KR20150030794A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescence device including the same. The organic compound of the present invention can be applied as a material for an organic electroluminescence device and preferably as a host material, so that the properties of the organic electroluminescence device such as light emitting efficiency, driving voltage, and life can be improved.

Description

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

The present invention relates to a novel organic compound that can be used as a material of an organic electroluminescent device, and an organic electroluminescent device including the same and having improved luminous efficiency, driving voltage, and life span of the device.

Studies on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') by blue electroluminescence using anthracene single crystals in 1965 have been carried out with reference to the observation of organic thin film luminosity 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. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies 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. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of light emission characteristics, but their thermal stability is lowered 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) or (2):

In the above Formulas 1 and 2,

Cy1 and Cy2 are the same or different and are each independently selected from the group consisting of C ₆ to C ₄₀ aromatic rings and heteroaromatic rings having 5 to 40 nuclear atoms,

R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl An amino group, 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 aryl boron group, by combining C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent group to form a condensed ring In addition,

X ₁ and X ₂ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ With the proviso that at least one of X ₁ and X ₂ is N (Ar ₁ )

Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group , A 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 C ₄₀ arylphosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of the group consisting of aryl silyl,

C ₆ to C ₄₀ aromatic rings of Cy 1 and Cy 2, heteroaromatic rings of 5 to 40 nuclear atoms, R ₁ to R ₄ And C ₁ to C ₄₀ alkyl groups of Ar ₁ to Ar ₅ , C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₄₀ aryl groups, heteroatoms having 5 to 40 nuclear atoms An aryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ aryl The phosphine oxide group and the C ₆ to C ₄₀ arylsilyl groups are each independently selected from the group consisting of deuterium (D), halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl an amine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl , 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 aryl of C ₆ ~ C ₄₀ And a silyl group, provided that when the substituent is plural, they may be the same or different from each other.

The organic electroluminescent device according to the present invention includes a cathode, an anode, 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 represented by the general formula A light emitting device is provided.

At least one of the organic layers including the compound of Formula 1 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. Preferably, The compound represented by the formula (1) is a blue, green or red phosphorescent host material.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence property and can be used as an organic material layer material of an organic electroluminescent device.

In particular, when the compound represented by the general formula (1) is used as a phosphorescent host material in the light emitting layer, an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, Further, a full color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compounds according to the present invention are particularly suitable for the preparation of fused aromatic rings or heteroaromatic rings at the ends of indenoindole moieties, indoloindole moieties or benzothianoindole moieties, ), Which has a basic skeleton and various substituents bonded to the basic skeleton, and is represented by the above formula (1) or (2).

The compound represented by Chemical Formula 1 or Chemical Formula 2 not only has a wide bandgap, but also has a bipolar property as a whole due to various aromatic ring substituents, so that the bonding force between holes and electrons can be enhanced. Accordingly, the compound represented by the above formula (1) or (2) can improve the phosphorescence property of the organic EL device and improve the hole injecting ability, transporting ability, or light emitting efficiency.

In addition, since the aromatic ring substituent introduced into the basic skeleton significantly increases the molecular weight of the compound, the glass transition temperature can be improved, which makes it possible to increase the molecular weight of the compound of the present invention, which is higher than that of conventional 4,4-dicarbazolylbiphenyl And may have thermal stability. When the compound represented by Formula 1 or 2 is contained in an organic material layer such as a light emitting layer, the organic EL device including the compound is effective in suppressing crystallization of the organic material layer due to the various aromatic ring substituents. Therefore, Can be greatly improved.

In addition, the compound represented by the formula (1) or (2) of the present invention can be used as a material for the hole injection / transport layer of the organic EL device or as a blue, green and / or red phosphorescent host material It is possible to exert an excellent effect in terms of the efficiency (for example, current efficiency, luminous efficiency) and life span of the device compared to the conventional CBP. Therefore, the compound according to the present invention can greatly contribute to the improvement of the performance and the life of the organic EL device, and in particular, the lifetime of the organic EL device is greatly improved in maximizing the performance of the full-color organic EL panel.

In the compounds represented by Chemical Formulas 1 and 2, Cy1 and Cy2 are the same or different from each other, and each independently selected from the group consisting of C ₆ to C ₄₀ aromatic rings and heteroaromatic rings having 5 to 40 nuclear atoms .

The C ₆ to C ₄₀ aromatic rings and the heteroaromatic rings having 5 to 40 nuclear atoms of the Cy 1 and Cy 2 are each independently selected from the group consisting of deuterium (D), halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to 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, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, an alkyl of C ₁ ~ C ₄₀ boron group, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C is selected from the ₄₀ arylsilyl group the group consisting of 1 When the substituent is plural, they may be the same or different and may form an aromatic ring or a heteroaromatic ring with an adjacent group. can do.

Examples of the C ₆ to C ₄₀ aromatic rings include, but are not limited to, benzene, indene, naphthalene, fluorene, anthracene, phenanthrene, naphthacene, pyrene and triphenylene.

The heteroaromatic ring having 5 to 40 nuclear atoms may be, but is not limited to, furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, thiazole, triazole, thiadiazole, oxadiazole , Pyridine, pyrimidine, triazine, indole, benzofuran, benzothiophene, benzoimidazole, benzothiazole, purine, quinoline, isoquinoline, quinoxaline, carbazole, dibenzothiophene, dibenzofuran, Dean, phenanthroline, and the like.

More specifically, it is most preferable that Cy1 and Cy2 are the same or different from each other and each independently selected from the group consisting of benzene, thiophene and thioindole.

Preferably, R ₁ to R ₄ and Ra are the same or different and each independently represents hydrogen, deuterium (D), a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, and C ₆ To C ₄₀ arylamine groups.

Also, R ₁ To R ₄ And Ra may be the same or different from each other, and each independently may be selected from the group consisting of hydrogen or the substituents represented by the following S1 to S222.

R ₁ to R ₄ And Ra of a C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, and a C ₆ ~ C ₄₀ group of arylamine each independently a heavy hydrogen (D), a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C ₄₀ of aryloxy A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl 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 And arylsilyl group, and when the substituent is plural, they may be the same as or different from each other.

X ₁ and X ₂ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ At least one of which is N (Ar ₁ ).

X ₁ and X ₂ are the same or different and are each independently selected from the group consisting of S, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ ).

According to one embodiment of the present invention, in the case where X ₁ is S or _{C (Ar 2) (Ar 3} ), X 2 is N (Ar _1), if X ₁ is N (Ar _1), X ₂ is S, N (Ar ₁ ) or C (Ar ₂ ) (Ar ₃ ).

The above-mentioned Ar ₁ to Ar ₅ are the same or different from each other and independently selected from the group consisting of an aryl group of C ₆ to C ₄₀ or a heteroaryl group of 5 to 40 nucleus atoms in consideration of the characteristics of the organic EL device .

In Ra and Ar ₁ to Ar ₅ , 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, to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 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 group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ arylphosphine oxide group and C ₆ to C ₄₀ arylsilyl group are each independently selected from the group consisting of deuterium (D), halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₄₀ heterocycloalkyl group of the arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ Alkyl silyl 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 arylsilyl group, and the like. At this time, when there are a plurality of substituents, they may be the same or different.

More preferably, the Ar &lt; _{1 &gt;} To Ar ₅ are the same or different and are each independently a C ₁ to C ₄₀ alkyl group or may be selected from the substituent groups represented by S 1 to S 222.

The formula (1) or (2) of the present invention can be more specifically represented by the following formulas (C-1) to (C-32).

In the above formulas C-1 to C-32,

Ar ₁ to Ar ₅ and R ₁ to R ₄ are the same as defined in Formula 1 or Formula 2,

Ra is a group selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ An arylamine group, 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 aryl boron group, C ₆ ~ C ₄₀ of an aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from the group consisting arylsilyl or in, or near the condensed ring groups bonded to the Lt; / RTI &gt;

n, m is an integer of 0 to 4, and 1 is an integer of 0 to 2.

More specific examples of the compounds represented by Formula 1 or Formula 2 include compounds consisting of the following Inv 1 to Inv 628, but are not limited thereto.

"Alkyl" in the present invention is a monovalent substituent derived from a linear 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, but are not limited thereto.

"Alkenyl" in the present invention 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, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

The term "alkynyl" in the present invention 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.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls 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. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . &Lt; / RTI &gt; Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

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

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon, preferably 1 to 3 carbons, of the ring is replaced by N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

"Alkylsilyl" in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

The "fused ring" in the present invention 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 in various ways with reference to the following Synthesis Examples. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

<Organic Field  Light emitting element>

The present invention provides an organic electroluminescent device comprising a compound represented by the above-mentioned formula (1) or (2).

Specifically, the organic electroluminescent device according to the present invention includes an anode, 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 (1) or (2). At this time, the compounds may be used alone or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of the organic layers may include a compound represented by Formula 1 or Formula 2 . Preferably, the organic compound layer containing the compound of Formula 1 or Formula 2 may be a light emitting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, which may include the compound of Formula 1 or Formula 2 as a host material. When the compound of Formula 1 or Formula 2 is contained in the light emitting layer material of the organic electroluminescent device, preferably blue, green, or red phosphorescent host material, the bonding strength between holes and electrons in the light emitting layer increases, The efficiency (luminous efficiency and power efficiency), lifetime, luminance and driving voltage of the light emitting device can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1 or Formula 2, And the like. Specifically, the compound of Formula 1 or Formula 2 can be used as a phosphorescent host material 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 can be formed by using a material and a method 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 Chemical Formula 1 or Chemical Formula 2 To form another organic material 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 a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

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

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

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

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

[ Preparation Example  One] IC Synthesis of -1

<Step 1> 2- bromophenanthro [9,10-b] thiophene

2,3,5-tribromothiophene (20 g, 62.34 mmol), 5,5-dimethyl-5H-dibenzo [b, d] stannole (18.76 g, 62.34 mmol), Pd (PtBu ₃ ) ₂ , 3.12 mmol), CsF (47.35 g, 311.69 mol) and THF (500 ml) were mixed and stirred at 60 ° C for 12 hours.

After the reaction was completed, the temperature was lowered to room temperature. The reaction mixture was filtered through a florisil, and the solvent was removed. The residue was purified by column chromatography (Hexane: MC = 10: 1 (v / v)) to obtain 2-bromophenanthro [ b] thiophene (6.25 g, yield 32%).

^{1 H-NMR: δ7.61 (m} , 4H), 7.88 (s, 1H), 7.94 (d, 1H), 8.15 (d, 1H), 8.65 (d, 2H)

<Step 2> Synthesis of 2- (2- nitrophenyl ) phenanthro [9,10-b] thiophene Synthesis of

2-Nitrophenylboronic acid (3.84 g, 22.99 mmol) and 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) obtained in the above Step 1 and K ₂ CO ₃ (7.94 g, 57.47 mmol) and THF / H ₂ O (a mixture of 100 ml / 50 ml), then insert the _{Pd (PPh 3) 4 (1.11} 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: MC = 5: 1 (v / v)) to obtain 4.29 g (yield 63%) of 2- (2-nitrophenyl) phenanthro [9,10- ).

^{1 H-NMR: δ7.41 (t} , 1H), 7.63 (m, 5H), 7.73 (s, 1H), 7.75 (d, 1H), 7.85 (d, 1H), 7.92 (d, 1H), 8.14 (d, 1 H), 8.62 (d, 2 H)

<Step 3> IC Synthesis of -1

(2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 11.25 mmol), triphenylphosphine (7.38 g, 28.14 mmol) and 1,2- dichlorobenzene ml) were mixed and 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 = 5: 1 (v / v)) to obtain IC-1 (2.04 g, yield 56%).

^{1 H-NMR: δ7.37 (m} , 2H), 7.62 (m, 5H), 7.89 (d, 1H), 7.91 (d, 1H), 8.12 (d, 1H), 8.60 (d, 2H), 11.32 (s, 1 H)

[ Preparation Example  2] IC Synthesis of -2

<Step 1> Synthesis of N- (2- bromophenyl ) phenanthro [9,10-b] thiophen -2- amine Synthesis of

2-bromophenanthro [9,10-b] thiophene (20.03 g, 63.95 mmol), 2-bromoaniline (10 g, 58.13 mmol), Pd (OAc) ₂ (0.65 g, 5 mol%), BINAP g, 7.5 mol%), t-BuONa (7.82 g, 81.39 mmol) and toluene (200 ml) were added and stirred at 100 ° C for 20 hours.

After completion of the reaction, the reaction mixture was extracted with dichloromethane. The obtained organic layer was washed with MgSO ₄ and purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain N- (2-bromophenyl) phenanthro [9,10-b] thiophen- -amine (9.17 g, yield 39%).

^{1 H-NMR: δ7.42 (t} , 1H), 7.62 (m, 5H), 7.71 (d, 1H), 7.73 (d, 1H), 7.87 (s, 1H), 7.93 (d, 1H), 8.15 (d, 1 H), 8.63 (d, 2H), 11.28 (s, 1 H)

<Step 2> IC Synthesis of -2

Phenanthro [9,10-b] thiophen-2-amine (9 g, 22.26 mmol), Pd (OAc) ₂ (0.5 g, 10 mol%), Na2CO3 (3.30 g, 2.23 mmol) and DMF (100 ml) were refluxed for 2 hours.

After completion of the reaction, the reaction mixture was extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO ₄ and purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IC-2 (3.82 g, yield 53%).

^{1 H-NMR: δ7.35 (m} , 2H), 7.64 (m, 5H), 7.87 (d, 1H), 7.92 (d, 1H), 8.15 (d, 1H), 8.62 (d, 2H), 11.31 (s, 1 H)

[ Preparation Example  3] IC Synthesis of -3

<Step 1> 2- bromo -1H- dibenzo Synthesis of [e, g] indole

Step 1> of Preparation Example 1 was repeated except that 2,3,5-tribromo-1H-pyrrole (20 g, 65.84 mmol) was used instead of 2,3,5-tribromothiophene (20 g, The same procedure was followed to obtain 2-bromo-1H-dibenzo [e, g] indole (6.04 g, yield 31%).

^{1 H-NMR: δ 7.63 (} m, 4H), 7.82 (s, 1H), 7.92 (d, 1H), 8.13 (d, 1H), 8.61 (d, 2H), 11.30 (s, 1H)

<Step 2> Synthesis of 2- (2- nitrophenyl ) -1H- dibenzo Synthesis of [e, g] indole

Except that 2-bromo-1H-dibenzo [e, g] indole (6 g, 20.26 mmol) was used in place of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) (2-nitrophenyl) -1H-dibenzo [e, g] indole (4.04 g, yield 59%).

^{1 H-NMR: δ7.43 (t} , 1H), 7.62 (m, 5H), 7.75 (m, 2H), 7.85 (d, 1H), 7.94 (d, 1H), 8.15 (d, 1H), 8.63 (d, 2 H), 11.28 (s, 1 H)

<Step 3> Synthesis of 2- (2- nitrophenyl )-One- phenyl -1H- dibenzo Synthesis of [e, g] indole

(2-nitrophenyl) -1H-dibenzo [e, g] indole (4 g, 11.82 mmol), iodobenzene (3.62 g, 17.73 mmol) and Cu powder (0.08 g, 1.18 mmol), K ₂ CO ₃ (1.63 g, 11.82 mmol), Na ₂ SO ₄ (1.68 g, 11.82 mmol) and nitrobenzene (50 ml) were mixed and stirred at 200 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 2- (2-nitrophenyl) indole (2.06 g, yield 42%).

^{1 H-NMR: δ 7.42 (} m, 2H), 7.51 (t, 2H), 7.60 (m, 7H), 7.72 (m, 2H), 7.83 (d, 1H), 7.91 (d, 1H), 8.13 ( d, 1 H), 8.62 (d, 2 H)

<Step 4> IC - 3 of  synthesis

1-phenyl-1H-dibenzo [e, g] indole (2 g, 4.83 mmol) instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene mmol), IC-3 (1.11 g, yield 60%) was obtained in the same manner as in <Step 3> of Preparation Example 1 above.

^{1 H-NMR: δ7.41 (m} , 2H), 7.50 (t, 2H), 7.59 (m, 7H), 7.70 (d, 1H), 7.81 (d, 1H), 7.92 (d, 1H), 8.14 (d, 1 H), 8.63 (d, 2H), 11.32 (s, 1 H)

[ Preparation Example  4] IC Synthesis of -4

<Step 1> 2- bromo -One- phenyl -1H- dibenzo Synthesis of [e, g] indole

Except that 2-bromo-1H-dibenzo [e, g] indole (15 g, 50.65 mmol) was used instead of 2- (2-nitrophenyl) -1H-dibenzo [e, g] indole 1-phenyl-1H-dibenzo [e, g] indole (7.54 g, yield 40%) was obtained in the same manner as in <Step 3> of Preparation Example 3.

^{1 H-NMR: δ7.42 (m} , 1H), 7.50 (t, 2H), 7.56 (t, 2H), 7.64 (m, 4H), 7.83 (s, 1H), 7.91 (d, 1H), 8.14 (d, 1 H), 8.62 (d, 2 H)

<Step 2> Synthesis of N- (2- bromophenyl )-One- phenyl -1H- dibenzo [e, g] indole-2- amine Synthesis of

Except that 2-bromo-1-phenyl-1H-dibenzo [e, g] indole (7.5 g, 20.15 mmol) was used in place of 2-bromophenanthro [9,10-b] thiophene (20.03 g, 63.95 mmol) 1H-dibenzo [e, g] indol-2-amine (3.14 g, yield 37%) was obtained in the same manner as in <Step 1> of Preparation Example 2 .

^{1 H-NMR: δ 7.42 (} m, 2H), 7.51 (m, 3H), 7.56 (m, 2H), 7.64 (m, 5H), 7.83 (s, 1H), 7.91 (d, 1H), 8.14 ( d, 1 H), 8.62 (d, 2H), 11.30 (s, 1 H)

<Step 3> IC Synthesis of -4

(2-bromophenyl) -1-phenyl-1H-dibenzo [e, g] indole-2-carboxylic acid in place of N- (2-bromophenyl) phenanthro [9,10b] thiophen- (1.29 g, yield 52%) was obtained in the same manner as in <Step 2> of Preparation Example 2 except that 2-amine (3 g, 6.47 mmol) was used.

^{1 H-NMR: δ7.41 (m} , 2H), 7.52 (m, 3H), 7.56 (m, 2H), 7.65 (m, 5H), 7.90 (d, 1H), 8.12 (d, 1H), 8.61 (d, 2 H), 11.29 (s, 1 H)

[ Preparation Example  5] IC Synthesis of -5

&Lt; Step 1 > 2- (2- ( 메틸 시ulfinyl ) phenyl ) -1H- dibenzo Synthesis of [e, g] indole

2-bromo-1H-dibenzo [e, g] indole (10 g, 20 mmol) was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.15 mmol) and 2-nitrophenyl boronic acid 33.77 mmol) and 4,4,5,5-tetramethyl-2- (2- (methylsulfinyl) phenyl) -1,3,2-dioxaborolane (10.78 g, 40.52 mmol) (Methylsulfinyl) phenyl] -1H-dibenzo [e, g] indole (7.56 g, yield 65%).

^{1 H-NMR: δ7.42 (t} , 1H), 7.56 (m, 2H), 7.63 (m, 3H), 7.74 (m, 2H), 7.85 (d, 1H), 7.92 (d, 1H), 8.14 (d, 1 H), 8.62 (d, 2H), 11.32 (s, 1 H)

<Step 2> IC Synthesis of -5

(Methylsulfinyl) phenyl] -1H-dibenzo [e, g] indole (7.5 g, mmol) obtained in the above Step 1 was added to CF ₃ SO ₃ H (100 ml) under a nitrogen stream, Lt; / RTI &gt; After 48 h, the reaction was slowly added to water-pyridine (1.2 ml, 5: 1) and refluxed for 12 h. The temperature was lowered to room temperature and the resulting solid was filtered to obtain IC-5 (5.42 g, yield 75%).

^{1 H-NMR: δ7.42 (t} , 1H), 7.63 (m, 5H), 7.74 (d, 1H), 7.85 (d, 1H), 7.92 (d, 1H), 8.14 (d, 1H), 8.62 (d, 2 H), 11.32 (s, 1 H)

[ Preparation Example  6] IC Synthesis of -6

&Lt; Step 1 > 2- (2- isopropylphenyl ) -1H- dibenzo Synthesis of [e, g] indole

2-bromo-1H-dibenzo [e, g] indole (10 g, 20 mmol) was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.15 mmol) and 2-nitrophenyl boronic acid (2-isopropylphenyl) -lH-dibenzo [e (2-isopropylphenyl) boronic acid was obtained by following the procedure of Step 2 of Preparation Example 1, , g] indole (6.68 g, yield 59%).

^{1 H-NMR: δ1.20 (s} , 6H), 2.88 (s, 1H), 7.43 (t, 1H), 7.58 (m, 2H), 7.62 (m, 3H), 7.73 (m, 2H), 7.84 (d, IH), 7.91 (d, IH), 8.15 (d, IH), 8.63

<Step 2> IC Synthesis of -6

The <step 1> 2- (2-isopropylphenyl) -1H-dibenzo [e, g] indole (6 g, 17.89 mmol) and _{RhCl (PPh 3) 3 (82.75} mg, 0.5 mol%) obtained in a nitrogen stream 1,4-dioxane (50 ml), and the mixture was stirred at 135 ° C for 3 hours.

After completion of the reaction, the solvent was removed and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v: v)) to obtain IC-6 (4.59 g, yield 77%).

^{1 H NMR: δ1.22 (s,} 6H), 7.40 (t, 1H), 7.56 (d, 1H), 7.63 (m, 3H), 7.71 (m, 2H), 7.83 (d, 1H), 7.92 ( (d, IH), 8.16 (d, IH), 8.62 (d, 2H), 11.32

[ Preparation Example  7] IC Synthesis of -7

<Step 1> IC Synthesis of -7-4

Naphthalene-2,3-diol (50 g, 312.17 mmol) and 2-mercaptoethanol (262.73 ml, 3.75 mol) were added to 1000 ml of chlorobenzene under nitrogen flow and stirred. TfOH (138.12 ml, 1.56 mol) was slowly added at room temperature and refluxed. After 6 hours, the temperature was lowered and the reaction was terminated by adding 5% NaOH. The organic layer was separated with methylene chloride and the water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 10: 1 (v / v)) to obtain IC-7-4 (23.65 g, yield 31%).

^{1 H-NMR: δ3.65 (m} , 8H), 7.39 (m, 2H), 7.64 (m, 2H)

<Step 2> IC Synthesis of -7-3

IC-7-4 (20 g, 81.84 mmol) and chloranil (72.25 g, 327.36 mmol) obtained in <Step 1> were added to toluene (400 ml) under a nitrogen stream and stirred at 100 ° C for 2 days.

After completion of the reaction, chloranil was removed by vacuum filtration, and the solvent was removed from the filtered filtrate and purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IC-7-3 %).

^{1 H-NMR: δ7.54 (d} , 2H), 7.65 (m, 2H), 8.02 (d, 2H), 8.39 (m, 2H)

<Step 3> IC Synthesis of -7-2

IC-7-3 (14.5 g, 60.33 mmol) obtained in the above Step 2 and NBS (11.81 g, 66.36 mmol) obtained in the above Step 2 were added to 200 ml of chloroform under reflux and refluxed for 12 hours.

After completion of the reaction, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 15: 1 (v / v)) to obtain IC-7-2 (11.75 g, yield 61%).

^{1 H-NMR: δ7.53 (d} , 1H), 7.67 (m, 2H), 8.04 (d, 1H), 8.12 (s, 1H), 8.41 (m, 2H)

<Step 4> IC Synthesis of -7-1

Except that IC-7-2 (11.5 g, 36.02 mmol) obtained in the above Step 3 was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) The same procedure as in <Step 2> was conducted to obtain IC-7-1 (7.03 g, yield 54%).

^{1 H-NMR: δ7.52 (d} , 1H), 7.68 (m, 3H), 7.96 (m, 2H), 8.04 (d, 2H), 8.13 (s, 1H), 8.43 (m, 2H)

<Step 5> IC Synthesis of -7

Step 1 of Preparation Example 1 was repeated except that IC-7-1 (7 g, 19.37 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-7 (3.76 g, yield 59%) was obtained.

^{1 H-NMR: δ7.53 (d} , 1H), 7.69 (m, 3H), 7.99 (m, 2H), 8.06 (d, 2H), 8.43 (m, 2H), 11.25 (s, 1H)

[ Preparation Example  8] IC Synthesis of -8

<Step 1> IC Synthesis of -8-2

The same procedure as in <Step 3> of Preparation Example 7 was conducted using IC-7-3 (20 g, 83.22 mmol) and NBS (32.58 g, 183.07 mmol) under a nitrogen stream to obtain IC- , Yield: 65%).

^{1 H-NMR: δ7.67 (d} , 2H), 8.13 (s, 2H), 8.42 (m, 2H)

<Step 2> IC Synthesis of -8-1

Except that IC-8-2 (20 g, 50.23 mmol) obtained in the above Step 3 was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) The same procedure as in <Step 2> was conducted to obtain IC-8-1 (10.17 g, yield 46%).

^{1 H-NMR: δ 7.66 (} m, 3H), 7.95 (m, 2H), 8.04 (d, 1H), 8.12 (s, 1H), 8.28 (s, 1H), 8.43 (m, 2H)

<Step 3> IC Synthesis of -8

Step 1 of Preparation Example 1 was repeated except that IC-8-1 (10 g, 22.71 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-8 (4.73 g, yield 51%) was obtained.

¹ H-NMR:? 7.65 (m, 3H), 7.94 (m, 2H), 8.03 (d,

[ Preparation Example  9] IC Synthesis of -9

<Step 1> IC Synthesis of -9-1

IC-8-2 (20 g, 50.23 mmol) obtained in the above Step 3 was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) and 2-nitrophenylboronic acid IC-9-1 (10.18 g, yield: 42%) was obtained by following the same procedure as in <Step 2> of Preparation Example 1 except that 2-nitrophenylboronic acid (18.45 g, 110.51 mmol) .

^{1 H-NMR: δ7.67 (m} , 4H), 7.96 (m, 2H), 8.05 (m, 4H), 8.26 (s, 2H), 8.42 (m, 2H)

<Step 2> IC Synthesis of -9

Step 1 of Preparation Example 1 was repeated except that IC-9-1 (10 g, 20.72 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-9 (4.16 g, yield 48%) was obtained.

^{1 H-NMR: δ7.67 (m} , 4H), 7.96 (m, 2H), 8.05 (m, 4H), 8.42 (m, 2H), 11.30 (s, 2H)

[ Preparation Example  10] IC Synthesis of -10

<Step 1> IC Synthesis of -10-4

Step 1 of Preparation Example 7 was repeated except that naphthalene-1,4-diol (50 g, 312.17 mmol) was used in place of naphthalene-2,3-diol (50 g, 312.17 mmol) To obtain IC-10-4 (25.17 g, yield 33%).

^{1 H-NMR: δ3.66 (m} , 8H), 7.38 (m, 2H), 7.65 (m, 2H)

<Step 2> IC Synthesis of -10-3

The procedure of Step 2 of Preparation Example 7 was repeated except that IC-10-4 (25, 102.30 mmol) was used instead of IC-7-4 (20 g, 81.84 mmol) 3 (18.19 g, yield 74%).

^{1 H-NMR: δ7.56 (d} , 2H), 7.64 (m, 2H), 8.03 (d, 2H), 8.40 (m, 2H)

<Step 3> IC Synthesis of -10-2

Step 3 of Preparation Example 7 was repeated except that IC-10-3 (15 g, 62.41 mmol) was used instead of IC-7-3 (14.5 g, 60.33 mmol) in a nitrogen stream IC-10-2 (11.76 g, yield 59%).

^{1 H-NMR: δ 7.52 (} d, 1H), 7.66 (m, 2H), 8.03 (d, 1H), 8.14 (s, 1H), 8.43 (m, 2H)

<Step 4> IC Synthesis of -10-1

Step 2 of Preparation Example 1 was repeated except that IC-10-2 (10 g, 31.32 mmol) was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) To obtain IC-10-1 (5.43 g, yield 48%).

^{1 H-NMR: δ7.51 (d} , 1H), 7.67 (m, 3H), 7.95 (m, 2H), 8.03 (d, 2H), 8.12 (s, 1H), 8.42 (m, 2H)

<Step 5> IC Synthesis of -10

Step 1 of Preparation Example 1 was repeated except that IC-10-1 (5 g, 13.83 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-10 (2.28 g, yield 50%) was obtained.

^{1 H-NMR: δ 7.54 (} d, 1H), 7.67 (m, 3H), 8.01 (m, 2H), 8.07 (d, 2H), 8.45 (m, 2H), 11.31 (s, 1H)

[ Preparation Example  11] IC Synthesis of -11

<Step 1> IC Synthesis of -11-2

Except that IC-10-3 (20 g, 83.22 mmol) and NBS (32.58 g, 183.07 mmol) were used instead of IC-7-3 (14.5 g, 60.33 mmol) and NBS (11.81 g, 66.36 mmol) IC-11-2 (20.21 g, yield 61%) was obtained by carrying out the same procedure as <Step 3> of Preparation Example 7 above.

^{1 H-NMR: δ7.67 (d} , 2H), 8.13 (s, 2H), 8.42 (m, 2H)

<Step 2> IC Synthesis of -11-1

Step 2 of Preparation Example 1 was repeated except that IC-11-2 (20 g, 50.23 mmol) was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) To obtain IC-11-1 (9.07 g, yield 41%).

^{1 H-NMR: δ 7.65 (} m, 3H), 7.95 (m, 2H), 8.04 (d, 1H), 8.13 (s, 1H), 8.31 (s, 1H), 8.45 (m, 2H)

<Step 3> IC Synthesis of -11

Step 1 of Preparation Example 1 was repeated except that IC-11-1 (9 g, 20.44 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-11 (3.59 g, yield 43%) was obtained.

^{1 H-NMR: δ7.64 (m} , 3H), 7.95 (m, 2H), 8.04 (d, 1H), 8.12 (s, 1H), 8.44 (m, 2H), 11.32 (s, 1H)

[ Preparation Example  12] IC Synthesis of -12

<Step 1> IC Synthesis of -12-4

Step 1 of Preparation Example 7 was repeated except that benzene-1,3,5-triol (50 g, 396.48 mmol) was used instead of naphthalene-2,3-diol (50 g, To give IC-12-4 (10 g, yield 10%).

^{1 H-NMR: δ3.12 (t} , 6H), 3.41 (t, 6H)

<Step 2> IC Synthesis of -12-3

Step 2 of Preparation Example 7 was carried out except that IC-12-4 (10 g, 39.62 mmol) was used instead of IC-7-4 (20 g, 81.84 mmol) -3 (9.68 g, yield 49%).

^{1 H-NMR: δ7.55 (d} , 3H), 7.65 (d, 3H)

<Step 3> IC Synthesis of -12-2

Step 3 of Preparation Example 7 was repeated except that IC-12-3 (9.5 g, 38.56 mmol) was used instead of IC-7-3 (14.5 g, 60.33 mmol) -2 (8.4 g, yield 67%).

^{1 H-NMR: δ7.53 (d} , 2H), 7.62 (d, 2H), 7.91 (s, 1H)

<Step 4> IC Synthesis of -12-1

Step 2 of Preparation Example 1 was repeated except that IC-12-2 (8 g, 24.60 mmol) was used in place of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) To obtain IC-12-1 (4.79 g, yield 53%).

^{1 H-NMR: δ 7.53 (} d, 2H), 7.65 (m, 3H), 7.91 (m, 2H), 8.01 (d, 1H), 8.09 (d, 1H)

<Step 5> IC Synthesis of -12

Step 1 of Preparation Example 1 was repeated except that IC-12-1 (4.5 g, 10.22 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-12 (2.13 g, yield 51%) was obtained.

¹ H-NMR:? 7.53 (d, 2H), 7.65 (m, 3H), 7.91 (d,

[ Preparation Example  13] IC Synthesis of -13

<Step 1> IC Synthesis of -13-2

Except that IC-12-3 (20 g, 81.18 mmol) and NBS (31.79 g, 178.59 mmol) were used in place of IC-7-3 (14.5 g, 60.33 mmol) and NBS (11.81 g, 66.36 mmol) IC-13-2 (20.34 g, yield 62%) was obtained in the same manner as in <Step 3> of Preparation Example 7 above.

^{1 H-NMR: δ7.56 (d} , 1H), 7.68 (d, 1H), 7.95 (s, 2H)

<Step 2> IC Synthesis of -13-1

Step 2 of Preparation Example 1 was repeated except that IC-13-2 (20 g, 49.49 mmol) was used instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) To obtain IC-13-1 (9.72 g, yield 44%).

¹ H-NMR: 隆 7.55 (d, 1H), 7.69 (m, 2H), 7.94 (m, 2H), 8.01

<Step 3> IC Synthesis of -13

Step 1 of Preparation Example 1 was repeated except that IC-13-1 (9.5 g, 21.28 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-13 (4.23 g, yield 48%) was obtained.

¹ H-NMR:? 7.54 (d, 1H), 7.68 (m, 2H), 7.95 (m, 2H), 8.02

[ Preparation Example  14] IC Synthesis of -14

<Step 1> IC Synthesis of -14-1

(20 g, 49.49 mmol) and 2-nitrophenylboronic acid (19.83 mmol) instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) and 2-nitrophenylboronic acid g, 118.77 mmol), IC-14-1 (11.36 g, yield 47%) was obtained in the same manner as in <Step 2> of Preparation Example 1 above.

^{1 H-NMR: δ 7.56 (} d, 1H), 7.70 (m, 3H), 7.95 (t, 2H), 8.00 (d, 2H), 8.05 (d, 2H), 8.11 (s, 2H)

<Step 2> IC Synthesis of -14

Step 1 of Preparation Example 1 was repeated except that IC-14-1 (10 g, 20.47 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-14 (3.91 g, yield 45%) was obtained.

^{1 H-NMR: δ7.54 (d} , 1H), 7.67 (m, 3H), 7.93 (t, 2H), 8.01 (d, 2H), 8.05 (d, 2H), 11.29 (s, 2H)

[ Preparation Example  15] IC Synthesis of -15

<Step 1> IC Synthesis of -15-2

Except that IC-12-3 (20 g, 81.18 mmol) and NBS (47.68 g, 267.89 mmol) were used in place of IC-7-3 (14.5 g, 60.33 mmol) and NBS (11.81 g, 66.36 mmol) The same procedure as in <Step 3> of Preparation Example 7 was conducted to obtain IC-15-2 (20.39 g, yield 52%).

^{1 H-NMR: δ7.94 (s} , 3H)

<Step 2> IC Synthesis of -15-1

(20 g, 41.40 mmol) and 2-nitrophenylboronic acid (8.29 mmol) instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) and 2-nitrophenylboronic acid g, 49.68 mmol), IC-15-1 (10.22 g, yield 41%) was obtained in the same manner as in <Step 2> of Preparation Example 1 above.

^{1 H-NMR: δ 7.67 (} t, 1H), 7.91 (t, 1H), 7.96 (s, 2H), 8.00 (d, 1H), 8.05 (d, 1H), 8.13 (s, 1H)

<Step 3> IC Synthesis of -15

Step 1 of Preparation Example 1 was repeated except that IC-15-1 (10 g, 19.04 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-15 (4.13 g, yield 44%) was obtained.

¹ H-NMR:? 7.67 (t, IH), 7.91 (t, IH), 7.96 (s, 2H)

[ Preparation Example  16] IC Synthesis of -16

<Step 1> IC Synthesis of -16-1

IC-15-2 (20 g, 41.40 mmol) and 2-nitrophenylboronic acid (16.59 g, 22.99 mmol) were used in the place of 2-bromophenanthro [9,10-b] thiophene g, 99.37 mmol), IC-16-1 (8.22 g, yield 35%) was obtained in the same manner as in <Step 2> of Preparation Example 1 above.

^{1 H-NMR: δ 7.65 (} t, 2H), 7.88 (t, 2H), 7.94 (m, 3H), 8.03 (d, 2H), 8.11 (s, 2H)

<Step 2> IC Synthesis of -16

Step 1 of Preparation Example 1 was repeated except that IC-16-1 (8 g, 14.10 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-16 (2.98 g, yield 42%) was obtained.

^{1 H-NMR: δ7.65 (t} , 2H), 7.88 (t, 2H), 7.94 (m, 3H), 8.03 (d, 2H), 11.30 (s, 2H)

[ Preparation Example  17] IC Synthesis of -17

<Step 1> IC Synthesis of -17-1

(20 g, 41.40 mmol) and 2-nitrophenylboronic acid (24.88 mmol) instead of 2-bromophenanthro [9,10-b] thiophene (6 g, 19.16 mmol) and 2-nitrophenylboronic acid g, 149.05 mmol), IC-17-1 (9.84 g, yield 39%) was obtained in the same manner as in <Step 2> of Preparation Example 1 above.

^{1 H-NMR: δ 7.67 (} t, 3H), 7.89 (t, 3H), 7.95 (d, 3H), 8.04 (d, 3H), 8.12 (s, 3H)

<Step 2> IC Synthesis of -17

Step 1 of Preparation Example 1 was repeated except that IC-16-1 (9 g, 14.76 mmol) was used instead of 2- (2-nitrophenyl) phenanthro [9,10-b] thiophene (4 g, 3 &gt;, IC-17 (3.11 g, yield 41%) was obtained.

^{1 H-NMR: δ7.66 (t} , 3H), 7.87 (t, 3H), 7.96 (d, 3H), 8.02 (d, 3H), 11.29 (s, 3H)

[ Synthetic example  One] Inv  Synthesis of 1

(3 g, 9.28 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.83 g, 11.13 mmol), Pd (OAc) ₂ g, 5 mol%), NaO (t-bu) (2.67 g, 27.83 mmol), P (t-bu) 3 (0.19 g, 0.93 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, and then the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain Inv 1 (4.15 g, yield 71% .

GC-Mass (calculated: 630.19 g / mol, measured: 630 g / mol)

[ Synthetic example  2] Inv  Synthesis of 36

4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.08 g, 11.13 mmol) instead of 2- (3- chlorophenyl) -4,6- diphenyl- g, 11.13 mmol) was used in place of the compound of Preparation Example 1 to obtain Inv 36 (2.91 g, yield 48%).

GC-Mass (calculated: 653.19 g / mol, measured: 653 g / mol)

[ Synthetic example  3] Inv  Synthesis of 10

IC-1 (3 g, 9.28 mmol) was dissolved in DMF (100 ml) under nitrogen, to which NaH (0.56 g, 23.19 mmol) was added and stirred for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.55 mmol) dissolved in 100 ml of DMF was added slowly. After stirring for 3 hours, the reaction was terminated and the mixture was filtered with silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give the desired compound Inv10 (2.21 g, yield 43%).

GC-Mass (calculated: 554.16 g / mol, measured: 554 g / mol)

[ Synthetic example  4] Inv  Synthesis of 25

B-d] thiophene (4.72 g, 13.91 mmol), Cu powder (0.06 g, 0.93 mmol), K ₂ CO ₃ (1.28 g, 9.28 mmol), Na 2 SO 4 (1.32 g, 9.28 mmol), and mixture of nitrobenzene (100 ml) was stirred at 200? 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 then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain Inv 25 (2.32 g, yield 43%).

GC-Mass (calculated: 581.13 g / mol, measured: 581 g / mol)

[ Synthetic example  5] Inv  Synthesis of 17

Except that 6-bromo-2,2'-bipyridine (3.27 g, 13.91 mmol) was used instead of 4- (3-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) 4] to obtain Inv 17 (1.82 g, yield 41%).

GC-Mass (calculated: 477.13 g / mol, measured: 477 g / mol)

[ Synthetic example  6] Inv  Synthesis of 37

The same procedure as in [Synthesis Example 1] was performed except that IC-2 (3 g, 9.28 mmol) was used in place of IC-1 (3 g, 9.28 mmol) to obtain Inv 37 (3.98 g, yield 68% .

GC-Mass (calculated: 630.19 g / mol, measured: 630 g / mol)

[ Synthetic example  7] Inv  Synthesis of 38

2 (3 g, 9.28 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- ) And 2- (3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (4.67 g, 11.13 mmol) were used in the same manner as in [Synthesis Example 1] Was performed to obtain Inv 38 (4.59 g, yield 70%).

GC-Mass (706.22 g / mol, measured: 706 g / mol)

[ Synthetic example  8] Inv  Synthesis of 46

The same procedure as in [Synthesis Example 3] was carried out except that IC-2 (3 g, 9.28 mmol) was used instead of IC-1 (3 g, 9.28 mmol) to obtain Inv 46 (2.11 g, yield 41% .

GC-Mass (calculated: 554.16 g / mol, measured: 554 g / mol)

[ Synthetic example  9] Inv  Synthesis of 48

2 (3 g, 9.28 mmol) and 4-bromo-2 (3 g, 9.28 mmol) were used instead of IC-1 (3 g, 9.28 mmol) and 4- (3- bromophenyl) dibenzo [b, d] thiophene , Inv 48 (2.73 g, yield 53%) was obtained by following the same procedure as in [Synthesis Example 4] except that 6-dipyridyl pyridine (4.34 g, 13.91 mmol) was used.

GC-Mass (calculated: 554.16 g / mol, measured: 554 g / mol)

[ Synthetic example  10] Inv  Synthesis of 59

2 (3 g, 9.28 mmol) and N- (4-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) Inv 59 (3.20 g, yield 56%) was obtained by following the same procedure as in [Synthesis Example 4], except using 5-bromophenyl) -N-phenylnaphthalen-2-amine (5.21 g, 13.91 mmol).

GC-Mass (theory: 616.20 g / mol, measured: 616 g / mol)

[ Synthetic example  11] Inv  Synthesis of 85

IC-3 (3 g, 7.84 mmol) and 2-bromo-4 (3-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) , Inv 8 (2.78 g, yield 58%) was obtained by following the same procedure as in [Synthesis Example 4], except that 6-diphenylpyridine (3.65 g, 11.77 mmol) was used.

GC-Mass (calculated: 611.24 g / mol, measured: 611 g / mol)

[ Synthetic example  12] Inv  Synthesis of 91

3 (3 g, 7.84 mmol) and 2- (4-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) Inv 91 (2.06 g, yield 49%) was obtained by carrying out the same procedure as in [Synthesis Example 4], except that bromophenyl) pyrimidine (2.77 g, 11.77 mmol) was used.

GC-Mass (calculated: 536.20 g / mol, measured: 536 g / mol)

[ Synthetic example  13] Inv  Synthesis of 75

3 (3 g, 7.84 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6- diphenyl-1,3,5- ) And 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -1,3,5-triazine (4.67 g, 9.41 mmol) (Inv36) (4.36 g, yield 66%).

GC-Mass (calculated: 841.32 g / mol, measured: 841 g / mol)

[ Synthetic example  14] Inv  Synthesis of 81

3 (3 g, 7.84 mmol) and 2- (5-aminopyridin-2-ylamine) instead of IC-1 (3 g, 9.28 mmol) and 4- (3- bromophenyl) dibenzo [ The same procedure as in [Synthesis Example 4] was carried out except that bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (5.46 g, 11.77 mmol) g, yield: 42%).

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

[ Synthetic example  15] Inv  Synthesis of 90

3 (3 g, 7.84 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6- diphenyl-1,3,5- ) And 2-chloro-4-phenylpyrimidine (1.79 g, 9.41 mmol) were used in the same manner as in [Synthesis Example 1] above to give Inv 90 (2.40 g, yield 57%).

GC-Mass (calculated: 536.20 g / mol, measured: 536 g / mol)

[ Synthetic example  16] Inv  116 Synthesis

4 (3 g, 7.84 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6- diphenyl-1,3,5- ) Was obtained in the same manner as in [Synthesis Example 1] except for using 2- (4-chlorophenyl) -4,6-diphenylpyrimidine (3.23 g, 9.41 mmol) ).

GC-Mass (calculated: 688.26 g / mol, measured: 688 g / mol)

[ Synthetic example  17] Inv  Synthesis of 138

4 (3 g, 7.84 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6- diphenyl-1,3,5- ) And 1-chlorophthalazine (1.55 g, 9.41 mmol) were used in the same manner as in [Synthesis Example 1], except that 1.5 g (yield 39%) of Inv 138 was obtained.

GC-Mass (calculated: 510.18 g / mol, measured: 510 g / mol)

[ Synthetic example  18] Inv  136 Synthesis

4 (3 g, 7.84 mmol) and 9- (4-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) Inv 136 (2.50 g, yield 51%) was obtained by carrying out the same procedure as in [Synthesis Example 4], except that 3-bromophenyl) -9H-carbazole (3.79 g, 11.77 mmol) was used.

GC-Mass (calculated: 623.24 g / mol, measured: 623 g / mol)

[ Synthetic example  19] Inv  Synthesis of 112

4 (3 g, 7.84 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6- diphenyl-1,3,5- ) And 4- (6-chloropyridin-2-yl) -2,6-diphenylpyrimidine (3.24 g, 9.41 mmol) were used in the same manner as in [Synthesis Example 1] , Yield: 37%).

GC-Mass (calculated: 689.26 g / mol, measured: 689 g / mol)

[ Synthetic example  20] Inv  Synthesis of 113

4 (3 g, 7.84 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6- diphenyl-1,3,5- ) And 2- (4-chlorophenyl) -4,6-di (naphthalen-1-yl) -1,3,5-triazine (4.18 g, 9.41 mmol) , To obtain Inv 113 (4.28 g, yield 69%).

GC-Mass (theory: 789.29 g / mol, measured: 789 g / mol)

[ Synthetic example  21] Inv  156 Synthesis

IC-5 (3 g, 9.28 mmol) and 6-bromo-2 (3 g) were used instead of IC-1 (3 g, 9.28 mmol) and 4- (3-bromophenyl) dibenzo [b, d] thiophene , And 4-dipyridyl pyridine (4.34 g, 13.91 mmol) were used in the same manner as in [Synthesis Example 4], to give Inv 156 (2.16 g, yield 42%).

GC-Mass (calculated: 554.16 g / mol, measured: 554 g / mol)

[ Synthetic example  22] Inv  Synthesis of 177

(3 g, 9.28 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- ) And 1-chloro-4-phenylphthalazine (2.68 g, 11.13 mmol) were used in the same manner as in [Synthesis Example 1].

GC-Mass (calculated: 527.15 g / mol, measured: 527 g / mol)

[ Synthetic example  23] Inv  150 Synthesis

(3 g, 9.28 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- ) And 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (3.82 g, 11.13 mmol) were used in the same manner as in [Synthesis Example 1] ).

GC-Mass (calculated: 629.19 g / mol, measured: 629 g / mol)

[ Synthetic example  24] Inv  Synthesis of 171

(3 g, 9.28 mmol) and 3- (3-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) Inv 171 (3.03 g, yield 51%) was obtained by following the same procedure as in [Synthesis Example 4], except using 5-bromophenyl-9-phenyl-9H-carbazole (5.54 g, 13.91 mmol).

GC-Mass (calculated: 640.20 g / mol, measured: 640 g / mol)

[ Synthetic example  25] Inv  Synthesis of 157

IC-5 (3 g, 9.28 mmol) and 2-bromo-4 (3-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) , Inv-157 (2.71 g, yield 53%) was obtained by following the same procedure as in [Synthesis Example 4] except that 6-diphenylpyridine (4.32 g, 13.91 mmol) was used.

GC-Mass (calculated: 552.17 g / mol, measured: 552 g / mol)

[ Synthetic example  26] Inv  Synthesis of 187

(3 g, 9.00 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl- ) In the same manner as in [Synthesis Example 1] except that 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.71 g, 10.80 mmol) (3.92 g, yield 68%).

GC-Mass (calculated: 640.26 g / mol, measured: 640 g / mol)

[ Synthetic example  27] Inv  Synthesis of 202

IC-6 (3 g, 9.00 mmol) and 4'-bromo-biphenyl were used instead of IC-1 (3 g, 9.28 mmol) and 4- (3-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) Inv 202 (2.70 g, yield 46%) was obtained in the same manner as in [Synthesis Example 4] except that N, N-diphenylbiphenyl-4-amine (5.40 g, 13.50 mmol) was used.

GC-Mass (calculated: 652.29 g / mol, measured: 652 g / mol)

[ Synthetic example  28] Inv  Synthesis of 204

6 (3 g, 9.00 mmol) and 2- (3-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) Inv 204 (2.18 g, yield 41%) was obtained by following the same procedure as in [Synthesis Example 4], except using bromophenyl dibenzo [b, d] thiophene (4.58 g, 13.50 mmol).

GC-Mass (calculated: 591.20 g / mol, measured: 591 g / mol)

[ Synthetic example  29] Inv  195 Synthesis

6 (3 g, 9.28 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, Inv 195 (2.28 g, 45% yield) was obtained in the same manner as in [Synthesis Example 3] except that chloro-4,6-diphenylpyrimidine (4.80 g, 18.00 mmol) was used.

GC-Mass (calculated: 563.24 g / mol, measured: 563 g / mol)

[ Synthetic example  30] Inv  Synthesis of 183

IC-6 (3 g, 9.00 mmol) was added to 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.55 mmol) The same procedure as in [Synthesis Example 3] was carried out except that 4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine (7.56 g, 18.00 mmol) (2.39 g, yield 37%).

GC-Mass (calculated: 716.29 g / mol, measured: 716 g / mol)

[ Synthetic example  31] Inv  Synthesis of 218

(3 g, 9.11 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl- ) And 2- (3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (4.59 g, 10.93 mmol) Was performed to obtain Inv 218 (4.22 g, yield 65%).

GC-Mass (calculated: 712.18 g / mol, measured: 712 g / mol)

[ Synthetic example  32] Inv  Synthesis of 245

(3 g, 9.11 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl- ) And 1-chloroisoquinoline (1.79 g, 10.93 mmol) were used in the same manner as in [Synthesis Example 1] above to give Inv 245 (1.95 g, yield 47%).

GC-Mass (theory: 456.08 g / mol, measured: 456 g / mol)

[ Synthetic example  33] Inv  232 Synthesis

IC-7 (3 g, 9.11 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.55 mmol) Inv 232 (2.15 g, yield 42%) was obtained by following the same procedure as in [Synthesis Example 3], except using 4-chloro-4,6-di (pyridin- 2- yl) pyrimidine (4.89 g, 18.21 mmol) ).

GC-Mass (calculated: 561.11 g / mol, measured: 561 g / mol)

[ Synthetic example  34] Inv  Synthesis of 253

(5 g, 12.25 mmol), phenylboronic acid (1.79 g, 14.69 mmol), K ₂ CO ₃ (5.08 g, 36.76 mmol) and THF / H ₂ O (200 ml / 100 ml) were mixed then, place the _{Pd (PPh 3) 4 (0.71} 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 resulting intermediate compound (3.87 g, 9.54 mmol, yield: 78%) was obtained as an intermediate compound (3.87 g, yield 78%) after purification by column chromatography (Hexane: MC = 5: 1 ) Was prepared by reacting 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.94 g, 11.45 mmol), Pd (OAc) ₂ (0.11 g, 5 mol%), NaO ) (2.75 g, 28.63 mmol), P (t-bu) ₃ (0.19 g, 0.9 mmol) and Toluene (150 ml) and stirred at 110? For 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain Inv 253 (5.10 g, yield 75% .

GC-Mass (calculated: 712.18 g / mol, measured: 712 g / mol)

[ Synthetic example  35] Inv  Synthesis of 289

phenyl-9H-carbazol-3-yl) phenylboronic acid (1.79 g, 14.69 mmol) and 2- (3- chlorophenyl) -4,6- diphenyl- The same procedure as in [Synthesis Example 34] was conducted, except that 2-chloro-4-phenylboronic acid (4.22 g, 14.69 mmol) and 2-chloro-4-phenylquinazoline (2.37 g, 9.84 mmol) 67%) and Inv 289 (2.48 g, yield 39%).

GC-Mass (calculated: 774.19 g / mol, measured: 774 g / mol)

[ Synthetic example  36] Inv  290

2-ylboronic acid (2.53 g, 14.69 mmol), K ₂ CO ₃ (5.08 g, 36.76 mmol) and THF / H ₂ O (100 ml / 50 mL) under a nitrogen stream, ml), and then, place the _{Pd (PPh 3) 4 (0.71} g, 5 mol%) at 40 ℃ was stirred at 80 ℃ for 12 hours the mixture.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The intermediate compound (3.63 g, yield 65%) was obtained by purification by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain the intermediate compound (3.63 g, 7.07 mmol ) Was dissolved in 100 ml of DMF, and NaH (0.42 g, 17.67 mmol) was added thereto, followed by stirring for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (3.78 g, 14.13 mmol) dissolved in 100 ml of DMF was added slowly. After stirring for 3 hours, the reaction was terminated and the mixture was filtered with silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give the desired compound Inv 290 (1.99 g, yield 41%).

GC-Mass (686.16 g / mol, measured: 686 g / mol)

[ Synthetic example  37] Inv  Synthesis of 300

Iodobenzene (3.57 g, 17.50 mmol), Cu powder (0.07 g, 1.17 mmol), K ₂ CO ₃ (1.61 g, 11.67 mmol), Na ₂ SO ₄ 1.66 g, 11.67 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 the water had been removed and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain an intermediate compound (2.71 g, yield 47% , 5.48 mmol) were dissolved in 100 ml of DMF, and NaH (0.33 g, 13.70 mmol) was added thereto, followed by stirring for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (2.93 g, 10.96 mmol) dissolved in 100 ml of DMF was added slowly. After stirring for 3 hours, the reaction was terminated and the mixture was filtered with silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give the desired compound Inv 300 (1.59 g, yield 40%).

GC-Mass (calculated: 725.17 g / mol, measured: 725 g / mol)

[ Synthetic example  38] Inv  Synthesis of 327

9 (3 g, 7.17 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.55 mmol) Inv 327 (1.96 g, yield 31%) was obtained by following the same procedure as in [Synthesis Example 3], except that chloro-4,6-diphenyl-1,3,5-triazine (7.68 g, 28.67 mmol) ).

GC-Mass (theory: 880.22 g / mol, measured: 880 g / mol)

[ Synthetic example  39] Inv  Synthesis of 328

IC-9 (5 g, 11.95 mmol) was dissolved in DMF (100 ml) under nitrogen, to which NaH (0.72 g, 29.87 mmol) was added and stirred for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (6.40 g, 23.89 mmol) dissolved in 100 ml of DMF was added slowly. After stirring for 3 hours, the reaction was terminated and the mixture was filtered with silica, washed with water and methanol, and then the solvent was removed. The resulting solid was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give the intermediate compound (2.87 g, yield 37% is 3- (3-bromophenyl) -9- phenyl-9H-carbazole (2.64 g, 6.63 mmol), Cu powder (0.03 g, 0.44 mmol), K 2 CO 3 (0.61 g, 4.42 mmol), Na 2 SO 4 (0.63 g, 4.42 mmol) and nitrobenzene (100 ml) and stirred at 200 &lt; 0 &gt; 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 then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain Inv 328 (1.45 g, yield 34%).

GC-Mass (calculated: 966.26 g / mol, measured: 966 g / mol)

[ Synthetic example  40] Inv  Synthesis of 336

(3 g, 9.11 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- ) And Inv 336 (3.71 g, yield 64%) was obtained by following the same procedure as in [Synthesis Example 1], except that 2- (4-chlorophenyl) -4,6-diphenylpyrimidine (3.75 g, 9.28 mmol) ).

GC-Mass (calculated: 635.15 g / mol, measured: 635 g / mol)

[ Synthetic example  41] Inv  Synthesis of 353

10 (3 g, 9.11 mmol) and 4- (3-bromophenyl) dibenzo [b, d] thiophene (4.72 g, 13.91 mmol) Inv 353 (2.03 g, yield 38%) was obtained by carrying out the same procedure as in [Synthesis Example 4], except that dibenzo [b, d] thiophene (4.63 g, 13.66 mmol)

GC-Mass (calculated: 587.08 g / mol, measured: 587 g / mol)

[ Synthetic example  42] Inv  Synthesis of 401

(1.94 g, 14.69 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.94 g, 11.45 mmol) instead of IC-8 (5 g, 12.25 mmol) 3-chloro-1- (6-phenylpyridin-2-yl) isoquinoline (3.31 g, 14.69 mmol) and IC-11 (5 g, 12.25 mmol) (4.85 g, 71%) and Inv 401 (2.62 g, yield 36%) were obtained in the same manner as in [Synthesis Example 34], except that the compound

GC-Mass (theory: 837.23 g / mol, measurement: 837 g / mol)

[ Synthetic example  43] Inv  Synthesis of 384

(5 g, 12.25 mmol), phenylboronic acid (1.79 g, 14.69 mmol), K ₂ CO ₃ (5.08 g, 36.74 mmol) and THF / H ₂ O (200 ml / 100 ml) were mixed Then, Pd (PPh ₃ ) ₄ (0.71 g, 5 mol%) was added at 40 ° C and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After the solvent was removed from the obtained organic layer, the intermediate compound (3.72 g, yield 75%) was obtained by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain the intermediate compound (3.72 g, 5.73 mmol ) Was reacted with 2- (3-bromophenyl) -4-phenylpyrimidine (2.67 g, 8.59 mmol), Cu powder (0.04 g, 0.57 mmol), K ₂ CO ₃ (0.79 g, 5.73 mmol), Na ₂ SO ₄ , 5.73 mmol) and nitrobenzene (100 ml), and the mixture was 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 then purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain Inv 384 (1.53 g, yield 42%).

GC-Mass (calculated: 635.15 g / mol, measured: 635 g / mol)

[ Synthetic example  44] Inv  Synthesis of 374

2-chloro-4,6-diphenyl-1,3,5-triazine (3.78 g, 14.13 mmol) instead of IC-8 (5 g, 12.25 mmol), naphthalen-2-ylboronic acid (2.53 g, The use of IC-11 (5 g, 12.25 mmol), phenylboronic acid (1.79 g, 14.69 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.79 g, , The intermediate compound (3.77 g, yield 76%) and Inv 374 (2.51 g, yield 44%) were obtained in the same manner as in [Synthesis Example 36].

GC-Mass (calculated: 636.14 g / mol, measured: 636 g / mol)

[ Synthetic example  45] Inv  Synthesis of 435

12 (3 g, 8.94 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- ) And Inv 435 (2.04 g, yield 37%) were obtained by following the same procedure as in [Synthesis Example 1] except that 4- (biphenyl-4-yl) -2-chloroquinazoline (3.40 g, 10.73 mmol) ).

GC-Mass (calculated: 615.09 g / mol, measured: 615 g / mol)

[ Synthetic example  46] Inv  Synthesis of 411

IC-12 (3 g, 8.94 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.55 mmol) Inv 411 (2.33 g, yield 46%) was obtained by carrying out the same procedure as in [Synthesis Example 3] except that chloro-4,6-diphenyl-1,3,5-triazine (4.79 g, 17.89 mmol) ).

GC-Mass (calculated: 566.07 g / mol, measured: 566 g / mol)

[ Synthetic example  47] Inv  Synthesis of 475

13 (5 g, 12.07 mmol) instead of IC-11 (5 g, 12.25 mmol), phenylboronic acid (1.79 g, 14.69 mmol) and 2- (3- bromophenyl) -4-phenylpyrimidine (2.67 g, 8.59 mmol) ), Phenylboronic acid (1.77 g, 14.48 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (5.10 g, 14.10 mmol) were used in the same manner as in [Synthesis Example 43] Compound (3.87 g, yield 78%) and Inv 475 (2.93 g, yield 45%).

GC-Mass (691.12 g / mol, measured: 691 g / mol)

[ Synthetic example  48] Inv  Synthesis of 448

2-chloro-4,6-diphenyl-1,3,5-triazine (3.78 g, 14.13 mmol) instead of IC-8 (5 g, 12.25 mmol), naphthalen-2-ylboronic acid (2.53 g, The use of IC-13 (5 g, 12.25 mmol), phenylboronic acid (1.79 g, 14.69 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.56 mmol) , The intermediate compound (3.82 g, yield: 77%) and Inv 448 (2.51 g, yield: 42%) were obtained in the same manner as in [Synthesis Example 36].

GC-Mass (calculated: 642.10 g / mol, measured: 642 g / mol)

[ Synthetic example  49] Inv  Synthesis of 474

2-chloro-4,6-diphenyl-1,3,5-triazine (3.78 g, 14.13 mmol) instead of IC-8 (5 g, 12.25 mmol), naphthalen-2-ylboronic acid (2.53 g, Carbodi-9-yl) phenylboronic acid (4.16 g, 14.48 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.45 g, yield 64%) and Inv 474 (2.43 g, yield 39%) were obtained in the same manner as in [Synthesis Example 36] except that the compound (4.13 g, 15.43 mmol)

GC-Mass (theory: 807.16 g / mol, measurement: 807 g / mol)

[ Synthetic example  50] Inv  Synthesis of 512

14 (3 g, 7.07 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.55 mmol) Inv 512 (2.70 g, yield 43%) was obtained by following the same procedure as in [Synthesis Example 3], except that chloro-4,6-diphenyl-1,3,5-triazine (7.57 g, 28.27 mmol) ).

GC-Mass (calculated: 886.18 g / mol, measured: 886 g / mol)

[ Synthetic example  51] Inv  Synthesis of 485

IC-14 (5.7 g, 17.6 mmol) was used instead of IC-9 (5 g, 11.67 mmol), iodobenzene (3.57 g, 17.50 mmol) and 2-chloro- 5 g, 11.78 mmol), iodobenzene (3.60 g, 17.67 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.40 g, 8.95 mmol) The intermediate compound (2.24 g, yield 38%) and Inv 485 (1.08 g, yield 33%) were obtained by the same procedure as in Example 37].

GC-Mass (731.13 g / mol, measured: 731 g / mol)

[ Synthetic example  52] Inv  Synthesis of 513

14 (3 g, 7.07 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6- diphenyl- ) And 2-chloroquinazoline (2.91 g, 17.67 mmol) were used in the same manner as in [Synthesis Example 1], to obtain Inv 513 (1.68 g, yield 35%).

GC-Mass (calculated: 680.09 g / mol, measured: 680 g / mol)

[ Synthetic example  53] Inv  Synthesis of 523

2-chloro-4,6-diphenyl-1,3,5-triazine (3.78 g, 14.13 mmol) instead of IC-8 (5 g, 12.25 mmol), naphthalen-2-ylboronic acid (2.53 g, The use of IC-15 (5 g, 10.14 mmol), phenylboronic acid (2.97 g, 24.33 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (3.80 g, 14.19 mmol) , The intermediate compound (3.46 g, yield 70%) and Inv 523 (2.30 g, yield 45%) were obtained in the same manner as in [Synthesis Example 36].

GC-Mass (718.13 g / mol, measured: 718 g / mol)

[ Synthetic example  54] Inv  Synthesis of 550

2-chloro-4,6-diphenyl-1,3,5-triazine (3.78 g, 14.13 mmol) instead of IC-8 (5 g, 12.25 mmol), naphthalen-2-ylboronic acid (2.53 g, (7.0 g, 24.33 mmol) and 4- chloro-4,6-diphenyl-1,3,5-triazine (3.37 g, 12.58 mmol, (5.17 g, yield 62%) and Inv 550 (2.58 g, yield 39%) were obtained in the same manner as in [Synthesis Example 36].

GC-Mass (calculated: 1052.28 g / mol, measured: 1052 g / mol)

[ Synthetic example  55] Inv  Synthesis of 545

(1.94 g, 14.69 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.94 g, 11.45 mmol) instead of IC-8 (5 g, 12.25 mmol) Except that IC-15 (5 g, 10.14 mmol), phenylboronic acid (2.97 g, 24.33 mmol) and 2-chloro-4-phenylquinazoline (2.08 g, 8.64 mmol) The same procedure was carried out to obtain an intermediate compound (3.51 g, yield 71%) and Inv 545 (1.59 g, yield 32%).

GC-Mass (691.12 g / mol, measured: 691 g / mol)

[ Synthetic example  56] Inv  Synthesis of 587

2-chloro-4,6-diphenyl-1,3,5-triazine (3.78 g, 14.13 mmol) instead of IC-8 (5 g, 12.25 mmol), naphthalen-2-ylboronic acid (2.53 g, Phenylboronic acid (1.45 g, 11.92 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (8.19 g, 30.60 mmol) , The intermediate compound (3.83 g, yield 77%) and Inv 587 (2.21 g, yield 30%) were obtained in the same manner as in [Synthesis Example 36].

GC-Mass (theory: 962.21 g / mol, measured: 962 g / mol)

[ Synthetic example  57] Inv  Synthesis of 588

(3.45 g, 11.92 mmol), K ₂ CO ₃ (4.12 g, 29.79 mmol) and THF / H ₂ O (100 ml / min) were added to a solution of 4- (diphenylamino) phenyl boronic acid Pd (PPh ₃ ) ₄ (0.57 g, 5 mol%) was added thereto at 40 ° C, and the mixture was stirred at 80 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The resulting intermediate compound (4.78 g, 7.16 mmol, yield: 72%) was obtained as an intermediate compound (4.78 g, yield 72%) after purification by column chromatography (Hexane: MC = 1: 1 ), Iodobenzene (2.19 g, 10.74 mmol), Cu powder (0.05 g, 0.72 mmol), K ₂ CO ₃ (0.99 g, 7.16 mmol), Na ₂ SO ₄ (1.02 g, 7.16 mmol) And stirred at 200 &lt; 0 &gt; 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 intermediate compound (2.18 g, yield 41%) was obtained by purification by column chromatography (Hexane: MC = 2: 1 (v / v)). The resulting intermediate compound (2.18 g, 2.93 mmol) was reacted with 4- (biphenyl-4-yl) -2-chloroquinazoline (1.11 g, 3.52 mmol), Pd (OAc) ₂ (0.03 g, Bu) (0.84 g, 8.79 mmol), P (t-bu) ₃ (0.06 g, 0.29 mmol) and Toluene (100 ml) and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to obtain Inv 588 (1.14 g, yield 38% .

GC-Mass (calculated: 1023.25 g / mol, measured: 1023 g / mol)

[ Synthetic example  58] Inv  Synthesis of 589

(1.94 g, 14.69 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.94 g, 11.45 mmol) instead of IC-8 (5 g, 12.25 mmol) 3-ylboronic acid (2.36 g, 11.92 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (5.98 g, , 17.39 mmol), and the intermediate compound (4.18 g, yield 73%) and Inv 589 (4.40 g, yield 51%) were obtained in the same manner as in [Synthesis Example 34].

GC-Mass (calculated: 1190.30 g / mol, measured: 1190 g / mol)

[ Synthetic example  59] Inv  Synthesis of 626

(5.69 g, 29.20 mmol), iodobenzene (5.96 g, 29.20 mmol), Cu powder (0.12 g, 1.95 mmol), K ₂ CO ₃ (2.69 g, 19.47 mmol), Na ₂ SO ₄ 2.77 g, 19.47 mmol) and nitrobenzene (150 ml) and stirred at 200 &lt; 0 &gt; 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 the water had been removed, and then the residue was purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain an intermediate compound (2.27 g, yield 35%). The obtained intermediate compound (2.27 g, 3.41 mmol) is 2-chloro-4- (4- ( naphthalen-1-yl) phenyl) quinazoline (1.50 g, 4.09 mmol), Pd (OAc) 2 (0.04 g, 5 mol% ), NaO (t-bu) (0.98 g, 10.23 mmol), P (t-bu) ₃ (0.07 g, 0.34 mmol) and Toluene (100 ml) and stirred at 110 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and then the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain Inv 626 (1.12 g, yield 33% .

GC-Mass (995.22 g / mol, measured: 995 g / mol)

[ Synthetic example  60] Inv  Synthesis of 627

17 (3 g, 5.84 mmol) instead of IC-1 (3 g, 9.28 mmol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- ) And 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (7.50 g, 20.44 mmol) were used in the same manner as in [Synthesis Example 1] 2.55 g, yield 29%).

GC-Mass (theory: 1503.39 g / mol, measurement: 1503 g / mol)

[ Synthetic example  61] Inv  Synthesis of 628

17 (3 g, 5.84 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (4.97 g, 18.55 mmol) Inv 628 (2.33 g, yield 33%) was obtained by following the same procedure as in [Synthesis Example 3], except that chloro-4,6-diphenyl-1,3,5-triazine (9.38 g, ).

GC-Mass (theory: 1206.28 g / mol, measurement: 1206 g / mol)

[ Example  1] Green organic EL  Device fabrication

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

First, a glass substrate coated with ITO (Indium tin oxide) thin film having a thickness of 1500 Å 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) / lnv 1 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

[ Example  2 ~ 48] Green organic EL  Device fabrication

4 to 16, 18 to 21, 23 to 35, 37 to 41, 43, 44, 46, 48 to 51, 53, 54, and 56 in place of the compound lnv 1 in Synthetic Example 1 as a luminescent host material, Lnv 17, lnv 37, lnv 38, lnv 46, lnv 48, lnv 59, lnv 85, lnv 91, lnv 75, lnv 81, lnv 90, lnv 116, lnv 136, lnv 112, lnv 113, lnv 156, lnv 150, lnv 171, lnv 157, lnv 187, lnv 202, lnv 204, lnv 195, lnv 183, lnv 218, lnv 245, lnv 232, lnv 253, lnv 289, lnv 300, lnv 327, lnv 328, lnv 336, lnv 353, lnv 384, lnv 374, lnv 411, lnv 448, lnv 474, lnv 512, lnv 485, lnv 523, lnv 550, lnv 587, lnv 589, lnv 628 The organic EL device was fabricated in the same manner as in Example 1.

[ Comparative Example  1] Organic EL  Device fabrication

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

The structure of CBP used is as follows.

[ Evaluation example  One]

The organic EL devices prepared in Examples 1-48 and Comparative Example 1 were measured for driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2, 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 6.71 518 39.9 Example 2 Inv25 6.78 519 40.9 Example 3 Inv 17 6.77 516 41.2 Example 4 Inv 37 6.69 517 42.5 Example 5 Inv 38 6.72 515 40.7 Example 6 Inv 46 6.75 516 41.1 Example 7 Inv 48 6.74 516 41.6 Example 8 Inv 59 6.79 517 39.7 Example 9 Inv 85 6.80 515 39.5 Example 10 Inv 91 6.81 516 39.8 Example 11 Inv 75 6.78 518 40.4 Example 12 Inv 81 6.72 519 41.8 Example 13 Inv 90 6.75 516 41.2 Example 14 Inv 116 6.78 515 40.9 Example 15 Inv 136 6.82 515 40.2 Example 16 Inv 112 6.83 516 40.5 Example 17 Inv 113 6.76 516 39.8 Example 18 Inv 156 6.69 517 40.5 Example 19 Inv 150 6.69 515 41.0 Example 20 Inv 171 6.74 515 40.6 Example 21 Inv 157 6.76 516 41.1 Example 22 Inv 187 6.81 517 40.7 Example 23 Inv 202 6.76 516 40.5 Example 24 Inv 204 6.72 518 39.7 Example 25 Inv 195 6.71 516 40.2 Example 26 Inv 183 6.79 517 39.8 Example 27 Inv 218 6.75 515 41.5 Example 28 Inv 245 6.71 516 38.4 Example 29 Inv 232 6.72 517 41.2 Example 30 Inv 253 6.68 516 41.9 Example 31 Inv 289 6.72 515 40.7 Example 32 Inv 300 6.77 516 38.6 Example 33 Inv 327 6.81 517 39.2 Example 34 Inv 328 6.83 518 38.8 Example 35 Inv 336 6.88 519 38.5 Example 36 Inv 353 6.88 516 39.2 Example 37 Inv 384 6.79 515 38.6 Example 38 Inv 374 6.82 516 40.4 Example 39 Inv 411 6.84 517 41.0 Example 40 Inv 448 6.87 518 39.3 Example 41 Inv 474 6.80 519 38.8 Example 42 Inv 512 6.83 516 39.2 Example 43 Inv 485 6.80 517 38.7 Example 44 Inv 523 6.82 515 39.0 Example 45 Inv 550 6.85 516 38.4 Example 46 Inv 587 6.77 515 40.1 Example 47 Inv 589 6.79 516 39.7 Example 48 Inv 628 6.83 517 39.1 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound according to the present invention was used as a light emitting layer of a green organic EL device (Example 1-48), compared with a green organic EL device (Comparative Example 1) using conventional CBP, And shows excellent performance in terms of driving voltage.

[ Example  49] Red organic EL  Device fabrication

Compound lnv 36 synthesized in Synthesis Example 2 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å 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) / lnv 36 + 10% (piq) ₂ Ir (acac) (300 nm) / BCP (10 nm) / Alq ₃ 30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structures of m-MTDATA, TCTA and BCP used are the same as in Example 1, and the structure of (piq) ₂ Ir (acac) is as follows.

[ Example  49] Red organic EL  Device fabrication

17, 22, 36, 37, 39, 42, 45, 47, 50, 52, 55 to 57 and 59 to 61 were used instead of the compound lnv 36 of the above Synthesis Example 2 Lnv 10, lnv 138, lnv 177, lnv 290, lnv 300, lnv 328, lnv 401, lnv 435, lnv 475, lnv 512, lnv 513, lnv 545, lnv 587, lnv 588, lnv 626, lnv 627, lnv 628 was used instead of lnv 628, a red organic electroluminescent device was fabricated in the same manner as in Example 49.

[ Comparative Example  2] Red organic EL  Device fabrication

A red organic electroluminescent device was fabricated in the same manner as in Example 49, except that CBP was used instead of the compound lnv 36 in Synthesis Example 2 as a luminescent host material in forming the light emitting layer.

The structure of CBP used is the same as that of Comparative Example 1.

[ Evaluation example  2]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 49 to 66 and Comparative Example 2, respectively, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 49 Inv 36 4.89 12.4 Example 50 Inv 10 4.91 11.5 Example 51 Inv 138 4.93 11.9 Example 52 Inv 177 4.92 12.0 Example 53 Inv 290 5.12 10.5 Example 54 Inv 300 5.17 9.8 Example 55 Inv 328 5.20 8.8 Example 56 Inv 401 4.97 11.0 Example 57 Inv 435 4.88 11.8 Example 58 Inv 475 5.07 10.4 Example 59 Inv 512 5.11 9.5 Example 60 Inv 513 4.84 10.6 Example 61 Inv 545 4.95 12.1 Example 62 Inv 587 5.10 10.0 Example 63 Inv 588 5.21 9.4 Example 64 Inv 626 5.05 10.9 Example 65 Inv 627 5.08 9.0 Example 66 Inv 628 5.11 9.4 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used as a material for the light emitting layer of a red organic electroluminescent device (Examples 49 to 66), a red organic electroluminescent device using conventional CBP as a material for the light emitting layer (Example 2), it shows that the current efficiency and the driving voltage are superior.

Claims (11)

[Chemical Formula 1]

(2)

In the above Formulas 1 and 2,
Cy1 and Cy2 are the same or different and are each independently selected from the group consisting of C ₆ to C ₄₀ aromatic rings and heteroaromatic rings having 5 to 40 nuclear atoms,
R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl An amino group, 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 aryl boron group, by combining C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent group to form a condensed ring In addition,
X ₁ and X ₂ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ from the group consisting of (Ar ₅₎ With the proviso that at least one of X ₁ and X ₂ is N (Ar ₁ )
Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group , A 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 C ₄₀ arylphosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of the group consisting of aryl silyl,
C ₆ to C ₄₀ aromatic rings of Cy 1 and Cy 2, heteroaromatic rings of 5 to 40 nuclear atoms, R ₁ to R ₄ And C ₁ to C ₄₀ alkyl groups of Ar ₁ to Ar ₅ , C ₂ to C ₄₀ alkenyl groups, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₄₀ aryl groups, heteroatoms having 5 to 40 nuclear atoms An aryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ aryl The phosphine oxide group and the C ₆ to C ₄₀ arylsilyl groups are each independently selected from the group consisting of deuterium (D), halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl an amine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl , 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 aryl of C ₆ ~ C ₄₀ And a silyl group, provided that when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
Wherein Cy1 and Cy2 are the same or different and are each independently selected from the group consisting of benzene, indene, naphthalene, fluorene, anthracene, phenanthrene, naphthacene, pyrene, triphenylene, furan, thiophene, pyrrole, pyrazole, imidazole Benzothiophene, benzimidazole, benzothiazole, purine, quinoline, isoquinoline, benzothiazole, benzothiazole, benzothiazole, benzothiazole, thiazole, thiazole, thiazole, thiazole, oxadiazole, pyridine, pyrimidine, , Quinoxaline, carbazole, dibenzothiophene, dibenzofuran, acridine and phenanthroline,
The above Cy1 and Cy2 benzene, indene, naphthalene, fluorene, anthracene, phenanthrene, naphthacene, pyrene, triphenylene, furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, thiazole, triazole , Thiadiazole, oxadiazole, pyridine, pyrimidine, triazine, indole, benzofuran, benzothiophene, benzimidazole, benzothiazole, purine, quinoline, isoquinoline, quinoxaline, carbazole, dibenzo Thiophene, dibenzofuran, acridine and phenanthroline are each independently selected from the group consisting of deuterium (D), halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ An arylamine group, 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 Group ₄₀ arylboronic of, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C over ₄₀ per selected from the group consisting of aryl silyl species substituted with a substituent or unsubstituted When the substituent is plural, they may be the same or different and form an aromatic ring or a heteroaromatic ring with an adjacent group. The method according to claim 1,
Wherein Cy1 and Cy2 are the same or different and are each independently selected from the group consisting of benzene, thiophene, and thioindole,
Above Cy1 and Cy2 benzene, thiophene and Im cyano indole are each independently a heavy hydrogen (D), a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl An amino group, 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 aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group of, C ₆ ~ C ₄₀ substituted to the aryl phosphine oxide group, and a C ₆ ~ 1 substituent at least one selected from an aryl silyl group consisting of C ₄₀ or unsubstituted be ring When the substituent is plural, they may be the same or different and form an aromatic ring or a heteroaromatic ring with an adjacent group. The method according to claim 1,
The R ₁ To R ₄ are the same or different, each independently represent hydrogen, deuterium _{(D), C 6 ~ C} 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ C ₄₀ aryl group consisting of an amine group of one another &Lt; / RTI &gt; The method according to claim 1,
Wherein Ar ₁ to Ar ₅ are the same or different from each other and each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms. The method according to claim 1,
Wherein R ₁ to R ₄ are the same or different and are each independently hydrogen or a substituent represented by the formula selected from the following formulas (S1) to (S211)
The Ar ₁ To Ar ₅ are the same or different and are each independently a C ₁ to C ₄₀ alkyl group or a substituent represented by the formula selected from the following formulas (S1) to (S222).

The method according to claim 1,
The compound represented by Formula 1 or Formula 2 is represented by any one of formulas C-1 to C-32.

In the above formulas C-1 to C-32,
Ar ₁ to Ar ₅ and R ₁ to R ₄ are the same as defined in claim 1,
Ra is hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, an aryl group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ of the nuclear A heteroaryl group having 5 to 40 atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nucleus A heterocyclic alkyl group having 3 to 40 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 C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting arylsilyl of C ₄₀ of, or by groups coupled to or adjacent to can form a fused ring, wherein when Ra is a plurality, equal to each other Or may be different,
C ₁ ~ C ₄₀ alkyl group of Ra, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ of ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₄₀ group, and C ₆ ~ C ₄₀ aryl silyl groups are each independently a heavy hydrogen (D), a halogen, a cyano group, an alkynyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ - a heteroaryl group of C ₄₀ aryl group, the number of nuclear atoms of 5 to 40, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₄₀ aryl amine group, C ₃ a ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ Kill boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C ₄₀ of the aryl silyl group consisting And may be substituted or unsubstituted with one or more substituents, provided that when the substituents are plural, they may be the same or different,
n and m are each an integer of 0 to 4,
and l is an integer of 0 to 2. 8. The method of claim 7,
Wherein Ra is hydrogen, deuterium _{(D), C 6 ~ C} 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ C ₄₀ compounds selected from the group consisting of arylamine of. 8. The method of claim 7,
Wherein Ra is hydrogen or a substituent represented by any one of formulas (S1) to (S222), wherein when Ra is plural, the compound is the same as or different from each other.

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 the compound according to any one of claims 1 to 9. 11. The method of claim 10,
Wherein at least one of the one or more organic layers including the compound is a light emitting layer.