KR101571591B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound in which an indole moiety is fused at the terminal of a carbazole moiety to form a basic skeleton and various substituents are bonded to the basic skeleton, and an organic electroluminescent device including the novel compound , The luminous efficiency, driving voltage, lifetime, etc. of the device can be improved by including the compound in at least one organic layer, preferably a light emitting layer.

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 observation 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): < EMI ID =

In Formula 1,

At least one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is bonded to the following formula 2 to form a condensed ring;

In Formula 2,

At least one of R ₉ and R _10, R ₁₀ and R ₁₁ , and at least one of R ₁₁ and R ₁₂ is bonded to Formula 1 to form a condensed ring;

R ₁ to R ₁₂ 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 alkylamine group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, of ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nuclear atoms to C40 heterocycloalkyl group, substituted or non-substituted of unsubstituted C ₁ ~ C ₄₀ alkyl a silyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group of boron, and a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted of Is selected from the group C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted aryl silyl group of the C ₆ ~ C ₄₀ ring consisting of, all of which are adjoining To form a condensed ring,

X ₁ and X ₂ are each independently selected from O, S, Se, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ ), at least one of X ₁ and X ₂ is N (Ar ₁ )

Y ₁ and Y ₂ are each independently selected from N and C (R ₁₃ )

R ₁₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkenyl, substituted or unsubstituted C ₂ to C ₄₀ 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 C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, An unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a C ₆ to C ₄₀ arylalkyl group, a substituted or 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 ₁ to C ₄₀ alkylboron group, unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide of the 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 ₃ are the same or different, each independently represent a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ 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 alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a C ₆ to C ₄₀ arylalkyl group, a substituted or unsubstituted C ₃ to C _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 alkyl group, , And 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 to 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,

In the above R ₁ to R _{13 and} Ar ₁ to Ar ₃ , 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 nucleus atoms of 5 to 40 heteroaryl group, an aryloxy group of a _{C 6 ~ C 40, C 1} ~ C 40 alkyloxy group, the C ₆ ~ C ₄₀ aryl amine group, C ₆ ~ C ₄₀ aryl group, C of _A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to an alkyl group of C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl phosphine oxide group, and a C ₆ to C ₄₀ aryl silyl groups are each independently selected from deuterium, halogen, cyano group, C ₁ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms heteroaryl of 5 to 40 group, C ₆ ~ aryloxy C _40, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₄₀ aryl amine group, C ₆ ~ C ₄₀ aryl group, a cycloalkyl group of C ₃ ~ C ₄₀ of, An aryl phosphine group of atoms, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ of, A C ₆ to C ₄₀ arylphosphine oxide group, and a C ₆ to C ₄₀ arylsilyl group. When a plurality of substituents are introduced at this time, these substituents may be the same as 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 at the terminal of a carbazole moiety to form a basic skeleton and various substituents are bonded to the basic skeleton. .

The compound represented by Formula 1 has a larger molecular weight than a conventional organic EL device material (e.g., 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), and has a wide energy band gap, 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 compound has a broad bandgap due to an indole moiety bonded to the carbazole moiety at the terminal thereof, and has a bipolar characteristic due to various aromatic ring substituents , It is possible to exhibit excellent characteristics as a 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. In addition, the indole moiety bonded to the carbazole moiety may be fused to improve the thermal stability of the compound. In addition, the crystallization inhibition of the organic compound layer containing the compound of Formula 1 There is also an effect. 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.

The compound represented by the formula (1) of the present invention which forms a condensed ring in combination with the formula (2) may be further represented by a compound represented by any one of the following formulas (3) to (20)

In the above Chemical Formulas 3 to 20,

R ₁ to R _12, X ₁ and X ₂ , Y ₁ and Y ₂ are as defined in the above formula (1).

More specifically, X ₁ and X ₂ are each independently selected from O, S, Se, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ ), and at least one of X ₁ and X ₂ is N Ar ₁ ). Preferably, both X ₁ and X ₂ are N (Ar ₁ ). When X ₁ and X ₂ are N (Ar ₁ ), each Ar ₁ is the same or different.

Y ₁ and Y ₂ are each independently selected from N and C (R ₁₃ ), preferably all C (R ₁₃ ). When Y ₁ and Y ₂ are C (R ₁₃ ), each R ₁₃ is the same or different.

Also, R ₁ to R ₁₂ excluding at least one of R ₅ and R ₆ , R ₆ and R ₇ , and / or R ₇ and R ₈ substituents which form the non-forming group of the formula (2) 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 aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a 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, substituted or non-substituted of unsubstituted C ₆ ~ C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a C ₆ to C ₄₀ arylalkyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted 3 to 40 nuclear atoms of the heterocycloalkyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted Or an unsubstituted C ₁ to C ₄₀ alkylboron group and 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 A 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.

In the present invention, R ₁ to R ₁₂ and R ₁₃ are each independently selected from the group consisting of hydrogen, deuterium (D), a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl And a substituted or unsubstituted C ₆ to C ₄₀ arylamine group.

Wherein Ar ₁ to Ar ₃ 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 of 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 heteroaryl group, a substituted or unsubstituted in the ring C ₆ ~ C ₄₀ aryl Substituted or unsubstituted C ₁ to C ₄₀ alkyloxy groups, substituted or unsubstituted C ₆ to C ₄₀ arylamine groups, C ₆ to C ₄₀ arylalkyl groups, substituted or unsubstituted C ₃ to C ₄₀ arylalkyl groups, C ₄₀ cycloalkyl group, a substituted or unsubstituted nuclear atoms of 3 to 40 heterocycloalkyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C alkyl boron of ₁ ~ C ₄₀ And 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 A C ₆ to C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group.

In the present invention, Ar ₁ to Ar ₃ are preferably 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.

Here, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group of R ₁ to R ₁₃ and Ar ₁ to Ar ₃ , alkyl group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group each independently selected from deuterium, halogen, cyano, C alkyl group of _{1 ~ C 40, C 2 ~} C 40 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 alkyl oxy group, C ₆ ~ C ₄₀ aryl amine group, C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl of the group, C ₁ ~ C ₄₀ group of an alkyl boron, 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 of Arylsilyl Which may be substituted with one or more substituents selected from the group consisting of, wherein if a plurality of substituents substituted, which are the same or different from each other.

In the compound represented by the formula (1) of the present invention, when X ₁ and X ₂ are N (Ar ₁ ) and Y ₁ and Y ₂ are C (R ₁₃ ), a compound represented by any one of the following formulas As shown in FIG.

In the above Formulas 21 to 38,

R ₁ to R ₁₃ and Ar ₁ are the same as defined in claim ₁ , respectively.

More specifically, R ₁ to R ₁₂ and R ₁₃ are selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, and And a substituted or unsubstituted C ₆ to C ₄₀ arylamine group.

It is preferable that Ar ₁ is 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.

In the compound represented by formula (1) according to the present invention, R ₁ to R ₁₃ and Ar ₁ to Ar ₃ are each independently hydrogen or more preferably selected from the group consisting of substituents S1 to S196 shown below. However, the present invention is not limited thereto.

More preferably Ar ₁ to Ar ₃ may be selected from the following substituent groups.

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 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 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 is represented by Formula 1 Compound, preferably a compound represented by the general formula (3) to a compound represented by the general formula (20), more preferably any one of the compounds represented by the general formulas (21) to (38). At this time, the compounds of formulas (3) to (20) may be used singly 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 compound represented by Formula 1 may be included in an organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material.

The structure of the organic electroluminescent device according to the present invention is not particularly limited 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 stacked. 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 . At this time, the compound of the present invention can be used as a phosphorescent host of the light emitting layer. 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.

Non-limiting examples of usable cathode materials 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.

Non-limiting examples of usable cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

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

[Preparation Example 1] Synthesis of IC-1

<Step 1> Synthesis of 6-bromo-1H-benzo [g] indole

1-Bromo-5-nitronaphthalene (20 g, 79.35 mmol) was dissolved in 800 ml of THF under a nitrogen stream and then cooled to -40 ° C and vinylmagnesium bromide (31.24 g, 238.04 mmol) was added. Using MgSO ₄ to remove water and the organic layer was separated with ethyl acetate After completion of the reaction by using a saturated aqueous solution of NH4Cl and then stirred for 20 minutes. The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 6-bromo-1H- benzo [g] indole (12.69 g, yield 65% .

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.46 (t, 1H), 7.57 (d, 1H), 7.97 (d, 1H), 8.12 (d, 2H), 10.14 ( s, 1 H)

<Step 2> Synthesis of 6- (2-nitrophenyl) -1H-benzo [g] indole

6-bromo-1H-benzo [ g] indole (12 g, 48.76 mmol) and 2-nitrophenylboronic acid (9.77 g, 58.51 mmol), K 2 CO 3 (20.22 g, 146.28 mmol) and THF / H ₂ in a nitrogen atmosphere O a mixture (300 ml / 150 ml), then insert the _{Pd (PPh 3) 4 (2.82} g, 5 mol%) at 40 ℃ was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain 6- (2-nitrophenyl) -1H-benzo [g] indole (11.53 g, 82 %).

^{1 H-NMR: δ 6.44 (} d, 1H), 7.26 (d, 1H), 7.45 (t, 1H), 7.56 (d, 1H), 7.67 (t, 1H), 7.91 (t, 1H), 8.01 ( m, 2H), 8.10 (m, 3H), 10.18 (s, 1H)

&Lt; Step 3 > 6- (2- nitrophenyl )-One- phenyl -1H- benzo Synthesis of [g] indole

Iodobenzene (11.68 g, 57.23 mmol), Cu powder (0.24 g, 3.82 mmol), and K ₂ CO ₃ (11 g, 38.15 mmol) were added to a solution of 6- (2-nitrophenyl) 5.27 g, 38.15 mmol), Na ₂ SO ₄ (5.42 g, 38.15 mmol) and nitrobenzene (200 ml) were mixed and stirred at 200 ° C for 24 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 . After removing the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain 6- (2-nitrophenyl) 7.09 g, yield: 51%).

^{1 H-NMR: δ 6.43 (} d, 1H), 7.28 (d, 1H), 7.43 (m, 2H), 7.50 (d, 2H), 7.58 (m, 3H), 7.66 (t, 1H), 7.90 ( t, 1 H), 8.00 (m, 2 H), 8.13 (m, 3 H)

<Step 4> Synthesis of IC-1

Indole (7 g, 19.46 mmol), triphenylphosphine (12.76 g, 48.64 mmol), and 1,2-dichlorobenzene (100 ml) were added to a solution of 6- (2-nitrophenyl) The mixture was stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO ₄ and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain IC-1 (3.04 g, yield 47%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.30 (d, 1H), 7.44 (m, 2H), 7.52 (d, 2H), 7.59 (m, 3H), 7.69 (t, 1H), 7.91 ( 1H), 8.02 (m, 2H), 8.14 (m, 2H), 10.15

[Preparation Example 2] Synthesis of IC-2

<Step 1> Synthesis of 2-bromo-6- (2-nitrophenyl) naphthalene

2,6-dibromonaphthalene (30 g, 104.91 mmol), 2-nitrophenylboronic acid (21.02 g, 125.89 mmol), Pd (PPh 3) 4 (6.06 g, 5 mol%), K 2 CO 3 (43.50 g, 314.73 mmol ) and _{THF / H 2 O (500 ml} / 200 ml) using the same procedure as in <step 2> the preparation example 1, the desired compound of 2-bromo-6- (2- nitrophenyl) naphthalene (22.03 g, Yield 64%).

^{1 H-NMR: δ 7.46 (} d, 1H), 7.51 (s, 1H), 7.67 (t, 1H), 7.80 (d, 1H), 7.91 (m, 3H), 8.03 (m, 2H), 8.21 ( s, 1 H)

<Step 2> Synthesis of 6- (2-nitrophenyl) naphthalen-2-amine

Aqueous ammonia (22.8 ml, 335.2 mmol) and Cu (0.21 g, 5 mol%) were dissolved in 250 ml of THF under a nitrogen atmosphere. , And the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . The solvent was removed from the filtered organic layer and the residue was purified by column chromatography (hexane: EA = 5: 1 (v / v)) to obtain 6- (2-nitrophenyl) naphthalen-2-amine (14.17 g, yield 80% Respectively.

^{1 H-NMR: δ 4.62 (} s, 2H), 7.47 (d, 1H), 7.52 (s, 1H), 7.66 (t, 1H), 7.74 (s, 1H), 7.82 (d, 1H), 7.92 ( m, 3 H), 8.02 (m, 2 H)

<Step 3> Synthesis of 7- (2-nitrophenyl) -3H-benzo [e] indole

(14 g, 52.97 mmol) was dissolved in H ₂ O / dioxane (10 ml / 90 ml), and triethanolammonium chloride (0.98 g, 5.30 mmol) and RuCl ₃ put the <sub>`H 2 O (0.12 g,</sub> 0.5 mmol) and <sub>PPh 3 (0.42 g, 1.59 mmol</sub> ), SnCl 2` 2H 2 O (1.20 g, 5.30 mmol), and stirred at 180 ℃ for 20 hours. After the reaction was completed, the reaction mixture was poured into aqueous 5% HCl, extracted with methylene chloride, and charged with MgSO ₄ . After removing the solvent of the filtered organic layer, the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain 7- (2-nitrophenyl) -3H- ).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.58 (s, 1H), 7.65 (m, 3H), 7.73 (d, 1H), 7.90 (t, 1H), 8.00 ( d, 1 H), 8.05 (m, 2H), 10.20 (s, 1 H)

<Step 4> Synthesis of 7- (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole

Step 3> of Preparation Example 1 was repeated except that 7- (2-nitrophenyl) -3H-benzo [e] indole was used instead of 6- (2-nitrophenyl) The same procedure was followed to obtain 7- (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.26 (d, 1H), 7.46 (m, 1H), 7.51 (d, 2H), 7.59 (m, 3H), 7.66 (m, 3H), 7.72 ( (d, IH), 7.91 (t, IH), 8.01 (d, IH), 8.07

<Step 5> Synthesis of IC-2

Except that 7- (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole was used in place of 6- (2-nitrophenyl) -1-phenyl- IC-2 was obtained by performing the same procedure as < Step 4 >.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.25 (d, 1H), 7.47 (m, 1H), 7.52 (m, 3H), 7.58 (m, 2H), 7.65 (m, 3H), 7.92 ( t, 1 H), 8.02 (d, 1 H), 8.09 (m, 2 H), 11.70 (s, 1 H).

[Preparation Example 3] Synthesis of IC-3

Except that 7- (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole was used in place of 6- (2-nitrophenyl) -1-phenyl- IC-3 was obtained by carrying out the same procedure as < Step 4 >

^{1 H-NMR: δ 6.46 (} d, 1H), 7.26 (d, 1H), 7.46 (m, 1H), 7.51 (d, 2H), 7.57 (m, 2H), 7.64 (m, 3H), 7.91 ( (d, 1H), 8.00 (d, 1H), 8.08 (m, 2H), 8.12

[Preparation Example 4] Synthesis of IC-4

<Step 1> Synthesis of 6- (2-nitrophenyl) -1H-benzo [f] indole

The procedure of Step 3 of Preparation Example 2 was repeated except that 6- (2-nitrophenyl) naphthalen-2-amine was used in place of 9-phenyl-9H-carbazol- 2-nitrophenyl) -1H-benzo [f] indole.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.40 (s, 1H), 7.55 (s, 1H), 7.58 (s, 1H), 7.67 (t, 1H), 7.73 ( (d, IH), 7.91 (m, 2H), 8.02 (d, 2H), 10.13

&Lt; Step 2 > 6- (2- nitrophenyl )-One- phenyl -1H- benzo Synthesis of [f] indole

Step 3 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1H-benzo [f] indole was used instead of 6- (2-nitrophenyl) -1H- (2-nitrophenyl) -1-phenyl-1H-benzo [f] indole was obtained.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.42 (m, 2H), 7.50 (d, 2H), 7.55 (s, 1H), 7.58 (m, 3H), 7.67 ( (d, IH), 7.73 (d, IH), 7.91 (m, 2H), 8.02

<Step 3> IC Synthesis of -4

1H-benzo [f] indole was used instead of 6- (2-nitrophenyl) -1-phenyl-1H-benzo [ 1 < Step 4 > to obtain IC-4.

^{1 H-NMR: δ 6.46 (} d, 1H), 7.28 (d, 1H), 7.41 (m, 2H), 7.49 (d, 2H), 7.54 (m, 2H), 7.59 (m, 2H), 7.66 ( t, 1 H), 7.92 (m, 2 H), 8.04 (d, 2H), 10.73

[Preparation Example 5] Synthesis of IC-5

1H-benzo [f] indole was used instead of 6- (2-nitrophenyl) -1-phenyl-1H-benzo [ IC-5 was obtained by performing the same procedure as in < Step 4 >

^{1 H-NMR: δ 6.44 (} d, 1H), 7.26 (d, 1H), 7.41 (m, 2H), 7.50 (d, 2H), 7.54 (s, 1H), 7.58 (m, 2H), 7.68 ( 1H), 7.91 (m, 2H), 8.01 (d, 2H), 8.11

[Preparation Example 6] Synthesis of IC-6

<Step 1> Synthesis of 2-bromo-7- (2-nitrophenyl) naphthalene

2,7-dibromonaphthalene (30 g, 104.91 mmol), 2-nitrophenylboronic acid (21.02 g, 125.89 mmol), Pd (PPh 3) 4 (6.06 g, 5 mol%), K 2 CO 3 (43.50 g, 314.73 mmol ) and _{THF / H 2 O (500 ml} / 200 ml) to the preparation example 1 <step 2> the same manner as the desired compound of 2-bromo-6- (2- nitrophenyl) naphthalene (21.34 g, and the yield using 62%).

^{1 H-NMR: δ 7.46 (} d, 1H), 7.59 (s, 1H), 7.67 (t, 1H), 7.78 (d, 1H), 7.84 (d, 1H), 7.90 (m, 2H), 8.00 ( d, 1 H), 8.05 (d, 1 H), 8.21 (s, 1 H)

<Step 2> Synthesis of 7- (2-nitrophenyl) naphthalen-2-amine

The procedure of Step 2 of Preparation Example 2 was repeated except that 2-bromo-7- (2-nitrophenyl) naphthalene was used instead of 2-bromo-6- (2-nitrophenyl) (2-nitrophenyl) naphthalen-2-amine.

^{1 H-NMR: δ 4.63 (} s, 2H), 7.49 (d, 1H), 7.58 (s, 1H), 7.66 (t, 1H), 7.75 (m, 2H), 7.85 (d, 1H), 7.91 ( m, 2 H), 8.02 (d, 1 H), 8.08 (d, 1 H)

<Step 3> Synthesis of 8- (2-nitrophenyl) -3H-benzo [e] indole

The procedure of Step 3 of Preparation Example 2 was repeated except that 7- (2-nitrophenyl) naphthalen-2-amine was used in place of 9-phenyl-9H-carbazol- 2-nitrophenyl) -3H-benzo [e] indole.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.27 (d, 1H), 7.58 (s, 1H), 7.66 (m, 2H), 7.77 (d, 1H), 7.85 (d, 1H), 7.91 ( (d, IH), 8.08 (d, IH), 10.11 (s, IH)

<Step 4> Synthesis of 8- (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole

Step 3 of Preparation Example 1 was repeated except that 8- (2-nitrophenyl) -3H-benzo [e] indole was used instead of 6- (2-nitrophenyl) (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole was obtained.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.45 (m, 1H), 7.51 (d, 2H), 7.59 (m, 3H), 7.67 (m, 2H), 7.78 ( (d, IH), 7.86 (d, IH), 7.92 (m, 2H), 8.04

<Step 5> Synthesis of IC-6

Except that 8- (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole was used in place of 6- (2-nitrophenyl) -1-phenyl- IC-6 was obtained by performing the same procedure as in < Step 4 >

^{1 H-NMR: δ 6.46 (} d, 1H), 7.26 (d, 1H), 7.44 (m, 1H), 7.52 (d, 2H), 7.57 (t, 2H), 7.66 (m, 2H), 7.85 ( (d, IH), 7.91 (m, 2H), 8.02 (d, IH), 8.09

[Preparation Example 7] Synthesis of IC-7

Except that 8- (2-nitrophenyl) -3-phenyl-3H-benzo [e] indole was used in place of 6- (2-nitrophenyl) -1-phenyl- 1 < Step 4 >.

^{1 H-NMR: δ 6.46 (} d, 1H), 7.26 (d, 1H), 7.43 (m, 2H), 7.51 (d, 1H), 7.56 (s, 1H), 7.60 (m, 2H), 7.69 ( (m, 2H), 7.85 (d, 1H), 7.91 (m, 2H), 8.03

[Preparation Example 8] Synthesis of IC-8

<Step 1> Synthesis of 7- (2-nitrophenyl) -1H-benzo [f] indole

The procedure of Step 3 of Preparation Example 2 was repeated except that 7- (2-nitrophenyl) naphthalen-2-amine was used instead of 9-phenyl-9H-carbazol- 2-nitrophenyl) -1H-benzo [f] indole.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.40 (s, 1H), 7.55 (s, 1H), 7.58 (s, 1H), 7.67 (t, 1H), 7.73 ( (d, IH), 7.91 (m, 2H), 8.03 (m, 2H), 10.11

<Step 2> Synthesis of 7- (2-nitrophenyl) -1-phenyl-1H-benzo [f] indole

Step 3 of Preparation Example 1 was repeated except that 7- (2-nitrophenyl) -1H-benzo [f] indole was used instead of 6- (2-nitrophenyl) -1H- To obtain 7- (2-nitrophenyl) -1-phenyl-1H-benzo [f] indole.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.42 (m, 2H), 7.50 (d, 2H), 7.55 (s, 1H), 7.58 (m, 3H), 7.67 ( t, 1 H), 7.73 (d, 1 H), 7.91 (m, 2 H), 8.03 (m,

<Step 3> Synthesis of IC-8

Except that 7 (2-nitrophenyl) -1-phenyl-1H-benzo [f] indole was used instead of 6- (2-nitrophenyl) 1 < Step 4 >.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.42 (m, 2H), 7.50 (d, 2H), 7.55 (s, 1H), 7.58 (m, 2H), 7.67 ( 1H), 7.91 (m, 2H), 8.03 (m, 2H), 8.11

[Preparation Example 9] Synthesis of IC-9

Except that 7 (2-nitrophenyl) -1-phenyl-1H-benzo [f] indole was used instead of 6- (2-nitrophenyl) 1 < Step 4 > to obtain IC-9.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.42 (m, 2H), 7.50 (d, 2H), 7.55 (s, 1H), 7.58 (m, 2H), 7.67 ( 1H), 7.91 (m, 2H), 8.03 (m, 2H), 8.09

[Preparation Example 10] Synthesis of IC-10

<Step 1> Synthesis of 1-bromo-8- (2-nitrophenyl) naphthalene

1,8-dibromonaphthalene (30 g, 104.91 mmol), 2-nitrophenylboronic acid (21.02 g, 125.89 mmol), Pd (PPh 3) 4 (6.06 g, 5 mol%), K 2 CO 3 (43.50 g, 314.73 mmol ) and _{THF / H 2 O (500 ml} / 200 ml), the preparation of example 1 <step 2> the same manner as the desired compound of 1-bromo-8- (2- nitrophenyl) naphthalene (21.00 g , and using, Yield: 61%).

^{1 H-NMR: δ 7.46 (} t, 1H), 7.67 (t, 1H), 7.72 (t, 1H), 7.90 (t, 1H), 7.98 (d, 2H), 8.05 (d, 1H), 8.09 ( d, 1 H), 8.12 (d, 2H)

<Step 2> Synthesis of 8- (2-nitrophenyl) naphthalen-1-amine

Step 2 of Preparation Example 2 was carried out except that 1-bromo-8- (2-nitrophenyl) naphthalene was used in place of 2-bromo-6- (2-nitrophenyl) (2-nitrophenyl) naphthalen-1-amine.

^{1 H-NMR: δ 5.79 (} s, 2H), 7.45 (t, 1H), 7.66 (t, 1H), 7.73 (t, 1H), 7.81 (t, 1H), 7.89 (d, 2H), 7.94 ( d, 1 H), 8.00 (d, 1 H), 8.09 (d, 2 H)

<Step 3> Synthesis of 9- (2-nitrophenyl) -1H-benzo [g] indole

The procedure of Step 3 of Preparation Example 2 was repeated except that 8- (2-nitrophenyl) naphthalen-1-amine was used instead of 9-phenyl-9H-carbazol- 2-nitrophenyl) -1H-benzo [g] indole.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.26 (d, 1H), 7.45 (t, 1H), 7.66 (t, 1H), 7.73 (d, 1H), 7.81 (d, 1H), 7.89 ( (d, IH), 8.09 (d, IH), 10.15 (s, IH)

<Step 4> Synthesis of 9- (2-nitrophenyl) -1-phenyl-1H-benzo [g] indole

Step 3 of Preparation Example 1 was repeated except that 9- (2-nitrophenyl) -1H-benzo [g] indole was used instead of 6- (2-nitrophenyl) (2-nitrophenyl) -1-phenyl-1H-benzo [g] indole was obtained.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.26 (d, 1H), 7.45 (m, 2H), 7.50 (d, 2H), 7.57 (t, 2H), 7.66 (t, 1H), 7.73 ( (d, IH), 7.81 (d, IH), 7.89 (d,

<Step 5> Synthesis of IC-10

Except that 9- (2-nitrophenyl) -1-phenyl-1H-benzo [g] indole was used in place of 6- (2-nitrophenyl) 1 < Step 4 > to obtain IC-10.

^{1 H-NMR: δ 6.43 (} d, 1H), 7.25 (d, 1H), 7.44 (m, 2H), 7.51 (d, 2H), 7.56 (d, 1H), 7.65 (d, 1H), 7.72 ( (d, 1H), 7.80 (d, 1H), 7.90 (d, 2H), 7.95

[Preparation Example 11] Synthesis of IC-11

<Step 1> Synthesis of 6- (2-nitronaphthalen-1-yl) -1H-benzo [g] indole

6-bromo-1H-benzo [ g] indole (30 g, 121.90 mmol), 2-nitronaphthalen-1-ylboronic acid (31.74 g, 146.28 mmol), Pd (PPh 3) 4 (7.04 g, 5 mol%), (2-nitronaphthalen-1-ylamine) was obtained in the same manner as in <Step 2> of Preparation Example 1, using K ₂ CO ₃ (50.54 g, 365.70 mmol) and THF / H ₂ O -1-yl) -1H-benzo [g] indole (31.34 g, yield 76%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.59 (m, 2H), 7.80 (m, 2H), 8.04 (d, 1H), 8.12 (d, 1H), 8.24 ( (d, IH), 8.34 (d, IH), 8.43 (d,

<Step 2> Synthesis of 6- (2-nitronaphthalen-1-yl) -1-phenyl-1H-benzo [g]

Except that 6- (2-nitronaphthalen-1-yl) -1H-benzo [g] indole was used in place of 6- (2-nitrophenyl) -1H- 3] was carried out to obtain 6- (2-nitronaphthalen-1-yl) -1-phenyl-1H-benzo [g] indole.

^{1 H-NMR: δ 6.44 (} d, 1H), 7.26 (d, 1H), 7.45 (m, 1H), 7.50 (d, 2H), 7.58 (m, 4H), 7.81 (m, 2H), 8.02 ( (d, IH), 8.11 (d, IH), 8.23 (d, 2H), 8.32

<Step 3> Synthesis of IC-11

Except that 6- (2-nitronaphthalen-1-yl) -1-phenyl-1H-benzo [g] indole was used instead of 6- (2-nitrophenyl) -1-phenyl- , &Lt; Step 4 > of Preparation Example 1 was performed to obtain IC-11.

^{1 H-NMR: δ 6.46 (} d, 1H), 7.27 (d, 1H), 7.44 (m, 1H), 7.51 (d, 2H), 7.61 (m, 4H), 7.80 (m, 2H), 8.01 ( (d, IH), 8.10 (d, IH), 8.22 (d, 2H), 8.31

[Preparation Example 12] Synthesis of IC-12

Synthesis of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [g] indole

Indole (30 g, 121.90 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi Dioxane (800 ml), Pd (dppf) Cl ₂ (4.98 g, 5 mol%), KOAc (35.89 g, 365.70 mmol), and 1,3-dioxaborolane (37.15 g, 146.28 mmol) Were mixed and stirred at 130 ° 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 purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 6- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-benzo [g] indole (26.45 g, yield 74%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.45 (d, 1H), 7.28 (d, 2H), 7.56 (d, 2H), 8.08 (d, 1H), 8.12 (d, 1H), 10.12 ( s, 1 H)

<Step 2> Synthesis of 6- (5-bromo-2-nitrophenyl) -1H-benzo [g] indole

2-yl) -1H-benzo [g] indole (25 g, 85.27 mmol), 2,4-dibromo-1-nitrobenzene using (28.74 g, 102.33 mmol), Pd (PPh 3) 4 (4.93 g, 5 mol%), K 2 CO 3 (35.36 g, 255.82 mmol) and _{THF / H 2 O (500 ml} / 200 ml) , 5-bromo-2-nitrophenyl) -1 H-benzo [g] indole (13.46 g, yield 43%) was obtained in the same manner as in <Step 2> of Preparation Example 1.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 8.12 (d, 1H), 7.57 (d, 1H), 7.72 (s, 1H), 7.98 (d, 1H), 8.21 ( 1H), 8.42 (d, 1H), 7.61 (t, 1H), 8.04

Step 3 Synthesis of 6- (5-bromo-2-nitrophenyl) -1-phenyl-1H-benzo [g] indole

Except that 6- (5-bromo-2-nitrophenyl) -1H-benzo [g] indole was used in place of 6- (2-nitrophenyl) -1H- 3] was performed to obtain 6- (5-bromo-2-nitrophenyl) -1-phenyl-1H-benzo [g] indole.

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.45 (m, 1H), 7.50 (d, 2H), 7.61 (t, 2H), 8.12 (d, 1H), 7.57 ( (d, IH), 7.72 (s, IH), 7.98 (d, IH), 8.21

<Step 4> Synthesis of 9-bromo-3-phenyl-3,6-dihydroindolo [7,6-c] carbazole

Except that 6- (5-bromo-2-nitrophenyl) -1-phenyl-1H-benzo [g] indole was used instead of 6- (2-nitrophenyl) Bromo-3-phenyl-3,6-dihydroindolo [7,6-c] carbazole was obtained in the same manner as in <Step 4> of Preparation Example 1 above.

^{1 H-NMR: δ 6.51 (} d, 1H), 7.43 (m, 2H), 7.51 (d, 3H), 7.59 (m, 3H), 7.64 (d, 2H), 7.88 (d, 1H), 8.05 ( s, 1 H), 8.43 (d, 1 H), 11.70 (s, 1 H)

<Step 5> Synthesis of IC-12

Except that 9-bromo-3-phenyl-3,6-dihydroindolo [7,6-c] carbazole was used in place of 6- (2-nitrophenyl) -1H- IC-12 was obtained by performing the same procedure as in < Step 3 >.

^{1 H-NMR: δ 6.50 (} d, 1H), 7.41 (m, 3H), 7.50 (m, 5H), 7.57 (m, 5H), 7.65 (d, 2H), 7.89 (d, 1H), 8.06 ( s, 1 H), 8.41 (d, 1 H)

[Preparation Example 13] Synthesis of IC-13

Synthesis of 1- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-benzo [g] indole

Indole (20 g, 69.37 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (28.61 g, , 83.25 mmol), Pd (OAc ) 2 (0.78 g, 5 mol%), NaO (t-bu) (16.67 g, 173.43 mmol), P (t-bu) 3 (1.40 g, 3.47 mmol) and Toluene ( 500 ml) were mixed and stirred at 110 ° C for 12 hours. The reaction was extracted with ethyl acetate and then terminated, and then remove the water with MgSO ₄ and purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to give 1- (3- (4,6-diphenyl- 1,3,5-triazin-2-yl) phenyl) -6- (2-nitrophenyl) -1H-benzo [g] indole (28.10 g, yield 68%).

GC-Mass (theory: 595.20 g / mol, measured: 595 g / mol)

<Step 2> Synthesis of IC-13

(4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -6- (2-pyridyl) IC-13 was obtained in the same manner as in <Step 4> of Preparation Example 1 except that 2-nitrophenyl-1H-benzo [g] indole was used.

GC-Mass (calculated: 563.21 g / mol, measured: 563 g / mol)

[Preparation Example 14] Synthesis of IC-14

<Step 1> Synthesis of 1- (4,6-diphenylpyridin-2-yl) -6- (2-nitrophenyl) -1H-benzo [g] indole

(4,6-diphenylpyridin-2-yl) -6- (4-methylphenyl) pyridine was prepared by following the procedure of Step 3 of Preparation Example 1, except that 2-bromo-4,6-diphenylpyridine was used in place of iodobenzene. (2-nitrophenyl) -1H-benzo [g] indole.

GC-Mass (calculated: 517.18 g / mol, measured: 517 g / mol)

<Step 2> Synthesis of IC-14

(4-diphenylpyridin-2-yl) -6- (2-nitrophenyl) -1H-benzo [g] indole instead of 6- (2-nitrophenyl) IC-14 was obtained by carrying out the same procedure as < Step 4 >

GC-Mass (calculated: 485.19 g / mol, measured: 485 g / mol)

[Preparation Example 15] Synthesis of IC-15

<Step 1> Synthesis of 6- (2-nitrophenyl) -1-o-tolyl-1H-benzo [g] indole

2-nitrophenyl) -1-o-tolyl-1H-benzo [b] thiophene was carried out by following the procedure of Step 3 of Preparation Example 1, except that 1-iodo-2- g] indole.

^{1 H-NMR: δ 1.92 (} s, 3H), 6.52 (d, 1H), 7.22 (d, 1H), 7.33 (t, 1H), 7.39 (t, 1H), 7.48 (d, 1H), 7.60 ( 2H), 8.12 (d, 2H), 7.87 (m, 2H)

<Step 2> Synthesis of IC-15

Except that 6- (2-nitrophenyl) -1-o-tolyl-1H-benzo [g] indole was used instead of 6- (2-nitrophenyl) IC-15 was obtained by carrying out the same procedure as <Step 4> of Preparation Example 1.

^{1 H-NMR: δ 1.91 (} s, 3H), 6.53 (d, 1H), 7.23 (d, 1H), 7.34 (t, 1H), 7.40 (t, 1H), 7.50 (d, 1H), 7.61 ( 2H), 8.14 (d, 1H), 10.67 (s, 1H), 8.08 (d,

[Synthesis Example 1] Synthesis of Inv-1

2-bromo-4,6-diphenylpyridine (4.20 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol) mmol), Na ₂ SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene (100 ml) were mixed and stirred at 200 ° C for 24 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 = 1: 1 (v / v)) to obtain the target compound Inv-1 (2.74 g, yield 54%).

GC-Mass (calculated: 561.22 g / mol, measured: 561 g / mol)

[Synthesis Example 2] Synthesis of Inv-2

Under nitrogen, 0.32 g (13.54 mmol) of NaH was added to 50 ml of DMF and stirred. 3 g (9.03 mmol) of IC-1 dissolved in 50 ml of DMF was added slowly and stirred for about 1 hour. Then 3.62 g (13.54 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine dissolved in 100 ml of DMF was added slowly and stirred for 12 hours. After completion of the reaction, the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed to obtain the objective compound Inv-2 (3.87 g, yield 76%).

GC-Mass (calculated: 563.21 g / mol, measured: 563 g / mol)

[Synthesis Example 3] Synthesis of Inv-3

(3 g, 9.03 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.72 g, 10.83 mmol), Pd (OAc) ₂ g, 5 mol%), NaO (t-bu) (2.17 g, 22.56 mmol), P (t-bu) 3 (0.18 g, 0.90 mmol) and a mixture of Toluene (100 ml) and for 12 hours at 110 ℃ Lt; / RTI &gt; 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 = 2: 1 (v / v)) to obtain 4.0 g of the objective compound Inv-3 %).

GC-Mass (calculated: 639.24 g / mol, measured: 639 g / mol)

[Synthesis Example 4] Synthesis of Inv-4

(3.18 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), IC-1 (3 g, 9.03 mmol), 6-bromo-2,3'-bipyridine , using _{Na 2 SO 4 (1.28 g,} 9.03 mmol), nitrobenzene (100 ml), was obtained in Inv-4 (2.28 g, yield 52%) of the target compound in the same manner as in synthesis example 1.

GC-Mass (calculated: 486.18 g / mol, measured: 486 g / mol)

[Synthesis Example 5] Synthesis of Inv-5

IC-1 (3 g, 9.03 mmol), 3-bromo-9-phenyl-9H-carbazole (4.36 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K 2 CO 3 (1.25 g, 9.03 mmol _{), Na 2 SO 4 (1.28} g, using 9.03 mmol), nitrobenzene (100 ml ), was obtained in Inv-5 (3.11 g, yield 60%) of the target compound in the same manner as in synthesis example 1.

GC-Mass (calculated: 573.22 g / mol, measured: 573 g / mol)

[Synthesis Example 6] Synthesis of Inv-6

3-yl) -4,6-diphenyl-1,3,5-triazine (4.56 g, 10.83 mmol), Pd (OAc) ₂ (0.10 g, 5 mol%), NaO (t-bu) (2.17 g, 22.56 mmol), P (t-bu) ₃ (0.18 g, 0.90 mmol) and Toluene 3, the objective compound Inv-6 (4.39 g, yield 68%) was obtained.

GC-Mass (calculated: 715.27 g / mol, measured: 715 g / mol)

[Synthesis Example 7] Synthesis of Inv-7

(2.82 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), Na ₂ SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene (100 ml), the target compound Inv-7 (1.99 g, yield 48%) was obtained in the same manner as in Synthesis Example 1. [

GC-Mass (459.17 g / mol, measured: 459 g / mol)

[Synthesis Example 8] Synthesis of Inv-8

(3.72 g, 10.83 mmol), Pd (OAc) ₂ (0.10 g, 5 mmol), IC-2 (3 g, 9.03 mmol), 2- (4- chlorophenyl) -4,6- mol%), using NaO (t-bu) (2.17 g, 22.56 mmol), P (t-bu) 3 (0.18 g, 0.90 mmol) and Toluene (100 ml), in the same manner as in synthesis example 3 The target compound Inv-8 (3.87 g, yield 67%) was obtained.

GC-Mass (calculated: 639.24 g / mol, measured: 639 g / mol)

[Synthesis Example 9] Synthesis of Inv-9

Pd (OAc) ₂ (0.10 g, 5 mol%), NaO (t-Butylpyrimidine) (3.71 g, 10.83 mmol), IC- bu) (2.17 g, 22.56 mmol ), P (t-bu) 3 (0.18 g, 0.90 mmol) and Toluene (100 ml), the same method the desired compound Inv-9 (3.92 g in the above synthesis example 3 using , Yield 68%).

GC-Mass (calculated: 638.25 g / mol, measured: 638 g / mol)

[Synthesis Example 10] Synthesis of Inv-10

(3.16 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), Na ₂ SO ₄ using a (1.28 g, 9.03 mmol), nitrobenzene (100 ml), was obtained in Inv-10 (1.80 g, yield 41%) of the desired compound in the same manner as in synthesis example 1.

GC-Mass (calculated: 485.19 g / mol, measured: 485 g / mol)

[Synthesis Example 11] Synthesis of Inv-11

Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), IC-4 (3 g, 9.03 mmol), 4-bromo- N, N diphenylaniline (4.39 g, 13.54 mmol) using _{Na 2 SO 4 (1.28 g,} 9.03 mmol), nitrobenzene (100 ml), was obtained in Inv-11 (2.86 g, yield 55%) of the target compound in the same manner as in synthesis example 1.

GC-Mass (calculated: 575.24 g / mol, measured: 575 g / mol)

[Synthesis Example 12] Synthesis of Inv-12

(3.85 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), Na Inv-12 (2.32 g, yield 48%) was obtained in the same manner as in Synthesis Example 1, using _2- SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene (100 ml).

GC-Mass (calculated: 535.20 g / mol, measured: 535 g / mol)

[Synthesis Example 13] Synthesis of Inv-13

3-bromo-9- (4,6-diphenylpyridin-2-yl) -9H-carbazole (6.44 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), IC- Inv-4 (2.56 g, 0.032 mmol) was obtained in the same manner as in Synthesis Example 1, using K ₂ CO ₃ (1.25 g, 9.03 mmol), Na ₂ SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene , Yield 39%).

GC-Mass (calculated: 726.28 g / mol, measured: 726 g / mol)

[Synthesis Example 14] Synthesis of Inv-14

(3.72 g, 10.83 mmol), Pd (OAc) ₂ (0.10 g, 5 mmol), IC-5 (3 g, 9.03 mmol), 2- (4- chlorophenyl) -4,6- mol%), using NaO (t-bu) (2.17 g, 22.56 mmol), P (t-bu) 3 (0.18 g, 0.90 mmol) and Toluene (100 ml), in the same manner as in synthesis example 3 The target compound Inv-14 (3.75 g, yield 65%) was obtained.

GC-Mass (calculated: 639.24 g / mol, measured: 639 g / mol)

[Synthesis Example 15] Synthesis of Inv-15

(0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), IC-6 (3 g, 9.03 mmol), 4-bromo-2,6-diphenylpyridine (4.20 g, 13.54 mmol) Na ₂ SO ₄ using a (1.28 g, 9.03 mmol), nitrobenzene (100 ml), to obtain the desired compound of Inv-15 (1.77 g, yield 35%) in the same manner as in synthesis example 1.

GC-Mass (calculated: 561.22 g / mol, measured: 561 g / mol)

[Synthesis Example 16] Synthesis of Inv-16

(5.45 g, 13.54 mmol), Cu powder (0.06 g, 13.54 mmol), IC-6 (3 g, 9.03 mmol), 2- (3-bromo- _{0.90 mmol), K 2 CO 3} (1.25 g, 9.03 mmol), Na 2 SO 4 (1.28 g, 9.03 mmol), using the nitrobenzene (100 ml), the objective compound in the same manner as in synthesis example 1 Inv- 16 (2.36 g, yield 40%).

GC-Mass (calculated: 653.26 g / mol, measured: 653 g / mol)

[Synthesis Example 17] Synthesis of Inv-17

3-yl) -6- (3-chlorophenyl) -1,3,5-triazine (5.37 g, 10.83 mmol), Pd (OAc ) ₂ (0.10 g, 5 mol%), NaO (t-bu) (2.17 g, 22.56 mmol), P (t-bu) ₃ (0.18 g, 0.90 mmol) and Toluene In the same manner as in Synthesis Example 3, the desired compound Inv-17 (4.79 g, yield 67%) was obtained.

GC-Mass (calculated: 791.30 g / mol, measured: 791 g / mol)

[Synthesis Example 18] Synthesis of Inv-18

(3.00 g, 10.83 mmol), Pd (OAc) ₂ (0.10 g, 5 mmol), IC-7 (3 g, 9.03 mmol), 2- (3- chlorophenyl) -4,6- mol%), using NaO (t-bu) (2.17 g, 22.56 mmol), P (t-bu) 3 (0.18 g, 0.90 mmol) and Toluene (100 ml), in the same manner as in synthesis example 3 The target compound Inv-18 (3.41 g, yield 59%) was obtained.

GC-Mass (calculated: 640.24 g / mol, measured: 640 g / mol)

[Synthesis Example 19] Synthesis of Inv-19

3-yl) -4,6-diphenyl-1,3,5-triazine (6.29 g, 13.54 mmol), Cu powder (0.06 g, _{0.90 mmol), K 2 CO 3} (1.25 g, 9.03 mmol), Na 2 SO 4 (1.28 g, 9.03 mmol), using the nitrobenzene (100 ml), the objective compound in the same manner as in synthesis example 1 Inv- 19 (2.46 g, yield 38%).

GC-Mass (calculated: 715.27 g / mol, measured: 715 g / mol)

[Synthesis Example 20] Synthesis of Inv-20

D] imidazole (4.73 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ (4 g, Inv-20 (2.11 g, yield: 97%) was obtained in the same manner as in Synthesis Example 1, using the compound CO ₃ (1.25 g, 9.03 mmol), Na ₂ SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene 39%).

GC-Mass (theory: 600.23 g / mol, measurement: 600 g / mol)

[Synthesis Example 21] Synthesis of Inv-21

(3.16 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), Na Inv-21 (1.84 g, yield 42%) was obtained in the same manner as in Synthesis Example 1, using _2- SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene (100 ml).

GC-Mass (calculated: 485.19 g / mol, measured: 485 g / mol)

[Synthesis Example 22] Synthesis of Inv-22

2-chloro-4,6-diphenylpyrimidine (2.89 g, 10.83 mmol), Pd (OAc) ₂ (0.10 g, 5 mol%), NaO (t-Bu) g, 22.56 mmol), P ( t-bu) 3 (0.18 g, 0.90 mmol) and Toluene (100 ml), the same method the desired compound Inv-22 (3.66 g in the above synthesis example 3 using a yield of 72% ).

GC-Mass (calculated: 562.22 g / mol, measured: 562 g / mol)

[Synthesis Example 23] Synthesis of Inv-23

2-bromoquinoline (2.82 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), Na ₂ SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene (100 ml), the target compound Inv-23 (2.32 g, yield 56%) was obtained in the same manner as in Synthesis Example 1. [

GC-Mass (459.17 g / mol, measured: 459 g / mol)

[Synthesis Example 24] Synthesis of Inv-24

(3.85 g, 13.54 mmol), Cu powder (0.06 g, 0.90 mmol), K ₂ CO ₃ (1.25 g, 9.03 mmol), Na ₂ Inv-24 (2.56 g, yield 53%) was obtained in the same manner as in Synthesis Example 1, using SO ₄ (1.28 g, 9.03 mmol) and nitrobenzene (100 ml).

GC-Mass (calculated: 535.20 g / mol, measured: 535 g / mol)

[Synthesis Example 25] Synthesis of Inv-25

4-yl) -4,6-diphenyl-1,3,5-triazine (3.95 g, 9.41 mmol), Pd (OAc) ₂ (0.09 g, 5 mol%) , using NaO (t-bu) (1.88 g, 19.61 mmol), P (t-bu) 3 (0.16 g, 0.78 mmol) and Toluene (100 ml), the above synthesis example The target compound Inv-25 (3.90 g, yield 65%) was obtained in the same manner as in 3).

GC-Mass (calculated: 765.29 g / mol, measured: 765 g / mol)

[Synthesis Example 26] Synthesis of Inv-26

(3 g, 6.16 mmol), 3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenylboronic acid (2.61 g, 7.39 mmol) and K ₂ CO ₃ 2.55 g, 18.47 mmol) and THF / H ₂ O (a mixture of 100 ml / 50 ml), then insert the _{Pd (PPh 3) 4 (0.36} g, 5 mol%) at 40 ℃ stirred at 80 ℃ for 12 hours Respectively. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain the target compound Inv-26 (3.48 g, 79%).

GC-Mass (calculated: 715.27 g / mol, measured: 715 g / mol)

[Synthesis Example 27] Synthesis of Inv-27

IC-12 (3 g, 6.16 mmol), 4- (diphenylamino) phenylboronic acid (2.14 g, 7.39 mmol), Pd (PPh 3) 4 (0.36 g, 5 mol%), K 2 CO 3 (2.55 g, 18.47 Inv-27 (3.33 g, yield 83%) was obtained in the same manner as in Synthesis Example 26, using _2-

GC-Mass (calculated: 651.27 g / mol, measured: 651 g / mol)

[Synthesis Example 28] Synthesis of Inv-28

3-ylboronic acid (3.27 g, 7.39 mmol), Pd (3 g, 6.16 mmol), IC- with _{(PPh 3) 4 (0.36 g} , 5 mol%), K 2 CO 3 using a (2.55 g, 18.47 mmol) and _{THF / H 2 O (100 ml} / 50 ml), the same procedure as in synthesis example 26 The target compound Inv-28 (3.82 g, yield 77%) was obtained.

GC-Mass (theory: 804.30 g / mol, measurement: 804 g / mol)

[Synthesis Example 29] Synthesis of Inv-29

K ₂ CO ₃ (0.74 g, 5.32 mmol), Na ₂ SO ₄ (0.76 g, 0.53 mmol), IC powder (3 g, 5.32 mmol), iodobenzene (1.63 g, 5.32 mmol) and nitrobenzene (100 ml), Inv-29 (1.87 g, yield 55%) was obtained in the same manner as in Synthesis Example 1. [

GC-Mass (calculated: 639.24 g / mol, measured: 639 g / mol)

[Synthesis Example 30] Synthesis of Inv-30

Cu powder (0.03 g, 0.53 mmol), K ₂ CO ₃ (0.74 g, 5.32 mmol), IC-13 (3 g, 5.32 mmol), 1-bromo-3,5- , Na ₂ using _{SO 4 (0.76 g, 5.32 mmol} ), nitrobenzene (100 ml), was obtained in Inv-30 (1.81 g, yield 43%) of the target compound in the same manner as in synthesis example 1.

GC-Mass (calculated: 791.30 g / mol, measured: 791 g / mol)

[Synthesis Example 31] Synthesis of Inv-31

K ₂ CO ₃ (1.25 g, 6.18 mmol), Na ₂ SO ₄ (1.28 g, 0.62 mmol), IC powder 14 (3 g, 6.18 mmol), iodobenzene (1.89 g, 6.18 mmol) and nitrobenzene (100 ml), Inv-31 (2.08 g, yield 60%) was obtained in the same manner as in Synthesis Example 1. [

GC-Mass (calculated: 561.22 g / mol, measured: 561 g / mol)

[Synthesis Example 32] Synthesis of Inv-32

Cu powder (0.06 g, 0.62 mmol), K ₂ CO ₃ (1.25 g, 6.18 mmol), IC-14 (3 g, 6.18 mmol), 1-bromo-3,5- , Na ₂ SO ₄ using a (1.28 g, 6.18 mmol), nitrobenzene (100 ml), was obtained in Inv-32 (1.90 g, yield 43%) of the target compound in the same manner as in synthesis example 1.

GC-Mass (calculated: 713.28 g / mol, measured: 713 g / mol)

[Synthesis Example 33] Synthesis of Inv-33

(3.57 g, 10.39 mmol), Pd (OAc) ₂ (0.10 g, 5 mmol), IC-15 (3 g, 8.66 mmol), 2- (3- chlorophenyl) mol%), using NaO (t-bu) (2.08 g, 21.65 mmol), P (t-bu) 3 (0.18 g, 0.87 mmol) and Toluene (100 ml), in the same manner as in synthesis example 3 The target compound Inv-33 (3.62 g, yield 64%) was obtained.

GC-Mass (calculated: 653.26 g / mol, measured: 653 g / mol)

[Synthesis Example 34] Synthesis of Inv-34

3-yl) -4,6-diphenyl-1,3,5-triazine (4.36 g, 10.39 mmol), Pd (OAc) ₂ (0.10 g, 5 mol%), NaO (t-bu) (2.08 g, 21.65 mmol), P (t-bu) ₃ (0.18 g, 0.87 mmol) and Toluene The objective compound Inv-34 (3.73 g, yield 59%) was obtained in the same manner as in 3).

GC-Mass (calculated: 729.29 g / mol, measured: 729 g / mol)

[Examples 1 to 34] Fabrication of organic EL device

Each of the compounds Inv-1 to Inv-34 synthesized in Synthesis Examples 1 to 34 was subjected to high purity sublimation purification by a known method, and then a green organic EL device was manufactured according to the following procedure.

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

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / Inv-1 to Inv-34 + 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 are as follows.

[Comparative Example 1] Fabrication of organic EL device

An organic EL device was fabricated in the same manner as in Example 1 except that CBP was used instead of the compound Inv-1 as a luminescent host material in forming the light emitting layer.

[Evaluation example]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for each of the organic EL devices manufactured in Example 1-34 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 Inv-1 6.65 516 41.8 Example 2 Inv-2 6.63 517 40.7 Example 3 Inv-3 6.62 516 43.2 Example 4 Inv-4 6.65 516 43.5 Example 5 Inv-5 6.70 516 41.7 Example 6 Inv-6 6.67 516 41.1 Example 7 Inv-7 6.62 517 42.6 Example 8 Inv-8 6.83 517 39.6 Example 9 Inv-9 6.75 518 39.8 Example 10 Inv-10 6.72 518 39.3 Example 11 Inv-11 6.74 515 40.2 Example 12 Inv-12 6.62 516 41.0 Example 13 Inv-13 6.65 517 41.3 Example 14 Inv-14 6.81 518 39.7 Example 15 Inv-15 6.72 516 40.2 Example 16 Inv-16 6.63 517 41.3 Example 17 Inv-17 6.84 517 39.7 Example 18 Inv-18 6.63 516 40.5 Example 19 Inv-19 6.68 518 41.3 Example 20 Inv-20 6.64 517 41.5 Example 21 Inv-21 6.78 516 41.2 Example 22 Inv-22 6.65 517 40.5 Example 23 Inv-23 6.80 516 39.3 Example 24 Inv-24 6.81 515 39.6 Example 25 Inv-25 6.85 517 38.8 Example 26 Inv-26 6.75 516 39.6 Example 27 Inv-27 6.65 517 42.5 Example 28 Inv-28 6.67 518 41.0 Example 29 Inv-29 6.68 517 40.5 Example 30 Inv-30 6.71 517 41.4 Example 31 Inv-31 6.73 518 40.3 Example 32 Inv-32 6.69 518 40.2 Example 33 Inv-33 6.78 517 41.1 Example 34 Inv-34 6.83 516 39.5 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL device of Example 1-34, in which the compound (Inv-1 to Inv-34) according to the present invention was used as a light emitting layer, It can be seen that the EL device exhibits excellent performance in terms of efficiency and driving voltage.

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 (9)

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

In Formula 1,
At least one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is bonded to the following formula 2 to form a condensed ring;
(2)

In Formula 2,
At least one of R ₉ and R _10, R ₁₀ and R ₁₁ , and at least one of R ₁₁ and R ₁₂ is bonded to Formula 1 to form a condensed ring;
R ₁ to R ₁₂ which do not form a condensed ring are the same as or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl And a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, wherein R ₁ and R ₂ , R ₂ and R ₃ , or R ₃ and R ₄ combine to form a condensed ring In addition,
X ₁ and X ₂ are each independently N (Ar ₁ )
Y ₁ and Y ₂ are the same or different and are each independently selected from N and C (R ₁₃ )
R ₁₃ is a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms &Lt; / RTI &gt;
Ar ₁ is the same or different and is 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,
When the C ₁ to C ₄₀ alkyl group, the C ₆ to C ₄₀ aryl group, and the heteroaryl group having 5 to 40 nuclear atoms are substituted, each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ An aryl group, a heteroaryl group having 5 to 40 nuclear atoms, and an arylamine group having ₆ to ₄₀ carbon atoms. 2. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (20)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

In the above Chemical Formulas 3 to 20,
R ₁ to R _12, X ₁ and X ₂ , Y ₁ and Y ₂ are as defined in claim 1, respectively. The compound according to claim 1, wherein Y ₁ and Y ₂ are C (R ₁₃ )
R ₁₃ is a compound characterized in that each independently hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, and the number of nuclear atoms selected from the group consisting of 5 to 40 heteroaryl group of. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (21) to (38)
[Chemical Formula 21]

[Chemical Formula 22]

(23)

&Lt; EMI ID =

(25)

(26)

(27)

(28)

[Chemical Formula 29]

(30)

(31)

(32)

(33)

(34)

(35)

(36)

(37)

(38)

In the above Formulas 21 to 38,
R ₁ to R ₁₃ and Ar ₁ are the same as defined in claim ₁ , respectively. delete delete 2. A compound according to claim 1, wherein Ar &lt; ₁ &gt; is each independently selected from the following Substituent group.

A cathode, and at least one organic 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 4 or 7. The organic electroluminescent device according to claim 8, wherein at least one organic compound layer containing the compound is a light emitting layer.