to a preferred embodiment of the present invention, the substituent represented by any one of formulas (A-1) to (A-5) is selected from the group consisting of the following substituents.

In the above substituents, * denotes a portion where a bond is formed.

In addition, the present invention provides a cathode active material comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode, The organic electroluminescent device comprising the compound represented by formula (I).

According to a preferred embodiment of the present invention, at least one of the one or more organic layers including the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, Preferably, the compound represented by Formula 1 may be used as a green or red phosphorescent host of the light emitting layer.

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

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

The term "alkynyl" in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

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

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

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon of the ring, preferably 1 to 3 carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

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

In the present invention, 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 is excellent in thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 according to the present invention is used as a phosphorescent host material, it is possible to manufacture an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, and long life time, Further, a full color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The present invention relates to a novel carbazole-based compound having excellent thermal stability and phosphorescence characteristics, and more particularly to a carbazole-based compound having at least two or more carbazole moieties, a dibenzo-moiety bonded to form a basic skeleton, A compound having a structure in which various substituents are bonded to such basic skeleton. However, the bonding position of these is not particularly limited.

Specifically, the novel organic compound provided by the present invention is characterized by being represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X ₁ and X ₂ are the same or different and are each independently selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ , Wherein at least one of X ₁ and X ₂ is N (Ar ₁ ), preferably X ₁ and X ₂ are all N (Ar ₁ ), a plurality of Ar ₁ are the same or different from each other;

L ₁ is a divalent group linker known in the art and is selected from the group consisting of a single bond, a C ₆ to C ₄₀ arylene group, and a heteroarylene group having 5 to 40 nucleus atoms, A phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, a prinylene group, a quinolinylene group, , An imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group and a pyrimidinylene group, more preferably a single bond, a phenylene group or a biphenylene group;

Ar ₁ to Ar ₅ and R ₁ to R ₆ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ alkynyl group of C _40, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C of ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the A phosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , or may combine with adjacent groups to form a condensed ring. Preferably, Ar ₁ to Ar ₅ and R ₁ to R ₄ are each independently selected from the group consisting of , Hydrogen, deuterium (D), C ₆ -C An aryl group having 1 to ₆₀ carbon atoms, a heteroaryl group having 5 to 40 nuclear atoms, and R ₅ and R ₆ are both hydrogen;

a, b, c and d are each independently an integer of 0 to 4;

e is an integer from 0 to 3;

f is an integer from 0 to 2;

Arylene group and a heteroarylene group and Ar ₁ to Ar ₅ and R ₁ to the alkyl group of R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group of the L _1, an arylamine group, An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkylboron group, an arylboron group, an alkylphosphine group, , A cyano group, 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 40 nuclear atoms, An aryloxy group of C ₆ to C ₆₀ , an alkyloxy group of C ₁ to C ₄₀ , an arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, group C ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic Blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C substituted with one or more substituents selected from the ₆₀ arylsilyl group the group consisting of or being unsubstituted , When they are substituted with a plurality of substituents, they may be the same or different.

The dibenzo moiety which may be included in the compound represented by formula (1) of the present invention may be selected from the following structures.

On the other hand, carbazole moieties are widely used as materials for organic electroluminescent devices, particularly phosphorescent host materials. The carbazole moiety is mainly used for the blue phosphorescent host, with a triple energy as large as 3.0 eV and a low HOMO energy level of 6.0 eV. Therefore, in the case of the compound represented by Formula 1 of the present invention in which two dibenzo-moieties are bonded to one benzene ring of the carbazole moiety, the triplet energy is smaller than 3.0 eV, the HOMO energy level is increased, The band gap becomes suitable for the blue / green / red phosphorescent host.

In the compound of Formula 1 of the present invention, a carbazole moiety and one of the dibenzo-moieties are bonded to one benzene ring of the carbazole moiety to form a steric hinderance. Cause. Therefore, compound molecules are distorted to solve the problem of lowering the luminescence property due to pi-pi-stacking, thereby preventing the formation of an excimer (excimer), thereby improving the luminous efficiency do.

Further, in the compound represented by Formula 1 of the present invention, the carbazole moiety has a characteristic of an electron donating group (EDG). When an electron withdrawing group (EWG) is introduced as a substituent at the 9-position of the carbazole moiety, the compound of the present invention has an electron withdrawing group (EWG) The whole molecule contains bipolar, including electron donating group (EDG). The bipolar compound represented by the formula (1) of the present invention can be used not only as a host in a phosphorescent light emitting layer but also as a hole transport layer, a hole injection layer, and an electron transport layer since it can increase the bonding force between holes and electrons.

Meanwhile, the compound represented by the formula (1) of the present invention has a higher thermal stability than the conventional CBP (4,4-dicarbazolylbiphenyl) as the molecular weight of the compound is significantly increased due to the substituent introduced into the molecule and the glass transition temperature is improved . Further, the compound represented by the general formula (1) of the present invention is also effective for inhibiting crystallization of the organic material layer.

According to a preferred embodiment of the present invention, the compound represented by the formula (1) may be a compound represented by any one of the following formulas (2) to (7).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 2 to 7,

Each of L ₁ , X ₁ to X ₂ , R ₁ to R ₆ , Ar ₁ to Ar ₅ and a to f is as defined in the above formula (1).

According to a preferred embodiment of the present invention, at least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ in Formula 1 may be a substituent represented by Formula 8 below.

[Chemical Formula 8]

In Formula 8,

* Represents a moiety bonded to Formula 1;

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nucleus atoms;

Z ₁ to Z ₅ are the same or different from each other and each independently N or C (R ₁₁ ), at least one of Z ₁ to Z ₅ is N;

When the R ₁₁ multiple individuals, all of which are the same or different, R ₁₁ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₆₀ C ₁ ~ alkyloxy group of C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or a neighboring tile that To form a condensed ring;

Alkyl group of the R _11, 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 alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 40 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of 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, at least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ in Formula 1 may be a substituent represented by any of Formulas A-1 to A-15.

In the above formulas A-1 to A-15,

* Denotes the part where the bond is made;

n is an integer of 0 to 4, and when n is 0, hydrogen means not substituted by substituent R ₂₁ , and when n is an integer of 1 to 4, R ₂₁ is each independently selected from the group consisting of deuterium, 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 alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms , C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C of aryloxy ₆₀ C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryl amine 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 arylphosphine group, a C ₆ to C ₆₀ mono or diaryl A phosphinyl group and an arylsilyl group having ₆ to ₆₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring;

Alkyl group of the R _21, 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 alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 40 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of And when they are substituted with a plurality of substituents, they are the same as or different from each other;

L < ₂ > and R < ₁₁ > are the same as defined in the above formula (8).

According to a preferred embodiment of the present invention, the substituent represented by any one of formulas A-1 to A-15 is preferably selected from the group consisting of the following substituents. However, it is not particularly limited.

In the above substituents, * denotes a moiety in which a bond is formed.

According to one preferred embodiment of the present invention, the compound represented by formula (1) of the present invention may be selected from the group consisting of the following compounds, but is not limited thereto.

In the present invention, the compound represented by Formula 1 may be synthesized according to a general synthesis method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic electroluminescent device

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 organic electroluminescent device according to the present invention includes one or more organic layers interposed between the anode and the cathode, (i) an anode, (ii) a cathode, and (iii) At least one of the one or more organic layers includes a compound represented by the general formula (1). At this time, the compound represented by the formula (1) may be used alone or in combination of two or more.

According to an embodiment of the present invention, in the organic electroluminescent device, 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, an electron transporting layer and an electron injecting layer, (1). ≪ / RTI > Preferably, the organic compound layer containing the compound of Formula 1 may be a light emitting layer.

In addition, according to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). When the compound of Formula 1 is included in the light emitting layer material of the organic electroluminescent device, preferably blue, green, and red phosphorescent host materials, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved. The compound represented by Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.

Here, the structure of the organic electroluminescent device is not particularly limited, and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At least one or more of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer may be laminated on the electron transport layer as described above. ≪ / RTI > compounds.

In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic layers and an anode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one layer (for example, a light emitting layer) of the organic material layer includes the compound represented by Formula 1 Other organic material layers and electrodes.

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

On the other hand, a ceramic crucible having a high thermal conductivity is used as a method of forming an organic material layer of an organic electroluminescent device through a vacuum deposition method, and a stepwise and continuous evaporation control is possible, and an organic material should not be spattered. The temperature rise of the evaporation source is not properly performed, and the organic material having reached the evaporation temperature in an excessively short time causes a phenomenon of splashing and clogging of the inlet of the evaporation source. As a result, the deposition rate of the organic material becomes unstable, . Also, there is a high possibility that the organic material is discolored or discolored during the deposition. Organic materials have the property of being melted or sublimated depending on the material. When the organic material is deposited by the sublimation method, the organic material layer is formed immediately after the sublimation process in the solid state, whereas in the case of the melting method The solid is vaporized through the liquid to form an organic layer. It is difficult to control the deposition temperature and the uniformity because the melting method is one step higher than the phase change of the material as compared with the sublimation method. At this time, the compound represented by the formula (1) according to the present invention can be deposited by the sublimation method to have uniform thin film characteristics, thereby improving the luminescent characteristics.

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

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

Examples of the positive electrode material that can be used 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.

Examples of the cathode material which can be used include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional materials known in the art can be used.

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

[Preparation Example 1] Synthesis of TCZ-1

<Step 1> Synthesis of 1-chloro-9-phenyl-9H-3,9'-bicarbazole

Carbazole (17.8 g, 50.0 mmol), 9H-carbazole (8.35 g, 50.0 mmol) and Pd ₂ (dba) ₃ (2.30 g, 2.5 mmol), (t-Bu) ₃ P (1.01 g, 5.0 mmol) and sodium tertiary-butoxide (14.7 g, 150.0 mmol) were placed in 500 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 1-chloro-9-phenyl-9H-3,9'-bicarbazole (14.8 g, yield 67%) was obtained by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 443

Elemental Analysis: C, 81.35; H, 4.32; Cl, 8.00; N, 6.32

<Step 2> Synthesis of TCZ-1

Carbazole (13.3 g, 30.0 mmol), (9H-carbazol-3-yl) boronic acid (6.33 g, 30.0 mmol), K 250 ml / 120 ml THF / H ₂ O was added to a solution of _2- CO ₃ (12.8 g, 90.0 mmol), Pd (PPh ₃ ) ₄ (1.73 g, 5 mol%) and X- Phos 90 C &lt; / RTI &gt; for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, TCZ-1 (10.5 g, yield 61%) was obtained by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 574

^{1 H-NMR: δ 7.16 (} m, 2H), 7.20 (m, 2H), 7.35 (m, 2H), 7.52 (m, 7H), 7.67 (m, 3H), 7.74 (m, 2H), 7.95 ( 2H), 8.52 (m, 2H), 11.54 (s, 1H)

[Preparation Example 2] Synthesis of TCZ-2

Step 2 of Preparation Example 1 was repeated except that (9H-carbazol-2-yl) boronic acid (6.33 g, 30.0 mmol) was used in place of (9H-carbazol- To obtain TCZ-2 (11.2 g, yield 65%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 574

^{1 H-NMR: δ 7.19 (} m, 4H), 7.35 (m, 2H), 7.54 (m, 7H), 7.62 (m, 3H), 7.75 (m, 2H), 7.94 (m, 3H), 8.19 ( (m, 2H), 8.31 (t, 1H), 8.55 (m, 2H), 11.55

[Preparation Example 3] Synthesis of TCZ-3

Step 2 of Preparation Example 1 was repeated except that (9H-carbazol-4-yl) boronic acid (6.33 g, 30.0 mmol) was used in place of (9H-carbazol- To obtain TCZ-3 (8.95 g, yield 52%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 574

^{1 H-NMR: δ 7.19 (} m, 4H), 7.35 (m, 2H), 7.55 (m, 8H), 7.62 (m, 3H), 7.75 (m, 2H), 7.94 (m, 2H), 8.20 ( m, 2 H), 8.54 (m, 2 H), 11.56 (s, 1 H)

[Preparation Example 4] Synthesis of TCZ-4

<Step 1> Synthesis of 9- (4-chlorodibenzo [b, d] thiophen-2-yl) -9H-carbazole

Except that 2-bromo-4-chlorodibenzo [b, d] thiophene (14.9 g, 50.0 mmol) was used instead of 3-bromo-1-chloro-9- (4-chlorodibenzo [b, d] thiophen-2-yl) -9H-carbazole (14.6 g, yield 76%) was obtained by carrying out the same procedure as in <Step 1> of Example 1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 384

Elemental Analysis: C, 75.09; H, 3.68; Cl, 9.23; N, 3.65; S, 8.35

<Step 2> Synthesis of TCZ-4

Carbodiazepine (11.5 g, 30.0 mmol) instead of 9-chloro-9-phenyl-9H-3,9'- (10.2 g, yield 66%) was obtained in the same manner as in < Step 2 > of Preparation Example 1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 515

^{1 H-NMR: δ 7.18 (} m, 3H), 7.35 (t, 1H), 7.51 (m, 5H), 7.63 (d, 1H), 7.77 (m, 2H), 7.92 (m, 4H), 8.00 ( (s, 1H), 8.20 (m, 2H), 8.50 (m, 2H), 11.56

[Preparation Example 5] Synthesis of TCZ-5

Carbodiazepine (11.5 g, 30.0 mmol) instead of 9-chloro-9-phenyl-9H-3,9'- (9.12 g, yield 59%) was obtained in the same manner as in < Step 1 >

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 515

^{1 H-NMR: δ 7.16 (} t, 1H), 7.21 (m, 2H), 7.35 (t, 1H), 7.53 (m, 5H), 7.63 (d, 1H), 7.75 (m, 2H), 7.92 ( 2H), 8.50 (m, 2H), 8.01 (s, 1H), 8.20

[Preparation Example 6] Synthesis of TCZ-6

Carbodiazepine (11.5 g, 30.0 mmol) instead of 9-chloro-9-phenyl-9H-3,9'- (7.57 g, yield 49%) was obtained by carrying out the same procedure as <Step 1> of Preparation Example 3, except that

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 515

¹ H-NMR:? 7.19 (m, 3H), 7.35 (t, IH), 7.52 (m, 6H), 7.64 (s, 1H), 8.19 (m, 2H), 8.50 (m, 2H), 11.56

[Preparation Example 7] Synthesis of TCZ-7

<Step 1> Synthesis of 9- (4-chlorodibenzo [b, d] furan-2-yl) -9H-carbazole

Except that 2-bromo-4-chlorodibenzo [b, d] furan (14.1 g, 50.0 mmol) was used instead of 3-bromo-1-chloro-9- (4-chlorodibenzo [b, d] furan-2-yl) -9H-carbazole (13.1 g, yield 71%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 368

Elemental Analysis: C, 78.37; H, 3.84; Cl, 9.64; N, 3.81; O, 4.35

<Step 2> Synthesis of TCZ-7

(11.0 g, 30.0 mmol) instead of 9- (4-chlorodibenzo [b, d] furan-2-yl) -9H- carbazole in place of 1-chloro-9- (8.38 g, yield: 56%) was obtained in the same manner as in &lt; Step 2 &gt; of Preparation Example 1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 499

^{1 H-NMR: δ 7.19 (} m, 3H), 7.35 (m, 3H), 7.52 (m, 4H), 7.62 (m, 2H), 7.71 (m, 2H), 7.93 (m, 4H), 8.19 ( m, 2H), 8.55 (d, 1H), 11.55 (s, 1H)

[Preparation Example 8] Synthesis of TCZ-8

(11.0 g, 30.0 mmol) instead of 9- (4-chlorodibenzo [b, d] furan-2-yl) -9H- carbazole in place of 1-chloro-9- (8.68 g, yield: 58%) was obtained in the same manner as in &lt; Step 1 &gt;

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 499

^{1 H-NMR: δ 7.20 (} m, 3H), 7.37 (m, 3H), 7.52 (m, 4H), 7.65 (m, 2H), 7.71 (m, 2H), 7.92 (m, 3H), 8.19 ( (d, IH), 8.55 (d, IH), 11.55 (s, IH)

[Preparation Example 9] Synthesis of TCZ-9

(11.0 g, 30.0 mmol) instead of 9- (4-chlorodibenzo [b, d] furan-2-yl) -9H- carbazole in place of 1-chloro-9- TCZ-9 (6.59 g, 44% yield) was obtained by following the procedure of <Step 1> of Preparation Example 3, except that

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 499

^{1 H-NMR: δ 7.19 (} m, 3H), 7.33 (m, 3H), 7.55 (m, 5H), 7.65 (m, 2H), 7.71 (m, 2H), 7.93 (m, 3H), 8.20 ( m, 2H), 8.55 (d, 1H), 11.55 (s, 1H)

[Preparation Example 10] Synthesis of TCZ-10

Step 1 Synthesis of 9- (1-chloro-9,9-dimethyl-9H-fluoren-3-yl) -9H-carbazole

Except that 3-bromo-1-chloro-9,9-dimethyl-9H-fluorene (15.4 g, 50.0 mmol) was used instead of 3-bromo-1-chloro-9- 9-dimethyl-9H-fluoren-3-yl) -9H-carbazole (14.4 g, yield 73%) was obtained in the same manner as in <Step 1> &Lt; / RTI &gt;

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 394

Elemental Analysis: C, 82.33; H, 5.12; Cl, 9.00; N, 3.56

<Step 2> Synthesis of TCZ-10

(9-dimethyl-9H-fluoren-3-yl) -9H-carbazole (11.8 g, The procedure of Step 2 of Preparation Example 1 was repeated to obtain TCZ-10 (8.03 g, yield 51%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 525

^{1 H-NMR: δ 1.64 (} s, 6H), 7.21 (m, 4H), 7.35 (m, 2H), 7.52 (m, 4H), 7.63 (d, 1H), 7.73 (m, 2H), 7.99 ( 2H), 8.52 (d, 1H), 11.56 (s, 1H)

[Preparation Example 11] Synthesis of TCZ-11

Synthesis of 4-bromo-2-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole

(14.0 g, 50.0 mmol), NaH (1.2 g, 50.0 mmol) and DMF (150 ml) were mixed under nitrogen atmosphere and stirred at room temperature for 10 minutes, and 2 -Chloro-4,6-diphenyl-1,3,5-triazine (13.4 g, 50.0 mmol) was added and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water was added thereto, and the solid compound was filtered, and then purified by column chromatography to obtain 4-bromo-2-chloro-9- (4,6-diphenyl- Azin-2-yl) -9H-carbazole (20.7 g, yield 81%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 511, 513

Elemental Analysis: C, 63.36; H, 3.15; Br, 15.61; Cl, 6.93; N, 10.95

<Step 2> Synthesis of TCZ-11

Bromo-2-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl) (10.4 g, yield: 58%) was obtained in the same manner as in <Step 1> of Preparation Example 1 except that -9H-carbazole (15.3 g, 30.0 mmol)

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 598

^{1 H-NMR: δ 7.13 (} s, 1H), 7.19 (m, 3H), 7.33 (m, 3H), 7.51 (m, 8H), 7.94 (m, 2H), 8.19 (d, 1H), 8.36 ( d, 4H), 8.55 (d, IH)

[Synthesis Example 1] Synthesis of C21

(5.74 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.0 mmol) and Pd ₂ (dba) ₃ (0.46 g , 0.5 mmol), (t-Bu) ₃ P (0.20 g, 1.0 mmol) and sodium tertiary-butoxide (2.94 g, 30.0 mmol) were placed in 500 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent of the filtered organic layer was removed, and the desired compound C21 (6.20 g, yield 77%) was obtained by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 805

[Synthesis Example 2] Synthesis of C 23

2- (3-Chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol) instead of 2-chloro-4,6- ), The target compound C23 (7.75 g, yield: 88%) was obtained by carrying out the same procedure as in Synthesis Example 1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 881

[Synthesis Example 3] Synthesis of C28

The procedure of Synthesis Example 1 was repeated except that TCZ-2 (5.74 g, 10.00 mmol) was used in place of TCZ-1 to obtain the desired compound C28 (6.44 g, yield 80%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 805

[Synthesis Example 4] Synthesis of C 29

The procedure of Synthesis Example 2 was repeated except that TCZ-2 (5.74 g, 10.00 mmol) was used instead of TCZ-1 to obtain the desired compound C 29 (7.14 g, yield 81%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 881

[Synthesis Example 5] Synthesis of C 30

The procedure of Synthesis Example 1 was repeated except that TCZ-3 (5.74 g, 10.00 mmol) was used instead of TCZ-1 to obtain the target compound C30 (5.64 g, yield 70%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 805

[Synthesis Example 6] Synthesis of C 51

The procedure of Synthesis Example 1 was repeated except that TCZ-4 (5.15 g, 10.00 mmol) was used in place of TCZ-1 to obtain the target compound C 51 (5.37 g, yield 72%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 746

[Synthesis Example 7] Synthesis of C 53

The procedure of Synthesis Example 2 was repeated except that TCZ-4 (5.15 g, 10.00 mmol) was used instead of TCZ-1 to obtain C 53 (6.49 g, yield 79%) as a target compound.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 822

[Synthesis Example 8] Synthesis of C 58

The procedure of Synthesis Example 1 was repeated except that TCZ-5 (5.15 g, 10.00 mmol) was used in place of TCZ-1 to obtain the target compound C 58 (5.30 g, yield 71%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 746

[Synthesis Example 9] Synthesis of C 59

The procedure of Synthesis Example 2 was repeated except that TCZ-5 (5.15 g, 10.00 mmol) was used in place of TCZ-1 to obtain the desired compound C 59 (6.74 g, yield 82%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 822

[Synthesis Example 10] Synthesis of C 60

The procedure of Synthesis Example 1 was repeated except that TCZ-6 (5.15 g, 10.00 mmol) was used in place of TCZ-1 to obtain C 60 (5.30 g, yield 71%) as a target compound.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 746

[Synthesis Example 11] Synthesis of C 81

The procedure of Synthesis Example 1 was repeated except that TCZ-7 (4.99 g, 10.00 mmol) was used in place of TCZ-1 to obtain C 81 (5.40 g, yield 74%) as a target compound.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 730

[Synthesis Example 12] Synthesis of C 83

The procedure of Synthesis Example 2 was repeated except that TCZ-7 (4.99 g, 10.00 mmol) was used instead of TCZ-1 to obtain the desired compound C83 (6.69 g, yield 83%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 806

[Synthesis Example 13] Synthesis of C 88

The procedure of Synthesis Example 1 was repeated except that TCZ-8 (4.99 g, 10.00 mmol) was used instead of TCZ-1 to obtain the desired compound C88 (5.11 g, yield 70%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 730

[Synthesis Example 14] Synthesis of C 89

The procedure of Synthesis Example 2 was repeated except that TCZ-8 (4.99 g, 10.00 mmol) was used instead of TCZ-1 to obtain the desired compound C 89 (7.01 g, yield 87%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 806

[Synthesis Example 15] Synthesis of C 90

(5.26 g, yield 72%) was obtained in the same manner as in Synthesis Example 1, except that TCZ-9 (4.99 g, 10.00 mmol) was used instead of TCZ-1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 730

[Synthesis Example 16] Synthesis of C 111

The procedure of Synthesis Example 1 was repeated except that TCZ-10 (5.25 g, 10.00 mmol) was used in place of TCZ-1 to obtain C 111 (5.37 g, yield 71%) as a target compound.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 756

[Synthesis Example 17] Synthesis of C 113

The procedure of Synthesis Example 2 was repeated except that TCZ-10 (5.25 g, 10.00 mmol) was used in place of TCZ-1 to obtain C 113 (6.41 g, yield 77%) as a target compound.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 832

[Synthesis Example 18] Synthesis of C 123

(2.87 g, 30.0 mmol) and K ₂ CO ₃ (4.27 g, 30.0 mmol) were added to a solution of the compound 120 ml / 40 ml / 40 ml of Tol / EtOH / H ₂ O were added to Pd (PPh ₃ ) ₄ (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, C123 (4.51 g, yield 56%) was obtained by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 805

[Examples 1 to 18] Fabrication of green organic EL device

The compounds C 21 to C 123 synthesized in Synthesis Examples 1 to 18 were subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / each compound of C 21 to C 123 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ 30 nm) / LiF (1 nm) / Al (200 nm) in this order to form an organic EL device.

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

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound C 21 as a luminescent host material in forming the light emitting layer.

[Evaluation example]

The driving voltage, current efficiency and emission peak at the current density (10) mA / cm2 were measured for each of the green organic EL devices manufactured in Examples 1 to 18 and Comparative Example 1, and the results are shown in the following Table 1 .

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 C 21 6.61 518 38.6 Example 2 C 23 6.70 517 39.3 Example 3 C 28 6.49 518 38.5 Example 4 C 29 6.81 518 39.9 Example 5 C 30 6.73 517 40.2 Example 6 C 51 6.74 518 40.8 Example 7 C 53 6.77 518 40.7 Example 8 C 58 6.71 516 39.2 Example 9 C 59 6.68 517 39.8 Example 10 C 60 6.63 517 39.4 Example 11 C 81 6.49 518 38.5 Example 12 C 83 6.87 517 39.1 Example 13 C 88 6.66 517 41.3 Example 14 C 89 6.70 517 40.4 Example 15 C 90 6.82 517 42.2 Example 16 C 111 6.81 518 41.5 Example 17 C 113 6.82 518 41.7 Example 18 C 123 6.81 518 39.6 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound (C 21 to C 123) according to the present invention was used as a light emitting layer of a green organic EL device (Examples 1 to 18), a green organic EL device (Comparative Example 1 ), It can be seen that it shows better performance in terms of efficiency and driving voltage.

Claims (13)

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

In Formula 1,
X ₁ and X ₂ are the same or different and are each independently selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ At least one of X ₁ to X ₂ is N (Ar ₁ );
L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nucleus atoms;
Ar ₁ to Ar ₅ and R ₁ to R ₆ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ alkynyl group of C _40, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C of ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the A phosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , or is bonded to an adjacent group to form a condensed ring;
a, b, c and d are each independently an integer of 0 to 4;
e is an integer from 0 to 3;
f is an integer from 0 to 2;
Arylene group and a heteroarylene group and Ar ₁ to Ar ₅ and R ₁ to the alkyl group of R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group of the L _1, an arylamine group, An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heterocyclic group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an alkylboron group, an arylboron group, an alkylphosphine group, , A cyano group, 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 40 nuclear atoms, An aryloxy group of C ₆ to C ₆₀ , an alkyloxy group of C ₁ to C ₄₀ , an arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, group C ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic Blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C substituted with one or more substituents selected from the ₆₀ arylsilyl group the group consisting of or being unsubstituted , When they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein the compound represented by Formula 1 is a compound represented by any one of Chemical Formulas 2 to 7:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 2 to 7,
L ₁ , X ₁ to X ₂ , R ₁ to R ₆ , Ar ₁ to Ar ₅ and a to f each are as defined in claim 1. The method according to claim 1,
X ₁ and X ₂ are both N (Ar ₁ ), and a plurality of Ar _{1 s} are the same or different from each other. The method according to claim 1,
Wherein L &lt; _{1 &gt;} is a single bond, a phenylene group or a biphenylene group. The method according to claim 1,
Ar ₁ to Ar ₅ and R ₁ to R ₄ are each independently selected from the group consisting of hydrogen, deuterium (D), an aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 40 nuclear atoms,
R &lt; ₅ &gt; and R &lt; ₆ &gt; are both hydrogen. The method according to claim 1,
At least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ is a substituent represented by the following formula (8):
[Chemical Formula 8]

In Formula 8,
* Represents a moiety bonded to Formula 1;
L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₄₀ arylene group and a heteroarylene group having 5 to 40 nucleus atoms;
Z ₁ to Z ₅ are the same or different from each other and each independently N or C (R ₁₁ ), at least one of Z ₁ to Z ₅ is N;
When the R ₁₁ multiple individuals, all of which are the same or different, R ₁₁ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₆₀ C ₁ ~ alkyloxy group of C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or a neighboring tile that To form a condensed ring;
Alkyl group of the R _11, 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 alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 40 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 6,
Wherein the substituent represented by the formula (8) is a substituent represented by any one of the following formulas (A-1) to (A-15):

In the above formulas A-1 to A-15,
* Denotes the part where the bond is made;
n is an integer of 0 to 4, and when n is 0, hydrogen means not substituted by substituent R ₂₁ , and when n is an integer of 1 to 4, R ₂₁ is each independently selected from the group consisting of deuterium, 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 alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms , C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C of aryloxy ₆₀ C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryl amine 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 arylphosphine group, a C ₆ to C ₆₀ mono or diaryl A phosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , or is bonded to an adjacent group to form a condensed ring;
Alkyl group of the R _21, 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 alkenyl group, a substituted or unsubstituted aryl group, A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ 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 or different from each other;
L &lt; ₂ &gt; and R &lt; ₁₁ &gt; are as defined in claim 6, respectively. 8. The method of claim 7,
The substituent represented by any one of the above-mentioned Formulas A-1 to A-5 is selected from the group consisting of the following substituents:

In the above substituents, * denotes a portion where a bond is formed. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds:

(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 according to any one of claims 1 to 9. 11. The method of claim 10,
Wherein the organic compound layer containing the compound represented by Formula 1 is selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, and an electron injecting layer. 12. The method of claim 11,
Wherein the organic compound layer including the compound represented by Formula 1 is a light emitting layer. 13. The method of claim 12,
Wherein the compound is used as a phosphorescent host of the light emitting layer.