KR20160076881A - Organic light-emitting compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel condensed phenanthrene-based compound with excellent electron transfer ability and luminosity. The present invention further relates to an organic electroluminescent device which includes the same in at least one organic layer, thereby exhibiting improved luminous efficiency, driving voltage, and lifespan.

Description

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

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device comprising the same. More particularly, the present invention relates to a novel condensed phenanthrene compound having excellent hole injection and transport ability, To an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and life span.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") that resulted in blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film emission of Bernanose in the 1950s A layered organic EL device was proposed in 1987 by Tang divided into a hole layer and a functional layer of a light emitting layer. In order to produce high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

The light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve the luminous efficiency up to four times that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. As the hole blocking layer and the electron transporting layer, NPB, BCP and Alq ₃ represented by the following formulas are widely known, and an anthracene derivative as a luminescent material has been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in terms of efficiency improvement of a light emitting material, a metal complex compound containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like is a blue, green, It is used as a material. Up to now, 4,4-dicarbazolylbiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, conventional host materials are advantageous from the viewpoint of luminescence characteristics, but have low glass transition temperature and very poor thermal stability, and thus are not satisfactory in terms of lifetime in organic EL devices.

An object of the present invention is to provide a novel organic compound which is excellent in hole injection and transporting ability, light emitting ability and the like.

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

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1) or (2).

[Chemical Formula 1]

(2)

In the above formulas (1) and (2)

At least _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula (3) fused to form a condensed ring;

(3)

In Formula 3,

The dotted line is a moiety which is condensed with Formula 1 or Formula 2;

In the above Chemical Formulas 1 to 3,

X ₁ and X ₄ are the same or different and are each independently selected from _{O, S, N (Ar 1} ), C (Ar 2) (Ar 3) and Si (Ar ₄₎ are selected from guneu consisting of (Ar ₅₎ , Preferably at least one of X ₁ and X ₄ is N (Ar ₁ ), more preferably X ₁ is selected from O, S, N (Ar ₁ ) and X ₄ is N (Ar ₁ );

X ₂ and X ₃ are the same or different and are each independently N or C (R ₉ ), preferably X ₂ and X ₃ are both C (R ₉ ) or X ₂ is C (R ₉ ) , X < ₃ > may be N;

Y ₁ to Y ₄ are the same or different and are each independently N or C (R ₁₀ ), and in one example, Y ₁ to Y ₄ are both C (R ₁₀ ) or at least one of Y ₁ to Y ₄ is N Lt; / RTI >

R ₁ to R ₁₀ which do not form a condensation with the ring represented by the general formula (3) are the same as or different from each other and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to the 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ groups of an alkyl boron, C ₆ ~ 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 ~ consisting of an aryl amine of the C ₆₀ of the Or may combine with adjacent groups to form a condensed ring;

Ar ₁ to Ar ₇ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, 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 ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine 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;

The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group and aryl group of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ A halogen atom, 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 alkenyl group, a substituted or unsubstituted aryl group, _A C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkenyl group, C ₆ -C ₆₀ alkyloxy, C ₆ -C ₆₀ aryloxy, C ₃ -C ₄₀ alkylsilyl, C ₆ -C ₆₀ arylsilyl, C ₁ -C ₄₀ alkylboron, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ one or more substituents selected from the group consisting of C ₆₀ arylamine If substituted or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₁ to R ₁₀ and Ar ₁ to Ar ₇ , which do not form a condensation with the ring represented by the formula (3), are the same as or different from each other, and R At least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ is 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 a C ₆ to C ₆₀ arylamine ≪ / RTI >

The alkyl, aryl, heteroaryl and arylamine groups of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms , A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group , C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ one or more aryl group consisting of an amine group of the C ₆₀ of the 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 R ₁ to R ₁₀ and Ar ₁ to Ar ₇ which do not form a condensation with the ring represented by the general formula (3) in the general formulas (1) and (2) Is a substituent represented by the general formula (4).

[Chemical Formula 4]

In Formula 4,

* Means a moiety bonded to Formula 1 or Formula 2;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

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

R ₁₁ is the same or different from each other and each of R ₁₁ is independently hydrogen, 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, 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 ₃ ~ 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;

Arylene group, heteroarylene group, an alkyl group of the R ₁₁ of the L, 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 alkyl 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, a substituted or unsubstituted aryl group, aryloxy C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₃ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylene groups, C ₆ to C ₆₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl silyl When substituted by one or more substituent species selected from the group consisting of or being substituted by plural substituents Beach and ring, they may be the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by the formula (4) is selected from the group consisting of substituents represented by the following formulas (A-1) to (A-15).

In the above A-1 to A-15,

* Means a moiety bonded to Formula 1 or Formula 2;

n is an integer of 0 to 4, and when n is 0, hydrogen means that hydrogen is not substituted with substituent R ₁₂ ; when n is 1 to 4, R ₁₂ is independently selected from the group consisting of deuterium, halogen, cyano , nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryl of C ₆₀ amine groups, A C ₃ 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 _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, heteroaryl group, aryloxy group, 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 60 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 heteroaryl group having 3 to 40 nuclear atoms, a C ₃ 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 may be the same or different from each other;

L and R < ₁₁ > are the same as defined in the above formula (4).

According to one preferred embodiment of the present invention, at least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ which do not form a condensation with the ring represented by the formula (3) in the above-mentioned formulas (1) and (2) And R < 2 >

[Chemical Formula 5]

In Formula 5,

* Means a moiety bonded to Formula 1 or Formula 2;

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₃ and R ₁₄ 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, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine group or, wherein R ₁₃ and R ₁₄ may form a condensed ring by combining to each other, and;

The alkyl, aryl, heteroaryl and arylamine groups of R ₁₃ and R ₁₄ 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, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₃ ~ C ₄₀ alkylsilyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and one substituent at least one selected from the group consisting arylsilyl of C ₆ ~ C ₆₀ of When they are substituted or unsubstituted and substituted by a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, the compound represented by the formula (1) is represented by any one of the following formulas (6) to (11).

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above Chemical Formulas 6 to 11,

X ₁ to X ₄ , Y ₁ to Y _4, and R ₁ to R ₈ are the same as defined in Formula 1, respectively.

According to a preferred embodiment of the present invention, the compound represented by the formula (2) is represented by any one of the following formulas (12) to (17).

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

In the above Formulas 12 to 17,

X ₁ , X ₄ , Y ₁ to Y _4, Ar ₆ to Ar _7, and R ₁ to R ₈ are as defined in Formula 2, respectively.

The present invention also provides an organic electroluminescent device comprising (i) a positive electrode, (ii) a negative electrode, and (iii) at least one organic material layer interposed between the positive electrode and the negative electrode, One of the organic electroluminescent devices includes a compound represented by Formula 1 or Formula 2.

Here, the organic material layer including the compound represented by Formula 1 or Formula 2 may be selected from the group consisting of an electron transporting layer, an electron transporting auxiliary layer, and a light emitting layer. Preferably, the organic material layer including the compound may be a light emitting layer. Preferably, the compound may be used as a phosphorescent host, a fluorescent host, or a dopant material thereof in the light emitting layer.

In the present invention, "alkyl" means a monovalent substituent derived from a linear 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 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "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.

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.

"Alkylsilyl" in the present invention means a silyl substituted with alkyl having 3 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) or (2) according to the present invention is excellent in thermal stability and luminescence characteristics and can be used as a material of an organic material layer of an organic electroluminescence device.

In particular, when the compound represented by Formula 1 or Formula 2 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, A full color display panel having improved performance and life span can be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The present invention relates to a novel condensed phenanthrene compound having a higher molecular weight than that of a conventional organic EL device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')] and having excellent electron transporting ability, to provide.

Specifically, the novel organic compound according to the present invention is characterized in that any one of indene moiety, indole moiety, benzothiophene, benzofuran and benzosilole is condensed with a condensed phenanthrene moiety to form a basic skeleton, It has a structure in which various substituents are bonded to the skeleton.

Preferably, the novel organic compound of the present invention can be represented by the following general formula (1) or (2).

[Chemical Formula 1]

(2)

In the above formulas (1) and (2)

R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , At least one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by Formula 3 to form a fused ring;

(3)

In Formula 3,

The dotted line is a moiety which is condensed with the formula (1) or (2);

In the above Chemical Formulas 1 to 3,

X ₁ and X ₄ are the same or different and are each independently selected from O, S, N (Ar _1), is selected from the group consisting of _{C (Ar 2) (Ar 3} ) and _{Si (Ar 4) (Ar 5} ) , Preferably at least one of X ₁ and X ₄ is N (Ar ₁ ), more preferably X ₁ is selected from O, S, N (Ar ₁ ) and X ₄ is N (Ar ₁ );

X ₂ and X ₃ are the same or different and are each independently N or C (R ₉₎ with each other, one example in the X ₂ and X ₃ are either both C (R _9), X ₂ is C (R ₉₎ And X < ₃ > may be N;

Y ₁ to Y ₄ are the same or different and are each independently N or C (R ₁₀ ), and in one example, Y ₁ to Y ₄ are both C (R ₁₀ ) or at least one of Y ₁ to Y ₄ is N Lt; / RTI >

R ₁ to R ₁₀ which do not form a condensation with the ring represented by the general formula (3) are the same as or different from each other and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to the 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ groups of an alkyl boron, C ₆ ~ 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 ~ consisting of an aryl amine of the C ₆₀ of the Or may combine with adjacent groups to form a condensed ring;

Ar ₁ to Ar ₇ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, 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 ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine 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;

The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group and aryl group of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ A halogen atom, 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 alkenyl group, a substituted or unsubstituted aryl group, _A C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkenyl group, C ₆ -C ₆₀ alkyloxy, C ₆ -C ₆₀ aryloxy, C ₃ -C ₄₀ alkylsilyl, C ₆ -C ₆₀ arylsilyl, C ₁ -C ₄₀ alkylboron, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ one or more substituents selected from the group consisting of C ₆₀ arylamine If substituted or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

The compound represented by Formula 1 or Formula 2 provided in the present invention has a higher molecular weight than conventional organic EL device materials such as 4,4-dicarbazolylbiphenyl (hereinafter, referred to as 'CBP'), It has excellent ability to discharge water and has excellent luminous efficiency. Therefore, when the compound of Formula 1 or Formula 2 is used as at least one of the organic material layer of the organic electroluminescence device, preferably, the electron transport layer material, the hole transport layer material, and the light emitting layer material, , Current efficiency) and life can be improved.

Generally, in a phosphorescent light emitting layer of an organic electroluminescent device, the host material should have a triplet energy gap higher than the triplet energy gap of the dopant. That is, when the lowest excitation state of the host is higher in energy than the lowest emission state of the dopant, the phosphorescence efficiency can be improved. Therefore, in the present invention, the compound of formula (1) or (2) can be used as a phosphorescent host material since a specific substituent is introduced into a basic skeleton having a high triplet energy, so that the energy level can be controlled to be higher than that of the dopant.

In addition, the compound of Formula 1 or Formula 2 may have a wide band gap (sky blue to red) by controlling the energy level according to the substituents bonded to the basic skeleton. As a result, And it is also possible to prevent the excitons formed in the light emitting layer from migrating (spreading) to the surrounding organic material layer. Therefore, the compound of Formula 1 or Formula 2 can improve the phosphorescence characteristics of the device and improve the electron and / or hole transporting ability, luminescence efficiency, driving voltage, lifetime characteristics, etc., compared to CBP.

In addition to the host materials of the light emitting layer, the present invention can be applied to a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a light emitting auxiliary layer, In particular, the compound of Formula 1 or Formula 2 may have a bipolar property as a whole depending on the characteristics of the substituent bonded to the basic skeleton. According to one example, when the substituent bonded to the basic skeleton is an electron withdrawing group (EWG) having a high electron absorbing property, the compound of Formula 1 or Formula 2 has a bipolar, thereby having a wide band gap , The bonding force between holes and electrons can be increased. Therefore, the compound of the present invention can improve the hole injection ability, the transport ability, or the light emitting efficiency while improving the phosphorescence property of the organic EL device.

In addition, the compound of Formula 1 or Formula 2 has an aromatic ring substituent introduced into the basic skeleton, whereby the molecular weight of the compound is significantly increased. As a result, the glass transition temperature is improved, Stability can be obtained. Therefore, the organic electroluminescent device comprising the compound represented by the formula (1) or (2) of the present invention can greatly improve durability and lifetime characteristics.

When the compound represented by Formula 1 or Formula 2 of the present invention is used as a material for the hole injection layer, the hole transporting layer, or the light emitting layer of the organic electroluminescent device, The efficiency and lifetime of the light emitting device can be improved. In addition, the lifetime of the organic electroluminescent device can be maximized to maximize the performance of the full color organic electroluminescent panel.

According to one preferred embodiment of the present invention, considering the wide band gap, the light emitting property and the thermal stability, R ₁ to R ₁₀ which do not form a condensation with the ring represented by the formula (3) Ar ₁ to Ar ₇ are the same or different from each other, and at least one is 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 a C ₆ to C ₆₀ aryl And an amine group.

The alkyl, aryl, heteroaryl and arylamine groups of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ An alkynyl group of C ₂ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroatom having 5 to 60 nuclear atoms An aryl group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkyl A boron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group When they are substituted or unsubstituted by one or more substituents, and when they are substituted by a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, at least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ which do not form a condensation with the ring represented by the general formula (3) in the general formulas (1) and (2) Is a substituent represented by the general formula (4).

[Chemical Formula 4]

In Formula 4,

* Means a moiety bonded to Formula 1 or Formula 2;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

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

R ₁₁ is the same or different from each other and each of R ₁₁ is independently hydrogen, 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, 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 ₃ ~ 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;

Arylene group, heteroarylene group, an alkyl group of the R ₁₁ of the L, 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 alkyl 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, a substituted or unsubstituted aryl group, aryloxy C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₃ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylene groups, C ₆ to C ₆₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl silyl When substituted by one or more substituent species selected from the group consisting of or being substituted by plural substituents Beach and ring, they may be the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by the formula (4) is selected from the group consisting of substituents represented by the following formulas (A-1) to (A-15).

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

* Means a moiety bonded to Formula 1 or Formula 2;

n is an integer of 0 to 4, and when n is 0, hydrogen means that hydrogen is not substituted with substituent R ₁₂ ; when n is 1 to 4, R ₁₂ is independently selected from the group consisting of deuterium, halogen, cyano , nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryl of C ₆₀ amine groups, A C ₃ 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 _12, 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 60 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 heteroaryl group having 3 to 40 nuclear atoms, a C ₃ 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 may be the same or different from each other;

L and R < ₁₁ > are the same as defined in the above formula (4).

According to one preferred embodiment of the present invention, at least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ which do not form a condensation with the ring represented by the formula (3) in the above-mentioned formulas (1) and (2) And R < 2 >

[Chemical Formula 5]

In Formula 5,

* Means a moiety bonded to Formula 1 or Formula 2;

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₃ and R ₁₄ 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, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine group or, wherein R ₁₃ and R ₁₄ may form a condensed ring by combining to each other, and;

The alkyl, aryl, heteroaryl and arylamine groups of R ₁₃ and R ₁₄ 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, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₃ ~ C ₄₀ alkylsilyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ - a group arylboronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ - mono or diaryl phosphine of C ₆₀ blood group and one substituent at least one selected from the group consisting arylsilyl of C ₆ - C ₆₀ When they are substituted or unsubstituted and substituted by a plurality of substituents, they may be the same or different.

According to one preferred embodiment of the present invention, in the compound represented by Formula 1, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , At least one of R ₇ and R ₈ may be fused with the ring represented by the formula (3) to form a condensed ring to form a compound represented by any one of the following formulas (6) to (11) no.

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above Chemical Formulas 6 to 11,

X ₁ to X ₄ , Y ₁ to Y ₄ and R ₁ to R ₈ are as defined in the above formula (1).

According to a preferred embodiment of the present invention, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , And any one of R ₇ and R ₈ may be condensed with a ring represented by Formula 3 to form a condensed ring to form a compound represented by any of Formula 12 to Formula 17, but is not limited thereto .

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

In the above Chemical Formulas 12 to 17,

X ₁ , X ₄ , Y ₁ to Y ₄ , Ar ₆ to Ar _7, and R ₁ to R ₈ are the same as defined in Formula 2, respectively.

The compounds represented by formula (1) or (2) according to the present invention can be represented by the following formulas, but are not limited thereto.

The compound of formula (1) or (2) of the present invention can 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

According to another aspect of the present invention, there is provided an organic electroluminescent device (organic EL device) comprising a compound represented by Formula 1 or Formula 2 described above.

Specifically, the organic electroluminescent device according to the present invention includes (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode, , And at least one of the organic material layers includes a compound represented by the formula (1) or (2). At this time, the compounds represented by the formulas (1) and (2) may be used singly or in combination of two or more.

According to an embodiment of the present invention, the at least one organic material layer may include 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. 2 < / RTI >

Preferably, the organic material layer including the compound of Formula 1 or Formula 2 may be selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer, and more preferably, it may be a light emitting layer.

In particular, when the compound represented by Formula 1 or Formula 2 is included in the organic electroluminescent device as the light emitting layer material, the luminous efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.

For example, the compound represented by Formula 1 or Formula 2 may be used as a phosphorescent host or a fluorescent host or a dopant material of the light emitting layer.

Preferably, the compound represented by Formula 1 or Formula 2 may be included in the organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material.

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated on the substrate, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer Lt; / RTI >

Specifically, the organic electroluminescent device may have a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated on a substrate, and if necessary, It may be located.

At this time, at least one of the electron transporting layer, the hole transporting layer, and the light emitting layer may include the compound represented by Chemical Formula 1 or Chemical Formula 2, and preferably the light emitting layer may include the compound represented by Chemical Formula 1 or 2 The compound of Formula 1 or Formula 2 may be used as a phosphorescent host or an electron transport layer of the light emitting layer.

In addition, the organic electroluminescent device may include a life improving layer or an electron transporting layer between the light emitting layer and the electron transporting layer. At this time, the compound of Formula 1 or Formula 2 may also be used as a life improving layer or an electron transporting auxiliary layer.

The organic electroluminescent device of the present invention can be produced by forming organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers includes the compound of Formula 1 or Formula 2 .

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 that can be used in the fabrication of the organic electroluminescent device in the present invention is not particularly limited and includes, for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or a sheet.

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 and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Further, the hole injection layer material, the hole transport layer material, the electron injection layer material, and the electron transport layer material 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 the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

The schematic reaction scheme used in the preparation of Core I to VI in the preparation examples described below is as follows.

[Core synthesis reaction formula I & II]

[Core synthesis reaction formula III & IV]

[Core synthesis reaction formula V & VI]

[Preparation Example 1] Synthesis of Core I

<Step 1> Synthesis of 3-bromophenanthrene-9,10-dione

To 50 g (0.24 mol) of phenanthrene-9,10-dione was added 1.0 L of AcOH. The reaction solution was heated to reflux for 1 hour, and 5.8 g (0.024 mol) of dibenzoyl peroxide was added. After the reaction solution was heated for 1 hour, 37 mL (0.72 mol) of bromine was slowly added dropwise. The mixture was heated under reflux for 4 hours, cooled to room temperature, and stirred for 12 hours. The resulting solid was filtered under reduced pressure and dried in a warm air. The resulting solid was recrystallized from 300 mL of dimethylformamide to obtain 40.0 g (yield: 58%) of the target compound.

^{1 H-NMR (300Mz, DMSO} -d6): δ 8.51 (s, 1H), 8.35 (d, 1H), 8.00 (d, 1H), 7.79 (d, 1H), 7.75 (t, 1H), 7.74 ( dd, 1 H), 7.55 (t, 1 H)

[LCMS]: 287

Step 2 Synthesis of 6-bromo-1,2-diphenyl-1H-phenanthro [9,10-d] imidazole

800 mL of AcOH was added to 40.0 g (0.14 mol) of 3-bromophenanthrene-9,10-dione, 51.9 g (0.56 mol) of aniline, 16.3 g (0.153 mol) of benzaldehyde and 43.0 g . The reaction solution was heated to reflux at 110 DEG C for 12 hours and cooled to room temperature. It was neutralized with 500 mL of NaOH aqueous solution, extracted with 2.0 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 52.0 g (yield: 83%) of the desired compound.

^{1 H-NMR (300Mz, DMSO} -d6): δ 9.10 (dd, 1H), 8.93 (dd, 1H), 8.65 (dd, 1H), 7.90 (m, 1H), 7.70 (m, 5H), 7.58 ( (m, 2H), 7.54 (dd, 1 H), 7.35 (m, 4H), 7.06

[LCMS]: 449

Step 3: Synthesis of 1,2-diphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-phenanthro [ -d] imidazole < / RTI >

A mixture of 52.0 g (0.12 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-dicyclohexylcarbodiimide '-Octamethyl-2,2' -bis (1,3,2-dioxaborolane) (38.2 g, 0.15 mol) was added 1.0 L of dioxane. 4.7 g (5.9 mmol) of Pd (dppf) Cl ₂ and 34.1 g (0.35 mol) of KOAc were added to the reaction solution. The mixture was heated to reflux at 130 占 폚 for 12 hours. 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 (41.4 g, yield 72%).

^{1 H-NMR (300Mz, DMSO} -d6): δ 9.11 (s, 1H), 8.84 (d, 1H), 8.70 (d, 1H), 8.03 (d, 1H), 7.71 (m, 5H), 7.60 ( m, 3H), 7.37 (m, 4H), 7.08 (d,

[LCMS]: 496

<Step 4> Synthesis of 6- (2-nitrophenyl) -1,2-diphenyl-1H-phenanthro [9,10-d] imidazole

(4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -1H-phenanthro [9,10- 800.0 mL of toluene, 200 mL of EtOH and 200 mL of H ₂ O were added to 41.0 g (82.6 mmol) of dicazole and 20.0 g (99.1 mmol) of 1-bromo-2-nitrobenzene. 4.8 g (4.1 mmol) of Pd (PPh ₃ ) _{4 and} 34.2 g (248 mmol) of K ₂ CO ₃ were added, and the mixture was refluxed at 120 ° C. for 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 34.5 g (yield: 85%) of the desired compound.

^{1 H-NMR (300Mz, DMSO} -d6): δ 8.90 (m, 1H), 8.72 (t, 1H), 8.08 (dd, 1H), 7.82 (m, 1H), 7.71 (m, 8H), 7.60 ( (m, 2H), 7.48 (m, IH), 7.37 (m, 5H), 7.11

[LCMS]: 491

<Step 5> Core I Synthesis of

34 g (69.8 mmol) of 6- (2-nitrophenyl) -1,2-diphenyl-1H-phenanthro [9,10-d] imidazole and 54.4 g - Dichlorobenzene (600 mL) was added. The reaction solution was heated to reflux at 200 占 폚 for 12 hours. The reaction mixture was cooled to room temperature, 500 mL of purified water was added thereto, and the reaction was terminated. The reaction mixture was extracted with 1.0 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 the desired compound (14.0 g, yield 44%).

¹ H-NMR (300 MHz, DMSO-d 6):? 11.91 (s, IH), 9.29 (m, IH), 8.52 (m, 2H), 7.81 (d, 1H), 7.31 (m, 5H), 7.60 (m, 2H), 7.46 , 1H)

[LCMS]: 459

[Preparation Example 2] Synthesis of Core II

The same procedure as in steps 1 to 5 of Preparation Example 1 was carried out to obtain 9.0 g of the objective compound (yield: 28%).

¹ H-NMR (300 Mz, DMSO-d 6):? 11.95 (s, IH), 9.32 (d, IH), 8.68 2H), 7.48 (t, 1H), 7.35 (m, 4H), 7.26 (m, 2H)

[LCMS]: 459

[Preparation Example 3] Synthesis of Core III

<Step 1> Synthesis of (Z) -3-bromo-10- (hydroxyimino) phenanthrene-9 (10H)

To the solution was added 1.0 L of EtOH to 50.0 g (0.17 mol) of 3-bromophenanthrene-9,10-dione, 12.1 g (0.17 mol) of hydroxylamine and 35.1 mL (0.44 mol) of pyridine. The reaction solution was heated to reflux at 100 占 폚 for 12 hours. The reaction solution was cooled to room temperature, and the resulting solid was filtered under reduced pressure, washed with purified water and dried under a humid atmosphere to obtain 40.5 g (yield 77%) of the desired compound.

[LCMS]: 302

<Step 2> Synthesis of 6-bromo-2-phenylphenanthro [9,10-d] oxazole

DMF was added to 800 mL on 40.0 g (0.13 mol) and _{K 2 CO 3 36.6 g (0.26} mol) - (Z) -3- bromo-10- (hydroxyimino) phenanthrene -9 (10H). 23.6 mL (0.20 mol) of benzyl bromide was slowly added dropwise to the reaction solution. The reaction mixture was stirred at room temperature for 12 hours and 500 mL of purified water was added thereto. The reaction was terminated, and the mixture was extracted with 1.0 L of EA, followed by washing 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 aimed compound (30.8 g, yield 62%).

[LCMS]: 374

<Step 3> Synthesis of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenanthro [9,10- synthesis

The procedure of Step 3 of Preparation Example 1 was repeated except that 30.0 g (80.2 mmol) of 6-bromo-2-phenylphenanthro [9,10-d] oxazole was used as a reactant, g (yield: 80%).

[LCMS]: 421

<Step 4> Synthesis of 6- (2-nitrophenyl) -2-phenylphenanthro [9,10-d] oxazole

27.0 g of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenanthro [9,10- 64.1 mmol), the procedure of Step 4 of Preparation Example 1 was carried out to obtain 22.7 g (yield: 85%) of the target compound.

[LCMS]: 416

<Step 5> Core III Synthesis of

The same procedure as in Step 5 of Preparation Example 1 was carried out except that 22.0 g (52.8 mmol) of 6- (2-nitrophenyl) -2-phenylphenanthro [9,10-d] To obtain 8.0 g of the desired compound (yield 39%).

[LCMS]: 384

[Preparation Example 4] Synthesis of Core IV

The procedure of steps 1 to 5 of Preparation Example 3 was repeated to obtain 7.4 g of the title compound (yield: 36%).

[LCMS]: 384

[Preparation Example 5] Synthesis of Core V

<Step 1> Synthesis of 6-bromo-2,2-dimethylphenanthro [9,10-d] [1,3] dioxole

3.0 L (1: 1: 1) of a mixed solvent of ACN, THF and H ₂ O was added to 50 g (0.17 mol) of 3-bromophenanthrene-9,10-dione and 72.2 g (0.52 mol) of K ₂ CO ₃ Respectively. 155 g (1.74 mol) of 2-nitropropane was added to the reaction solution, and the mixture was heated to reflux for 12 hours. The reaction was terminated by addition of 1.5 L of purified water, extracted with 3.0 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 the desired compound (41.3 g, yield 72%).

^{1 H-NMR (300Mz, CDCl} 3): δ 8.79 (s, 1H), 8.57 (d, 1H), 7.90 (d, 1H), 7.77 (d, 1H), 7.70 (m, 1H), 7.64 (t , 7.55 (t, 1 H), 1.85 (s, 6 H)

[LCMS]: 329

Step 2 2- (2,2-Dimethylphenanthro [9,10-d] [1,3] dioxol-6-yl) -4,4,5,5-tetramethyl- - Synthesis of dioxaborolane

The procedure of Step 3 of Preparation Example 1 was repeated except for using 6-bromo-2,2-dimethylphenanthro [9,10-d] [1,3] dioxole as a reactant, 35.1 g (yield 75%) was obtained.

^{1 H-NMR (300Mz, CDCl} 3): δ 9.04 (s, 1H), 8.79 (d, 1H), 7.88 (d, 1H), 7.82 (m, 2H), 7.67 (t, 1H), 7.62 (t , &Lt; / RTI &gt; 1H), 1.81 (s, 6H), 1.34 (s,

[LCMS]: 376

Step 3 Synthesis of 2,2-dimethyl-6- (2-nitrophenyl) phenanthro [9,10-d] [1,3] dioxole

The reaction was carried out in the same manner as in Example 1 except that 2- (2,2-dimethylphenanthro [9,10-d] [1,3] dioxol-6-yl) -4,4,5,5-tetramethyl- The procedure of Step 4 of Preparation Example 1 was repeated except for using oxaboronane to obtain 28.3 g of the title compound (yield: 82%).

^{1 H-NMR (300Mz, CDCl} 3): δ 8.61 (m, 2H), 7.94 (d, 1H), 7.91 (m, 2H), 7.67 (m, 1H), 7.60 (m, 2H), 7.50 (m , &Lt; / RTI &gt; 3H), 1.86 (s, 6H)

[LCMS]: 371

<Step 4> Synthesis of Core V

The procedure of Preparation Example 1 was repeated except for using 28.0 g (75.4 mol) of 2,2-dimethyl-6- (2-nitrophenyl) phenanthro [9,10- The procedure of Step 5 was followed to obtain 5.0 g of the title compound (yield 20%).

[LCMS]: 339

[Preparation Example 6] Synthesis of Core VI

The procedure of Steps 1 to 4 of Preparation Example 5 was repeated to obtain 11.6 g of the desired compound (yield: 45%).

¹ H-NMR (300 Mz, CDCl ₃ ):? 9.10 (s, IH), 8.90 (m, IH), 8.32 , 7.69 (m, 3H), 7.47 (t, 1 H), 7.32 (t,

[LCMS]: 339

[Synthesis Example 1] Synthesis of Compound 1

To 100 mL of DMF was added 6.0 g (13.1 mmol) of the Core I compound of Preparation Example 1 and 4.5 g (17.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine. 0.78 g (19.6 mmol) of 60% NaH was added to the reaction solution. After stirring at room temperature for 12 hours, 100 mL of purified water was added to terminate the reaction. The mixture was extracted with 300 mL of EA and washed twice 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 4.70 g (yield 52%) of the desired compound.

[LCMS]: 690

[Synthesis Example 2] Synthesis of Compound 4

100 mL of dioxane was added to 4.5 g (9.8 mmol) of the Core I compound of Preparation Example 1 and 5.1 g (14.7 mmol) of 2- (3-chlorophenyl) . Was Pd (OAc) ₂ 0.11 g was added to (0.49 mmol), P (t -Bu) 3 0.40 g (0.98 mmol), K 2 CO 3 4.1 g (29.4 mmol) and the reaction mixture heated under reflux for 12 hours at 120 ℃ . 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 (3.6 g, yield 48%).

[LCMS]: 766

[Synthesis Example 3] Synthesis of Compound 7

100 mL of toluene was added to 5.0 g (10.9 mmol) of the Core I compound of Preparation Example 1 and 5.6 g (16.3 mmol) of 2- (4-chlorophenyl) -4,6-diphenyl- Respectively. 0.1 g (0.54 mmol) of Pd (OAc) ₂ , 0.44 g (1.1 mmol) of P (t-Bu) _{3 and} 2.1 g (21.8 mmol) of NaOt-Bu were added to the reaction solution and refluxed at 120 ° C for 12 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 (5.0 g, yield 60%).

[LCMS]: 766

[Synthesis Example 4] Synthesis of Compound 10

5.5 g (12.0 mmol) of the Core I compound of Preparation Example 1 and 7.5 g (18.0 mmol) of 2- (3'-chlorobiphenyl-3-yl) Was added 100 mL of dioxane. 0.13 g (0.60 mmol) of Pd (OAc) ₂ , 0.57 g (1.2 mmol) of XPhos and 7.8 g (23.9 mmol) of Cs ₂ CO ₃ were added to the reaction solution and the mixture was refluxed at 120 ° C for 12 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 4.0 g (yield 40%) of the desired compound.

[LCMS]: 842

[Synthesis Example 5] Synthesis of Compound 11

To a solution of 7.2 g (16.5 mmol) of the Core I compound of Preparation Example 1 and 150 mL of toluene in 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5- Respectively. 1.4 g (1.6 mmol) of Pd ₂ (dba) ₃ , 0.98 g (1.6 mmol) of BINAP and 10.2 g (31.3 mmol) of Cs ₂ CO ₃ were added to the reaction solution and refluxed at 120 ° C for 12 hours. 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 (7.3 g, yield 55%).

[LCMS]: 842

[Synthesis Example 6] Synthesis of Compound 16

The same procedure as in Synthesis Example 4 was carried out except that 4- (3'-chlorobiphenyl-3-yl) -2,6-diphenylpyrimidine was used in combination with the Core I compound of Preparation Example 1 as a reactant To obtain 5.7 g (yield: 62%) of the desired compound.

[LCMS]: 842

[Synthesis Example 7] Synthesis of Compound 22

The procedure of Synthesis Example 2 was repeated except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine was used in combination with the Core II compound of Preparation Example 2 as a reactant, 5.3 g (yield 53%) of the compound was obtained.

[LCMS]: 766

[Synthesis Example 8] Synthesis of Compound 33

The same procedure as in Synthesis Example 5 was carried out except that the core II compound of Preparation Example 2 and 2- (4'-chlorobiphenyl-4-yl) -4,6-diphenylpyrimidine were used as a reactant, (Yield: 38%) of the aimed compound.

[LCMS]: 842

[Synthesis Example 9] Synthesis of Compound 43

The same procedure as in Synthesis Example 3 was carried out, except that Core III compound of Preparation Example 3 and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine were used as a reactant To obtain 5.6 g (yield 52%) of the desired compound.

[LCMS]: 691

[Synthesis Example 10] Synthesis of Compound 51

The same procedure as in Synthesis Example 5 was carried out except that the core III compound of Preparation Example 3 and 2- (4'-chlorobiphenyl-4-yl) -4,6-diphenylpyrimidine were used as a reaction product To obtain 5.8 g (yield 65%) of the desired compound.

[LCMS]: 766

[Synthesis Example 11] Synthesis of Compound 60

The same procedure as in Synthesis Example 2 was carried out, except that Core IV compound of Preparation Example 4 and 4- (3-chlorophenyl) -2,6-diphenylpyrimidine were used as a reactant, to obtain 3.9 g 44%).

[LCMS]: 690

[Synthesis Example 12] Synthesis of Compound 71

The same procedure as in Synthesis Example 5 was carried out except that the core IV compound of Preparation Example 4 and 4- (4'-chlorobiphenyl-3-yl) -2,6-diphenylpyrimidine were used as a reactant, 4.4 g (the yield: 35%) of the aimed compound was obtained.

[LCMS]: 766

[Synthesis Example 13] Synthesis of Compound 84

Except that the Core V compound of Preparation Example 5 and 2- (4'-chlorobiphenyl-4-yl) -4,6-diphenyl-1,3,5-triazine were used as a reaction product. 5, the title compound (6.1 g, yield: 55%) was obtained.

[LCMS]: 722

[Synthesis Example 14] Synthesis of Compound 94

The same procedure as in Synthesis Example 2 was carried out except that the Core VI compound of Preparation Example 6 and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine were used as a reactant To obtain 4.7 g (yield 53%) of the desired compound.

[LCMS]: 646

[Synthesis Example 15] Synthesis of Compound 100

Except that the Core VI compound of Preparation Example 6 and 2- (3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used as a reaction product, 4, 3.2 g (yield: 60%) of the desired compound was obtained.

[LCMS]: 722

[Synthesis Example 16] Synthesis of Compound 103

The procedure of Synthesis Example 4 was repeated except that the Core VI compound of Preparation Example 6 and 2- (3'-chlorobiphenyl-3-yl) -4,6-diphenylpyrimidine were used as a reactant, To obtain 5.6 g (yield 55%) of the desired compound.

[LCMS]: 721

[Synthesis Example 17] Synthesis of Compound 108

The procedure of Synthesis Example 5 was repeated except that the Core VI compound of Preparation Example 6 and 4- (4'-chlorobiphenyl-4-yl) -2,6-diphenylpyrimidine were used as a reactant, 5.3 g (the yield: 47%) of the desired compound was obtained.

[LCMS]: 721

[Example 1] Production of blue organic EL device

The compound Inv-3 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a conventionally known method, and a blue organic EL device was fabricated according to the following procedure.

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, 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.

(15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound 1 (5 nm) / Alq ₃ (25 nm) on the ITO transparent electrode prepared as above. ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structures of NPB, ADN and Alq ₃ used in this case are as follows.

[Example 2] - [Example 10] Production of blue organic EL device

A blue organic EL device was prepared in the same manner as in Example 1 except that the compound shown in Table 1 was used as an electron transporting auxiliary layer material instead of the compound 1 used in Example 1.

[Comparative Example 1] Production of blue organic electroluminescent device

The procedure of Example 1 was repeated except that the compound 1 used as the electron transporting auxiliary layer material in Example 1 was not used and the electron transporting layer material Alq ₃ was deposited at 30 nm instead of 25 nm, The device was fabricated.

[Evaluation Example 1]

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

Sample Electron transporting auxiliary layer The driving voltage (V) Emission peak (nm) Current efficiency cd / A) Example 1 Compound 1 4.3 442 6.6 Example 2 Compound 4 4.4 448 6.8 Example 3 Compound 7 4.0 445 6.9 Example 4 Compound 10 4.1 440 7.1 Example 5 Compound 22 4.3 456 6.8 Example 6 Compound 43 4.4 458 6.3 Example 7 Compound 60 4.3 455 6.0 Example 8 Compound 84 4.5 458 6.7 Example 9 Compound 94 4.8 459 5.9 Example 10 Compound 100 4.4 458 7.1 Comparative Example 1 - 4.7 458 6.0

As shown in Table 1, the blue organic EL devices of Examples 1 to 10 including the electron transporting auxiliary layer formed of the compound according to the present invention were prepared in the same manner as in Comparative Example 1 containing the electron transporting layer of Alq ₃ without the electron transporting auxiliary layer It was found that the organic EL device exhibited better current efficiency and better driving voltage than the blue organic EL device.

[Example 11] Fabrication of green organic EL device

Compound 1 synthesized in Synthesis Example 1 was 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, 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.

The compound 1 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / 90% of m-MTDATA (60 nm) / TCTA LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device. The structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP used are as follows.

[Example 12] - [Example 20] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 11, except that the compound described in the following Table 2 was used instead of the compound 1 used as the luminescent host material in Example 11.

[Comparative Example 2] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 11, except that CBP was used instead of Compound 1 as a luminescent host material in Example 11. The structure of CBP used is as follows.

[Evaluation Example 2]

The driving voltage, current efficiency and emission peak at the current density (10) mA / cm &lt; 2 &gt; were measured for the green organic EL devices manufactured in Examples 11 to 20 and Comparative Example 2, Respectively.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 11 Compound 4 6.2 513 44.5 Example 12 Compound 10 6.5 516 46.3 Example 13 Compound 11 6.3 519 45.0 Example 14 Compound 16 6.0 520 48.2 Example 15 Compound 22 6.3 515 46.0 Example 16 Compound 33 6.9 510 47.6 Example 17 Compound 51 6.6 512 43.3 Example 18 Compound 71 6.6 525 45.9 Example 19 Compound 84 6.3 514 46.0 Example 20 Compound 94 6.3 518 47.5 Comparative Example 2 CBP 6.9 516 41.5

As shown in Table 2, in the case of the green organic EL devices of Examples 11 to 20 using the compound according to the present invention as a light emitting layer material, compared with the green organic EL device of Comparative Example 2 using conventional CBP, .

[Example 21] Production of red organic EL device

Compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, 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.

(60 nm) / TCTA (80 nm) / 90% compound 1 + 10% (piq) ₂ Ir (acac) (30 nm) / BCP (10 nm) / Alq ₃ ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device. The structures of m-MTDATA, TCTA, and BCP used are as described in Example 1, and the structure of (piq) ₂ Ir (acac) is as follows.

[Examples 22 to 26] Preparation of red organic EL device

A red organic EL device was prepared in the same manner as in Example 21 except that the compound described in the following Table 3 was used in place of the compound 1 used as a luminescent host material in forming the light emitting layer in Example 21.

[Comparative Example 3]

A red organic electroluminescent device was fabricated in the same manner as in Example 21 except that CBP was used instead of the compound 1 used as the light emitting host material in the light emitting layer formation in Example 21. The structure of the CBP used is as described in Comparative Example 2.

[Evaluation Example 3]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 21 to 26 and Comparative Example 3, respectively, and the results are shown in Table 3 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 21 Compound 1 4.4 12.5 Example 22 Compound 33 4.6 13.8 Example 23 Compound 60 4.8 11.5 Example 24 Compound 71 4.4 10.8 Example 25 Compound 84 4.3 12.8 Example 26 Compound 103 4.5 11.9 Comparative Example 3 CBP 4.8 10.5

As shown in Table 3, in the case of the red organic EL devices of Examples 21 to 26 using the compound according to the present invention as a light emitting layer material, compared with the red organic electroluminescent device of Comparative Example 3 using conventional CBP, It was confirmed that the voltage was excellent.

Claims (14)

A compound represented by the following formula (1) or (2):
[Chemical Formula 1]

(2)

In the above formulas (1) and (2)
At least _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula (3) fused to form a condensed ring;
(3)

In Formula 3,
The dotted line is a moiety which is condensed with the formula (1) or (2);
In the above Chemical Formulas 1 to 3,
X ₁ and X ₄ are the same or different and are each independently selected from O, S, N (Ar _1), is selected from the group consisting of _{C (Ar 2) (Ar 3} ) and _{Si (Ar 4) (Ar 5} ) ;
X ₂ and X ₃ are the same or different and are each independently N or C (R ₉ );
Y ₁ to Y ₄ are the same or different and are each independently N or C (R ₁₀ );
R ₁ to R ₁₀ which do not form a condensation with the ring represented by the general formula (3) are the same as or different from each other and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to the 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ groups of an alkyl boron, C ₆ ~ 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 ~ consisting of an aryl amine of the C ₆₀ of the Selected from the group, or combine with adjacent groups to form a condensed ring;
Ar ₁ to Ar ₇ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, 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 ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine 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;
The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group and aryl group of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and the arylamine groups are each independently a C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ aryl amine, or is 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 at least one of X ₁ and X ₄ is N (Ar ₁ ). 3. The method of claim 2,
Wherein X ₁ is selected from the group consisting of O, S and N (Ar ₁ ), and X ₄ is N (Ar ₁ ). The method according to claim 1,
R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are the same or different and at least one of them is 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 of C ₆ to C ₆₀ ;
The alkyl, aryl, heteroaryl and arylamine groups of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ , A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms , A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group , C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ one or more aryl group consisting of an amine group of the C ₆₀ of the 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 1,
At least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ is a phenyl group or a substituent represented by the following formula (4):
[Chemical Formula 4]

In Formula 4,
* Means a moiety bonded to Formula 1 or Formula 2;
L is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₁ );
R ₁₁ is the same or different from each other and each of R ₁₁ is independently hydrogen, 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, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₃ 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;
Arylene group, heteroarylene group, an alkyl group of the R ₁₁ of the L, 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 alkyl 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, a substituted or unsubstituted aryl group, aryloxy C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₃ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylene groups, C ₆ to C ₆₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl silyl Substituted by one or more substituent species selected from the group consisting of or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same as or different from each other. 6. The method of claim 5,
Wherein the substituent represented by the formula (4) is selected from the group consisting of substituents represented by at least one of the following formulas (A-1) to (A-15):

In the above formulas A-1 to A-15,
* Means a moiety bonded to Formula 1 or Formula 2;
n is an integer of 0 to 4, and when n is 0, hydrogen means that hydrogen is not substituted with substituent R ₁₂ ; when n is 1 to 4, R ₁₂ is independently selected from the group consisting of deuterium, halogen, cyano , nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ of alkyloxy, C of ₆ ~ C ₆₀ aryl amine group, A C ₃ 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;
Arylene group, heteroarylene group, the R ₁₁ and the alkyl group of R ₁₂ of the L, 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 aryl amine A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 nuclear heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₃ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylene group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a ~ C ₄₀ alkyl group of boron, C ₆ ~ 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 ~ C ₆₀ of the O If or substituted with one or more substituents selected from the group consisting of a silyl Beach and ring, which is substituted by plural substituents, these are the same or different, and,
L and R &lt; ₁₁ &gt; are as defined in claim 5. The method according to claim 1,
At least one of R ₁ to R ₁₀ and Ar ₁ to Ar ₇ is a substituent represented by the following formula (5):
[Chemical Formula 5]

In Formula 5,
* Means a moiety bonded to Formula 1 or Formula 2;
L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R ₁₃ and R ₁₄ 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, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine group Or R ₁₃ and R ₁₄ are bonded to each other to form a condensed ring;
The alkyl, aryl, heteroaryl and arylamine groups of R ₁₃ and R ₁₄ 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, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₃ ~ C ₄₀ alkylsilyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ - a group arylboronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ - mono or diaryl phosphine of C ₆₀ blood group and one substituent at least one selected from the group consisting arylsilyl of C ₆ - C ₆₀ When they are substituted or unsubstituted and are substituted by a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
The compound represented by Formula 1 is represented by any one of the following Chemical Formulas 6 to 11:
[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above Chemical Formulas 6 to 11,
X ₁ to X ₄ , Y ₁ to Y ₄ and R ₁ to R ₈ are as defined in claim 1, respectively. The method according to claim 1,
Wherein the compound represented by Formula 2 is represented by any one of the following Chemical Formulas 12 to 17:
[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

In the above Chemical Formulas 12 to 17,
X ₁ , X ₄ , Y ₁ to Y _4, Ar ₆ to Ar ₇ and R ₁ to R ₈ are as defined in claim 1, respectively. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 10. 12. The method of claim 11,
Wherein the organic compound layer containing the compound is selected from the group consisting of an electron transporting layer, an electron transporting auxiliary layer, and a light emitting layer. 13. The method of claim 12,
Wherein the organic compound layer containing the compound is a light emitting layer. 14. The method of claim 13,
The compound is used as a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer.