KR101548040B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel structure compound having a basic skeleton formed by fusing an indole moiety to the terminal of a pyrrolocarbazole moiety and various substituents bonded to the basic skeleton, and an organic electroluminescent device including the novel structure compound.
In the present invention, by including the aforementioned compound in one or more organic layers, preferably a light emitting layer, the luminous efficiency, driving voltage, lifetime, etc. of the device can be improved.

Description

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

The present invention relates to a novel organic compound which can be used as a material for an organic electroluminescent device, and an organic electroluminescent device including the same, which improves the luminous efficiency, driving voltage and lifetime of the device.

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

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

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, researches on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. In particular, the phosphor has a great advantage in improving the efficiency aspects of the light-emitting material materials _{Firpic, Ir (ppy) 3,} (acac) Ir (btp) 2 Ir metal complex compound is blue (blue), which includes the same as the green ( green and red dopant materials, and CBP is a phosphorescent host material.

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

An object of the present invention is to provide a novel organic compound capable of improving the bonding force between holes and electrons while having excellent thermal stability due to a high glass transition temperature.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and having improved driving voltage, luminous efficiency, and the like.

The present invention provides a compound represented by the following formula (1).

In Formula 1,

At least one of R ₃ and R _4, R ₄ and R ₅ , and R ₅ and R ₆ is bonded to the following formula 2 to form a condensed ring;

In the formula (2), the dashed line represents the condensation site;

At least one of R ₇ and R _8, R ₈ and R ₉ , and R ₉ and R ₁₀ is bonded to the following formula 3 to form a condensed ring;

In the formula (3), the dashed line represents the condensation site;

X ₁ is O, S, Se, N ( Ar 3), is selected from _{C (Ar 4) (Ar 5} ) and _{Si (Ar 6) (Ar 7} )

R ₁ to R ₁₄ which form a condensed ring are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, of a C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 of the A substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, Or an unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, an aryl phosphonic a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ of pingi, A substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, which may be bonded to adjacent groups to form a condensed ring, ,

Ar ₁ to Ar ₇ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ alkylsulfonyl group, C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted aryl phosphine oxide of a C ₆ ~ C ₄₀ ring Is selected from, the group consisting of aryl silyl substituted or unsubstituted C ₆ ~ C _40,

In R ₁ to R ₁₄ and Ar ₁ to Ar ₇ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a nuclear atom the number of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C arylamine group of ₆ ~ C _40, aryl group of C ₆ ~ C _40, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _40, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl groups are each independently selected from deuterium, halogen, a cyano group, an alkyl group of C ₁ ~ C ₄₀ of, C ₂ ~ aryloxy C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of, C ₁ ~ C ₄₀ the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 KV A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ Aryl phosphine oxide groups, and arylsilyl groups of C ₆ to C ₄₀ . At this time, when a plurality of substituents are introduced, the plurality of substituents are the same or different from each other.

Also, the present invention is an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound of the above formula The organic electroluminescent device comprising:

At least one of the one or more organic layers may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a light emitting layer, and is preferably a light emitting layer. At this time, the compound represented by Formula 1 is a blue, green or red phosphorescent host material.

The compound represented by the general formula (1) of the present invention is excellent in thermal stability and phosphorescence properties and can be applied to a light emitting layer of an organic electroluminescent device.

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

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compound according to the present invention has a structure in which an indole moiety is fused to the terminal of a pyrrolocarbazole moiety to form a basic skeleton and various substituents are bonded to the basic skeleton. Is displayed.

The compound represented by the formula (1) has a larger molecular weight than the conventional organic EL device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as "CBP")] The bonding force of electrons can be increased. Accordingly, when the compound of Formula 1 is used in an organic EL device, the driving voltage, efficiency (luminous efficiency, power efficiency), lifetime and brightness of the device can be improved.

In particular, the compounds have broad bandgaps due to indole moieties attached to the ends of pyrrolocarbazole moieties, and because of the various aromatic ring substituents, the whole molecule has a bipolar characteristic It is possible to enhance the bonding force between the hole and the electron, and thus it is possible to exhibit excellent characteristics as the host material of the light emitting layer as compared with the conventional CBP. Thus, the phosphorescent characteristics of the device can be improved, and the hole injecting ability and / or transporting ability, luminous efficiency, driving voltage, lifetime characteristics and the like can be improved. Further, the energy level can be controlled by the above-mentioned substituents, and thus it can have a wide band gap (sky blue to red), so that it can be applied not only as a light emitting layer but also as a hole transport layer and a hole injection layer.

On the other hand, due to various aromatic ring substituents introduced in many of the bonded indole moieties, the molecular weight of the compound is significantly increased, so that the glass transition temperature (Tg) can be improved. As a result, It can have high thermal stability. Also, the indole moiety bonded to the end of the pyrrolocarbazole moiety is fused. Not only the thermal stability of the compound can be improved, but also the effect of inhibiting the crystallization of the organic layer containing the compound of the formula (1). Therefore, the device including the compound of Formula 1 according to the present invention can greatly improve durability and lifetime characteristics.

In addition, when the compound of Formula 1 according to the present invention is used as a positive hole injection / transport layer material, a blue, green and / or red phosphorescent host material of an organic EL device, it exerts an excellent effect in terms of efficiency and life . Therefore, the compound according to the present invention can greatly contribute to the improvement of the performance and lifetime of the organic EL device, and particularly the lifetime improvement of the device has a great effect for maximizing the performance in the full-color organic light emitting panel.

In the compound represented by formula (1) according to the present invention, at least one of R ₃ and R _4, R ₄ and R ₅ , R ₅ and R ₆ is bonded to the following formula (2) to form a pyrrolocarbazole skeleton condensation ring, At the same time, at least one of R ₇ and R _8, R ₈ and R ₉ , R ₉ and R ₁₀ in Formula 2 is bonded to the following Formula 3 of the indole structure to form a condensed ring.

More specifically, the compound represented by the formula (1) of the present invention can be further represented by a compound represented by any of the following formulas (C-1) to (C-36).

In Formulas C-1 to C-36, R ₁ to R ₁₄ , X ₁ and Ar ₁ to Ar ₂ are the same as defined in Formula 1, respectively.

In Formula 1 according to the present invention, X ₁ may be selected from O, S, Se, N (Ar ₃ ), C (Ar ₄ ) (Ar ₅ ) and Si (Ar ₆ ) (Ar ₇ ) Is S or N (Ar ₃ ), and more preferably N (Ar ₃ ).

Also, at least one of R ₃ and R _4, R ₄ and R ₅ , R ₅ and R ₆ is a substituent which forms a non-forming group with the formula (2) and / or the condensation ring; And R ₁ to R ₁₄ , excluding at least one of R ₇ and R _8, R ₈ and R ₉ , R ₉ and R ₁₀ , are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ An aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted Or an unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or Substituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ of is selected from an aryl silyl group the group consisting of, all of which are of the May be bonded to adjacent groups to form a condensed ring.

In this case, considering the characteristics of the organic electroluminescent device, R ₁ to R ₁₄ , except for the substituent forming the condensed ring, are the same or different and each independently represents hydrogen, deuterium (D), substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, and is preferably a substituted or unsubstituted nucleus atoms selected from the group consisting of a heteroaryl group of from 5 to 40.

In the formula (1) according to the present invention, Ar ₁ to Ar ₇ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group , A substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted A C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkylcarbonyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, A substituted or unsubstituted C ₆ to C ₄₀ arylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide is selected from the pin group and a substituted or unsubstituted C ₆ ~ arylsilyl group consisting of C ₄₀ ring.

Here, the alkyl group of the R ₁ to R ₁₄ and Ar ₁ to Ar _7, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an aryl group, a cycloalkyl group, a heterocycloalkyl the alkyl group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide groups and arylsilyl groups each of one or more substituents to be introduced are each independently a heavy hydrogen, a halogen, cyano group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ 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, group C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C _And an arylsilyl group having 1 to ₄₀ carbon atoms. When a plurality of substituents are substituted, they may be the same or different from each other.

More specifically, each of Ar ₁ to Ar ₇ is independently selected from the group consisting of a substituted or unsubstituted C ₆ to C ₄₀ aryl group and a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms Do.

The substituents on the aryl and heteroaryl groups of Ar ₁ to Ar ₇ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, and a C ₆ ~ C ₄₀ group consisting arylsilyl of &Lt; / RTI &gt; When a plurality of substituents are introduced at this time, these substituents may be the same as or different from each other.

In the compound represented by the formula (1) according to the present invention, each of R ₁ to R ₁₄ and Ar ₁ to Ar ₇ is independently hydrogen or more preferably selected from the substituent group consisting of the following substituent groups S1 to S204. However, the present invention is not limited thereto.

More preferably, R ₁ to R ₁₄ , Ar ₁ to Ar ₇ each independently may be selected from hydrogen or the following substituent group.

The compounds of the present invention described above can be further exemplified by the following exemplified structures. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

As used herein, "unsubstituted alkyl" is a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso -Amyl, hexyl, and the like.

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

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

"Unsubstituted aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either alone or in combination with at least two rings. Two or more rings may be attached to each other in a pendant or condensed form. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Unsubstituted heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. One or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom such as N, O, S or Se. It is interpreted that two or more rings may be attached to each other in a pendant or condensed form together with a condensed form with an aryl group. Examples of heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. Includes rings and is also meant to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

"Unsubstituted aryloxy" is a monovalent substituent represented by RO-, wherein R is aryl having 5 to 60 carbon atoms. Examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

"Unsubstituted alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents an alkyl having 1 to 40 carbon atoms, and may have a linear, branched or cyclic structure . Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Unsubstituted arylamine" means an amine substituted with aryl having 6 to 60 carbon atoms.

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

"Unsubstituted heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, is replaced by N, O, or S Lt; / RTI &gt; Non-limiting examples thereof include morpholine, piperazine, and the like.

"Alkylsilyl" is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

"Condensation ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

&Lt; Organic electroluminescent device &

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

Specifically, the organic electroluminescent device of the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Includes a compound represented by the above formula (1), preferably a compound represented by the formula (C-1) to a compound represented by the formula (C-36). At this time, the compounds represented by any one of formulas C-1 to C-36 may be used alone or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one organic layer may include a compound represented by Formula 1. Preferably, the organic compound layer containing the compound of Compound 1 may be an emissive layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). Thus, when the compound of Formula 1 is incorporated into a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host, the bonding strength between holes and electrons in the light emitting layer is increased. (Luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include a compound represented by Formula 1, and preferably, the emitting layer includes a compound represented by Formula 1 . Specifically, the compound of the present invention can be used as a phosphorescent host of the light emitting layer. On the other hand, an electron injection layer may be further stacked on the electron transport layer.

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

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

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

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

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

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

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

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

[Preparation Example 1] Synthesis of CNB-1 and CNB-2

<Step 1> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole

(25 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3 , 2-dioxaborolane) (48.58 g , 0.191 mol), mixed with _{Pd (dppf) Cl 2 (5.2} g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) and 130 ℃ Lt; / RTI &gt; for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 5- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-indole (22.32 g, yield 72%).

¹ H-NMR:? 1.24 (s, 12H), 6.45 (d, IH), 7.27 (d, IH), 7.42 s, 1 H)

<Step 2> Synthesis of 5- (5-bromo-2-nitrophenyl) -1H-indole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-one) obtained in the above Step 1 was reacted with 2,4-dibromo-1-nitrobenzene (21.18 g, 75.41 mmol) yl) -1H-indole (22 g , 90.49 mmol), K 2 CO 3 (31.26 g, 226.24 mmol) and _{THF / H 2 O (400 ml} / 200 ml) , and then, Pd (PPh ₃ at 40 ℃ mixing ) ₄ (4.36 g, 5 mol%) were added, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. 5-bromo-2-nitrophenyl) -1H-indole (9.1 g, yield 38%) was obtained by removing the solvent from the obtained organic layer and then purifying by column chromatography (Hexane: EA = 3: 1 (v / &Lt; / RTI &gt;

^{1 H NMR: δ 6.45 (d} , 1H), 7.26 (d, 1H), 7.45 (d, 1H), 7.55 (d, 1H), 7.64 (d, 1H), 7.85 (d, 1H), 7.96 (s , &Lt; / RTI &gt; 1H), 8.13 (s, 1H), 8.21

<Step 3> Synthesis of 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole

Indole (9 g, 28.38 mmol), iodobenzene (11.58 g, 56.76 mmol), Cu powder (0.18 g, 2.84 mmol) obtained in the above Step 2 ), K ₂ CO ₃ (3.92 g, 28.38 mmol), Na ₂ SO ₄ (4.03 g, 28.38 mmol) and nitrobenzene (150 ml) were mixed and stirred at 210 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give 5- (5-bromo- 2-nitrophenyl) 8.03 g, yield 72%).

^{1 H NMR: δ 6.44 (d} , 1H), 7.25 (d, 1H), 7.46 (m, 3H), 7.56 (m, 4H), 7.65 (d, 1H), 7.86 (d, 1H), 7.95 (s , &Lt; / RTI &gt; 1H), 8.11 (s, 1H)

<Step 4> Synthesis of CNB-1 and CNB-2

5-bromo-2-nitrophenyl) -1-phenyl-1H-indole (8 g, 20.34 mmol), triphenylphosphine (13.34 g, 50.86 mmol) obtained in Step 3, dichlorobenzene (100 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The obtained organic layer was washed with MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain CNB-1 (3.89 g, yield 53%) and CNB- , Yield: 18%).

Of ^{CNB-1 1 H-NMR:} δ 6.45 (d, 1H), 7.26 (d, 1H), 7.38 (m, 2H), 7.45 (d, 1H), 7.51 (d, 1H), 7.57 (m, 3H ), 7.64 (d, IH), 7.85 (d, IH), 8.10 (s,

Of ^{CNB-2 1 H-NMR:} δ 6.45 (d, 1H), 7.26 (d, 1H), 7.38 (m, 2H), 7.41 (s, 1H), 7.48 (s, 1H), 7.54 (m, 3H ), 7.61 (d, IH), 7.87 (d, IH), 8.10 (s,

[Preparation Example 2] Synthesis of CPB-1

<Step 1> Synthesis of CPB-1

Except that CNB-1 (10.26 g, 0.028 mmol) obtained in Step 4 of Preparation Example 1 was used instead of 5- (5-bromo-2-nitrophenyl) 3], CPB-1 (9.81 g, yield 79%) was obtained.

¹ H NMR: 8 6.48 (d, 1 H), 7.42 (m, 6 H), 7.51 (m, 4 H)

[Preparation Example 3] Synthesis of CPBO-1

<Step 1> Synthesis of CPBO-1

Step 1 of Preparation Example 1 was repeated except that CPB-1 (55.98 g, 0.128 mmol) obtained in Step 4 of Preparation Example 1 was used instead of 5-bromo-1H-indole, 1 (55.18 g, yield 89%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.48 (d, 1H), 7.25 (d, 1H), 7.45 (m, 2H), 7.57 (m, 9H), 7.78 (s, 1H), 7.89 ( d, 1 H), 7.93 (m, 2 H)

[Preparation Example 4] Synthesis of CPB-2

<Step 1> Synthesis of CPB-2

Except that CNB-2 (10.26 g, 0.028 mol) obtained in Step 4 of Preparation Example 1 was used instead of 5- (5-bromo-2-nitrophenyl) 3], CPB-2 (9.81 g, yield 79%) was obtained.

^{1 H NMR: δ 6.48 (d} , 1H), 7.25 (d, 1H), 7.45 (m, 2H), 7.57 (m, 9H), 7.78 (s, 1H), 7.89 (d, 1H), 7.93 (m , 2H)

[Preparation Example 5] Synthesis of CPBO-2

<Step 1> Synthesis of CPBO-2

Except that CPB-2 (55.98 g, 0.128 mol) obtained in Step 1 of Preparation Example 4 was used instead of 5-bromo-1H-indole in Step 1 of Preparation Example 1, 2 (58.90 g, yield 95%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.48 (d, 1H), 7.25 (d, 1H), 7.45 (m, 2H), 7.57 (m, 9H), 7.78 (s, 1H), 7.89 ( d, 1 H), 7.93 (m, 2 H)

[Preparation Example 6] Synthesis of PCI-1 and PCI-2

<Step 1> Synthesis of 7- (2-nitrophenyl) -3,10-diphenyl-3,10-dihydropyrrolo [3,2-a]

Was obtained in the same manner as in Step 1 of Preparation Example 3 instead of 2,4-dibromo-1-nitrobenzene and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- 2-nitrophenyl) -3,10-diphenyl-2-nitrobenzene was obtained in the same manner as in [Step 2] of Preparation Example 1 except that CPBO-1 (58.0 g, 119.73 mmol) and 1-bromo- 3,10-dihydropyrrolo [3,2-a] carbazole (41.34 g, yield 72%).

¹ H NMR:? 6.54 (d, 1 H), 7.45 (m, 9H), 7.68 (m, 6H)

<Step 2> Synthesis of PCI-1 and PCI-2

(2-nitrophenyl) -3,10-diphenyl-3,10-dihydropyrrolo [3 (5-bromophenyl) , PCI-1 (19.52 g, yield 51%) and PCI-2 (41.0 g, 85.56 mmol) were obtained in the same manner as in Step 4 of Synthesis Example 1, 6.50 g, yield: 17%).

¹ H-NMR of PCI-1: δ 6.54 (d , 1H), 7.30 (t, 1H), 7.58 (m, 13H), 7.96 (m, 4H), 8.15 (d, 1H), 10.01 (s, 1H )

¹ H-NMR:? 6.54 (d, 1H), 7.28 (t, 1H), 7.56 (m, 13H), 7.93 )

[Preparation Example 7] Synthesis of PCI-3, PCI-4

<Step 1> Synthesis of 6- (2-nitrophenyl) -1,9-diphenyl-1,9-dihydropyrrolo [2,3-b] carbazole

Was obtained in the same manner as in Step 1 of Preparation Example 5 instead of 2,4-dibromo-1-nitrobenzene and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-nitrophenyl) -1,9-dihydroxybenzoate was obtained in the same manner as in [Step 2] of Preparation Example 1 except that CPBO-2 (58.0 g, 119.73 mmol) and 1-bromo- diphenyl-1,9-dihydropyrrolo [2,3-b] carbazole (41.34 g, yield 72%).

^{1 H NMR: δ 6.54 (d} , 1H), 7.45 (m, 5H), 7.56 (m, 5H), 7.69 (m, 5H), 7.90 (m, 2H), 8.05 (m, 2H)

<Step 2> Synthesis of PCI-3 and PCI-4

(2-nitrophenyl) -1,9-diphenyl-1,9-dihydropyrrolo [2 (2-nitrophenyl) -1H-indole was used in place of 5- (5-bromo- 3 (19.52 g, yield 51%) and PCI-4 (51.5%) were obtained in the same manner as in <Step 4> of Synthesis Example 1, 6.50 g, yield: 17%).

¹ H-NMR:? 6.54 (d, 1H), 7.35 (t, 1H), 7.60 (m, 13H), 8.05 )

¹ H-NMR:? 6.54 (d, 1H), 7.32 (t, 1H), 7.56 (m, 13H), 7.95 )

 [Preparation Example 8] Synthesis of PCI-5, PCI-6

Synthesis of 3- (6-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole

9-phenyl-9H-carbazol-3-ylboronic acid, 18.6 g (18.06 mmol) of 20.0 g (63.06 mmol) of 5-bromo-6-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 62) of the target compound, 3- (6-nitro-1-phenyl-1H-indol- %).

^{1 H NMR: δ 6.54 (d} , 1H), 7.30 (t, 1H), 7.50 (m, 13H), 7.80 (s, 1H), 8.80 (m, 2H), 8.15 (m, 2H), 9.10 (s , 1H)

<Step 2> Synthesis of PCI-5, PCI-6

9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine and 120 ml of distilled water were added to a solution of 12.0 g (25.02 mmol) of 3- (6-nitro- DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.91 g (yield: 35%) of PCI-5 and 3.81 g (yield: 32%) of PCI-6 were obtained using column chromatography.

A ^{PCI-5 1 H-NMR:} δ 6.54 (d, 1H), 7.35 (t, 1H), 7.60 (m, 13H), 8.05 (m, 4H), 8.15 (d, 1H), 10.01 (s, 1H )

¹ H-NMR:? 6.54 (d, 1H), 7.32 (t, 1H), 7.56 (m, 13H), 7.95 )

[Preparation Example 9] Synthesis of PCI-7, PCI-8

Synthesis of 2- (6-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole

Phenyl-9H-carbazol-2-ylboronic acid, 18.6 g (18.06 mmol) of 5-bromo-6-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 62) of the target compound, 2- (6-nitro- 1-phenyl-1H-indol-5-yl) -9- %).

^{1 H NMR: δ 6.54 (d} , 1H), 7.30 (m, 2H), 7.52 (m, 12H), 7.82 (d, 1H), 8.02 (d, 1H), 8.03 (s, 1H), 8.20 (d , &Lt; / RTI &gt; 1H), 8.55 (d, 1H), 9.16

<Step 2> Synthesis of PCI-7, PCI-8

9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine and 120 ml of a solution of 12.0 g (25.02 mmol) of 2- DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.91 g (yield: 35%) of PCI-7 and 3.81 g (yield: 32%) of PCI-8 were obtained using column chromatography.

A ^{PCI-7 1 H-NMR:} δ 6.54 (d, 1H), 7.58 (m, 16H), 7.94 (d, 1H), 8.14 (d, 1H), 8.54 (d, 1H), 10.01 (s, 1H )

A ^{PCI-8 1 H-NMR:} δ 6.54 (d, 1H), 7.55 (m, 17H), 7.90 (d, 1H), 8.60 (d, 1H), 10.01 (s, 1H)

[Preparation Example 10] Synthesis of PCI-9, PCI-10

Synthesis of 3- (5-nitro-1-phenyl-1H-indol-6-yl) -9-phenyl-9H-carbazole

9-phenyl-9H-carbazol-3-ylboronic acid, 18.6 g (18.06 mmol) of 20.0 g (63.06 mmol) of 6-bromo-5-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 62) of the target compound, 3- (5-nitro-1-phenyl-1H-indol- %).

^{1 H NMR: δ 6.50 (d} , 1H), 7.32 (m, 2H), 7.50 (m, 12H), 7.90 (d, 1H), 8.02 (d, 1H), 8.03 (s, 1H), 8.20 (d , &Lt; / RTI &gt; 1H), 8.54 (d, 1H), 9.10

<Step 2> Synthesis of PCI-9, PCI-10

9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine and 120 ml of distilled water were added to a solution of 12.0 g (25.02 mmol) of 3- (5-nitro- DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.91 g (yield: 35%) of PCI-9 and 3.81 g (yield: 32%) of PCI-10 were obtained using column chromatography.

A ^{PCI-9 1 H-NMR:} δ 6.52 (d, 1H), 7.50 (m, 16H), 7.98 (d, 1H), 8.14 (d, 1H), 8.50 (d, 1H), 10.01 (s, 1H )

Of ^{PCI-10 1 H-NMR:} δ 6.52 (d, 1H), 7.52 (m, 17H), 7.90 (d, 1H), 8.60 (d, 1H), 10.00 (s, 1H)

[Preparation Example 11] Synthesis of PCI-11, PCI-12

Synthesis of 2- (5-nitro-1-phenyl-1H-indol-6-yl) -9-phenyl-9H-carbazole

Phenyl-9H-carbazol-2-ylboronic acid, 18.6 g (18.06 mmol) of 20.0 g (63.06 mmol) of 6-bromo-5-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 62%) of the target compound, 2- (5-nitro-1-phenyl-1H-indol- %).

^{1 H NMR: δ 6.50 (d} , 1H), 7.30 (m, 2H), 7.50 (m, 12H), 7.94 (d, 1H), 8.12 (d, 1H), 8.03 (s, 1H), 8.21 (d , &Lt; / RTI &gt; 1H), 8.50 (d, 1H), 9.10

<Step 2> Synthesis of PCI-11 and PCI-12

9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine and 120 ml of a solution of 12.0 g (25.02 mmol) of 2- DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.91 g (yield: 35%) of PCI-11 and 3.81 g (yield: 32%) of PCI-12 were obtained using column chromatography.

¹ H-NMR:? 6.52 (d, 1H), 7.58 (m, 17H), 7.90

Of ^{PCI-12 1 H-NMR:} δ 6.52 (d, 1H), 7.52 (m, 16H), 7.90 (d, 1H), 8.60 (d, 1H), 10.02 (s, 1H)

[Preparation Example 12] Synthesis of PCI-13, PCI-14

Synthesis of 3- (4-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole

9-phenyl-9H-carbazol-3-ylboronic acid, 186.1 g (63.0 mmol) of 5-bromo-4-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 62) of 3- (4-nitro-1-phenyl-1H-indol- %).

^{1 H NMR: δ 6.52 (d} , 1H), 7.42 (m, 2H), 7.58 (m, 12H), 7.94 (d, 1H), 8.20 (d, 1H), 8.03 (s, 1H), 8.30 (d , &Lt; / RTI &gt; 1H), 8.50 (d, 1H), 9.10

<Step 2> Synthesis of PCI-13 and PCI-14

9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine and 120 ml of distilled water were added to a solution of 12.0 g (25.02 mmol) of 3- (4-nitro- DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.91 g (yield: 35%) of PCI-13 and 3.81 g (yield: 32%) of PCI-14 were obtained using column chromatography.

¹ H-NMR of the PCI-13: δ 6.54 (d , 1H), 7.60 (m, 17H), 7.68 (d, 1H), 8.50 (d, 1H), 10.02 (s, 1H)

¹ H-NMR of the PCI-14: δ 6.52 (d , 1H), 7.52 (m, 16H), 7.90 (d, 1H), 8.60 (d, 1H), 10.02 (s, 1H)

[Preparation Example 13] Synthesis of PCI-15 and PCI-16

Synthesis of 2- (4-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole

9-phenyl-9H-carbazol-2-ylboronic acid, 18.6 g (18.06 mmol) of 20.0 g (63.06 mmol) of 5-bromo-4-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 62) of the target compound, 2- (4-nitro-1-phenyl-1H-indol- %).

^{1 H NMR: δ 6.54 (d} , 1H), 7.40 (m, 2H), 7.65 (m, 12H), 7.60 (d, 1H), 8.28 (d, 1H), 8.03 (s, 1H), 8.36 (d , &Lt; / RTI &gt; 1H), 8.50 (d, 1H), 9.10

<Step 2> Synthesis of PCI-15 and PCI-16

9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine and 120 ml of a solution of 12.0 g (25.02 mmol) of 2- DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.91 g (yield: 35%) of PCI-15 and 3.81 g (yield: 32%) of PCI-16 were obtained using column chromatography.

Of ^{PCI-15 1 H-NMR:} δ 6.54 (d, 1H), 7.60 (m, 17H), 7.68 (d, 1H), 8.50 (d, 1H), 10.02 (s, 1H)

¹ H-NMR of the PCI-16: δ 6.52 (d , 1H), 7.52 (m, 16H), 7.90 (d, 1H), 8.60 (d, 1H), 10.02 (s, 1H)

[Preparation Example 14] Synthesis of PCB-1 and PCB-2

Synthesis of 5- (dibenzo [b, d] thiophen-2-yl) -6-nitro-1-phenyl-1H-indole

Dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18 mmol) of 20.0 g (63.06 mmol) of 5-bromo-6-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of 5- (dibenzo [b, d] thiophen-2-yl) -6-nitro- %).

^{1 H NMR: δ 6.52 (d} , 1H), 7.50 (m, 8H), 7.86 (d, 1H), 8.00 (m, 4H), 8.45 (d, 1H), 9.15 (s, 1H)

<Step 2> Synthesis of PCB-1 and PCB-2

(Dibenzo [b, d] thiophen-2-yl) -6-nitro-1-phenyl-1H-indole and 22.45 g (85.61 mmol) of triphenylphosphine in 120 ml DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.88 g (yield: 35%) of PCB-1 and 3.54 g (yield: 32%) of PCB-2 were obtained using column chromatography.

A ^{PCB-1 1 H-NMR:} δ 6.52 (d, 1H), 7.50 (m, 10H), 7.80 (d, 1H), 8.00 (d, 1H), 8.10 (d, 1H), 8.50 (d, 1H ), 10.10 (s, 1 H)

A ^{PCB-2 1 H-NMR:} δ 6.52 (d, 1H), 7.55 (m, 10H), 7.78 (s, 1H), 7.86 (s, 1H), 8.10 (d, 1H), 8.50 (d, 1H ), 10.10 (s, 1 H)

[Preparation Example 15] Synthesis of PCB-3 and PCB-4

Synthesis of 5- (dibenzo [b, d] thiophen-3-yl) -6-nitro-1-phenyl-1H-indole

Dibenzo [b, d] thiophen-3-ylboronic acid, 7.56 g (189.18 mmol) of 20.0 g (63.06 mmol) of 5-bromo-6-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of 5- (dibenzo [b, d] thiophen-3-yl) -6-nitro- %).

^{1 H NMR: δ 6.52 (d} , 1H), 7.54 (m, 8H), 7.90 (d, 1H), 8.12 (m, 4H), 8.50 (d, 1H), 9.15 (s, 1H)

<Step 2> Synthesis of PCB-3 and PCB-4

(Dibenzo [b, d] thiophen-3-yl) -6-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine and 120 ml DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.88 g (yield: 35%) of PCB-3 and 3.54 g (yield: 32%) of PCB-4 were obtained by column chromatography.

A ^{PCB-3 1 H-NMR:} δ 6.52 (d, 1H), 7.60 (m, 10H), 7.75 (d, 1H), 8.15 (d, 1H), 8.15 (d, 1H), 8.55 (d, 1H ), 10.10 (s, 1 H)

A ^{PCB-4 1 H-NMR:} δ 6.52 (d, 1H), 7.50 (m, 10H), 7.78 (s, 1H), 7.86 (s, 1H), 8.10 (d, 1H), 8.50 (d, 1H ), 10.10 (s, 1 H)

[Preparation Example 16] Synthesis of PCB-5 and PCB-6

Synthesis of 6- (dibenzo [b, d] thiophen-2-yl) -5-nitro-1-phenyl-1H-indole

Dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18 mmol) of 20.0 g (63.06 mmol) of 6-bromo-5-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of 6- (dibenzo [b, d] thiophen-2-yl) -5-nitro- %).

^{1 H NMR: δ 6.52 (d} , 1H), 7.54 (m, 8H), 7.88 (m, 2H), 8.00 (m, 3H), 8.45 (d, 1H), 9.80 (s, 1H)

<Step 2> Synthesis of PCB-5 and PCB-6

(Dibenzo [b, d] thiophen-2-yl) -5-nitro-1-phenyl-1H- indole and 22.45 g (85.61 mmol) of triphenylphosphine were added to a solution of 12.0 g (28.53 mmol) DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.88 g (yield: 35%) of PCB-5 and 3.54 g (yield: 32%) of PCB-6 were obtained by column chromatography.

A ^{PCB-5 1 H-NMR:} δ 6.52 (d, 1H), 7.70 (m, 10H), 7.80 (d, 1H), 8.00 (d, 1H), 8.08 (d, 1H), 8.45 (d, 1H ), 10.10 (s, 1 H)

A ^{PCB-6 1 H-NMR:} δ 6.50 (d, 1H), 7.50 (m, 10H), 7.78 (s, 1H), 7.88 (s, 1H), 8.15 (d, 1H), 8.50 (d, 1H ), 10.10 (s, 1 H)

[Preparation Example 17] Synthesis of PCB-7 and PCB-8

Synthesis of 6- (dibenzo [b, d] thiophen-3-yl) -5-nitro-1-phenyl-1H-indole

Dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18 mmol) of 20.0 g (63.06 mmol) of 6-bromo-5-nitro- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of the desired compound, 6- (dibenzo [b, d] thiophen-3-yl) -5-nitro- %).

^{1 H NMR: δ 6.52 (d} , 1H), 7.50 (m, 8H), 7.90 (m, 2H), 8.12 (m, 3H), 8.50 (d, 1H), 9.84 (s, 1H)

<Step 2> Synthesis of PCB-7 and PCB-8

(Dibenzo [b, d] thiophen-3-yl) -5-nitro-1-phenyl-1H-indole and 22.45 g (85.61 mmol) of triphenylphosphine were added to a solution of 12.0 g (28.53 mmol) DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.88 g (yield: 35%) of PCB-7 and 3.54 g (yield: 32%) of PCB-8 were obtained using column chromatography.

A ^{PCB-7 1 H-NMR:} δ 6.52 (d, 1H), 7.80 (m, 10H), 8.30 (d, 1H), 8.40 (d, 1H), 8.80 (d, 1H), 8.90 (d, 1H ), 10.10 (s, 1 H)

A ^{PCB-8 1 H-NMR:} δ 6.52 (d, 1H), 7.52 (m, 10H), 7.82 (s, 1H), 7.90 (s, 1H), 8.45 (d, 1H), 8.50 (d, 1H ), 10.10 (s, 1 H)

[Preparation Example 18] Synthesis of PCB-9 and PCB-10

<Step 1> Synthesis of 5- (dibenzo [b, d] thiophen-2-yl) -4-nitro-1-phenyl-

Dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18 mmol) of 20.0 g (63.06 mmol) of 5-bromo- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of the objective compound, 5- (dibenzo [b, d] thiophen-2-yl) -4-nitro- %).

^{1 H NMR: δ 6.52 (d} , 1H), 7.54 (m, 8H), 7.86 (d, 1H), 8.00 (m, 3H), 8.44 (m, 3H)

<Step 2> Synthesis of PCB-9 and PCB-10

(Dibenzo [b, d] thiophen-2-yl) -4-nitro-1-phenyl-1H-indole and 22.45 g (85.61 mmol) of triphenylphosphine in 120 ml DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.88 g (yield: 35%) of PCB-9 and 3.54 g (yield: 32%) of PCB-10 were obtained using column chromatography.

A ^{PCB-9 1 H-NMR:} δ 6.52 (d, 1H), 7.58 (m, 8H), 7.80 (d, 1H), 8.00 (m, 3H), 8.08 (d, 1H), 8.50 (d, 1H ), 10.10 (s, 1 H)

A ^{PCB-10 1 H-NMR:} δ 6.52 (d, 1H), 7.50 (m, 8H), 7.80 (s, 1H), 7.86 (s, 1H), 8.00 (m, 3H), 8.55 (d, 1H ), 10.10 (s, 1 H)

[Preparation Example 19] Synthesis of PCB-11 and PCB-12

<Step 1> Synthesis of 5- (dibenzo [b, d] thiophen-3-yl) -4-nitro-1-phenyl-

Dibenzo [b, d] thiophen-3-ylboronic acid, 7.56 g (189.18 mmol) of 20.0 g (63.06 mmol) of 5-bromo- mmol) of NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ 2.18 g (1.89 mmol) of Pd (PPh _{3) 4} into the mixture was stirred at 100 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of the target compound, 5- (dibenzo [b, d] thiophen-3-yl) -4-nitro- %).

^{1 H NMR: δ 6.52 (d} , 1H), 7.60 (m, 8H), 8.08 (m, 4H), 8.44 (m, 3H)

<Step 2> PCB -11, PCB Synthesis of -12

(Dibenzo [b, d] thiophen-3-yl) -4-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine and 120 ml DCB was added and stirred. Stir at 180 &lt; 0 &gt; C for 14 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3.88 g (yield: 35%) of PCB-11 and 3.54 g (yield: 32%) of PCB-12 were obtained by column chromatography.

A ^{PCB-11 1 H-NMR:} δ 6.52 (d, 1H), 7.58 (m, 8H), 7.78 (s, 1H), 7.88 (s, 1H), 7.96 (m, 3H), 8.50 (d, 1H ), 10.10 (s, 1 H)

A ^{PCB-12 1 H-NMR:} δ 6.52 (d, 1H), 7.58 (m, 9H), 8.05 (m, 4H), 8.50 (d, 1H), 10.10 (s, 1H)

[ Synthetic example  1] 1 Synthesis of 1

(3.0 g, 6.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.15 g, 8.04 mmol), NaH g, 8.04 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 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 the desired compound 1 (3.2 g, yield 71%).

GC-Mass (theory: 678.78 g / mol, measured: 678 g / mol)

[Synthesis Example 2] Synthesis of 2

(3.0 g, 6.7 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.12 g, 8.04 mmol ), Cu powder (0.21 g, 3.35 mmol), K ₂ CO ₃ (0.92 g, 6.7 mmol), Na ₂ SO ₄ (1.9 g, 13.4 mmol) and nitrobenzene (80 ml) Lt; / RTI &gt;

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound 2 (2.8 g, yield 56%).

GC-Mass (calculated: 754.88 g / mol, measured: 754 g / mol)

[Synthesis Example 3] Synthesis of 3

Except that 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.0 g, 6.7 mmol) was used instead of 2- (3-bromophenyl) -4,6- diphenyl- The procedure of Synthesis Example 2 was repeated to obtain the target compound 3 (2.9 g, yield 57%).

GC-Mass (calculated: 753.89 g / mol, measured: 753 g / mol)

[Synthesis Example 4] Synthesis of 4

Except that 2- (3-bromophenyl) pyridine (3.0 g, 6.7 mmol) was used in place of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- The target compound 4 (2.2 g, yield 55%) was obtained by carrying out the same procedure.

GC-Mass (theory: 600.71 g / mol, measurement: 600 g / mol)

[ Synthetic example  5] 5 Synthesis of 5

(3.0 g, 6.7 mmol) and 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine 1.93 g, 8.04 mmol), Pd (OAc) 2 (0.07 g, 0.33 mmol), NaO (t-bu) (1.28 g, 13.4 mmol), P (t-bu) 3 (0.13 g, 0.67 mmol) and Toluene (100 ml) were mixed, followed by stirring at 110 DEG C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain the desired compound 5 (1.9 g, yield 44% ).

GC-Mass (calculated: 651.76 g / mol, measured: 651 g / mol)

[Synthesis Example 6] Synthesis of 6

(Biphenyl-4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluorene- 6 (3.7 g, yield 61%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that 2-amine (3.0 g, 6.7 mmol) was used.

GC-Mass (calculated: 757.96 g / mol, measured: 757 g / mol)

[Synthesis Example 7] Synthesis of 7

(2.7 g, yield 60%) was obtained in the same manner as in Synthesis Example 1, except that PCI-2 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 678.78 g / mol, measured: 678 g / mol)

[Synthesis Example 8] Synthesis of 8

(2.6 g, yield 52%) was obtained in the same manner as in Synthesis Example 2, except that PCI-2 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 754.88 g / mol, measured: 754 g / mol)

[Synthesis Example 9] Synthesis of 9

(2.8 g, yield 55%) was obtained in the same manner as in Synthesis Example 3, except that PCI-2 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 753.89 g / mol, measured: 753 g / mol)

[ Synthetic example  10] Synthesis of 10

10 (2.3 g, yield: 57%) was obtained by carrying out the same procedure as in Synthesis Example 4, except that PCI-2 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 600.71 g / mol, measurement: 600 g / mol)

[Synthesis Example 11] Synthesis of 11

(3.0 g, yield 65%) was obtained in the same manner as in Synthesis Example 1, except that PCI-4 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 678.78 g / mol, measured: 678 g / mol)

[Synthesis Example 12] Synthesis of 12

12 (3.3 g, yield 66%) was obtained in the same manner as in Synthesis Example 2, except that PCI-4 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 754.88 g / mol, measured: 754 g / mol)

[Synthesis Example 13] Synthesis of 13

(3.1 g, yield 62%) was obtained in the same manner as in Synthesis Example 3, except that PCI-4 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 753.89 g / mol, measured: 753 g / mol)

[Synthesis Example 14] Synthesis of 14

(2.4 g, yield 60%) was obtained in the same manner as in Synthesis Example 4, except that PCI-4 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 600.71 g / mol, measurement: 600 g / mol)

[Synthesis Example 15] Synthesis of 15

(2.9 g, yield 63%) was obtained in the same manner as in Synthesis Example 1, except that PCI-13 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 678.78 g / mol, measured: 678 g / mol)

[Synthesis Example 16] Synthesis of 16

(3.0 g, yield 60%) was obtained in the same manner as in Synthesis Example 2, except that PCI-13 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 754.88 g / mol, measured: 754 g / mol)

[Synthesis Example 17] Synthesis of 17

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine using PCI-13 (3.0 g, 6.7 mmol) The target compound 17 (3.2 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that 6-diphenylpyridine (3.1 g, 8.04 mmol) was used.

GC-Mass (calculated: 752.9 g / mol, measured: 752 g / mol)

[Synthesis Example 18] Synthesis of 18

PCI-13 (3.0 g, 6.7 mmol) was used in place of PCI-1 and 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5 (3.1 g, yield: 54%) was obtained by carrying out the same procedure as in Synthesis Example 5, except that -triazine (3.37 g, 8.04 mmol) was used.

GC-Mass (calculated: 830.97 g / mol, measured: 830 g / mol)

[Synthesis Example 19] Synthesis of 19

Except that PCI-13 (3.0 g, 6.7 mmol) was used in place of PCI-1 and 2- (3-chlorophenyl) -4-phenylquinazoline (2.55 g, 8.04 mmol) was used in place of 2-chloro-4-phenylquinazoline , The same procedure as in Synthesis Example 5 was carried out to obtain 19 (2.7 g, yield 55%) of the target compound.

GC-Mass (calculated: 727.85 g / mol, measured: 727 g / mol)

[Synthesis Example 20] Synthesis of 20

Except that PCI-13 (3.0 g, 6.7 mmol) was used instead of PCI-1 and N- (biphenyl-4-yl) - 20 (3.5 g, yield 62%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that N- (4-bromophenyl) biphenyl-4-amine (3.8 g, 8.04 mmol) .

GC-Mass (calculated: 843.02 g / mol, measured: 843 g / mol)

[Synthesis Example 21] Synthesis of 21

(3.1 g, yield 68%) was obtained in the same manner as in Synthesis Example 1, except that PCI-14 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 678.78 g / mol, measured: 678 g / mol)

[Synthesis Example 22] Synthesis of 22

(3.2 g, yield 64%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that PCI-14 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 754.88 g / mol, measured: 754 g / mol)

[Synthesis Example 23] Synthesis of 23

(3.0 g, yield 59%) was obtained in the same manner as in Synthesis Example 3, except that PCI-14 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 753.89 g / mol, measured: 753 g / mol)

[Synthesis Example 24] Synthesis of 24

24 (2.5 g, yield 62%) was obtained by carrying out the same procedure as in Synthesis Example 4, except that PCI-14 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 600.71 g / mol, measurement: 600 g / mol)

[Synthesis Example 25] Synthesis of 25

25 (2.9 g, yield 63%) was obtained in the same manner as in Synthesis Example 1, except that PCI-15 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 678.78 g / mol, measured: 678 g / mol)

[ Synthetic example  26] Synthesis of 26

(2.9 g, yield 58%) was obtained in the same manner as in Synthesis Example 2, except that PCI-15 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 754.88 g / mol, measured: 754 g / mol)

[Synthesis Example 27] Synthesis of 27

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, using PCI-15 (3.0 g, 6.7 mmol) The target compound 27 (3.0 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that 6-diphenylpyridine (3.1 g, 8.04 mmol) was used.

GC-Mass (calculated: 752.9 g / mol, measured: 752 g / mol)

[Synthesis Example 28] Synthesis of 28

Instead of PCI-1, PCI-15 (3.0 g, 6.7 mmol) was used and 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5 -triazine (3.37 g, 8.04 mmol), the target compound 28 (3.3 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 5.

GC-Mass (calculated: 830.97 g / mol, measured: 830 g / mol)

[Synthesis Example 29] Synthesis of 29

(3.1 g, yield 68%) was obtained in the same manner as in Synthesis Example 1, except that PCI-16 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 678.78 g / mol, measured: 678 g / mol)

[Synthesis Example 30] Synthesis of 30

(3.3 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that PCI-16 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 754.88 g / mol, measured: 754 g / mol)

[Synthesis Example 31] Synthesis of 31

31 (3.1 g, yield 62%) was obtained in the same manner as in Synthesis Example 3, except that PCI-16 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 753.89 g / mol, measured: 753 g / mol)

[Synthesis Example 32] Synthesis of 32

32 (2.4 g, yield 60%) was obtained in the same manner as in Synthesis Example 4, except that PCI-16 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (theory: 600.71 g / mol, measurement: 600 g / mol)

[ Synthetic example  33] Synthesis of 33

33 (2.9 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that PCB-9 (3.0 g, 7.72 mmol) was used instead of PCI-1.

GC-Mass (theory: 619.74 g / mol, measured: 619 g / mol)

[Synthesis Example 34] Synthesis of 34

(3.3 g, yield 59%) was obtained in the same manner as in Synthesis Example 2, except that PCB-9 (3.0 g, 7.72 mmol) was used instead of PCI-1.

GC-Mass (calculated: 695.83 g / mol, measured: 695 g / mol)

[Synthesis Example 35] Synthesis of 35

Instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, PCB-9 (3.0 g, 7.72 mmol) (2.5 g, yield 59%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that 6-diphenylpyridine (3.58 g, 9.26 mmol) was used.

GC-Mass (calculated: 693.86 g / mol, measured: 693 g / mol)

[Synthesis Example 36] Synthesis of 36

PCB-9 (3.0 g, 7.72 mmol) was used instead of PCI-1, and 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5 -triazine (3.9 g, 9.26 mmol), the objective compound 36 (3.5 g, yield 58%) was obtained by carrying out the same procedure as in Synthesis Example 5.

GC-Mass (calculated: 771.93 g / mol, measured: 771 g / mol)

[Synthesis Example 37] Synthesis of 37

Except that PCB-9 (3.0 g, 7.72 mmol) was used in place of PCI-1 and 2- (3-chlorophenyl) -4-phenylquinazoline (2.9 g, 9.26 mmol) was used in place of 2-chloro-4-phenylquinazoline , The same procedure as in Synthesis Example 5 was carried out to obtain the desired compound 37 (2.4 g, yield 46%).

GC-Mass (calculated: 668.81 g / mol, measured: 668 g / mol)

[Synthesis Example 38] Synthesis of 38

Except that PCB-9 (3.0 g, 7.72 mmol) was used instead of PCI-1 and N- (biphenyl-4-yl) - The same procedure as in Synthesis Example 2 was carried out except that N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (4.7 g, 9.26 mmol) (3.7 g, yield 58%).

GC-Mass (calculated: 824.04 g / mol, measured: 824 g / mol)

[ Synthetic example  39] Synthesis of 39

(2.8 g, yield 59%) was obtained in the same manner as in Synthesis Example 1, except that PCB-10 (3.0 g, 7.72 mmol) was used instead of PCB-9.

GC-Mass (theory: 619.74 g / mol, measured: 619 g / mol)

[Synthesis Example 40] Synthesis of 40

(3.3 g, yield 65%) was obtained in the same manner as in Synthesis Example 2, except that PCB-10 (3.0 g, 7.72 mmol) was used instead of PCB-9.

GC-Mass (calculated: 695.83 g / mol, measured: 695 g / mol)

[Synthesis Example 41] Synthesis of 41

(3.0 g, yield 55%) was obtained in the same manner as in Synthesis Example 3, except that PCB-10 (3.0 g, 7.72 mmol) was used instead of PCB-9.

GC-Mass (calculated: 693.86 g / mol, measured: 693 g / mol)

[Synthesis Example 42] Synthesis of 42

(2.2 g, yield 62%) was obtained in the same manner as in Synthesis Example 4, except that PCB-10 (3.0 g, 7.72 mmol) was used instead of PCB-9.

GC-Mass (calculated: 541.66 g / mol, measured: 541 g / mol)

[Synthesis Example 43] Synthesis of 43

2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, , 8.04 mmol), the objective compound 43 (3.2 g, yield 57%) was obtained by carrying out the same procedure as in Synthesis Example 2.

GC-Mass (calculated: 830.97 g / mol, measured: 830 g / mol)

[Synthesis Example 44] Synthesis of 44

44 (3.5 g, yield 62%) was obtained in the same manner as in Synthesis Example 43, except that PCB-13 (3.0 g, 6.7 mmol) was used instead of PCI-1.

GC-Mass (calculated: 830.97 g / mol, measured: 830 g / mol)

[Synthesis Example 45] Synthesis of 45

(3.4 g, yield: 57%) was obtained in the same manner as in Synthesis Example 43, except that PCB-9 (3.0 g, 7.72 mmol) was used instead of PCI-1.

GC-Mass (calculated: 771.93 g / mol, measured: 771 g / mol)

[Example 1] Production of green organic EL device

Compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was produced as follows.

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

M-MTDATA (60 nm) / TCTA (80 nm) / Compound 1 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in that order.

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

[Examples 2 to 45] Preparation of organic EL device

Organic EL devices were prepared in the same manner as in Example 1 except for using the compounds 2 to 45 synthesized in Synthesis Examples 2 to 45 instead of the compound 1 used as a host material in the formation of the light emitting layer in Example 1, .

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1 except that CBP was used instead of the compound 1 used as a host material in the formation of the light emitting layer in Example 1. The structure of CBP used is as follows.

[Experimental Example]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic EL devices prepared in Examples 1 to 45 and Comparative Example 1, respectively, and the results are shown in Table 1 below .

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 1 Compound 1 6.55 41.5 Example 2 Compound 2 6.45 41.9 Example 3 Compound 3 6.40 42.1 Example 4 Compound 4 6.50 41.7 Example 5 Compound 5 6.55 41.8 Example 6 Compound 6 6.50 41.3 Example 7 Compound 7 6.55 41.4 Example 8 Compound 8 6.49 41.9 Example 9 Compound 9 6.50 41.9 Example 10 Compound 10 6.50 41.8 Example 11 Compound 11 6.55 41.5 Example 12 Compound 12 6.50 42.1 Example 13 Compound 13 6.47 42.2 Example 14 Compound 14 6.50 42.0 Example 15 Compound 15 6.60 42.1 Example 16 Compound 16 6.55 41.9 Example 17 Compound 17 6.50 41.5 Example 18 Compound 18 6.50 42.0 Example 19 Compound 19 6.45 41.8 Example 20 Compound 20 6.50 41.8 Example 21 Compound 21 6.55 41.9 Example 22 Compound 22 6.55 42.2 Example 23 Compound 23 6.50 42.0 Example 24 Compound 24 6.55 41.8 Example 25 Compound 25 6.49 41.9 Example 26 Compound 26 6.62 41.5 Example 27 Compound 27 6.60 42.2 Example 28 Compound 28 6.55 41.5 Example 29 Compound 29 6.50 41.9 Example 30 Compound 30 6.45 41.5 Example 31 Compound 31 6.55 41.8 Example 32 Compound 32 6.50 42.1 Example 33 Compound 33 6.45 41.5 Example 34 Compound 34 6.50 41.8 Example 35 Compound 35 6.60 42.0 Example 36 Compound 36 6.50 41.5 Example 37 Compound 37 6.50 42.0 Example 38 Compound 38 6.55 41.5 Example 39 Compound 39 6.45 41.9 Example 40 Compound 40 6.50 42.3 Example 41 Compound 41 6.55 41.4 Example 42 Compound 42 6.55 42.0 Example 43 Compound 43 6.59 41.7 Example 44 Compound 44 6.55 41.8 Example 45 Compound 45 6.50 41.5 Comparative Example 1 CBP 6.93 38.2

As a result of the experiment, the green organic EL devices prepared in Examples 1 to 45 using the compounds represented by Chemical Formula 1 (Compound 1 to Compound 45) according to the present invention as the host material of the light emitting layer, It was confirmed that the organic EL device exhibited better current efficiency and better driving voltage than the green organic EL device.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

Claims (8)

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

In Formula 1,
At least one of R ₃ and R _4, R ₄ and R ₅ , and R ₅ and R ₆ is bonded to the following formula 2 to form a condensed ring;
(2)

In the formula (2), the dashed line represents the condensation site;
At least one of R ₇ and R _8, R ₈ and R ₉ , and R ₉ and R ₁₀ is bonded to the following Formula 3 to form a condensed ring;
(3)

In the formula (3), the dashed line represents the condensation site;
X ₁ is selected from O, S, Se, and N (Ar ₃ )
R ₁ to R _{14 which} are not condensed with each other are each independently hydrogen,
Ar ₁ to Ar ₃ are the same or different and are each independently selected from the group consisting of a C ₆ to C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms,
In the Ar ₁ to Ar ₃ , the C ₆ to C ₄₀ aryl group and the heteroaryl group having 5 to 40 nuclear atoms are each independently a C ₆ to C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms Lt; / RTI &gt; may be substituted with one or more substituents selected from the group consisting of The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (C-1) to (C-36)

In the above formulas, R ₁ to R ₁₄ , Ar ₁ , Ar ₂ and X ₁ are the same as defined in claim 1, respectively. The compound according to claim 1, wherein X ₁ is N (Ar ₃ )
Ar ₃ is selected from the group consisting of a C ₆ to C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms. delete delete The compound according to claim 1, wherein Ar ₁ to Ar ₃ are each independently selected from the group consisting of the following structures.

1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 3 or 6. The organic electroluminescent device according to claim 7, wherein at least one organic compound layer containing the compound is a light emitting layer.