KR101641410B1 - Organic light-emitting compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel indole compound having excellent hole injecting and transporting ability and light emitting ability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime by incorporating it into one or more organic layers.

Description

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

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device including the same. More particularly, the present invention relates to a novel organic compound having excellent hole injection and transport ability, An organic electroluminescent device having improved characteristics such as driving voltage, lifetime and the like.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film luminosity of Bernanose in the 1950s, (Tang) and a functional layer of a light emitting layer. In order to produce high efficiency and high number of organic EL devices, the organic EL device has been developed to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

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

The light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve the luminous efficiency up to four times that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. As the hole blocking layer and the electron transporting layer, NPB, BCP and Alq ₃ represented by the following formulas are widely known, and an anthracene derivative as a luminescent material has been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in terms of efficiency improvement of a light emitting material, a metal complex compound containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like is a blue, green, It is used as a material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional host materials are advantageous from the viewpoint of luminescence characteristics, but have low glass transition temperature and very poor thermal stability, and thus are not satisfactory in terms of lifetime in organic EL devices.

It is an object of the present invention to provide a novel organic compound having excellent hole injecting and transporting ability, light emitting ability and the like.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having an improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

In Formula 1,

Any _one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula Form a fused ring;

In Formula 2,

The dotted line represents a moiety which is condensed with the formula (1)

X ₁ and X ₂ are the same or different and are each independently _{C (Ar 1) (Ar 2} ), N (Ar 3), O, S , and is selected from the group consisting of _{Si (Ar 4) (Ar 5} ) ;

R ₁ to R ₈ and R ₉ to R _{14 which} are not condensed with the ring of Formula 2 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, A C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C to ₄₀ groups of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C of ₆ ~ C ₆₀ aryl phosphine oxide group, and an aryl amine of the C ₆ ~ C ₆₀ group Or may combine with adjacent groups to form a condensed ring,

Ar ₁ to Ar ₅ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , is selected from the aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₆₀ aryl amine of the C ₆ ~ C _60,

The alkyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, and the alkylboron group of the above R ₁ to R ₁₄ and Ar ₁ to Ar ₅ , an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ substituted from the group consisting of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine, with one or more substituents selected or is unsubstituted, but the When there are plural substituents, they may be the same as or different from each other.

The present invention also provides an organic electroluminescent device comprising (i) a positive electrode, (ii) a negative electrode, and (iii) at least one organic material layer interposed between the positive electrode and the negative electrode, One is an organic electroluminescent device comprising a compound represented by the general formula (1).

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and luminescence properties and can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emitting performance, a low driving voltage, a high efficiency and a long life can be manufactured as compared with a conventional host material, Full color display panels with improved performance and lifetime can also be fabricated.

Hereinafter, the present invention will be described in detail.

The novel organic compound according to the present invention is obtained by condensing any one of an indene moiety, indole moiety, benzothiophene, benzofuran, and benzosilole with a dibenzoisoindole moiety (2H-dibenzo [e, g] isoindole moiety) Which is a structure having a basic skeleton and various substituents bonded to the basic skeleton, and is characterized by being represented by the above formula (1). The compound represented by Chemical Formula 1 has a higher molecular weight than conventional materials for organic EL devices such as 4,4-dicarbazolybiphenyl (hereinafter, referred to as 'CBP'), and has excellent hole injection ability, Therefore, when the compound of Formula 1 is used as at least one of the organic compound layer material of the organic electroluminescence device, preferably the hole injection layer material, the hole transport layer material and the light emitting layer material, the driving voltage, efficiency ) And life can be improved.

The compound represented by Formula 1 has the basic skeleton, so that the triplet energy is higher than about 2.3 eV. Therefore, when the compound is used as a host of an organic electroluminescent device, the energy of triplet energy is higher than that of a dopant known in the art (for example, Ir (ppy) _3, etc.) It is possible to improve the luminous efficiency of the device.

In addition, the compound of Formula 1 may have a broad band gap (sky blue to red) by controlling the energy level according to the substituents bonded to the basic skeleton, so that the carrier can be easily transferred to the dopant , And the migration (diffusion) of excitons formed in the light emitting layer to the surrounding organic material layer can be prevented. Therefore, the compound of Formula 1 can improve the phosphorescence characteristics of the device and improve the electron and / or hole transporting ability, luminescence efficiency, driving voltage, lifetime characteristics, and the like compared to the conventional CBP.

In addition to the host materials of the light emitting layer, the present invention can be applied to a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a light emitting auxiliary layer and the like in accordance with the above substituents. In particular, the compound of Formula 1 may have a bipolar characteristic as a whole depending on the characteristics of the substituent bonded to the basic skeleton. According to an example, when the substituent bonded to the basic skeleton is an electron withdrawing group (EWG) having a high electron absorbing property, the compound of Formula 1 has a bipolar, thereby having a wide band gap, The bonding force of electrons can be increased. Accordingly, the compound of Formula 1 can improve the phosphorescence characteristics of the organic EL device, and improve the hole injecting ability, transporting ability, or light emitting efficiency.

In addition, the compound of formula (1) has an aromatic ring substituent introduced into the basic skeleton, thereby significantly increasing the molecular weight of the compound, thereby improving the glass transition temperature and having higher thermal stability than conventional CBP . Accordingly, the organic electroluminescent device comprising the compound represented by Formula 1 of the present invention can greatly improve the durability and lifetime characteristics.

As described above, when the compound represented by Formula 1 of the present invention is used as a material for a hole injection layer, a hole transporting layer, or a light emitting layer of an organic electroluminescent device, the organic electroluminescent device (for example, Efficiency and life can be improved. In addition, the lifetime of the organic electroluminescent device can be maximized to maximize the performance of the full color organic electroluminescent panel.

In the compound represented by Formula 1 according to the present invention, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R _4, R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ When one is condensed with the ring represented by the formula (2) to form a fused ring, the compound may be represented by any one of the following formulas (3) to (8).

In the above Formulas 3 to 8,

X ₁ , X ₂ and R ₁ to R ₁₄ are each as defined in formula (1).

In the compound of Formula 1, X ₁ and X ₂ are the same or different, and each independently _{C (Ar 1) (Ar 2} ), N (Ar 3), O, S and Si (Ar ₄₎ (Ar ₅ , Preferably X ₁ is selected from the group consisting of C (Ar ₁ ) (Ar ₂ ), N (Ar ₃ ), O, S and Si (Ar ₄ ) (Ar ₅ ) X ₂ may be N (Ar ₃ ), and more preferably, X ₁ and X ₂ may all be N (Ar ₃ ).

For example, when X ₁ and X ₂ are both N (Ar ₃ ), the compound represented by formula (1) according to the present invention can be represented by any of the following formulas (9) to (14).

In the above Chemical Formulas 9 to 14,

R ₁ to R ₁₄ , and Ar ₃ Are as defined in formula (1), respectively.

In the compound of Formula 1, in consideration of a wide band gap and thermal stability, Ar ₁ to Ar ₅ are the same or different from each other, and each independently represents an aryl group of C ₆ to C _{60 and} an aryl group of 5 to 60 And a heteroaryl group.

The C ₆ -C ₆₀ aryl group and the heteroaryl group having 5 to 60 nuclear atoms of Ar ₁ to Ar ₅ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C _A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, an aryl group having 5 to 60 nuclear atoms A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ one selected from the aryl group consisting of an amine group of the C ₆₀ of the Lt; / RTI > or more of the above substituents. However, when there are a plurality of substituents, they may be the same or different.

In the compound represented by the general formula (1) according to the present invention, R ₁ to R ₈ and R ₉ to R _{14 which} are not condensed with the ring of the general formula (2) are the same or different and are each independently hydrogen, halogen, cyano , A C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ arylamine group.

The R ₁ to R ₈ and R ₉ to R ₁₄ C ₁ to C ₄₀ alkyl groups, C ₆ to C ₆₀ aryl groups, heteroaryl groups having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryl amine groups are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₆₀ heteroaryl group, -aryl silyl group of C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ of, C ₁ - C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine group, C ₆ of the C ₆₀ - substituted aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group consisting of an amine group in the C ₆₀ with one or more substituents selected or may be unsubstituted. However, when there are a plurality of substituents, they may be the same or different.

In the compound of formula (I) according to the present invention, Ar ₁ to Ar ₅ and R ₁ to R ₈ and R ₉ to R _{14, which} are not condensed with the ring of formula (2), are each independently hydrogen, Can be selected from the group.

The compounds represented by formula (I) according to the present invention can be further formulated by the following illustrated formulas, but are not limited thereto.

In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

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

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

"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 of the carbons, preferably one to three carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. 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, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and may be a linear, branched or cyclic structure . ≪ / RTI > Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

In the present invention, "alkylboron group" means a boron group substituted with alkyl having 1 to 40 carbon atoms, "arylboron group" means a boron group substituted with aryl having 6 to 60 carbon atoms, Means a phosphine group substituted with aryl of 1 to 60, and the term "arylphosphine oxide group" means a phosphine oxide group substituted with aryl having 1 to 60 carbon atoms.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.

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

The compound of formula (I) of the present invention can be synthesized according to a general synthesis method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

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

Specifically, the organic electroluminescent device according to the present invention includes at least one organic layer interposed between the anode and the cathode, (iii) an anode, (ii) a cathode, and (iii) at least one organic compound layer interposed between the anode and the cathode, Include the compounds represented by the above formula (1). At this time, the compound represented by the formula (1) may be used singly or in combination of two or more.

According to an example, the at least one organic material layer includes a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. Preferably, the organic compound layer containing the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer, and more preferably, a light emitting layer. In particular, when the compound represented by Formula 1 is included in the organic electroluminescent device as a light emitting layer material, the luminous efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.

For example, the compound represented by Formula 1 may be used as a phosphorescent host or a fluorescent host or a dopant material of the light emitting layer. Preferably, the compound represented by Formula 1 may be included in the organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material.

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated on the substrate, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer Lt; / RTI >

Specifically, the organic electroluminescent device may have a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked on a substrate. Alternatively, an electron injection layer may be disposed on the electron transporting layer. At least one of the hole injecting layer, the hole transporting layer, and the light emitting layer may include the compound represented by Formula 1, and the light emitting layer may include the compound of Formula 1, May be used as a phosphorescent host or a fluorescent host of the light emitting layer.

The organic electroluminescent device of the present invention may be formed by using a material known in the art (for example, a hole injecting layer, a hole transporting layer, and a light emitting layer), except that at least one of the organic layers And forming an organic layer and an electrode using a method.

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 includes, for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or a sheet, but is not limited thereto.

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 and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Further, the hole injection layer material, the hole transport layer material, the electron injection layer material, and the electron transport layer material 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 the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Preparation Example 1] Synthesis of Compound A3

<Step 1> Synthesis of 4-bromo-2-phenyl-2H-dibenzo [e, g] isoindole

Dibenzo [b, d] stannole (18.7 g, 62.1 mmol), 4-bromo-5,5-dimethyl-5H-dibenzo [b, pyrrole (18.7 g, 62.1 mmol), Pd (PtBu ₃ ) ₂ (1.6 g, 5 mol) and THF (900 ml) Lt; 0 &gt; C for 10 hours.

After completion of the reaction, the temperature was lowered to room temperature and the reaction product was filtered with Florisil. Then, the solvent was removed and the residue was purified by column chromatography to obtain 4-bromo-2-phenyl-2H-dibenzo [e, g] isoindole (7.4 g, 20.0 mmol, yield 32%).

GC-Mass (theory: 372.26 g / mol, measurement: 372 g / mol)

<Step 2> Synthesis of 4- (2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole

2-phenyl-2H-dibenzo [e, g] isoindole (7.4 g, 20.0 mmol), 2-nitrophenylboronic acid (3.3 g, 20.0 mmol) obtained in the above Step 1, Pd ₃ ) ₄ (1.1 g, 5 mol), potassium carbonate (8.3 g, 60.0 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) were mixed and stirred at 110 ° C for 2 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . Then, the solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain 6.3 g (15.2 mmol, yield: 76%) of 4- (2-nitrophenyl) -2-phenyl- 2H- dibenzo [e, g] isoindole.

GC-Mass (calculated: 414.45 g / mol, measured: 414 g / mol)

<Step 3> Synthesis of Compound A3

(2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole (6.3 g, 15.2 mmol) obtained in the above Step 2 and triphenylphosphine (10.0 g, 38.0 mmol) 2-dichlorobenzene (60 ml) were mixed and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and then water was removed using MgSO ₄ . Thereafter, the solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain Compound A3 (4.7 g, 12.3 mmol, yield 81%).

GC-Mass (theory: 382.46 g / mol, measured: 382 g / mol)

[Preparation Example 2] Synthesis of compounds B3 and B4

<Step 1> Synthesis of 5-bromo-2-phenyl-2H-dibenzo [e, g] isoindole

Dibenzo [b, d] stannole (16.6 g, 55.2 mmol) and 3-bromo-5,5-dimethyl-5H-dibenzo [b, d] stannole (21.0 g, 55.2 mmol) (16.6 g, 55.2 mmol), Pd (PtBu ₃ ) ₂ (1.4 g, 5 mol) and THF (800 ml) Stir for 10 hours.

After completion of the reaction, the temperature was lowered to room temperature and the reaction product was filtered with Florisil. Then, the solvent was removed, and the residue was purified by column chromatography to obtain 5-bromo-2-phenyl-2H-dibenzo [e, g] isoindole (7.4 g, 20.0 mmol, yield 36%).

GC-Mass (theory: 372.26 g / mol, measurement: 372 g / mol)

<Step 2> Synthesis of 5- (2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole

2H-dibenzo [e, g] isoindole used in Step 2 of Preparation Example 1 was used instead of 5-bromo-2-phenyl-2H- (2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole was obtained by following the procedure of <Step 2> of Preparation Example 1, [e, g] isoindole (6.4 g, 15.4 mmol, yield 77%).

GC-Mass (calculated: 414.45 g / mol, measured: 414 g / mol)

<Step 3> Synthesis of compounds B3 and B4

(2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole was used in place of 4- (2-nitrophenyl) -2-phenyl- 2H- The same procedure as in <Step 3> of Preparation Example 1 was conducted, except that the compound B3 (2.1 g, 5.4 mmol, yield 35%) and the compound B4 (5.4 mmol, 2.0 g, 5.1 mmol, yield: 33%).

GC-Mass of compound B3 (theoretical value: 382.46 g / mol, measured value: 382 g / mol)

GC-Mass of compound B4 (theoretical value: 382.46 g / mol, measured value: 382 g / mol)

[Preparation Example 3] Synthesis of Compound C3 and C4

<Step 1> Synthesis of 6-bromo-2-phenyl-2H-dibenzo [e, g] isoindole

Dibenzo [b, d] stannole (17.6 g, 58.5 mmol), 2-bromo-5,5-dimethyl-5H-dibenzo [b, d] stannole (22.2 g, 58.5 mmol) mmol), 3,4-dibromo-1 -phenyl-1H-pyrrole (17.6g, 58.5mmol), Pd (PtBu 3) 2 (1.5g, 5 mol), and into a THF (900ml), at 60 ℃ 10 Lt; / RTI &gt;

After completion of the reaction, the temperature was lowered to room temperature and the reaction product was filtered with Florisil. After removing the solvent, the residue was purified by column chromatography to obtain 7.4 g (20.0 mmol, yield: 34%) of 6-bromo-2-phenyl-2H-dibenzo [e, g] isoindole as a target compound.

GC-Mass (theory: 372.26 g / mol, measurement: 372 g / mol)

<Step 2> Synthesis of 6- (2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole

6-bromo-2-phenyl-2H-dibenzo [e, g] isoindole (7.4 g, 10 mmol) instead of the 4-bromo-2- phenyl- 2H-dibenzo [e, g] isoindole used in <Step 2> 2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole (6.3 g, 15.2 mmol) was obtained by carrying out the same procedure as <Step 2> of Preparation Example 1, mmol, yield: 76%).

GC-Mass (calculated: 414.45 g / mol, measured: 414 g / mol)

<Step 3> Synthesis of Compounds C3 and C4

(2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole used in Step 3 of Preparation Example 1 was used instead of 4- The same procedure as in <Step 3> of Preparation Example 1 was conducted, except that the compound C3 (2.0 g, 5.3 mmol) was used, except that the compound mmol, yield 35%) and compound C4 (1.9 g, 5.0 mmol, 33% yield).

GC-Mass of compound C3 (theoretical value: 382.46 g / mol, measured value: 382 g / mol)

GC-Mass of compound C4 (theoretical value: 382.46 g / mol, measurement: 382 g / mol)

[Preparation Example 4] Synthesis of Compound D3

<Step 1> Synthesis of 7-bromo-2-phenyl-2H-dibenzo [e, g] isoindole

Dibenzo [b, d] stannole (19.3 g, 64.1 mmol) and 1-bromo-5,5-dimethyl-5H-dibenzo [b, d] stannole (24.4 g, 64.1 mmol) pyridine (19.3 g, 64.1 mmol), Pd (PtBu ₃ ) ₂ (1.6 g, 5 mol) and THF (1000 ml) Lt; / RTI &gt;

After completion of the reaction, the temperature was lowered to room temperature and the reaction product was filtered with Florisil. Thereafter, the solvent was removed, and the residue was purified by column chromatography to obtain 7-bromo-2-phenyl-2H-dibenzo [e, g] isoindole (7.4 g, 20.0 mmol, yield: 31%).

GC-Mass (theory: 372.26 g / mol, measurement: 372 g / mol)

<Step 2> Synthesis of 7- (2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole

Bromo-2-phenyl-2H-dibenzo [e, g] isoindole (7.4 g, 10 mmol) instead of the 4-bromo-2- phenyl- 2H-dibenzo [e, g] isoindole used in <Step 2> 2-nitrophenyl) -2-phenyl-2H-dibenzo [e, g] isoindole (6.5 g, 15.6 mmol) was obtained by following the procedure of Step 2 of Preparation Example 1, mmol, yield 78%).

GC-Mass (calculated: 414.45 g / mol, measured: 414 g / mol)

<Step 3> Synthesis of Compound D3

2-nitrophenyl-2-phenyl-2H-dibenzo [e, g] isoindole was used in place of 4- (2-nitrophenyl) , g] isoindole (6.5 g, 15.6 mmol) was used in place of 4-chloro-2-fluoroaniline to give compound D3 (4.5 g, 11.9 mmol, yield 76%).

GC-Mass (theory: 382.46 g / mol, measured: 382 g / mol)

[Synthesis Example 1] Synthesis of Compound R1

(4.7 g, 12.3 mmol), 5'-chloro-1, -1 ': 3', -1''-Terphenyl (3.6 g, 13.6 mmol) obtained in Preparation Example 1 and Pd _{2 ) 3 (0.6g, 5 mol)} , tri- tert- butylphosphine (0.1g, 0.5mmol) and Sodium tert-butoxide (3.6g, put 37.0mmol), and Toluene (60ml), stirred for 3 hours at 110 ℃ Respectively.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Thereafter, the resultant product was purified by column chromatography to obtain Compound R1 (5.6 g, 9.1 mmol, yield 74%).

GC-Mass (theory: 610.74, measured: 610 mol)

[Synthesis Example 2] Synthesis of compound R2

Except that 2-chloro-4,6-diphenylpyridine (3.6 g, 13.6 mmol) was used instead of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 1 , The same procedure as in Synthesis Example 1 was conducted to obtain compound R2 (5.4 g, 8.7 mmol, Yield 71).

GC-Mass (theory: 611.73, measurement: 611 / mol)

[Synthesis Example 3] Synthesis of Compound R4

Except that 4-chloro-2,6-dipheylpyrimidine (3.6 g, 13.6 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 1 , The same procedure as in Synthesis Example 1 was conducted to obtain compound R4 (5.5 g, 9.0 mmol, yield 73%).

GC-Mass (theory: 612.72, measurement: 612 / mol)

[Synthesis Example 4] Synthesis of Compound R20

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 10 mmol) instead of 5'-chloro-1, g, 13.6 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain compound R20 (5.9 g, 8.5 mmol, yield 69%).

GC-Mass (calculated: 689.80 g / mol, measured: 689 g / mol)

[Synthesis Example 5] Synthesis of Compound R25

Except that 2-chloro-4-phenylquinazoline (3.3 g, 13.6 mmol) was used in place of 5'-chloro-1, -1 ': 3', -1''-Terphenyl used in Synthesis Example 1, The procedure of Example 1 was repeated to obtain compound R25 (5.3 g, 9.0 mmol, yield 73%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 6] Synthesis of compound R26

(2.1 g, 5.4 mmol), 5'-chloro-1, -1 ': 3', -1''-Terphenyl (1.6 g, 5.9 mmol) and Pd _{2 dba) 3 (0.3g, 5 mol} ), tri- tert- butylphosphine (0.1g, 0.5mmol) and Sodium tert-butoxide (1.6g, 16.2mmol ), and put Toluene (60ml) was stirred at 110 for 4 hours ℃ Respectively.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Thereafter, the resultant was purified by column chromatography to obtain a compound R26 (2.5 g, 4.2 mmol, yield 77%).

GC-Mass (theory: 610.74, measured: 610 mol)

[Synthesis Example 7] Synthesis of compound R27

Except that 2-chloro-4,6-diphenylpyridine (1.6 g, 5.9 mmol) was used instead of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 6 , And the same procedure as in Synthesis Example 6 was carried out to obtain a compound R27 (2.5 g, 4.0 mmol, yield 75%).

GC-Mass (theory: 611.73, measurement: 611 / mol)

[Synthesis Example 8] Synthesis of Compound R29

Except that 4-chloro-2,6-dipheylpyrimidine (1.6 g, 5.9 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 6 , And the same procedure as in Synthesis Example 6 was carried out to obtain a compound R29 (2.5 g, 4.2 mmol, yield 77%).

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

[Synthesis Example 9] Synthesis of compound R45

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.0 g) was used instead of 5'-chloro-1,1 ': 3' g, 5.9 mmol), the same procedure as in Synthesis Example 6 was conducted to obtain a compound R45 (2.7 g, 3.9 mmol, yield 72%).

GC-Mass (calculated: 689.80 g / mol, measured: 689 g / mol)

[Synthesis Example 10] Synthesis of Compound R50

Except that 2-chloro-4-phenylquinazoline (1.4 g, 5.9 mmol) was used in place of 5'-chloro-1, -1 ': 3', -1''-Terphenyl used in Synthesis Example 6, The procedure of Example 6 was repeated to give compound R50 (2.5 g, 4.3 mmol, yield 79%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 11] Synthesis of Compound R51

(1.9 g, 5.1 mmol), 5'-chloro-1, -1 ': 3', -1''-Terphenyl (1.5 g, 5.6 mmol), Pd _{2 ) 3 (0.2g, 5 mol)} , tri- tert- butylphosphine (0.1g, 0.5mmol) and Sodium tert-butoxide (1.5g, put 15.2mmol), and Toluene (40ml) was stirred at 110 for 3 hours ℃ .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Thereafter, purification was conducted by column chromatography to obtain a compound R51 (2.2 g, 3.7 mmol, yield 72%).

GC-Mass (theory: 610.74, measured: 610 mol)

[Synthesis Example 12] Synthesis of Compound R52

Except that 2-chloro-4,6-diphenylpyridine (1.5 g, 5.9 mmol) was used instead of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 11 , The same procedure as in Synthesis Example 11 was carried out to obtain a compound R52 (2.1 g, 3.5 mmol, yield 68%).

GC-Mass (theory: 611.73, measurement: 611 / mol)

[Synthesis Example 13] Synthesis of Compound R54

Except that 4-chloro-2,6-dipheylpyrimidine (1.5 g, 5.9 mmol) was used instead of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 11 , And the procedure of Synthesis Example 11 was repeated to give compound R54 (2.2 g, 3.6 mmol, yield 71%).

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

[Synthesis Example 14] Synthesis of Compound R70

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g) was used in place of 5'-chloro-1,1 ': 3' g, 5.6 mmol), the same procedure as in Synthesis Example 11 was conducted to obtain compound R70 (2.5 g, 3.7 mmol, yield 72%).

GC-Mass (calculated: 689.80 g / mol, measured: 689 g / mol)

[Synthesis Example 15] Synthesis of Compound R75

Except that 2-chloro-4-phenylquinazoline (1.3 g, 5.6 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 11 The procedure of Example 11 was repeated to give compound R75 (2.4 g, 4.1 mmol, yield 81%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 16] Synthesis of Compound R76

(2.0 g, 5.3 mmol), 5'-chloro-1, -1 ': 3', -1''-Terphenyl (1.6 g, 5.9 mmol), Pd _{2 ) 3 (0.3g, 5 mol)} , tri- tert- butylphosphine (0.1g, 0.5mmol) and Sodium tert-butoxide (1.5g, put 16.0mmol), and Toluene (40ml) was stirred for 4 hours at 110 ℃ .

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain a compound R76 (2.2 g, 3.7 mmol, yield 69%).

GC-Mass (theory: 610.74, measured: 610 mol)

[Synthesis Example 17] Synthesis of Compound R77

Except that 2-chloro-4,6-diphenylpyridine (1.6 g, 5.9 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 16 , And the procedure of Synthesis Example 16 was repeated to give compound R77 (2.3 g, 3.8 mmol, yield 71%).

GC-Mass (theory: 611.73, measurement: 611 / mol)

[Synthesis Example 18] Synthesis of Compound R79

Except that 4-chloro-2,6-dipheylpyrimidine (1.6 g, 5.9 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 16 , And the same procedure as in Synthesis Example 16 was carried out to obtain a compound R79 (2.4 g, 4.0 mmol, yield 75%).

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

[Synthesis Example 19] Synthesis of Compound R95

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.1 g) was used in the place of 5'-chloro-1,1 ': 3' g, 5.9 mmol), the same procedure as in Synthesis Example 16 was conducted to obtain Compound R95 (2.7 g, 3.9 mmol, yield 74%).

GC-Mass (calculated: 689.80 g / mol, measured: 689 g / mol)

[Synthesis Example 20] Synthesis of Compound R100

Except that 2-chloro-4-phenylquinazoline (1.5 g, 5.9 mmol) was used in place of 5'-chloro-1, -1 ': 3', -1''-Terphenyl used in Synthesis Example 16 The procedure of Example 16 was repeated to obtain compound R100 (2.2 g, 3.8 mmol, yield 71%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 21] Synthesis of Compound R101

(1.9 g, 5.0 mmol), 5'-chloro-1, -1 ': 3', -1''-Terphenyl (1.5 g, 5.5 mmol) obtained in Preparation Example 3 and Pd _{2 ) 3 (0.2g, 5 mol)} , tri- tert- butylphosphine (0.1g, 0.5mmol), Sodium tert-butoxide (1.5g, 15.1mmol) and put Toluene (40ml) was stirred for 4 hours at 110 ℃.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain Compound R101 (2.0 g, 3.3 mmol, yield 66%).

GC-Mass (theory: 610.74, measured: 610 mol)

[Synthesis Example 22] Synthesis of Compound R102

Except that 2-chloro-4,6-diphenylpyridine (1.5 g, 5.5 mmol) was used instead of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 21 , The same procedure as in Synthesis Example 21 was conducted to obtain compound R102 (2.1 g, 3.4 mmol, yield 67%).

GC-Mass (theory: 611.73, measurement: 611 / mol)

[Synthesis Example 23] Synthesis of Compound R104

Except that 4-chloro-2,6-dipheylpyrimidine (1.5 g, 5.5 mmol) was used instead of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 21 , And the procedure of Synthetic Example 21 was repeated to give compound R104 (2.0 g, 3.2 mmol, yield 66%).

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

[Synthesis Example 24] Synthesis of Compound R120

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g) was used in place of 5'-chloro-1,1 ': 3' g, 5.5 mmol), the same procedure as in Synthesis Example 21 was conducted to obtain Compound R95 (2.3 g, 3.3 mmol, yield 65%).

GC-Mass (calculated: 689.80 g / mol, measured: 689 g / mol)

[Synthesis Example 25] Synthesis of Compound R125

Except that 2-chloro-4-phenylquinazoline (1.3 g, 5.5 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 21 The procedure of Example 21 was repeated to give compound R125 (2.0 g, 3.5 mmol, yield 69%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Synthesis Example 26] Synthesis of Compound R126

(4.5 g, 11.9 mmol), 5'-chloro-1, -1 ': 3', -1''-Terphenyl (3.5 g, 13.0 mmol) and Pd ₂ (dba _{) 3 (0.6g, 5 mol)} , tri- tert- butylphosphine (0.1g, 0.5mmol), Sodium tert-butoxide (3.4g, 35.6mmol) and put Toluene (90ml) was stirred at 110 ℃ for 5 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Purification by column chromatography afforded compound R126 (5.1 g, 8.4 mmol, yield 71%).

GC-Mass (theory: 610.74, measured: 610 mol)

[Synthesis 27] Synthesis of compound R127

Except that 2-chloro-4,6-diphenylpyridine (3.5 g, 13.0 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 26 , And the procedure of Synthesis Example 26 was performed to obtain a compound R127 (5.1 g, 8.3 mmol, yield 70%).

GC-Mass (theory: 611.73, measurement: 611 / mol)

[Synthesis Example 28] Synthesis of Compound R129

Except that 4-chloro-2,6-dipheylpyrimidine (3.5 g, 13.0 mmol) was used in place of 5'-chloro-1, -1 ': 3', - 1 '' - terphenyl used in Synthesis Example 26 , And the procedure was similar to that of Synthesis Example 26 to obtain the compound R129 (4.9 g, 8.1 mmol, yield 68%).

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

[Synthesis Example 29] Synthesis of Compound R145

(3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.5 g) was used in the place of 5'-chloro-1,1 ': 3' g, 13.0 mmol) was used in place of the compound obtained in Example 26 to obtain the compound R145 (5.4 g, 7.8 mmol, yield 66%).

GC-Mass (calculated: 689.80 g / mol, measured: 689 g / mol)

[ Synthetic example  30] Compound R150 Synthesis of

Except that 2-chloro-4-phenylquinazoline (3.1 g, 13.0 mmol) was used in place of 5'-chloro-1, -1 ': 3', -1''-Terphenyl used in Synthesis Example 26, The same procedure as in Example 26 was conducted to obtain a compound R150 (4.7 g, 8.1 mmol, yield 68%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[Example 1] Production of green organic EL device

Compound R1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was fabricated according to the following procedure.

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

(60 nm) / TCTA (80 nm) / Compound R1 + 10% Ir (ppy) ₃ (30 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.

At this time, the structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP are as follows.

[Example 2] - [Example 18] - Preparation of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1 except for using the compounds R4 to R145 described in Table 1 instead of the compound R1 used as a luminescent host material in the luminescent layer formation in Example 1.

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound R1 as a luminescent host material in forming the light emitting layer. The structure of CBP used is as follows.

[Evaluation Example 1]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic EL devices manufactured in Examples 1 to 18 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 R1 6.2 515 41.2 Example 2 R4 6.1 515 41.1 Example 3 R20 6.2 515 41.2 Example 4 R26 6.3 514 41.7 Example 5 R29 5.9 513 40.5 Example 6 R45 5.7 515 41.2 Example 7 R51 6.2 515 40.9 Example 8 R54 6.4 514 41.2 Example 9 R70 6.3 514 42.3 Example 10 R76 6.2 514 41.5 Example 11 R79 6.9 514 41.5 Example 12 R95 6.3 515 40.2 Example 13 R101 6.2 515 41.2 Example 14 R104 6.1 515 41.0 Example 15 R120 6.2 515 40.2 Example 16 R126 6.4 515 41.1 Example 17 R129 6.4 514 42.1 Example 18 R145 6.2 514 41.5 Comparative Example 1 CBP 7.2 518 35.2

As shown in Table 1, the compound (R1, R4, R20, R26, R29, R45, R51, R54, R70, T76, R79, R95, R101, R104, R120, R126, R129, Are used as light emitting layer materials, the green organic EL devices of Examples 1 to 18 show higher current efficiency and better driving voltage than the green organic EL device of Comparative Example 1 using CBP in the related art.

[Example 19] Production of red organic EL device

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

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

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

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

[Example 20] - [Example 30] - Preparation of red organic EL device

A red organic EL device was manufactured in the same manner as in Example 19 except that the compound A25 to R150 described in Table 2 was used instead of the compound R2 used as the luminescent host material in forming the light emitting layer in Example 19, respectively.

[Comparative Example 2]

A red organic electroluminescent device was fabricated in the same manner as in Example 19, except that CBP was used instead of the compound R 2 in Synthesis Example 2 as a luminescent host material in forming the light emitting layer. At this time, the structure of CBP used is as described in Comparative Example 1.

[Evaluation Example 2]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 19 to 30 and Comparative Example 2, respectively, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 19 R2 6.4 515 41.2 Example 20 R25 6.2 514 41.1 Example 21 R27 5.5 515 41.2 Example 22 R50 6.3 514 41.1 Example 23 R52 5.9 514 40.2 Example 24 R75 5.5 515 40.5 Example 25 R77 6.2 513 40.3 Example 26 R100 6.4 515 41.2 Example 27 R102 6.4 514 42.0 Example 28 R125 6.2 514 41.3 Example 29 R127 6.9 514 41.1 Example 30 R150 6.5 513 41.2 Comparative Example 2 CBP 7.1 517 37.0

As shown in Table 2, in the case of the red organic electroluminescent devices of Examples 19 to 30, in which the compounds (compounds R2 to R150) according to the present invention were used as light emitting layer materials, in Comparative Example 2 using CBP as the material of the light emitting layer It can be seen that the current efficiency and the driving voltage are superior to those of the red organic electroluminescent device.

Claims (7)

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

In Formula 1,
Any one of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by the following formula (2) to form a fused ring;
(2)

In Formula 2,
The dotted line represents a moiety which is condensed with the formula (1)
And X ₁ and X ₂ are each independently selected from N (Ar _3), wherein and Ar ₃ of X ₁ is phenyl, the X ₂ Ar ₃ is the nuclear atoms of 6 to 12 which contains one or two phenyl and N hetero An aryl group,
The phenyl and heteroaryl groups of Ar ₃ are each independently substituted with one or more substituents selected from the group consisting of C ₆ to C ₁₂ aryl groups and heteroaryl groups having 6 to 18 nucleus atoms containing 3 N, Provided that when the substituent is plural, they may be the same or different from each other,
R ₁ to R ₄ , R ₉ to R ₁₄ , and R ₅ to R _{8, which} are not condensed with the ring of Formula 2, are each independently hydrogen. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (3) to (8)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above Formulas 3 to 8,
X ₁ , X ₂ and R ₁ to R ₁₄ are as defined in claim 1, respectively. The method according to claim 1,
The compound represented by the formula (1) is represented by the following formulas (9) to (14).
[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

In the above formulas (9) to (14)
R ₁ to R ₁₄ , and Ar ₃ are as defined in claim 1, respectively. delete 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 3. 6. The method of claim 5,
Wherein the organic material layer is selected from the group consisting of a hole injection layer, a hole transporting layer, and a light emitting layer. 6. The method of claim 5,
Among the one or more organic layers, the organic layer including the compound is a light emitting layer,
Wherein the compound is used as a phosphorescent host of the light emitting layer.