KR20160079548A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound having excellent light-emitting ability, carrier transporting ability, and the like, and to an organic electroluminescent device comprising the same in at least one organic matter layer, thereby having properties such as a low driving voltage, a high light-emitting efficiency, a long lifespan, and the like. The compound is represented by chemical formula 1 to chemical formula 3.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

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 condensed benzocarbazole compound having excellent carrier transport ability and light emitting ability, And an organic electroluminescent device having improved luminous efficiency, lifetime characteristics, and the like.

A study on electroluminescent (EL) devices (hereinafter, simply referred to as "organic EL devices") which led to blue electroluminescence using anthracene single crystals in 1965 based on 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 EL 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 luminous efficiency up to four times that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

As the hole injecting layer, the hole transporting layer, the hole blocking layer, and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material . Particularly, as a phosphorescent material having a great advantage in improving the efficiency 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 used as a blue, green and red dopant material . Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of luminescence characteristics, but their glass transition temperature is low and their thermal stability is not very good, which is not satisfactory in terms of lifetime in an organic EL device. Therefore, development of materials with higher performance is required.

It is an object of the present invention to provide a novel organic compound that is applicable to an organic electroluminescent device, and has excellent carrier transporting ability and light emitting ability.

Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage, a high luminous efficiency, and a long life.

In order to achieve the above object, the present invention provides a compound represented by any one of the following general formulas (1) to (3).

[Chemical Formula 1]

(2)

(3)

In the above Chemical Formulas 1 to 3,

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 ₇ and R ₈ , R ₈ and R ₉ and R ₉ and R ₁₀ is represented by the following formula Lt; / RTI > to form a condensed ring;

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,

The dotted line is the part where the condensation occurs;

Each of X ₁ and X ₂ independently represent _{O, S, N (Ar 1} ), C (Ar 2) (Ar 3) and Si (Ar _4), but selected from the group consisting of (Ar ₅₎ wherein X ₁ and X At least one of ₂ is N (Ar ₁ ), preferably X ₁ and X ₂ are each independently selected from the group consisting of O, S and N (Ar ₁ ), more preferably X ₁ and X ₂ are both N (Ar < ₁ >);

Y ₁ and Y ₂ are each independently N or C (R ₁₁ ), preferably both Y ₁ and Y ₂ are C (R ₁₁ ), or at least one of Y ₁ and Y ₂ is N;

R ₁ to R ₁₁ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An 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 alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in the, form a condensed ring by combining adjacent tile You can;

Ar ₁ to Ar ₅ 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 ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ 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 ₁₁ and Ar ₁ to Ar ₅ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently 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 alkynyl group, ~ 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 ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C ₆₀ aryl phosphine group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group and a C ₆ ~ substituted by one or more selected from the group consisting of C ₆₀ aryl amine, or unsubstituted, and a plurality In the case of being substituted with a substituent which may be the same or different from each other.

According to a preferred embodiment of the present invention, in the compound represented by any one of Chemical Formulas 1 to 3, Ar ₁ is an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms do.

According to a preferred embodiment of the present invention, the compound represented by any one of Chemical Formulas 1 to 3 is a compound represented by any one of Chemical Formulas C-1 to C-20.

In the above formulas C-1 to C-20,

X ₁ , X ₂ , Y ₁ , Y ₂ and R ₁ to R ₁₀ are as defined in the above Chemical Formulas 1 to 4.

According to a preferred embodiment of the present invention, the compound represented by any one of Chemical Formulas 1 to 3 is a compound represented by any one of Chemical Formulas D-1 to D-20.

In the above formulas D-1 to D-20,

Ar ₁ and R ₁ to R ₁₁ are as defined in formulas (1) to (4).

According to one embodiment, preferred according to the present invention, in the compound represented by any one of the above Chemical Formulas 1 to 3 R ₁ to R ₁₁ and Ar ₁ to at least one of Ar ₅ represents an alkyl group of _{C 1 ~ C 40, C 6} ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60,

R ₁ to R ₁₁ and Ar ₁ to Ar ₅ Alkyl group, an aryl group, a heteroaryl group and an arylamine group, each independently, a deuterium, a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , An arylamine group of C ₆ to C ₆₀ , and when they are substituted with a plurality of substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, at least one of R ₁ to R ₁₁ and Ar ₁ to Ar ₅ is a phenyl group or a substituent group represented by the following general formula (5): .

[Chemical Formula 5]

In Formula 5,

* Represents a moiety bonded to any one of the above formulas (1) to (3);

L ₁ is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group and a nuclear atoms of 5 to 18 groups heteroarylene, preferably a single bond, phenylene group, biphenylene group or carbazolyl be an and ;

Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₂ ), at least one of Z ₁ to Z ₅ is N;

R ₁₂ is the same or different from each other and each of R ₁₂ independently represents 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 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 ~ of aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ 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 group and coupling to the C ₆₀ To form a condensed ring;

Alkyl group of the R _12, 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 (5) 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,

* Represents a moiety bonded to any one of the above formulas (1) to (3);

n is an integer of 0 to 4, and when n is 0, hydrogen means not substituted by substituent R ₁₃ , and when n is an integer of 1 to 4, R ₁₃ 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 _13, 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 of blood group and a C ₆ ~ C over ₆₀ one member selected from the group consisting of aryl silyl group coming , When they are substituted with a plurality of substituents, they may be the same or different from each other;

L ₁ and R ₁₂ are as defined in the above formula (5).

According to a preferred embodiment of the present invention, at least one of R ₁ to R ₁₁ and Ar ₁ to Ar ₅ may be a substituent represented by the following formula (6) .

[Chemical Formula 6]

In Formula 6,

* Represents a moiety bonded to any one of the above formulas (1) to (3);

L ₂ is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group and a nuclear atoms of 5 to 18 groups heteroarylene, preferably a single bond, phenylene group, biphenylene group or carbazolyl be an and ;

R ₁₄ and R ₁₅ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ Or R ₁₄ and R ₁₅ may combine with each other to form a condensed ring;

The alkyl, aryl, heteroaryl and arylamine groups of R ₁₄ and R ₁₅ 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 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ - substituted with C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ - mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ 1 or more selected from the group consisting of a arylsilyl of C ₆₀ And when they are unsubstituted or substituted with a plurality of substituents, they may be the same or different.

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 is an organic electroluminescent device comprising a compound represented by the general formula (1).

According to a preferred embodiment of the present invention, the organic material layer containing the compound represented by Formula 1 is selected from the group consisting of a light emitting layer, an electron transporting layer, an electron injecting layer, a hole transporting layer, a hole injecting layer, And may preferably be selected from the group consisting of a light emitting layer, an electron transporting layer, a light emitting auxiliary layer, and a life improving layer, and more preferably, it can be used as a phosphorescent host of a 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 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 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.

"Alkylsilyl" in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 40 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent properties and can be used as a material of an organic material layer of an organic electroluminescent device.

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

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The 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 condensed benzocarbazole compound having excellent carrier transport ability and light emitting ability, And an organic electroluminescent device having improved luminous efficiency, lifetime characteristics, and the like.

Specifically, the steric organic compound provided in the present invention has a basic skeleton formed by condensing a 5-membered heteroaromatic ring moiety in a 3,4-direction on a benzocarbazole moiety, Or a compound represented by any one of the following formulas.

[Chemical Formula 1]

(2)

(3)

In the above Chemical Formulas 1 to 3,

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 ₇ and R ₈ , R ₈ and R ₉ and R ₉ and R ₁₀ is represented by the following formula To form a five membered fused ring comprising at least one of N, O, S and Si;

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,

The dotted line is the part where the condensation occurs;

Each of X ₁ and X ₂ independently represent _{O, S, N (Ar 1} ), C (Ar 2) (Ar 3) and Si (Ar _4), but selected from the group consisting of (Ar ₅₎ wherein X ₁ and X At least one of ₂ is N (Ar ₁ ), preferably X ₁ and X ₂ are each independently selected from the group consisting of O, S and N (Ar ₁ ), more preferably X ₁ and X ₂ are both N (Ar < ₁ >);

Y ₁ and Y ₂ are each independently N or C (R ₁₁ ), preferably both Y ₁ and Y ₂ are C (R ₁₁ ), or at least one of Y ₁ and Y ₂ is N;

R ₁ to R ₁₁ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An 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 alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or a condensed ring by combining tile adjacent Lt; / RTI >

Ar ₁ to Ar ₅ 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 ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60, in particular wherein Ar ₁ is an aryl group of C ₆ ~ C ₆₀ or nuclear atoms of 5 to 60 Lt; / RTI > heteroaryl groups;

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 ₁₁ and Ar ₁ to Ar ₅ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently 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 alkynyl group, ~ 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 ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C ₆₀ aryl phosphine group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group and a C ₆ ~ substituted by one or more selected from the group consisting of C ₆₀ aryl amine, or unsubstituted, and a plurality In the case of being substituted with a substituent which may be the same or different from each other.

In the present invention, since the compound represented by any one of Chemical Formulas 1 to 3 has higher molecular weight than conventional organic EL device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')] It is excellent in thermal stability due to its high temperature, and excellent in carrier transporting ability and light emitting ability. Accordingly, when the organic electroluminescent device includes the compound of Formula 1, low driving voltage, high luminous efficiency, and long life characteristics of the device can be secured.

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. In the present invention, the compound represented by any one of Chemical Formulas 1 to 3 has a high triplet energy, a specific substituent is introduced into a basic skeleton in which an indole derivative having a broad singlet energy level and a high triplet energy level is condensed , The energy level can be controlled higher than that of the dopant and can be used as a host material.

The compound represented by any one of the above formulas (1) to (3) of the present invention has high triplet energies as described above, so that the excitons generated in the light emitting layer are prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer can do. Therefore, when an organic layer (hereinafter referred to as a "light-emission-assisting layer") is formed between the hole transporting layer and the light-emitting layer using any one of the compounds represented by Chemical Formulas 1 to 3, diffusion of the excitons is prevented by the compound Unlike the conventional organic electroluminescent device not including the first exciton diffusion preventing layer, the number of excitons contributing to light emission in the light emitting layer can be substantially increased to improve the light emitting efficiency of the device.

When an organic material layer (hereinafter referred to as a "life improving layer") is formed between the light emitting layer and the electron transporting layer by using the compound represented by any one of Chemical Formulas 1 to 3, It is possible to improve the durability and stability of the organic electroluminescent device, and thereby the half life time of the device can be efficiently increased. As described above, the compound represented by any one of the above formulas (1) to (3) can be used as a light-emitting auxiliary layer material or a life improving layer material other than the host of the light emitting layer.

In addition, in the present invention, any one of the compounds represented by Chemical Formulas 1 to 3 can control the HOMO and LUMO energy levels according to the kind of the substituent introduced into the basic skeleton as described above, and can have a wide band gap, It can have transportability. For example, when the electron donating group (EWG) having a high electron absorbing property such as a nitrogen-containing heterocycle (for example, a pyridine group, a pyrimidine group, a triazine group, etc.) is bonded to the basic skeleton, Since it has the property of bipolar, the bonding force between holes and electrons can be increased. As described above, the compound represented by any one of Chemical Formulas 1 to 3 wherein EWG is introduced into the basic skeleton is excellent in carrier transporting property and light emitting property. Therefore, in addition to the light emitting layer material of the organic electroluminescent device, the electron injection / Or may be used as a life improving material.

When the compound of any one of Chemical Formulas 1 to 3 of the present invention has a large electron donor group (EDG) such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group and the like in the basic skeleton, The hole injection and transport layer or the electron injection / transport layer material other than the light emitting layer material can be usefully used.

As described above, in the present invention, the compound represented by any one of Chemical Formulas 1 to 3 improves the luminescence characteristics of the organic electroluminescent device, and can improve the hole injecting / transporting ability, electron injecting / transporting ability, Life characteristics and the like can be improved. Therefore, the compound of any one of formulas (1) to (3) according to the present invention can be used as an organic layer material of an organic electroluminescence device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material) , A hole transporting / injecting layer material, a light emitting auxiliary layer material and a life improving layer material, more preferably a phosphorescent host material of a light emitting layer.

In addition, the compound of any one of the above-mentioned formulas (1) to (3) of the present invention has various substituents, especially an aryl group and / or a heteroaryl group, introduced into the basic skeleton and the molecular weight of the compound is significantly increased, And may have higher thermal stability than conventional light emitting materials (e.g., CBP).

Further, the compound represented by any one of the above formulas (1) to (3) of the present invention is also effective for inhibiting crystallization of the organic material layer. Therefore, the organic electroluminescent device comprising any one of the compounds of formulas (1) to (3) according to the present invention can be greatly improved in performance and lifetime, and the full-color organic electroluminescent panel Can be maximized.

According to a preferred embodiment of the present invention, the compound represented by any one of Chemical Formulas 1 to 3 may be a compound represented by any one of Chemical Formulas C-1 to C-20 shown below, no.

In the above formulas C-1 to C-20,

X ₁ , X ₂ , Y ₁ , Y ₂ and R ₁ to R ₁₀ are as defined in the above Chemical Formulas 1 to 4.

According to a preferred embodiment of the present invention, the compound represented by any one of formulas (1) to (3) may be represented by any one of the following formulas (D-1) to (D-20), but is not limited thereto.

In the above formulas D-1 to D-20,

Ar ₁ and R ₁ to R ₁₁ are as defined in the above Chemical Formulas 1 to 4.

According to a preferred embodiment of the present invention, R ₁ to R ₁₀ which do not form a condensation with the ring represented by the formula (4), R ₁₁ and Ar ₁ to Ar at least one of ₅ is selected from the group consisting of an aryl amine of the C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ C ₆₀ of,

R ₁ to R ₁₁ and Ar ₁ to Ar ₅ The alkyl group, aryl group, heteroaryl group and arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, , An arylamine group of C ₆ to C ₆₀ , and when they are substituted with a plurality of substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, in the compound represented by any one of Chemical Formulas 1 to 3, R ₁ to R ₁₀ , which do not form a condensation with the ring represented by Chemical Formula 4, and R ₁₁ and Ar _1, at least one of Ar ₅ may be a phenyl group or a substituent represented by the formula (5).

[Chemical Formula 5]

In Formula 5,

* Represents a moiety bonded to any one of the above formulas (1) to (3);

L ₁ is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group and a nuclear atoms of 5 to 18 groups heteroarylene, preferably a single bond, phenylene group, biphenylene group or carbazolyl be an and ;

Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₂ ), at least one of Z ₁ to Z ₅ is N;

R ₁₂ is the same or different from each other and each of R ₁₂ is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ 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 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 Group (e.g., L ₁ , adjacent R ₁₂ ) to form a condensed ring;

Alkyl group of the R _12, 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 of blood group and a C ₆ ~ C over ₆₀ one member selected from the group consisting of aryl silyl group coming , And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, examples of the substituent represented by the formula (5) include substituents represented by any one of the following formulas A-1 to A-15, but the present invention is not limited thereto.

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

* Represents a moiety bonded to any one of the above formulas (1) to (3);

n is an integer of 0 to 4, and when n is 0, hydrogen is not substituted by substituent R _13; when n is an integer of 1 to 4, R ₁₃ 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 ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, an arylamine group of C ₆ ~ C ₆₀ , 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 di A rephosphinyl group and an arylsilyl group of C ₆ to C ₆₀ , or may be bonded to an adjacent group (for example, L ₁ , R ₁₂ or other R ₁₃ ) to form a condensed ring;

Alkyl group of the R _13, 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 of blood group and a C ₆ ~ C over ₆₀ one member selected from the group consisting of aryl silyl group coming , When they are substituted with a plurality of substituents, they may be the same or different from each other,

L ₁ and R ₁₂ are as defined in the above formula (5).

According to a preferred embodiment of the present invention, R ₁ to R ₁₀ , R ₁₁ and Ar ₁ to Ar ₅ which do not form a condensation with the ring represented by the formula (4) At least one may be a substituent represented by the following formula (6)

[Chemical Formula 6]

In Formula 6,

* Represents a moiety bonded to any one of the above formulas (1) to (3);

L ₂ is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group and a nuclear atoms of 5 to 18 groups heteroarylene, preferably a single bond, phenylene group, biphenylene group or carbazolyl be an and ;

R ₁₄ and R ₁₅ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ Or R ₁₄ and R ₁₅ may combine with each other to form a condensed ring;

The alkyl, aryl, heteroaryl and arylamine groups of R ₁₄ and R ₁₅ 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 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ - substituted with C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ - mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ 1 or more selected from the group consisting of a arylsilyl of C ₆₀ And when they are unsubstituted or substituted with a plurality of substituents, they may be the same or different.

In the present invention, the compounds represented by any one of formulas (1) to (3) may be represented by the following structures, but are not limited thereto.

The compounds of the formulas (1) to (3) of the present invention can be synthesized according to a general synthetic 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 a compound represented by any one of formulas 1 to 3 according to the present invention.

More 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) , And at least one of the one or more organic layers includes a compound represented by any one of Chemical Formulas 1 to 3 above. At this time, the compounds may be used alone or in combination of two or more.

According to an embodiment of the present invention, the at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and an electron injecting layer, And a compound represented by any one of Chemical Formulas (3) and (3). Specifically, the organic compound layer containing the compound of Formula 1 may be selected from the group consisting of a light emitting layer, an electron transporting layer, an electron injecting layer, a hole transporting layer, a hole injecting layer, a light emitting auxiliary layer, A light-emitting layer, a light-emitting layer, a light-emitting layer, a light-emitting layer, and a light-emitting layer.

The light-emitting layer of the organic electroluminescent device of the present invention may include a host material. Preferably, the host material may include a compound represented by any one of formulas (1) to (3) of the present invention. In addition, the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than any one of the compounds represented by Chemical Formulas 1 to 3 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may be formed on the electron transporting layer, Or a compound represented by any one of < RTI ID = 0.0 >

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic 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 represented by any one of Chemical Formulas 1 to 3 may be used as a lifetime improving layer or an electron transporting auxiliary layer.

The organic electroluminescent device of the present invention may be formed by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes a compound represented by one of the above Chemical Formulas 1 to 3 Can be manufactured.

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

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

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

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and ordinary 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 PBC-1 and PBC-2

<Step 1> Synthesis of 2H-benzo [e] isoindole

Under nitrogen gas stream, _{Pd [P (t -Bu) 3} ] 2 (10.0 g, 20.0 mmol), 2,3- dihydro -1H- benzo [e] isoindole (67.6 g, 400.0 mmol), cyclohexene (164.0 g , 2000.0 mmol) and 600 ml of 1,4-dioxane were placed and stirred. Stir at 110 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with methylene chloride, added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 2H-benzo [e] isoindole (45.5 g, 272.0 mmol, yield 68%) was obtained by column chromatography.

^{1 H-NMR: δ 5.95-5.96 (} m, 2H), 7.66-7.77 (m, 2H), 7.81 (d, 1H), 8.16 (d, 2H), 8.54-8.55 (m, 1H), 9.10 (s , 1H)

<Step 2> Synthesis of 2-phenyl-2H-benzo [e] isoindole

Pd ₂ in a nitrogen atmosphere _{(dba) 3 (7.1 g,} 7.716 mmol), P (t-Bu) 3 (1.6 g, 7.716 mmol), NaOtBu (49.4 g, 514.4 mmol), bromobenzene (48.5 g, 308.6 mmol ), 2H-benzo [e] isoindole (43.0 g, 257.2 mmol) and toluene (600 ml) were mixed and stirred at 120 ° C for 12 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound, 2-phenyl-2H-benzo [e] isoindole (55.7 g, 228.9 mmol, yield 89%).

^{1 H-NMR: δ 6.95 (} s, 2H), 7.45-7.67 (m, 7H), 7.81 (. M 1H), 8.16 (m, 2H), 8.54 (t, 1H)

Step 3 Synthesis of 8-bromo-2-phenyl-2H-benzo [e] isoindole

Benzo [e] isoindole (53.0 g, 217.8 mmol), NBS (N-bromosuccinimide), 38.7 g (217.8 mmol) of DMF and 700 ml of DMF were mixed and heated at 60 ° C for 3 hours Lt; / RTI &gt;

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound, 8-bromo-2-phenyl-2H-benzo [e] isoindole (22.5 g, 69.7 mmol, yield 32%).

¹ H-NMR:? 6.95 (s, 2H), 7.45-7.58 (m, 6H), 7.70 (d,

<Step 4> Synthesis of 8- (2-nitrophenyl) -2-phenyl-2H-benzo [e] isoindole

2-phenyl-2H- benzo [e] isoindole (20.0 g, 62.1 mmol), 2-nitrophenylboronic acid (12.4 g, 74.5 mmol) and NaOH (7.5 g, 186.3 mmol) And 1000 ml / 500 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the _{Pd (PPh 3) 4 (3.6} g, 5 mol%) it was stirred at 80 ℃ 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, 8- (2-nitrophenyl) -2-phenyl-2H-benzo [e] isoindole (17.7 g, 48.4 mmol, yield 78% .

^{1 H-NMR: δ 6.95 (} s, 2H), 7.45-7.73 (m, 8H), 7.86-8.00 (m, 5H), 8.34 (s, 1H)

<Step 5> Synthesis of PBC-1 and PBC-2

Benzo [e] isoindole (15.0 g, 41.1 mmol), triphenylphosphine (27.0 g, 102.9 mmol) and 1,2-dichlorobenzene And the mixture was stirred for 12 hours. After completion of the reaction, the 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and PBC-1 (4.2 g, 12.7 mmol, yield: 31%) and PBC-2 (5.1 g, 15.2 mmol, yield: 37%) were separated by column chromatography, .

¹ H-NMR:? 6.95 (s, 2H), 7.29 (t, 1H), 7.45-7.64 (m, 8H), 7.81 (d, 1H), 8.12-8.16 (s, 1 H)

Of ^{PBC-2 1 H-NMR:} δ 6.95 (s, 2H), 7.29 (t, 1H), 7.40-7.68 (m, 9H), 7.81 (d, 1H), 8.12-8.16 (m, 2H), 10.10 (s, 1 H)

[Preparation Example 2] Synthesis of PBC-3 and PBC-4

<Step 1> Synthesis of 2H-benzo [f] isoindole

Under nitrogen gas stream, _{Pd [P (t -Bu) 3} ] 2 (10.0 g, 20.0 mmol), 2,3- dihydro -1H- benzo [f] isoindole (67.6 g, 400.0 mmol), cyclohexene (164.0 g , 2000.0 mmol) and 600 ml of 1,4-dioxane were placed and stirred. Stir at 110 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with methylene chloride, added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 2H-benzo [f] isoindole (47.5 g, 284.0 mmol, yield 71%) was obtained by column chromatography.

^{1 H-NMR: δ 5.96 (} s, 2H), 7.66-7.77 (m, 4H), 8.16 (t, 2H), 9.10 (s, 1H)

<Step 2> Synthesis of 1,3-diphenyl-2H-benzo [f] isoindole

2H-benzo [f] isoindole (46.0 g, 275.1 mmol), chlorobenzene (30.9 g, 275.1 mmol) and NaOH (14.7 g, 366.7 mmol) were added under nitrogen atmosphere and the mixture was stirred at 110 ° C for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with methylene chloride, added with MgSO ₄ and filtered. After removal of the solvent of the filtered organic layer, the desired compound 1,3-diphenyl-2H-benzo [f] isoindole (65.9 g, 206.3 mmol, yield 75%) was obtained by column chromatography.

^{1 H-NMR: δ 5.00 (} s, 1H), 7.41-7.51 (m, 6H), 7.67 (t, 4H), 7.79 (t, 4H), 8.16 (m, 2H)

<Step 3> Synthesis of 1,2,3-triphenyl-2H-benzo [f] isoindole

Pd ₂ (dba) ₃ in a nitrogen stream (5.7 g, 6.2 mmol), P (t-Bu) 3 (1.3 g, 6.2 mmol), NaOtBu (39.7 g, 412.6 mmol), bromobenzene (38.8 g, 247.6 mmol ), 1,3-diphenyl-2H-benzo [f] isoindole (65.9 g, 206.3 mmol) and toluene (600 ml) were mixed and stirred at 120 ° C for 12 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound, 1,2,3-triphenyl-2H-benzo [f] isoindole (65.2 g, 165.0 mmol, yield 80%).

^{1 H-NMR: δ 7.41-7.67 (} m, 13H), 7.78-7.79 (m, 2H), 7.91 (d, 4H), 8.16 (m, 2H)

Step 4 Synthesis of 6-bromo-1,2,3-triphenyl-2H-benzo [f] isoindole

Benzo [f] isoindole (65.0 g, 203.5 mmol), NBS (N-bromosuccinimide), 36.2 g (203.5 mmol) of DMF and 700 ml of DMF were mixed under a stream of nitrogen, Lt; / RTI &gt; for 3 h.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound, 6-bromo-1,2,3-triphenyl-2H-benzo [f] isoindole (31.8 g, 67.2 mmol, yield 33% .

¹ H-NMR:? 7.41-7.58 (m, 12H), 7.78-7.79 (m, 4H), 7.91 )

<Step 5> Synthesis of 6- (2-nitrophenyl) -1,2,3-triphenyl-2H-benzo [f] isoindole

(29.5 g, 62.1 mmol), 2-nitrophenylboronic acid (12.4 g, 74.5 mmol), NaOH (7.5 mmol) and triethylamine g, 186.3 mmol) and 1000 ml / 500 ml of THF / H ₂ O were added and stirred. At 40 ℃ put 3.6 g (5 mol%) of Pd (PPh _{3) 4} was stirred at 80 ℃ 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, the desired compound 6- (2-nitrophenyl) -1,2,3-triphenyl-2H- benzo [f] isoindole (23.1 g, 44.7 mmol, Yield: 72%).

¹ H-NMR:? 7.41-7.58 (m, 12H), 7.78-7.79 (m, 4H), 7.91 )

<Step 6> Synthesis of PBC-3 and PBC-4

Benzo [f] isoindole (21.3 g, 41.1 mmol), triphenylphosphine (27.0 g, 102.9 mmol), 1,6-dibromo- 250 ml of 2-dichlorobenzene was added thereto, followed by stirring for 12 hours. After completion of the reaction, the 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ and purified by column chromatography to obtain PBC-3 (6.2 g, 12.7 mmol, yield: 31%) and PBC-4 (6.4 g, 13.2 mmol, yield: 32% .

¹ H-NMR of PBC-3:? 7.29 (t, 1H), 7.41-7.64 (m, 16H), 7.78-7.79 (m, 4H)

¹ H-NMR of PBC-4:? 7.29 (t, 1H), 7.41-7.64 (m, 17H), 7.79

[Preparation Example 3] Synthesis of PBC-5

<Step 1> Synthesis of 2H-benzo [f] isoindole

Under nitrogen gas stream, _{Pd [P (t -Bu) 3} ] 2 (10.0 g, 20.0 mmol), 2,3- dihydro -1H- benzo [f] isoindole (67.6 g, 400.0 mmol), cyclohexene (164.0 g , 2000.0 mmol) and 600 ml of 1,4-dioxane were placed and stirred. Stir at 110 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with methylene chloride, added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 2H-benzo [f] isoindole (47.5 g, 284.0 mmol, yield 71%) was obtained by column chromatography.

^{1 H-NMR: δ 5.96 (} s, 2H), 7.66-7.77 (m, 4H), 8.16 (t, 2H), 9.10 (s, 1H)

<Step 2> Synthesis of 2-phenyl-2H-benzo [f] isoindole

Pd ₂ in a nitrogen atmosphere _{(dba) 3 (7.1 g,} 7.716 mmol), P (t-Bu) 3 (1.6 g, 7.716 mmol), NaOtBu (49.4 g, 514.4 mmol), bromobenzene (48.5 g, 308.6 mmol ), 2H-benzo [f] isoindole (43.0 g, 257.2 mmol) and toluene (600 ml) were mixed and stirred at 120 ° C for 12 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound, 2-phenyl-2H-benzo [f] isoindole (55.7 g, 228.9 mmol, yield 89%).

^{1 H-NMR: δ 6.95 (} s, 2H), 7.45-7.64 (m, 5H), 7.67-7.68 (m, 4H), 8.16 (t, 2H)

Step 3 Synthesis of 5-bromo-2-phenyl-2H-benzo [f] isoindole

Benzo [f] isoindole (53.0 g, 217.8 mmol), NBS (N-bromosuccinimide), 38.7 g (217.8 mmol) of DMF and 700 ml of DMF were mixed and stirred at 60 ° C for 3 hours Respectively.

After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound, 5-bromo-2-phenyl-2H-benzo [f] isoindole (21.1 g, 65.3 mmol, yield 30%).

¹ H-NMR:? 6.95 (s, 2H), 7.45-7.68 (m, 6H), 7.72 (s,

Step 4 Synthesis of 5- (4-nitro- [1,1'-biphenyl] -3-yl) -2-phenyl-2H- benzo [f] isoindole

Benzo [f] isoindole (20.0 g, 62.1 mmol) and (4-nitro- [1,1'-biphenyl] -3-yl) boronic acid 18.1 g, 74.5 mmol), NaOH (7.5 g, 186.3 mmol) and 1000 ml / 500 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the _{Pd (PPh 3) 4 (3.6} g, 5 mol%) it was stirred at 80 ℃ 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 removal of the solvent of the filtered organic layer, the desired compound 5- (4-nitro- [1,1'-biphenyl] -3-yl) -2-phenyl-2H- benzo [ Indole (19.1 g, 43.4 mmol, yield 70%).

^{1 H-NMR: δ 6.95 (} s, 2H), 7.41-7.61 (m, 13H), 7.76 (d, 1H), 7.96 (s, 1H), 8.04 (d, 1H), 8.38-8.42 (m, 2H )

<Step 5> Synthesis of PBC-5

Benzo [f] isoindole (18.1 g, 41.1 mmol) and triphenylphosphine (prepared as described in Example 1) 27.0 g, 102.9 mmol) and 1,2-dichlorobenzene (250 ml) were added thereto, followed by stirring for 12 hours. After completion of the reaction, the 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and the desired compound PBC-5 (5.2 g, 12.7 mmol, yield: 31%) was obtained by column chromatography.

¹ H-NMR of PBC-5:? 6.95 (s, 2H), 7.41-7.69 (m, 15H), 7.77 (s,

[Preparation Example 4] Synthesis of PBC-6 and PBC-7

<Step 1> Synthesis of 5- (1-nitronaphthalen-2-yl) -2-phenyl-2H-isoindole

(16.8 g, 62.1 mmol), (1-nitronaphthalen-2-yl) boronic acid (16.1 g, 74.5 mmol) and NaOH (7.5 g, 186.3 mmol) and 1000 ml / 500 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the _{Pd (PPh 3) 4 (3.6} g, 5 mol%) it was stirred at 80 ℃ 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, 5- (1-nitronaphthalen-2-yl) -2-phenyl-2H-isoindole (16.7 g, 45.9 mmol, yield 74%) as a target compound was purified by column chromatography .

^{1 H-NMR: δ 6.95 (} s, 2H), 7.19 (t, 1H), 7.45-7.63 (m, 7H), 7.75-7.76 (m, 1H), 7.87-7.88 (m, 1H), 8.09 (d , 8.33 (d, IH), 8.41 (d, IH), 8.93 (d, IH)

<Step 2> Synthesis of PBC-6 and PCB-7

2-yl) -2-phenyl-2H-isoindole (15.0 g, 41.1 mmol), triphenylphosphine (27.0 g, 102.9 mmol), 1,2-dichlorobenzene And the mixture was stirred for 12 hours. After completion of the reaction, the 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and the desired compound PBC-6 (4.0 g, 12.3 mmol, yield 30%) and PBC-7 (4.3 g, 13.1 mmol, yield 32% .

¹ H-NMR:? 6.95 (s, 2H), 7.45-7.67 (m, 9H), 8.12-8.16 (m, 3H), 8.51

¹ H-NMR of PBC-7:? 6.95 (s, 2H), 7.46-7.68 (m, 9H), 8.12-8.16

[Preparation Example 5] Synthesis of PBC-8 and PBC-9

<Step 1> Synthesis of 5-bromo-1,2,3-triphenyl-2H-isoindole

5-bromo-2-phenyl-2H-isoindole (25.2 g, 92.8 mmol), chlorobenzene (10.4 g, 92.8 mmol) and NaOH (5.0 g, 123.7 mmol) were added under nitrogen atmosphere and the mixture was stirred at 110 ° C for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with methylene chloride, added with MgSO ₄ and filtered. After removing the solvent of the filtered organic layer, 5-bromo-1,2,3-triphenyl-2H-isoindole (27.5 g, 65.0 mmol, yield 70%) was obtained by column chromatography.

¹ H-NMR: 8 7.24 (s, 1 H), 7.41-7.51 (m, 8H), 7.58-7.60 (m, 5H), 7.78-7.79

<Step 2> Synthesis of 5- (3-nitronaphthalen-2-yl) -1,2,3-triphenyl-2H-isoindole

(26.3 g, 62.1 mmol), 2-nitrophenylboronic acid (12.4 g, 74.5 mmol) and NaOH (7.5 g, 186.3 mmol) in a stream of nitrogen ) And 1000 ml / 500 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the _{Pd (PPh 3) 4 (3.6} g, 5 mol%) it was stirred at 80 ℃ 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, the desired compound 5- (3-nitronaphthalen-2-yl) -1,2,3-triphenyl-2H-isoindole (23.1 g, 44.7 mmol, Yield: 72%).

¹ H-NMR:? 7.19 (t, 1H), 7.41-7.63 (m, 13H), 7.79-7.83 (m, 6H), 8.18 (d, ), 9.05 (s, 1 H)

<Step 3> Synthesis of PBC-8 and PBC-9

Triphenyl-2H-isoindole (21.2 g, 41.1 mmol), triphenylphosphine (27.0 g, 102.9 mmol), and 1 (3-nitronaphthalen-2-yl) , And 250 ml of 2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, the 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and PBC-8 (6.1 g, 12.7 mmol, yield: 31%) and PBC-9 (6.1 g, 12.7 mmol, yield: 31%) were separated by column chromatography. .

¹ H-NMR of PBC-8: δ 7.40-7.50 (m , 10H), 7.51-7.58 (m, 5H), 7.67 (d, 2H), 7.79 (d, 4H), 8.16 (t, 2H), 10.10 (s, 1 H)

PBC-9 ¹ H-NMR of: δ 7.40-7.50 (m, 6H) , 7.51-7.58 (m, 8H), 7.67 (d, 2H), 7.79 (d, 4H), 8.12-8.16 (m, 3H) , 10.10 (s, 1 H)

[Preparation Example 6] Synthesis of PBC-10

<Step 1> Synthesis of 4- (3-nitro-7-phenylnaphthalen-2-yl) -2-phenyl-2H-isoindole

(16.9 g, 62.1 mmol), (3-nitro-7-phenylnaphthalen-2-yl) boronic acid (21.8 g, 74.5 mmol), NaOH 7.5 g, 186.3 mmol) and 1000 ml / 500 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the _{Pd (PPh 3) 4 (3.6} g, 5 mol%) it was stirred at 80 ℃ 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 the solvent of the filtered organic layer was removed, the desired compound, 21.3 g (48.4 mmol, Yield: 80%) was obtained from the target compound 4- (3-nitro-7-phenylnaphthalen- 78%).

^{1 H-NMR: δ 6.95 (} s, 2H), 7.41-7.58 (m, 12H), 7.76-7.79 (m, 2H), 7.97 (d, 1H), 8.18 (d, 1H), 8.52 (s, 1H ), 9.05 (s, 1 H)

<Step 2> Synthesis of PBC-10

(18.1 g, 41.1 mmol), triphenylphosphine (27.0 g, 102.9 mmol), 1, 3-dihydroxyphenyl- 250 ml of 2-dichlorobenzene was added thereto, followed by stirring for 12 hours. After completion of the reaction, the 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and the desired compound PBC-10 (5.3 g, 12.3 mmol, yield 30%) was obtained by column chromatography.

¹ of PBC-10 H-NMR: δ 6.95 (s, 2H), 7.49-7.51 (m, 7H), 7.52-7.65 (m, 8H), 7.73 (d, 1H), 7.92 (d, 1H), 10.10 (s, 1 H)

[Synthesis Example 1] Synthesis of Compound 12

(3.30 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) obtained in Preparation Example 1 and 0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 12 (4.99 g, yield 93%) as a target compound.

GC-Mass (calculated: 536.65 g / mol, measured: 536 g / mol)

[Synthesis Example 2] Synthesis of Compound 16

(3.90 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After the reaction was completed, water was added thereto, and the solid compound was filtered, and then purified by column chromatography to obtain Compound 16 as a target compound (3.85 g, yield 67%).

GC-Mass (calculated: 575.70 g / mol, measured: 575 g / mol)

[Synthesis Example 3] Synthesis of Compound 17

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 17 (4.86 g, yield 68%) was obtained in the same manner as in Synthesis Example 2, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 4] Synthesis of Compound 18

The procedure of Synthesis Example 2 was repeated except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (3.38 g, yield 63%).

GC-Mass (calculated: 536.62 g / mol, measured: 536 g / mol)

[Synthesis Example 5] Synthesis of Compound 23

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, Compound 23 (3.79 g, yield 62%) was obtained by carrying out the same procedure as in Synthesis Example 2.

GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[Synthesis Example 6] Synthesis of Compound 26

The title compound was synthesized in the same manner as in Synthesis Example 2, except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 4- The compound 26 (3.97 g, yield 60%) was obtained.

GC-Mass (theory: 662.78 g / mol, measured: 662 g / mol)

[Synthesis Example 7] Synthesis of Compound 111

(3.30 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) obtained in Preparation Example 1 and 0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into water, and the solid compound was filtered, and then purified by column chromatography to obtain Compound 111 (5.24 g, yield 93%) as a target compound.

GC-Mass (calculated: 563.65 g / mol, measured: 563 g / mol)

[Synthesis Example 8] Synthesis of Compound 113

(3.30 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered, and then purified by column chromatography to obtain Compound 113 as a target compound (4.03 g, yield 70%).

GC-Mass (calculated: 575.70 g / mol, measured: 575 g / mol)

[Synthesis Example 9] Synthesis of Compound 114

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 114 (4.93 g, yield 69%) was obtained in the same manner as in Synthesis Example 8, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 10] Synthesis of Compound 115

The procedure of Synthetic Example 8 was repeated except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (3.48 g, yield 65%).

GC-Mass (calculated: 536.62 g / mol, measured: 536 g / mol)

[Synthesis Example 11] Synthesis of Compound 120

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, Compound 120 (3.86 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 8.

GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[Synthesis Example 12] Synthesis of Compound 121

The title compound was synthesized in the same manner as in Preparation Example 8, except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 4- The compound 121 (4.30 g, yield 65%) was obtained.

GC-Mass (theory: 662.78 g / mol, measured: 662 g / mol)

[Synthesis Example 13] Synthesis of Compound 136

(5.38 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) obtained in Preparation Example 2 and 0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 136 as a target compound (6.44 g, yield 90%).

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 14] Synthesis of Compound 137

(5.38 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was poured into water and the solid compound was filtered and purified by column chromatography to obtain Compound 137 (4.44 g, yield 61%) as a target compound.

GC-Mass (calculated: 727.89 g / mol, measured: 727 g / mol)

[Synthesis Example 15] Synthesis of Compound 138

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 138 (5.46 g, yield 63%) was obtained in the same manner as in Synthesis Example 14, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 868.03 g / mol, measured: 868 g / mol)

[Synthesis Example 16] Synthesis of Compound 139

The same procedure as in Synthesis Example 14 was carried out except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (4.47 g, yield 65%).

GC-Mass (calculated: 688.82 g / mol, measured: 688 g / mol)

[Synthesis Example 17] Synthesis of Compound 140

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, The same procedure as in Synthesis Example 14 was conducted to obtain Compound 140 (4.58 g, yield 60%) as a target compound.

GC-Mass (calculated: 764.91 g / mol, measured: 764 g / mol)

[Synthesis Example 18] Synthesis of Compound 141

The title compound was synthesized in analogy to Synthesis Example 14 (2) except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) The compound 141 (5.13 g, yield 63%) was obtained.

GC-Mass (calculated: 814.97 g / mol, measured: 814 g / mol)

[Synthesis Example 19] Synthesis of Compound 142

(5.38 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) obtained in Preparation Example 2 and 0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 142 (6.44 g, yield 90%) as a target compound.

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 20] Synthesis of Compound 143

(5.38 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was poured into water, the solid compound was filtered, and the residue was purified by column chromatography to obtain the desired compound Compound 143 (4.87 g, yield 67%).

GC-Mass (calculated: 727.89 g / mol, measured: 727 g / mol)

[Synthesis Example 21] Synthesis of Compound 144

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 144 (5.46 g, yield 63%) was obtained in the same manner as in Synthesis Example 21, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 868.03 g / mol, measured: 868 g / mol)

[Synthesis Example 22] Synthesis of Compound 145

The procedure of Synthetic Example 21 was repeated, except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (4.12 g, yield 60%).

GC-Mass (calculated: 688.82 g / mol, measured: 688 g / mol)

[Synthesis Example 23] Synthesis of Compound 146

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, Compound 146 (4.66 g, yield 61%) was obtained by carrying out the same procedure as in Synthesis Example 21.

GC-Mass (calculated: 764.91 g / mol, measured: 764 g / mol)

[Synthesis Example 24] Synthesis of Compound 147

(4.40 g, 12.00 mmol) instead of 4-bromo-N, N-diphenyl aniline in place of 4-bromo-N, The compound 147 (5.13 g, yield 63%) was obtained.

GC-Mass (calculated: 814.97 g / mol, measured: 814 g / mol)

[Synthesis Example 25] Synthesis of Compound 171

(4.62 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) obtained in Preparation Example 3 and 0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 171 (5.82 g, yield 91%) as a target compound.

GC-Mass (calculated: 639.75 g / mol, measured: 639 g / mol)

[Synthesis Example 26] Synthesis of Compound 177

(4.62 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered and purified by column chromatography to obtain Compound 177 (4.10 g, yield 63%) as a target compound.

GC-Mass (calculated: 651.80 g / mol, measured: 651 g / mol)

[Synthesis Example 27] Synthesis of Compound 178

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 178 (4.75 g, yield 60%) was obtained in the same manner as in Synthesis Example 26, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (theory: 791.94 g / mol, measured: 791 g / mol)

[Synthesis Example 28] Synthesis of Compound 179

The procedure of Synthetic Example 26 was repeated, except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (3.86 g, yield 63%).

GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[Synthesis Example 29] Synthesis of Compound 185

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, The same procedure as in Synthesis Example 26 was conducted to obtain Compound 185 (4.13 g, yield 60%) as a target compound.

GC-Mass (calculated: 688.82 g / mol, measured: 688 g / mol)

[Synthesis Example 30] Synthesis of Compound 188

The title compound was synthesized in analogy to Synthesis Example 26 (2) except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 4- The target compound Compound 188 (4.58 g, yield 62%) was obtained.

GC-Mass (738.87 g / mol, measured: 738 g / mol)

[Synthesis Example 31] Synthesis of Compound 202

(3.86 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) obtained in Preparation Example 4 and 0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 202 (5.18 g, yield 92%) as a desired compound.

GC-Mass (calculated: 563.65 g / mol, measured: 563 g / mol)

[Synthesis Example 32] Synthesis of Compound 203

(3.86 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri-mixed butoxide (1.44 g, 15.00 mmol) and Toluene (50 ml) and stirred at room temperature for 6 hours-tert-butylphosphine (0.1 g, 0.5 mmol) and sodium tert. After completion of the reaction, water was added, and the solid compound was filtered, and then purified by column chromatography to obtain Compound 203 (3.45 g, yield 60%) as a target compound.

GC-Mass (calculated: 575.70 g / mol, measured: 575 g / mol)

[Synthesis Example 33] Synthesis of Compound 207

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 207 (4.22 g, yield 59%) was obtained in the same manner as in Synthesis Example 32, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 34] Synthesis of Compound 211

The same procedure as in Synthesis Example 32 was carried out except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (3.48 g, yield 65%).

GC-Mass (calculated: 536.62 g / mol, measured: 536 g / mol)

[Synthesis Example 35] Synthesis of Compound 217

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, The procedure of Synthesis Example 32 was repeated to obtain Compound 217 (3.67 g, yield 60%) as a target compound.

GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[Synthesis Example 36] Synthesis of Compound 222

The title compound was synthesized in the same manner as in Synthesis Example 32 (4) except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) The compound 222 (4.04 g, yield 61%) was obtained.

GC-Mass (theory: 662.78 g / mol, measured: 662 g / mol)

[Synthesis Example 37] Synthesis of Compound 233

(3.86 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) and NaH (0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 233 (5.01 g, yield 89%) as a target compound.

GC-Mass (calculated: 563.65 g / mol, measured: 563 g / mol)

[Synthesis Example 38] Synthesis of Compound 234

(3.86 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered, and then purified by column chromatography to obtain Compound 234 (3.45 g, yield 60%) as a target compound.

GC-Mass (calculated: 575.70 g / mol, measured: 575 g / mol)

[Synthesis Example 39] Synthesis of Compound 242

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- The compound 242 (4.15 g, yield 58%) was obtained in the same manner as in Synthesis Example 38, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 40] Synthesis of Compound 244

The procedure of Synthesis Example 38 was repeated, except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (3.38 g, yield 63%).

GC-Mass (calculated: 536.62 g / mol, measured: 536 g / mol)

[Synthesis Example 41] Synthesis of Compound 249

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, The procedure of Synthesis Example 38 was repeated to obtain Compound 249 (3.43 g, yield 56%) as a target compound.

GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[Synthesis Example 42] Synthesis of Compound 253

The title compound was synthesized in the same manner as in Synthesis Example 38 (2) except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 4- The compound 253 (3.97 g, yield 60%) was obtained.

GC-Mass (theory: 662.78 g / mol, measured: 662 g / mol)

[Synthesis Example 43] Synthesis of Ccompound 260

POC-8 (5.38 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) and NaH (0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 260 (6.30 g, yield 88%) as a target compound.

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 44] Synthesis of Compound 265

(5.38 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered, and then purified by column chromatography to obtain Compound 265 (4.14 g, yield 57%) as a target compound.

GC-Mass (calculated: 727.89 g / mol, measured: 727 g / mol)

[Synthesis Example 45] Synthesis of Compound 267

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 267 (5.12 g, yield 59%) was obtained in the same manner as in Synthesis Example 44, except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 868.03 g / mol, measured: 868 g / mol)

[Synthesis Example 46] Synthesis of Compound 277

The same procedure as in Synthesis Example 44 was conducted, except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (4.13 g, yield 60%).

GC-Mass (calculated: 688.82 g / mol, measured: 688 g / mol)

[Synthesis Example 47] Synthesis of Compound 278

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, The procedure of Synthesis Example 44 was repeated to obtain Compound 278 (4.35 g, yield 57%) as a target compound.

GC-Mass (calculated: 764.91 g / mol, measured: 764 g / mol)

[Synthesis Example 48] Synthesis of Compound 281

The title compound was synthesized in analogy to Synthesis Example 44 (5) except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 4- The compound 281 (4.88 g, yield 60%) was obtained.

GC-Mass (calculated: 814.97 g / mol, measured: 814 g / mol)

[Synthesis Example 49] Synthesis of Compound 282

POC-9 (5.38 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) and NaH (0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 the desired compound Compound 282 (6.51 g, yield 91%).

GC-Mass (calculated: 715.84 g / mol, measured: 715 g / mol)

[Synthesis Example 50] Synthesis of Compound 283

(5.38 g, 10.00 mmol), 4-bromo-N, N-diphenyl aniline (3.90 g, 12.00 mmol) and Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was poured into water, the solid compound was filtered, and the residue was purified by column chromatography to obtain Compound 283 (4.36 g, yield 60%) as a target compound.

GC-Mass (calculated: 727.89 g / mol, measured: 727 g / mol)

[Synthesis Example 51] Synthesis of Compound 284

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 284 (4.94 g, yield 57%) was obtained by carrying out the same procedure as in Synthesis Example 50 except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (calculated: 868.03 g / mol, measured: 868 g / mol)

[Synthesis Example 52] Synthesis of Compound 285

The procedure of Synthetic Example 50 was repeated, except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (4.06 g, yield 59%).

GC-Mass (calculated: 688.82 g / mol, measured: 688 g / mol)

[Synthesis Example 53] Synthesis of Compound 286

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, The procedure of Synthesis Example 50 was repeated to obtain Compound 286 (4.43 g, yield 58%) as a target compound.

GC-Mass (calculated: 764.91 g / mol, measured: 764 g / mol)

[Synthesis Example 54] Synthesis of Compound 287

Except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 4-bromo-N, The compound 287 (5.13 g, yield 63%) was obtained.

GC-Mass (calculated: 814.97 g / mol, measured: 814 g / mol)

[Synthesis Example 55] Synthesis of Compound 303

Phenyl-10 (4.08 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol) obtained in Preparation Example 6 and 0.24 g , 10.00 mmol) and DMF (50 ml) were mixed and 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 Compound 303 (5.95 g, yield 93%) as a target compound.

GC-Mass (calculated: 639.75 g / mol, measured: 639 g / mol)

[Synthesis Example 56] Synthesis of Compound 305

(3.90 g, 12.00 mmol), Pd ₂ (dba) ₃ (0.45 g, 0.50 mmol) obtained in Preparative Example 6 (4.08 g, 10.00 mmol), 4-bromo- mmol), tri- tert -butylphosphine (0.1 g, 0.5 mmol) and sodium tert-butoxide (1.44 g, 15.00 mmol) and toluene (50 ml) were mixed and stirred at room temperature for 6 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered, and then purified by column chromatography to obtain Compound 305 as a target compound (3.91 g, yield 60%).

GC-Mass (calculated: 651.80 g / mol, measured: 651 g / mol)

[Synthesis Example 57] Synthesis of Compound 306

(3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Compound 306 (4.43 g, yield 56%) was obtained by carrying out the same procedure as in Synthesis Example 56 except that triazine (5.57 g, 12.00 mmol) was used.

GC-Mass (theory: 791.94 g / mol, measured: 791 g / mol)

[Synthesis Example 58] Synthesis of Compound 307

The procedure of Synthesis Example 56 was repeated, except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 4-bromo-N, (3.61 g, yield 59%).

GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[Synthesis Example 59] Synthesis of Compound 309

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.80 g, 12.00 mmol) was used in the place of 4-bromo-N, Compound 309 (3.92 g, yield 57%) was obtained by carrying out the same procedure as in Synthesis Example 56.

GC-Mass (calculated: 688.82 g / mol, measured: 688.82 g / mol)

[Synthesis Example 60] Synthesis of Compound 310

The title compound was synthesized in analogy to Synthesis Example 56 (2) except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) The compound 310 (4.28 g, yield 58%) was obtained.

GC-Mass (738.87 g / mol, measured: 738 g / mol)

[Examples 1 to 60] Preparation of red organic EL device

As shown in the following Table 1, the compounds 1 to 312 synthesized in Synthesis Examples 1 to 60 were subjected to high purity sublimation purification by a conventionally known method, and red organic electroluminescent devices were 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.

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / 1 to 312 + 10% (piq) ₂ Ir (acac) (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[Comparative Example 1]

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

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 1 to 60 and Comparative Example 1 are as follows.

[Evaluation example]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 60 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 One 4.6 535 13.9 Example 2 2 4.1 528 13.0 Example 3 3 5.1 537 13.9 Example 4 14 5.2 535 13.1 Example 5 15 4.5 548 13.1 Example 6 18 4.3 535 13.0 Example 7 34 4.8 548 14.9 Example 8 37 4.9 537 15.0 Example 9 38 4.8 555 10.7 Example 10 78 4,5 538 10.8 Example 11 79 4.2 537 10.0 Example 12 84 5.2 538 13.9 Example 13 95 5.6 535 13.9 Example 14 96 4.7 548 10.2 Example 15 100 5.1 535 13.1 Example 16 101 5.1 548 12.8 Example 17 108 5.0 538 12.0 Example 18 109 4.5 537 12.9 Example 19 111 4.3 537 13.9 Example 20 115 5.1 547 14.1 Example 21 116 5.2 557 13.2 Example 22 117 5.1 528 10.3 Example 23 134 5.0 537 11.1 Example 24 136 4.7 535 14.5 Example 25 137 4.7 538 13.1 Example 26 148 4.8 538 13.9 Example 27 150 4.7 537 13.1 Example 28 151 5.0 545 12.8 Example 29 152 5.0 538 12.7 Example 30 156 4.9 548 11.9 Example 31 159 4.9 538 12.2 Example 32 176 4.8 538 13.0 Example 33 177 4.9 548 12.9 Example 34 178 4.9 537 13.1 Example 35 193 4.7 535 14.1 Example 36 194 4.7 538 11.1 Example 37 199 4.8 538 11.9 Example 38 204 4.7 537 13.1 Example 39 206 5.1 558 13.4 Example 40 221 4.5 538 10.1 Example 41 222 4.6 547 8.9 Example 42 245 4.9 535 10.9 Example 43 247 4.6 538 11.3 Example 44 267 4.8 535 12.5 Example 45 268 4.9 538 13.5 Example 46 271 5.1 538 14.1 Example 47 272 4.8 548 15.4 Example 48 281 4.9 538 12.1 Example 49 285 4.8 537 13.7 Example 50 286 4.9 547 13.6 Example 51 287 5.0 535 12.6 Example 52 297 5.0 548 13.1 Example 53 298 5.2 538 10.9 Example 54 299 5.1 537 10.1 Example 55 300 4.8 545 11.9 Example 56 301 4.9 538 12.0 Example 57 303 4.9 538 13.9 Example 58 306 4.9 545 13.3 Example 59 307 4.8 538 12.2 Example 60 309 4.9 538 12.8 Comparative Example 1 CBP 5.25 516 8.2

As shown in Table 1, when the compound according to the present invention was used as a material for a light emitting layer of a red organic electroluminescent device, compared with a red organic electroluminescent device (Comparative Example 1) using CBP as a material for a light emitting layer And the driving voltage.

[Examples 61 to 70] Fabrication of green organic EL device

As shown in the following Table 2, the compounds 1 to 312 synthesized in Synthesis Examples 1 to 60 were subjected to high purity sublimation purification by a conventionally known method, and a green 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, 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.

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / 1 to 312 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

[Comparative Example 2] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 61, except that CBP was used instead of the compound of Synthesis Example 10 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 / cm 2 were measured for each of the green organic EL devices manufactured in Examples 61 to 70 and Comparative Example 2, .

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 61 5 6.74 42.2 Example 62 35 6.46 43.1 Example 63 97 6.71 41.1 Example 64 121 6.79 42.0 Example 65 123 6.55 42.5 Example 66 140 6.69 41.3 Example 67 171 6.69 41.9 Example 68 213 6.70 41.6 Example 69 257 6.34 41.5 Example 70 289 6.70 41.4 Comparative Example 2 CBP 6.93 38.2

As shown in Table 2, when the compound according to the present invention was used as a material for a light emitting layer of a green organic electroluminescent device (Examples 61-70), a green organic electroluminescent device using conventional CBP as a material for a light emitting layer 2), it can be seen that it shows excellent performance in terms of efficiency and driving voltage.

Claims (19)

A compound represented by any one of the following formulas (1) to (3):
[Chemical Formula 1]

(2)

(3)

In the above Chemical Formulas 1 to 3,
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 ₇ and R ₈ , R ₈ and R ₉ and R ₉ and R ₁₀ is represented by the following formula Lt; / RTI &gt; to form a condensed ring;
[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,
The dotted line is the part where the condensation occurs;
Each of X ₁ and X ₂ independently represent _{O, S, N (Ar 1} ), C (Ar 2) (Ar 3) and Si (Ar _4), but selected from the group consisting of (Ar ₅₎ wherein X ₁ and X At least one of ₂ is N (Ar &lt; ₁ &gt;);
Y ₁ and Y ₂ are each independently N or C (R ₁₁ );
R ₁ to R ₁₁ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An 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 alkyl A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in the, form a condensed ring by combining adjacent tile ;
Ar ₁ to Ar ₅ 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 ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ 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 ₁₁ and Ar ₁ to Ar ₅ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently 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 alkynyl group, ~ 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 ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C ₆₀ aryl phosphine group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group and a C ₆ ~ substituted by one or more selected from the group consisting of C ₆₀ aryl amine, or unsubstituted, and a plurality In the case of being substituted with a substituent which is the same as or different from each other. The method according to claim 1,
X ₁ and X ₂ are each independently selected from the group consisting of O, S and N (Ar ₁ ). The method according to claim 1,
X ₁ and X ₂ are both N (Ar ₁ ). The method according to claim 1,
Ar &lt; _{1 &gt;} is an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms. The method according to claim 1,
Wherein both of Y ₁ and Y ₂ are C (R ₁₁ ), or at least one of Y ₁ and Y ₂ is N. The method according to claim 1,
The compound represented by any one of Chemical Formulas (1) to (3) is a compound represented by any one of Chemical Formulas (C-1) to (C-20)

In the above formulas C-1 to C-20,
X ₁ , X ₂ , Y ₁ , Y ₂ and R ₁ to R ₁₀ are as defined in claim 1, respectively. The method according to claim 1,
The compound represented by any one of Chemical Formulas 1 to 3 is represented by any one of the following Chemical Formulas D-1 to D-20:

In the above formulas D-1 to D-20,
Ar ₁ and R ₁ to R ₁₁ are as defined in claim 1, respectively. The method according to claim 1,
At least one of R ₁ to R ₁₁ and Ar ₁ to Ar ₅ 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 An amine group,
R ₁ to R ₁₁ and Ar ₁ to Ar ₅ The alkyl group, aryl group, heteroaryl group and arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group, , An arylamine group having ₆ to ₆₀ carbon atoms, 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 ₁₁ and Ar ₁ to Ar ₅ is a phenyl group or a substituent group represented by the following formula (5):
[Chemical Formula 5]

In Formula 5,
* Represents a moiety bonded to any one of the above formulas (1) to (3);
L ₁ 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;
Z ₁ to Z ₅ are the same or different and are each independently N or C (R ₁₂ ), at least one of Z ₁ to Z ₅ is N;
R ₁₂ is the same or different from each other and each of R ₁₂ is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ 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 _12, 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 of blood group and a C ₆ ~ C over ₆₀ one member selected from the group consisting of aryl silyl group coming , And when they are substituted with a plurality of substituents, they are the same as or different from each other. 9. The method of claim 8,
Wherein the substituent represented by the formula (5) is a substituent represented by any one of the following formulas (A-1) to (A-15):

In the above A-1 to A-15,
* Represents a moiety bonded to any one of the above formulas (1) to (3);
n is an integer of 0 to 4, and when n is 0, hydrogen is not substituted by substituent R _13; when n is an integer of 1 to 4, R ₁₃ 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 _13, 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 of blood group and a C ₆ ~ C over ₆₀ one member selected from the group consisting of aryl silyl group coming , When they are substituted with a plurality of substituents, they are the same or different from each other;
L ₁ and R ₁₂ are as defined in claim 8, respectively. 10. The method of claim 9,
L ₁ is a single bond, a phenylene group, a biphenylene group, or a carbazolyl group. The method according to claim 1,
At least one of R ₁ to R ₁₁ and Ar ₁ to Ar ₅ is a substituent represented by the following formula (6):
[Chemical Formula 6]

In Formula 12,
* Represents a moiety bonded to the above formulas (1) to (3);
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 ₁₄ and R ₁₅ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ Or R ₁₄ and R ₁₅ combine to form a condensed ring;
The alkyl, aryl, heteroaryl and arylamine groups of R ₁₄ and R ₁₅ 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 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ - substituted with C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ - mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ 1 or more selected from the group consisting of a arylsilyl of C ₆₀ Or when they are unsubstituted or substituted with a plurality of substituents, they are the same as or different from each other. 13. The method of claim 12,
L ₂ is a single bond, a phenylene group, a biphenylene group, or a carbazolyl group. The method according to claim 1,
The compound represented by any one of Chemical Formulas 1 to 3 is selected from the group consisting of the following compounds:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound represented by any one of formulas (1) to (3) according to any one of claims 1 to 14. 16. The method of claim 15,
The organic electroluminescent device according to any one of claims 1 to 3, wherein the organic compound layer 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. 17. The method of claim 16,
Wherein the organic material layer comprising a compound represented by any one of Chemical Formulas 1 to 3 is selected from the group consisting of a light emitting layer, a hole transporting layer, and an electron transporting layer. 18. The method of claim 17,
The organic electroluminescent device according to any one of claims 1 to 3, wherein the organic compound layer is a light emitting layer. 19. The method of claim 18,
Wherein the compound represented by any one of Chemical Formulas 1 to 3 is used as a phosphorescent host of the light emitting layer.