WO2014104663A1 - Organic compound and organic electroluminescent element comprising same - Google Patents

Abstract

The present invention relates to: a compound having a novel structure wherein an indole moiety is fused to the terminal of a pyrrolocarbazole moiety so as to constitute a basic skeleton, and various substituents are bonded to the basic skeleton; and an organic electroluminescent element comprising the compound. In the present invention, the compound can be incorporated in one or more organic layer and preferably a luminescent layer such that properties such as the light-emitting efficiency, the drive voltage and the life of the element can be improved.

Description

Organic compound and organic electroluminescent device comprising the same

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 in which the luminous efficiency, driving voltage, lifetime, etc. of the device are improved.

Based on Bernanose's observation of organic thin-film luminescence in the 1950s, the study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang proposed an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, long life organic EL device, it has evolved to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.

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

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) _2, and the like. Green and red dopant materials are used, and CBP is a phosphorescent host material.

However, existing materials have advantages in terms of luminescence properties, but due to low glass transition temperature and very poor thermal stability, they are not satisfactory in terms of lifespan in OLED devices. Therefore, the development of the material which is more excellent in performance is desired.

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

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

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

Formula 1

In Chemical Formula 1,

At least one of R ₃ and R _4, R ₄ and R ₅ , and R ₅ and R ₆ may be combined with Formula 2 to form a condensed ring;

Formula 2

In the formula (2), the dotted line is a condensation site;

At least one of R ₇ and R _8, R ₈ and R ₉ , and R ₉ and R ₁₀ may be combined with Formula 3 to form a condensed ring;

Formula 3

In Chemical Formula 3, the dotted line represents a site where condensation takes place;

X ₁ is selected from O, S, Se, N (Ar ₃ ), 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 from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted A 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 nuclear atom having 5 to 40 Heteroaryl group, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted Or an unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C An alkyl boron group of ₁ to C ₄₀ , a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, A substituted or unsubstituted C ₆ -C ₄₀ arylphosphine oxide group and a substituted or unsubstituted C ₆ -C ₄₀ arylsilyl group, or they can combine with adjacent groups to form a condensed ring And

Ar ₁ to Ar ₇ are the same as or different from each other, and each independently 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 Alkynyl group of -C ₄₀ , substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group of 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ -C ₄₀ aryl jade Periodic, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted Heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to 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,

C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, a nuclear atom in R ₁ to R ₁₄ and Ar ₁ to Ar ₇ 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, C 3 -C 40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ alkylboron group, C ₆ -C ₄₀ aryl boron group, 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 ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ An alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 he Tercyclocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ It may be substituted with one or more selected from the group consisting of an arylphosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group. At this time, when a plurality of substituents are introduced, the plurality of substituents are the same or different from each other.

The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer includes the compound of Formula 1 Provided is an organic electroluminescent device characterized by.

Here, at least one of the one or more organic material 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, it is preferable that the light emitting layer. In this case, the compound represented by Chemical Formula 1 is a blue, green or red phosphorescent host material.

Since the compound represented by Formula 1 of the present invention is excellent in thermal stability and phosphorescence properties, it may be applied to the light emitting layer of the organic EL device.

Therefore, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to the conventional host material can be manufactured, and further, performance In addition, a full color display panel with a greatly improved lifespan can be manufactured.

Hereinafter, the present invention will be described in detail.

<New compound>

The novel compound according to the present invention is a structure in which an indole moiety is fused to a terminal of a pyrrolocarbazole moiety to form a basic skeleton, and a variety of substituents are bonded to the basic skeleton. It is characterized by being displayed.

The compound represented by Formula 1 has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], and has a wide energy band gap, The bonding force of the electrons can be increased. Therefore, when the compound of Formula 1 is used in an organic EL device, the driving voltage, efficiency (light emitting efficiency, power efficiency), lifetime, and luminance of the device may be improved.

In particular, the compound not only has a wide bandgap due to the indole moiety bound to the terminal of the pyrrolocarbazole moiety, but also the bipolar properties of the entire molecule due to various aromatic ring substituents. Since the bonding force between the holes and the electrons can be increased, superior characteristics as the host material of the light emitting layer can be exhibited compared to the conventional CBP. As a result, the phosphorescent property of the device may be improved, and the hole injection ability and / or the transport ability, the luminous efficiency, the driving voltage, and the lifetime characteristics may be improved. In addition, the energy level may be controlled by the substituents to have a wide bandgap (sky blue to red), and thus may be applied to not only the light emitting layer but also a hole transport layer, a hole injection layer, and the like.

On the other hand, the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced to the bound indole moiety, the glass transition temperature (Tg) can be improved, which is why compared to the conventional CBP It can have high thermal stability. In addition, by fusing an indole moiety bound to the terminal of the pyrrolocarbazole moiety, not only thermal stability of the compound may be improved, but also an organic layer including the compound of Formula 1 It is also effective in suppressing crystallization. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.

In addition, when the compound of Chemical Formula 1 according to the present invention is adopted as a hole injection / transport layer material of an organic EL device, a phosphorescent host material of blue, green and / or red color, the compound having the excellent efficiency and lifespan may be superior to the conventional CBP. Can be. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect on 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 may be combined with Formula 2 to form a pyrrolocarbazole skeleton condensed 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 combined with Formula 3 of an indole-based structure to form a condensed ring.

In more detail, the compound represented by Chemical Formula 1 of the present invention may be further embodied as a compound represented by any one of the following Chemical 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 ), preferably Is S or N (Ar ₃ ), more preferably N (Ar ₃ ).

In addition, a substituent which does not form a condensed ring with Formula 2 and / or Formula 3, for example, at least one of R ₃ and R _4, R ₄ and R ₅ , R ₅ and R ₆ ; And R ₁ to R ₁₄ except for at least one of R ₇ and R _8, R ₈ and R ₉ , R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or Unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ Aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted Or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, 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, substituted or non-substituted is selected from unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of aryl silyl substituted or unsubstituted C ₆ ~ C ₄₀ of, or These may combine with adjacent groups to form a condensed ring.

At this time, considering the characteristics of the organic EL device, R ₁ to R ₁₄ except for the substituents forming the condensed ring are the same or different from each other, each independently hydrogen, deuterium (D), substituted or unsubstituted C ₆ It is preferably selected from the group consisting of an aryl group of -C ₄₀ , and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms.

In Formula 1 according to the present invention, Ar ₁ to Ar ₇ are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group , Substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, Substituted or unsubstituted C _{6 Through} C ₄₀ An aryl boron group, Substituted or unsubstituted C _{6 Through} C ₄₀ An arylphosphine group, 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, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl of R ₁ to R ₁₄ and Ar ₁ to Ar ₇ One or more substituents each introduced into an alkyl group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group, and an arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ to 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 nuclear atom having 5 to 40 heteroaryl groups, a C ₆ to C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ 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 It may be substituted with one or more substituents selected from the group consisting of ₄₀ arylsilyl groups, wherein when a plurality of substituents are substituted, they are the same or different from each other.

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

Here, one or more substituents respectively introduced into the aryl group and heteroaryl group of Ar ₁ to Ar ₇ are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, 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 A group consisting of -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, and C ₆ -C ₄₀ arylsilyl group It may be substituted with one or more substituents selected from. In this case, when a plurality of substituents are introduced, these substituents may be the same or different from each other.

In the compound represented by Formula 1 according to the present invention, R ₁ to R ₁₄ and Ar ₁ to Ar ₇ are each more preferably selected from hydrogen or a substituent group consisting of the following substituents S1 to S204. However, it is not limited thereto.

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

The compounds of the present invention described above can be further embodied in the structures illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.

As used herein, "unsubstituted alkyl" is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which are 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 chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, examples of which include vinyl, allyl (allyl), isopropenyl, 2-butenyl, and the like, but are not limited thereto.

"Unsubstituted alkynyl" is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, examples being ethynyl , 2-propynyl, and the like, but is not limited thereto.

"Unsubstituted aryl" means a monovalent substituent derived from an aromatic hydrocarbon of 6 to 60 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached in a simple or condensed form with one another. 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. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. It is understood that two or more rings may be attached in a simple or condensed form with each other and further include a condensed form with an aryl group. Examples of heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and 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 an aryl having 5 to 60 carbon atoms. Examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

"Unsubstituted alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and has a linear, branched or cyclic structure It is to be interpreted as including. Examples of such alkyloxy may 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 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 carbon in the ring, preferably 1 to 3 carbons, is N, O or S Is substituted with a hetero atom such as Non-limiting examples thereof include morpholine, piperazine and the like.

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

"Condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.

Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

<Organic EL device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.

Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, and at least one of the at least one organic layer Compound represented by the formula (1), preferably a compound represented by the formula (C-1) to a compound represented by the formula (C-36). In this case, the compounds represented by any one of the formulas C-1 to C-36 may be used alone or two or more may be mixed.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, at least one of the organic material layer may include a compound represented by the formula (1). Preferably, the organic material layer including the compound of Compound 1 may be a light emitting layer.

According to an example of the present invention, the light emitting layer of the organic EL device may include a host material, wherein the host material may include the compound of Formula 1 as a host material. As such, when the compound of Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green or red phosphorescent host, the binding force between holes and electrons in the light emitting layer is increased, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.

The structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be. Specifically, the compound of the present invention can be used as a phosphorescent host of the light emitting layer. On the other hand, the 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 material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, a light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.

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 silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

In addition, examples of the anode 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : 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 multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, 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

5-bromo-1H-indole (25 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3) under nitrogen stream , 2-dioxaborolane) (48.58 g, 0.191 mol), Pd (dppf) Cl ₂ (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) were mixed and 130 ° C Stir at 12 h.

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

¹ H-NMR: δ 1.24 (s, 12H), 6.45 (d, 1H), 7.27 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.95 (s, 1H), 8.21 ( s, 1 H)

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

2,4-dibromo-1-nitrobenzene (21.18 g, 75.41 mmol) under nitrogen stream and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- obtained in <Step 1> above 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) were mixed and then Pd (PPh ₃ ) ₄ (4.36 g, 5 mol%) was added thereto and stirred at 80 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give 5- (5-bromo-2-nitrophenyl) -1H-indole (9.1 g, 38% yield). Got.

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 , 1H), 8.13 (s, 1H), 8.21 (s, 1H)

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

5- (5-bromo-2-nitrophenyl) -1H-indole (9 g, 28.38 mmol), iodobenzene (11.58 g, 56.76 mmol) obtained in <Step 2> under a nitrogen stream, Cu powder (0.18 g, 2.84 mmol ), K ₂ CO ₃ (3.92 g, 28.38 mmol), Na ₂ SO ₄ (4.03 g, 28.38 mmol), nitrobenzene (150 ml) were mixed and stirred at 210 ° C. for 12 hours.

After completion of the reaction, 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, and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole ( 8.03 g, yield 72%) was obtained.

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 , 1H), 8.11 (s, 1H)

Step 4 Synthesis of CNB-1 and CNB-2

5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole (8 g, 20.34 mmol), triphenylphosphine (13.34 g, 50.86 mmol) and 1,2- obtained in the above <Step 3> under a nitrogen stream dichlorobenzene (100 ml) was mixed and stirred for 12 h.

After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. To the obtained organic layer, water was removed with MgSO _4, and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give CNB-1 (3.89 g, yield 53%) and CNB-2 (1.30 g). , Yield 18%) was obtained.

¹ H-NMR of CNB-1: 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, 1H), 7.85 (d, 1H), 8.10 (s, 1H), 8.23 (s, 1H)

¹ H-NMR of CNB-2: 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, 1H), 7.87 (d, 1H), 8.10 (s, 1H), 8.23 (s, 1H)

Preparation Example 2 Synthesis of CPB-1

Step 1 Synthesis of CPB-1

<Step of Synthesis Example 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) -1H-indole. CPB-1 (9.81 g, yield 79%) was obtained in the same manner as 3>.

¹ H NMR: δ 6.48 (d, 1H), 7.42 (m, 6H), 7.51 (m, 4H), 7.60 (m, 5H), 8.15 (s, 1H)

Preparation Example 3 Synthesis of CPBO-1

Step 1 Synthesis of CPBO-1

CPBO- in the same manner as in <Step 1> of Preparation Example 1, 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%) was obtained.

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

<Step of Preparation Example 1, 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) -1H-indole. CPB-2 (9.81 g, yield 79%) was obtained in the same manner as 3>.

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

CPBO- in the same manner as in <Step 1> of Preparation Example 1, 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. 2 (58.90 g, yield 95%) was obtained.

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] carbazole

Obtained 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-yl) -1H-indole 7- (2-nitrophenyl) -3,10-diphenyl- 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-2-nitrobenzene were used. 3,10-dihydropyrrolo [3,2-a] carbazole (41.34 g, yield 72%) was obtained.

¹ H NMR: δ 6.54 (d, 1H), 7.45 (m, 9H), 7.68 (m, 6H), 7.96 (m, 4H), 8.18 (d, 1H)

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

In <Step 4> of Preparation Example 1, instead of 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole, 7- (2-nitrophenyl) -3,10-diphenyl-3,10-dihydropyrrolo [3 PCI-1 (19.52 g, Yield 51%) and PCI-2 (Synthesis) in the same manner as in <Step 4> of Synthesis Example 1, except that 2,2-a] carbazole (41.0 g, 85.56 mmol) was used. 6.50 g, yield 17%) was obtained.

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 of PCI-2: δ 6.54 (d, 1H), 7.28 (t, 1H), 7.56 (m, 13H), 7.93 (m, 4H), 8.15 (d, 1H), 10.01 (s, 1H )

Preparation Example 7 Synthesis of PCI-3 and PCI-4

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

Obtained 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-yl) -1H-indole 6- (2-nitrophenyl) -1,9- 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-2-nitrobenzene were used. Diphenyl-1,9-dihydropyrrolo [2,3-b] carbazole (41.34 g, yield 72%) was obtained.

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

In <Step 4> of Preparation Example 1, 6- (2-nitrophenyl) -1,9-diphenyl-1,9-dihydropyrrolo [2 instead of 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indole [2]. PCI-3 (19.52 g, 51% yield) and PCI-4 (19.52 g, 51% yield) in the same manner as in <Step 4> of Synthesis Example 1, except that, 3-b] carbazole (41.0 g, 85.56 mmol) was used. 6.50 g, yield 17%) was obtained.

¹ H-NMR of PCI-3: 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 of PCI-4: δ 6.54 (d, 1H), 7.32 (t, 1H), 7.56 (m, 13H), 7.95 (m, 4H), 8.15 (d, 1H), 10.01 (s, 1H )

 Preparation Example 8 Synthesis of PCI-5 and PCI-6

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

20.0 g (63.06 mmol) of 5-bromo-6-nitro-1-phenyl-1H-indole, 18.10 g (63.06 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 18.74 g (yield: 62) of the target compound 3- (6-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole was removed by removing the solvent of the filtered organic layer using column chromatography. %) Was obtained.

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 and PCI-6

120 ml of 12.0 g (25.02 mmol) 3- (6-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removal of the solvent of the filtered organic layer, column chromatography was used to obtain 3.91 g (yield: 35%) of PCI-5 and 3.81 g (yield: 32%) of PCI-6, respectively.

¹ H-NMR of PCI-5: 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 of PCI-6: δ 6.54 (d, 1H), 7.32 (t, 1H), 7.56 (m, 13H), 7.95 (m, 4H), 8.15 (d, 1H), 10.01 (s, 1H )

Preparation Example 9 Synthesis of PCI-7 and PCI-8

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

20.0 g (63.06 mmol) of 5-bromo-6-nitro-1-phenyl-1H-indole, 18.10 g (63.06 mmol) of 9-phenyl-9H-carbazol-2-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 18.74 g (yield: 62) of the target compound 2- (6-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole was removed by removing the solvent of the filtered organic layer using column chromatography. %) Was obtained.

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 , 1H), 8.55 (d, 1H), 9.16 (s, 1H)

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

120 ml of 12.0 g (25.02 mmol) of 2- (6-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain 3.91 g (yield: 35%) of PCI-7 and 3.81 g (yield: 32%) of PCI-8, respectively.

¹ H-NMR of PCI-7: 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 )

¹ H-NMR of PCI-8: 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 and PCI-10

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

20.0 g (63.06 mmol) of 6-bromo-5-nitro-1-phenyl-1H-indole, 18.10 g (63.06 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 18.74 g (yield: 62) of the target compound 3- (5-nitro-1-phenyl-1H-indol-6-yl) -9-phenyl-9H-carbazole was removed by removing the solvent of the filtered organic layer using column chromatography. %) Was obtained.

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 , 1H), 8.54 (d, 1H), 9.10 (s, 1H)

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

120 ml of 12.0 g (25.02 mmol) of 3- (5-nitro-1-phenyl-1H-indol-6-yl) -9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain 3.91 g (yield: 35%) of PCI-9 and 3.81 g (yield: 32%) of PCI-10, respectively.

¹ H-NMR of PCI-9: 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 )

¹ H-NMR of PCI-10: 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 and PCI-12

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

20.0 g (63.06 mmol) of 6-bromo-5-nitro-1-phenyl-1H-indole, 18.10 g (63.06 mmol) of 9-phenyl-9H-carbazol-2-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 18.74 g (yield: 62) of the target compound 2- (5-nitro-1-phenyl-1H-indol-6-yl) -9-phenyl-9H-carbazole was removed by removing the solvent of the filtered organic layer using column chromatography. %) Was obtained.

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 , 1H), 8.50 (d, 1H), 9.10 (s, 1H)

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

120 ml of 12.0 g (25.02 mmol) of 2- (5-nitro-1-phenyl-1H-indol-6-yl) -9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain 3.91 g (yield: 35%) of PCI-11 and 3.81 g (yield: 32%) of PCI-12, respectively.

¹ H-NMR of PCI-11: δ 6.52 (d, 1H), 7.58 (m, 17H), 7.90 (d, 1H), 8.55 (d, 1H), 10.02 (s, 1H)

¹ H-NMR of PCI-12: 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 and PCI-14

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

20.0 g (63.06 mmol) of 5-bromo-4-nitro-1-phenyl-1H-indole, 18.10 g (63.06 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 18.74 g (yield: 62) of the target compound 3- (4-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole was removed by removing the solvent of the filtered organic layer using column chromatography. %) Was obtained.

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 , 1H), 8.50 (d, 1H), 9.10 (s, 1H)

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

120 ml of 12.0 g (25.02 mmol) 3- (4-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 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 by using column chromatography.

¹ H-NMR of 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 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

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

20.0 g (63.06 mmol) of 5-bromo-4-nitro-1-phenyl-1H-indole, 18.10 g (63.06 mmol) of 9-phenyl-9H-carbazol-2-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 18.74 g (yield: 62) of the target compound 2- (4-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole was removed by removing the solvent of the filtered organic layer using column chromatography. %) Was obtained.

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 , 1H), 8.50 (d, 1H), 9.10 (s, 1H)

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

120 ml of 12.0 g (25.02 mmol) of 2- (4-nitro-1-phenyl-1H-indol-5-yl) -9-phenyl-9H-carbazole, 19.68 g (75.06 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using the column chromatography to obtain 3.91 g (yield: 35%) of PCI-15 and 3.81 g (yield: 32%) of PCI-16, respectively.

¹ H-NMR of PCI-15: 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 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

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

20.0 g (63.06 mmol) of 5-bromo-6-nitro-1-phenyl-1H-indole, 14.38 g (63.06 mmol) of dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of the target compound 5- (dibenzo [b, d] thiophen-2-yl) -6-nitro-1-phenyl-1H-indole using column chromatography %) Was obtained.

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

120 ml of 12.0 g (28.53 mmol) of 5- (dibenzo [b, d] thiophen-2-yl) -6-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using a column chromatography to obtain 3.88 g (yield: 35%) of PCB-1 and 3.54 g (yield: 32%) of PCB-2, respectively.

¹ H-NMR of PCB-1: 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, 1H)

¹ H-NMR of PCB-2: 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, 1H)

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

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

20.0 g (63.06 mmol) of 5-bromo-6-nitro-1-phenyl-1H-indole, 14.38 g (63.06 mmol) of dibenzo [b, d] thiophen-3-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 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) -6-nitro-1-phenyl-1H-indole using column chromatography %) Was obtained.

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, PCB-4

120 ml of 12.0 g (28.53 mmol) of 5- (dibenzo [b, d] thiophen-3-yl) -6-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography to obtain 3.88 g (yield: 35%) of the PCB-3 and 3.54 g (yield: 32%) of PCB-4, respectively.

¹ H-NMR of PCB-3: 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, 1H)

¹ H-NMR of PCB-4: 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, 1H)

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

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

20.0 g (63.06 mmol) of 6-bromo-5-nitro-1-phenyl-1H-indole, 14.38 g (63.06 mmol) of dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of the target compound 6- (dibenzo [b, d] thiophen-2-yl) -5-nitro-1-phenyl-1H-indole using column chromatography %) Was obtained.

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

120 ml of 12.0 g (28.53 mmol) of 6- (dibenzo [b, d] thiophen-2-yl) -5-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain 3.88 g (yield: 35%) of PCB-5 and 3.54 g (yield: 32%) of PCB-6, respectively.

¹ H-NMR of PCB-5: 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, 1H)

¹ H-NMR of PCB-6: 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, 1H)

Preparation 17 Synthesis of PCB-7 and PCB-8

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

20.0 g (63.06 mmol) of 6-bromo-5-nitro-1-phenyl-1H-indole, 14.38 g (63.06 mmol) of dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of the target compound 6- (dibenzo [b, d] thiophen-3-yl) -5-nitro-1-phenyl-1H-indole using column chromatography %) Was obtained.

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

120 ml of 12.0 g (28.53 mmol) of 6- (dibenzo [b, d] thiophen-3-yl) -5-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography to obtain 3.88 g (yield: 35%) of PCB-7 and 3.54 g (yield: 32%) of PCB-8, respectively.

¹ H-NMR of PCB-7: 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, 1H)

¹ H-NMR of PCB-8: 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, 1H)

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-1H-indole

20.0 g (63.06 mmol) of 5-bromo-4-nitro-1-phenyl-1H-indole, 14.38 g (63.06 mmol) of dibenzo [b, d] thiophen-2-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, 16.43 g (yield: 62) of the target compound 5- (dibenzo [b, d] thiophen-2-yl) -4-nitro-1-phenyl-1H-indole using column chromatography %) Was obtained.

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

120 ml of 12.0 g (28.53 mmol) of 5- (dibenzo [b, d] thiophen-2-yl) -4-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography to obtain 3.88 g (yield: 35%) of PCB-9 and 3.54 g (yield: 32%) of PCB-10, respectively.

¹ H-NMR of PCB-9: 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, 1H)

¹ H-NMR of PCB-10: 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, 1H)

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-1H-indole

20.0 g (63.06 mmol) of 5-bromo-4-nitro-1-phenyl-1H-indole, 14.38 g (63.06 mmol) of dibenzo [b, d] thiophen-3-ylboronic acid, 7.56 g (189.18) under nitrogen stream mmol) NaOH and 200 ml / 40 ml of 1,4-dioxane / H ₂ O were added and stirred. 2.18 g (1.89 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. 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-phenyl-1H-indole using column chromatography %) Was obtained.

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

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

120 ml of 12.0 g (28.53 mmol) of 5- (dibenzo [b, d] thiophen-3-yl) -4-nitro-1-phenyl-1H-indole, 22.45 g (85.61 mmol) of triphenylphosphine under nitrogen stream DCB was added and stirred. Stir at 180 ° C. for 14 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography to obtain 3.88 g (yield: 35%) of PCB-11 and 3.54 g (yield: 32%) of PCB-12, respectively.

¹ H-NMR of PCB-11: 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, 1H)

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

Synthesis Example 1 Synthesis of 1

PCI-1 (3.0 g, 6.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.15 g, 8.04 mmol), NaH (0.19), which was a compound prepared in Preparation Example 6, under nitrogen stream. g, 8.04 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered, and then purified by column chromatography to obtain the title compound 1 (3.2 g, yield 71%).

GC-Mass (Theoretical value: 678.78 g / mol, Measured value: 678 g / mol)

Synthesis Example 2 Synthesis of 2

PCI-1 (3.0 g, 6.7 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.12 g, 8.04 mmol), which are the compounds prepared in Preparation Example 6, under a nitrogen stream. ), 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) were mixed and stirred at 190 ° C. for 12 hours. Stirred.

After the reaction was completed, nitrobenzene 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 was purified by column chromatography to give the title compound 2 (2.8 g, yield 56%).

GC-Mass (Theoretical value: 754.88 g / mol, Measured value: 754 g / mol)

Synthesis Example 3 Synthesis of 3

Except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine (3.0 g, 6.7 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, The same procedure as in Synthesis Example 2 was performed, to obtain 3 (2.9 g, yield 57%) as a target compound.

GC-Mass (Theoretical value: 753.89 g / mol, Measured value: 753 g / mol)

Synthesis Example 4 Synthesis of 4

Except for using 2- (3-bromophenyl) pyridine (3.0 g, 6.7 mmol) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, The same procedure was followed to obtain the title compound 4 (2.2 g, yield 55%).

GC-Mass (Theoretical value: 600.71 g / mol, Measured value: 600 g / mol)

Synthesis Example 5 Synthesis of 5

PCI-1 (3.0 g, 6.7 mmol), 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine, which are the compounds prepared in Preparation Example 6 under a nitrogen stream, 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) was mixed and then stirred at 110 ° C. for 12 h.

After completion of the reaction, the mixture was extracted with ethyl acetate, followed by removing moisture with MgSO ₄ , and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain the target compound 5 (1.9 g, yield 44%). )

GC-Mass (Theoretical value: 651.76 g / mol, Measured value: 651 g / mol)

Synthesis Example 6 Synthesis of 6

N- (biphenyl-4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using 2-amine (3.0 g, 6.7 mmol), to obtain the target compound 6 (3.7 g, 61% yield) by the same process as in Synthesis Example 2.

GC-Mass (Theoretical value: 757.96 g / mol, Measured value: 757 g / mol)

Synthesis Example 7 Synthesis of 7

Except for using PCI-2 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 7 (2.7 g, yield 60%) by the same procedure as in Synthesis Example 1.

GC-Mass (Theoretical value: 678.78 g / mol, Measured value: 678 g / mol)

Synthesis Example 8 Synthesis of 8

Except for using PCI-2 (3.0 g, 6.7 mmol) instead of PCI-1, the same process as in Synthesis Example 2 was carried out to obtain the title compound 8 (2.6 g, yield 52%).

GC-Mass (Theoretical value: 754.88 g / mol, Measured value: 754 g / mol)

Synthesis Example 9 Synthesis of 9

Except for using PCI-2 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 9 (2.8 g, yield 55%) in the same manner as in Synthesis Example 3.

GC-Mass (Theoretical value: 753.89 g / mol, Measured value: 753 g / mol)

Synthesis Example 10 Synthesis of 10

Except for using PCI-2 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 10 (2.3 g, yield 57%) by the same procedure as in Synthesis Example 4.

GC-Mass (Theoretical value: 600.71 g / mol, Measured value: 600 g / mol)

Synthesis Example 11 Synthesis of 11

Except for using PCI-4 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 11 (3.0 g, yield 65%) in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 678.78 g / mol, Measured value: 678 g / mol)

Synthesis Example 12 Synthesis of 12

Except for using PCI-4 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 12 (3.3 g, 66% yield) was carried out in the same manner as in Synthesis Example 2.

GC-Mass (Theoretical value: 754.88 g / mol, Measured value: 754 g / mol)

Synthesis Example 13 Synthesis of 13

Except for using PCI-4 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 13 (3.1 g, yield 62%) was carried out in the same manner as in Synthesis Example 3.

GC-Mass (Theoretical value: 753.89 g / mol, Measured value: 753 g / mol)

Synthesis Example 14 Synthesis of 14

Except for using PCI-4 (3.0 g, 6.7 mmol) instead of PCI-1, the same procedure as in Synthesis Example 4 was carried out to obtain the target compound 14 (2.4 g, yield 60%).

GC-Mass (Theoretical value: 600.71 g / mol, Measured value: 600 g / mol)

Synthesis Example 15 Synthesis of 15

Except for using PCI-13 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 15 (2.9 g, yield 63%) was carried out in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 678.78 g / mol, Measured value: 678 g / mol)

Synthesis Example 16 Synthesis of 16

Except for using PCI-13 (3.0 g, 6.7 mmol) instead of PCI-1, the same procedure as in Synthesis Example 2 was carried out to obtain the target compound 16 (3.0 g, yield 60%).

GC-Mass (Theoretical value: 754.88 g / mol, Measured value: 754 g / mol)

Synthesis Example 17 Synthesis of 17

PCI-13 (3.0 g, 6.7 mmol) is used instead of PCI-1, and 2- (3-bromophenyl) -4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-diphenylpyridine (3.1g 8.04 mmol), the same procedure as in Synthesis Example 2 was carried out to obtain 17 (3.2 g, yield 63%) as a target compound.

GC-Mass (Theoretical value: 752.9 g / mol, Measured value: 752 g / mol)

Synthesis Example 18 Synthesis of 18

Use PCI-13 (3.0 g, 6.7 mmol) instead of PCI-1, 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5 instead of 2-chloro-4-phenylquinazoline Except that -triazine (3.37g 8.04 mmol) was used, the same procedure as in Synthesis Example 5 was carried out to obtain 18 (3.1 g, yield 54%) as a target compound.

GC-Mass (Theoretical value: 830.97 g / mol, Measured value: 830 g / mol)

Synthesis Example 19 Synthesis of 19

Except for using PCI-13 (3.0 g, 6.7 mmol) instead of PCI-1 and 2- (3-chlorophenyl) -4-phenylquinazoline (2.55g 8.04 mmol) instead of 2-chloro-4-phenylquinazoline , 19 (2.7 g, yield 55%) was obtained by the same procedure as in Synthesis Example 5.

GC-Mass (Theoretical value: 727.85 g / mol, Measured value: 727 g / mol)

Synthesis Example 20 Synthesis of 20

Use PCI-13 (3.0 g, 6.7 mmol) instead of PCI-1, and N- (biphenyl-4-yl)-instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using N- (4-bromophenyl) biphenyl-4-amine (3.8 g 8.04 mmol), the same procedure as in Synthesis Example 2 was performed, to obtain 20 (3.5 g, yield 62%) of the title compound. .

GC-Mass (Theoretical value: 843.02 g / mol, Measured value: 843 g / mol)

Synthesis Example 21 Synthesis of 21

Except for using PCI-14 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 21 (3.1 g, yield 68%) in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 678.78 g / mol, Measured value: 678 g / mol)

Synthesis Example 22 Synthesis of 22

Except for using PCI-14 (3.0 g, 6.7 mmol) instead of PCI-1, the same procedure as in Synthesis Example 2 was carried out to obtain the target compound 22 (3.2 g, yield 64%).

GC-Mass (Theoretical value: 754.88 g / mol, Measured value: 754 g / mol)

Synthesis Example 23 Synthesis of 23

Except for using PCI-14 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 23 (3.0 g, 59% yield) by the same procedure as in Synthesis Example 3.

GC-Mass (Theoretical value: 753.89 g / mol, Measured value: 753 g / mol)

Synthesis Example 24 Synthesis of 24

Except for using PCI-14 (3.0 g, 6.7 mmol) instead of PCI-1, the same procedure as in Synthesis Example 4 was carried out to obtain the target compound 24 (2.5 g, yield 62%).

GC-Mass (Theoretical value: 600.71 g / mol, Measured value: 600 g / mol)

Synthesis Example 25 Synthesis of 25

Except for using PCI-15 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 25 (2.9 g, yield 63%) was carried out in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 678.78 g / mol, Measured value: 678 g / mol)

Synthesis Example 26 Synthesis of 26

Except for using PCI-15 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 26 (2.9 g, yield 58%) was carried out in the same manner as in Synthesis Example 2.

GC-Mass (Theoretical value: 754.88 g / mol, Measured value: 754 g / mol)

Synthesis Example 27 Synthesis of 27

Use PCI-15 (3.0 g, 6.7 mmol) instead of PCI-1, 2- (3-bromophenyl) -4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-diphenylpyridine (3.1g 8.04 mmol), to obtain the target compound 27 (3.0 g, yield 60%) was carried out in the same manner as in Synthesis Example 2.

GC-Mass (Theoretical value: 752.9 g / mol, Measured value: 752 g / mol)

Synthesis Example 28 Synthesis of 28

Use PCI-15 (3.0 g, 6.7 mmol) instead of PCI-1, 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5 instead of 2-chloro-4-phenylquinazoline Except that -triazine (3.37g 8.04 mmol) was used, the same procedure as in Synthesis Example 5 was carried out to obtain 28 (3.3 g, yield 60%) as a target compound.

GC-Mass (Theoretical value: 830.97 g / mol, Measured value: 830 g / mol)

Synthesis Example 29 Synthesis of 29

Except for using PCI-16 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 29 (3.1 g, yield 68%) was carried out in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 678.78 g / mol, Measured value: 678 g / mol)

Synthesis Example 30 Synthesis of 30

Except for using PCI-16 (3.0 g, 6.7 mmol) instead of PCI-1 to obtain the target compound 30 (3.3 g, 66% yield) by the same procedure as in Synthesis Example 2.

GC-Mass (Theoretical value: 754.88 g / mol, Measured value: 754 g / mol)

Synthesis Example 31 Synthesis of 31

Except for using PCI-16 (3.0 g, 6.7 mmol) instead of PCI-1, to obtain the target compound 31 (3.1 g, yield 62%) in the same manner as in Synthesis Example 3.

GC-Mass (Theoretical value: 753.89 g / mol, Measured value: 753 g / mol)

Synthesis Example 32 Synthesis of 32

Except for using PCI-16 (3.0 g, 6.7 mmol) instead of PCI-1, the same procedure as in Synthesis Example 4 was carried out to obtain the target compound 32 (2.4 g, yield 60%).

GC-Mass (Theoretical value: 600.71 g / mol, Measured value: 600 g / mol)

Synthesis Example 33 Synthesis of 33

Except for using PCB-9 (3.0 g, 7.72 mmol) instead of PCI-1, to obtain the target compound 33 (2.9 g, yield 60%) in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 619.74 g / mol, Measured value: 619 g / mol)

Synthesis Example 34 Synthesis of 34

Except for using PCB-9 (3.0 g, 7.72 mmol) instead of PCI-1, the same procedure as in Synthesis Example 2 was carried out to obtain the target compound 34 (3.3 g, yield 59%).

GC-Mass (Theoretical value: 695.83 g / mol, Measured value: 695 g / mol)

Synthesis Example 35 Synthesis of 35

Use PCB-9 (3.0 g, 7.72 mmol) instead of PCI-1, 2- (3-bromophenyl) -4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-diphenylpyridine (3.58g 9.26 mmol), the same procedure as in Synthesis Example 2 was carried out to obtain the target compound 35 (2.5 g, 59% yield).

GC-Mass (Theoretical value: 693.86 g / mol, Measured value: 693 g / mol)

Synthesis Example 36 Synthesis of 36

Use PCB-9 (3.0 g, 7.72 mmol) instead of PCI-1 and 2- (4'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5 instead of 2-chloro-4-phenylquinazoline Except that -triazine (3.9g 9.26 mmol) was used, the same procedure as in Synthesis Example 5 was carried out to obtain 36 (3.5 g, yield 58%) as a target compound.

GC-Mass (Theoretical value: 771.93 g / mol, Measured value: 771 g / mol)

Synthesis Example 37 Synthesis of 37

Except for using PCB-9 (3.0 g, 7.72 mmol) instead of PCI-1 and 2- (3-chlorophenyl) -4-phenylquinazoline (2.9g 9.26 mmol) instead of 2-chloro-4-phenylquinazoline , 37 (2.4 g, yield 46%) was obtained by the same procedure as in Synthesis Example 5.

GC-Mass (Theoretical value: 668.81 g / mol, Measured value: 668 g / mol)

Synthesis Example 38 Synthesis of 38

Use PCB-9 (3.0 g, 7.72 mmol) instead of PCI-1 and N- (biphenyl-4-yl)-instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (4.7g, 9.26 mmol), the same procedure as in Synthesis Example 2 was carried out, and the target compound was 38. (3.7 g, yield 58%) was obtained.

GC-Mass (Theoretical value: 824.04 g / mol, Measured value: 824 g / mol)

Synthesis Example 39 Synthesis of 39

Except for using PCB-10 (3.0 g, 7.72 mmol) instead of PCB-9, to obtain the target compound 39 (2.8 g, yield 59%) was carried out in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 619.74 g / mol, Measured value: 619 g / mol)

Synthesis Example 40 Synthesis of 40

Except for using PCB-10 (3.0 g, 7.72 mmol) instead of PCB-9, to obtain the target compound 40 (3.3 g, yield 65%) was carried out in the same manner as in Synthesis Example 2.

GC-Mass (Theoretical value: 695.83 g / mol, Measured value: 695 g / mol)

Synthesis Example 41 Synthesis of 41

Except for using PCB-10 (3.0 g, 7.72 mmol) instead of PCB-9, to obtain the target compound 41 (3.0 g, 55% yield) by the same procedure as in Synthesis Example 3.

GC-Mass (Theoretical value: 693.86 g / mol, Measured value: 693 g / mol)

Synthesis Example 42 Synthesis of 42

Except for using PCB-10 (3.0 g, 7.72 mmol) instead of PCB-9, to obtain the target compound 42 (2.2 g, yield 62%) was carried out in the same manner as in Synthesis Example 4.

GC-Mass (Theoretical value: 541.66 g / mol, Measured value: 541 g / mol)

Synthesis Example 43 Synthesis of 43

2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7g instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine , 8.04 mmol) was used in the same manner as in Synthesis Example 2 to obtain 43 (3.2 g, yield 57%) as a target compound.

GC-Mass (Theoretical value: 830.97 g / mol, Measured value: 830 g / mol)

Synthesis Example 44 Synthesis of 44

Except for using PCB-13 (3.0 g, 6.7 mmol) instead of PCI-1, the same process as in Synthesis Example 43 was carried out to obtain the target compound 44 (3.5 g, yield 62%).

GC-Mass (Theoretical value: 830.97 g / mol, Measured value: 830 g / mol)

Synthesis Example 45 Synthesis of 45

Except for using PCB-9 (3.0 g, 7.72 mmol) instead of PCI-1, the same procedure as in Synthesis Example 43 was carried out to obtain the title compound 45 (3.4 g, yield 57%).

GC-Mass (Theoretical value: 771.93 g / mol, Measured value: 771 g / mol)

Example 1 Manufacture 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 manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, using Compound 1 of Synthesis Example 1 as a host, 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 order to produce an organic EL device.

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

Examples 2 to 45 Fabrication of Organic EL Device

An organic EL device was manufactured in the same manner as in Example 1, except that Compounds 2 to 45, which were synthesized in Synthesis Examples 2 to 45, were used instead of Compound 1 used as the host material in forming the emission layer in Example 1. Prepared.

Comparative Example 1 Fabrication of Green Organic EL Device

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

Experimental Example

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

Table 1

Sample	Host	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 manufactured in Examples 1 to 45, respectively, using the compound represented by Chemical Formula 1 according to the present invention (Compounds 1 to 45) as the host material of the light emitting layer were prepared according to Comparative Example 1 It was confirmed that the green organic EL device exhibited better performance in terms of current efficiency and driving voltage.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.

Claims (8)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   At least one of R ₃ and R _4, R ₄ and R ₅ , and R ₅ and R ₆ may be combined with Formula 2 to form a condensed ring;

   [Formula 2]

   

   In the formula (2), the dotted line is a condensation site;

   At least one of R ₇ and R _8, R ₈ and R ₉ , and R ₉ and R ₁₀ may be combined with Formula 3 to form a condensed ring;

   [Formula 3]

   

   In Chemical Formula 3, the dotted line represents a site where condensation takes place;

   X ₁ is selected from O, S, Se, N (Ar ₃ ), 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 from each other, and each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ An alkenyl group of ˜C ₄₀ , a substituted or unsubstituted alkynyl group of C ₂ to C ₄₀ , a substituted or unsubstituted C ₆ ˜C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms , Substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group of boron, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, an aryl phosphonic a substituted or unsubstituted C ₆ ~ C ₄₀ pingi, Chi Or unsubstituted C ₆ ~ C ₄₀ aryl phosphine of the ring oxide groups, and substituted or unsubstituted selected from a C ₆ ~ group consisting arylsilyl of C ₄₀ ring, or they combine groups which are adjacent to form a condensed ring And

   Ar ₁ to Ar ₇ are the same as or different from each other, and each independently 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 Alkynyl group of -C ₄₀ , substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group of 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ -C ₄₀ aryl jade Periodic, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted Heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to 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,

   C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, a nuclear atom in R ₁ to R ₁₄ and Ar ₁ to Ar ₇ 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, C 3 -C 40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ alkylboron group, C ₆ -C ₄₀ aryl boron group, 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 ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ An alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 he Tercyclocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ It may be substituted with one or more substituents selected from the group consisting of an arylphosphine oxide group and a C ₆ to C ₄₀ arylsilyl group.
2. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas C-1 to C-36:

   

   In the above formula, R ₁ to R ₁₄ , Ar ₁ , Ar ₂ and X ₁ are the same as defined in claim 1, respectively.
3. The compound of claim 1, wherein X ₁ is N (Ar ₃ ).
4. According to claim 1, Ar ₁ to Ar ₇ are the same as or different from each other, each independently represent a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, and a substituted or unsubstituted 5 to 40 nuclear atoms Selected from the group consisting of heteroaryl groups,

   The aryl group and heteroaryl group in Ar ₁ to Ar ₇ are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to ₄₀ C ₆ ~ C 40 aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ groups of the cycloalkyl group, the nuclear atoms of 3 to 40 hetero cycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₄₀ group of the arylboronic, C substituted with ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group one or more substituents selected from the group consisting of or or characterized in that the unsubstituted compound.
5. The method of claim 1, wherein R ₁ to R ₁₄ are the same as or different from each other, and each independently hydrogen, deuterium (D), a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, and a substituted or unsubstituted It is selected from the group consisting of heteroaryl groups having 5 to 40 nuclear atoms,

   The C ₆ ~ C ₄₀ aryl group, the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, heterocycloalkyl groups of 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₄₀ of the arylboronic group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group substituted with one or more substituents selected from the group consisting of groups or Compound which is unsubstituted.
6. The compound of claim 1, wherein Ar ₁ to Ar ₇ and R ₁ to R ₁₄ are each independently selected from hydrogen or a substituent group consisting of the following structures.

   
7. In an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode,

   At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 6.
8. The organic electroluminescent device according to claim 7, wherein at least one organic material layer including the compound is a light emitting layer.