KR20170116500A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device having improved luminous efficiency, driving voltage, lifetime, and the like by incorporating a novel compound having excellent luminous efficiency into one or more organic layers.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel pyrimidine derivative compound having excellent electron injection and transport ability, And lifetime of the organic electroluminescent device.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1965 based on 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 4 times as compared with 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, Alq ₃ and the like represented by the following formulas are widely known, and an anthracene derivative as a light emitting material has been reported as a fluorescent dopant / host material. In particular Firpic, Ir as a phosphorescent material that has a great advantage in improving the efficiency aspects of the light-emitting material _{(ppy) 3, (acac)} Ir (btp) 2 Ir metal complex compound is a blue, green and red host material that includes such as . So far, CBP has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of light emitting properties, but their glass transition temperature is low and their thermal stability is not very good, which is not satisfactory in terms of lifetime in organic EL devices.

It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and has excellent electron injection and transporting ability.

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).

[Chemical Formula 1]

here,

L ₁ and L ₂ are the same or different and each is a single bond, a C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nuclear atoms,

R ₁ and R ₂ are the same or different and are each independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms;

Ar ₁ and Ar ₂ are different from each other and are each independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,

X ₁ , X ₂ and X ₃ are the same or different and are each independently N or C (R ₃ ), and at least two are N;

R ₃ 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, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 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 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, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of is selected from the group consisting of,

Aryl group and a heteroaryl group of L _1, L ₂ alkylene group and R ₁ to R ₃ and Ar ₁ to the aryl group Ar _2, and heteroaryl groups, each independently, a quartet cow, a cyano group, a halogen, C alkyl group of ₁ ~ C ₄₀ , 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, the number of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ alkylsilyl group of C _40, C ₆ ~ C ₆₀ aryl silyl group, C of ₁ ~ C ₄₀ group of an alkyl boron, 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 ~ arylamine group of C ₆₀ of And when they are substituted with a plurality of substituents, they may be the same 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).

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 linear or branched 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 (vinyl), allyl (all), isopropenyl (isopropenyl), and 2-butenyl (2-butenyl).

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 (ethyn yl), 2-propanyl (2-propynyl), 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 and triazinyl, phenoxathienyl, indolizinyl, indole, A polycyclic ring such as a carbamoyl group, a carbamoyl group, a carbamoyl group, a carbamoyl group, a carbamoyl group, a carbamoyl group, a carbamoyl group, a carbamoyl group, , 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 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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.

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

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

Since the compound of the present invention is excellent in thermal stability and luminescence properties, it can be used as a material of an organic material layer of an organic electroluminescent device.

In particular, when the compound of the present invention is used as an electron transporting material, it is possible to manufacture an organic electroluminescent device having superior light emitting performance, lower driving voltage, higher efficiency and longer life time than conventional host materials, A full color display panel can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The compound pyrimidine-based organic light-emitting compound of the present invention is superior in luminous efficiency and lifetime characteristics of a material compared with the conventional electron injection and transporting material, so that the device has an excellent driving life and induces an increase in power efficiency, There is an advantage that an improved OLED device can be manufactured.

Specifically, the novel organic compounds provided by the present invention are characterized by being represented by the following formula (1)

[Chemical Formula 1]

here,

L ₁ and L ₂ are the same or different and each is a single bond, a C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nuclear atoms,

R ₁ and R ₂ are the same or different and are each independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms;

Ar ₁ and Ar ₂ are different from each other and are each independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,

X ₁ , X ₂ and X ₃ are the same or different and are each independently N or C (R ₃ ), and at least two are N;

R ₃ 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, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 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 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, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of is selected from the group consisting of,

Aryl group and a heteroaryl group of L _1, L ₂ alkylene group and R ₁ to R ₃ and Ar ₁ to the aryl group Ar _2, and heteroaryl groups, each independently, a quartet cow, a cyano group, a halogen, C alkyl group of ₁ ~ C ₄₀ , 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 heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, the number of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ alkylsilyl group of C _40, C ₆ ~ C ₆₀ aryl silyl group, C of ₁ ~ C ₄₀ group of an alkyl boron, 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 ~ arylamine group of C ₆₀ of And when they are substituted with a plurality of substituents, they may be the same or different from each other.

Phenanthrene or carbazole-derived derivatives in the pyrimidine-based compounds are cores based on a structure having a high triplet energy and a stable structure. Especially, when the functional groups of phenanthrene or carbazole are substituted, electron transport ability is improved, So that it is advantageous as an electron injecting and transporting material capable of maximizing efficiency characteristics. In particular, when the aromatic ring and the heteroaromatic ring are independently substituted at the R ₁ , R ₂ , Ar ₁ and Ar ₂ positions, the planar structure is improved to improve the thermal stability as well as to improve the electron mobility, and thus it is suitable as an electron transport layer material.

According to a preferred embodiment of the present invention, Ar ₁ and Ar ₂ are different from each other, and each independently is a C ₆ to C ₆₀ aryl group.

According to a preferred embodiment of the present invention, X ₁ and X ₂ are each independently N, X ₃ is selected from N or C (R ₃ ), Ar ₁ and Ar ₂ are different from each other, May be selected from phenyl or biphenyl.

According to a preferred embodiment of the present invention, R ₁ and R ₂ may be the same or different and each independently selected from a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms , preferably at least one of R ₁ or R ₂ may be one selected from the group consisting of substituents of formulas 2 to 5:

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

here,

* Represents a moiety bonded to Formula 1;

X ₄ to X ₂₆ are the same or different and are each independently N or C (R ₅ )

R ₅ 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, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 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 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, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of is selected from the group consisting of,

R ₅ is an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, The oxides and arylamine groups are each independently selected from the group consisting of 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, 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 ₆ heteroaryl group, ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C aryl phosphine oxide group and a C ₆ ~ ₆₀ may be substituted with at least one member selected from the group consisting of an aryl amine of the C _60, the case be substituted with a plurality of substituents, they same or another It may be different.

According to one preferred embodiment of the present invention, the compound represented by formula (1) of the present invention may be selected from the group consisting of the following compounds, but is not limited thereto.

2. Organic electroluminescent device

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Preferably, the organic material layer containing the compound of Formula 1 may be an electron transporting layer.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary 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 auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, and preferably includes a hole transporting layer, The auxiliary layer may include a compound represented by the above formula (1). On the other hand, an electron injection layer may be further stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device of the present invention can be produced by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).

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 used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and 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 ordinary 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]

4 - ([1,1'- Biphenyl ] -4-yl) -6- (3- Bromo -5- (pyridin-3-yl) phenyl) -2- Phenylpyrimidine  synthesis

4 - ([1,1'-biphenyl] -4-yl) -6- (3,5-dibromophenyl) -2- phenylpyrimidine

(92.2 mmol) of pyridine-3-ylboronic acid and 250 mL of 1,4-dioxane were added. 5.32 g (4.61 mmol) of Pd (PPh ₃ ) ₄ and 31.85 g (230 mol) of K ₂ CO ₃ were added, and the mixture was refluxed at 120 ° C. for 24 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of an aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 30 g of the target compound (yield: 61%). 1H-NMR: 9.24 (s, 1H), 8.70 (d, 1H), 8.42-8.30 (m, 5H), 8.24 (s, 1H), 7.85-7.77 (m, 3H), 7.75 7.55-7.41 (m, 9H), HRMS [M] < ⁺ & gt ^; : 540.46

[ Preparation Example  2]

4 - ([1,1'- Biphenyl ] -4-yl) -6- (3- Bromo -5- (pyridin-4-yl) phenyl) -2- Phenylpyrimidine  synthesis

The procedure of Preparation Example 1 was repeated except that pyridine-4-ylboronic acid was used as a reactant to obtain 26 g of the target compound; HRMS [M] < + >: 540.46

[ Preparation Example  3]

8- (3- (6 - ([1,1'- Biphenyl ] -4-yl) -2- Phenylpyrimidine Yl) -5- Bromophenyl ) Quinoline

The procedure of Preparation Example 1 was repeated except that quinolin-8-ylboronic acid was used as a reactant to obtain 31 g of the target compound; HRMS [M] < + >: 590.52

[ Preparation Example  4]

4 - ([1,1'- Biphenyl ] -4-yl) -6- (5- Bromo -4 '- (pyridin-3-yl) - [1,1'- Biphenyl ] -3-yl) -2-phenylpyrimidine

The procedure of Preparation Example 1 was repeated except for using (4- (pyridin-3-yl) phenyl) boronic acid as a reactant to obtain 35 g of the target compound; HRMS [M] < + >: 616.56

[ Preparation Example  5]

2- (3- (6 - ([1,1'- Biphenyl ] -4-yl) -2- Phenylpyrimidine Yl) -5- Bromophenyl ) -1,10-phenanthroline Synthesis

Except that 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,10-phenanthroline was used as a reactant in Preparation Example 1 ] To obtain 31 g of the target compound; HRMS [M] < + >: 641.57

[ Preparation Example  6]

4 - ([1,1'- Biphenyl ] -4-yl) -6- (3- Bromo -5- (pyridin-3-yl) phenyl) -2- Phenylpyrimidine  synthesis

Except that 2 - ([1,1'-biphenyl] -4-yl) -4- (3,5-dibromophenyl) -6-phenyl-1,3,5-triazine was used as a reactant Was subjected to the same procedure as in [Preparation Example 1] to obtain 23 g of the target compound; HRMS [M] < + >: 541.45

[ Preparation Example  7]

4 - ([1,1'- Biphenyl ] -4-yl) -6- (3- Bromo -5- (pyridin-4-yl) phenyl) -2- Phenylpyrimidine  synthesis

Except that 2 - ([1,1'-biphenyl] -4-yl) -4- (3,5-dibromophenyl) -6-phenyl-1,3,5-triazine was used as a reactant Was subjected to the same procedure as in [Preparation Example 2] to obtain 22 g of the target compound; HRMS [M] < + >: 541.45

[ Preparation Example  8]

8- (3- (6 - ([1,1'- Biphenyl ] -4-yl) -2- Phenylpyrimidine Yl) -5- Bromophenyl ) Quinoline

Except that 2 - ([1,1'-biphenyl] -4-yl) -4- (3,5-dibromophenyl) -6-phenyl-1,3,5-triazine was used as a reactant Was subjected to the same procedure as in [Preparation Example 3] to obtain 26 g of the target compound; HRMS [M] < + >: 591.51

[ Preparation Example  9]

4 - ([1,1'- Biphenyl ] -4-yl) -6- (5- Bromo -4 '- (pyridin-3-yl) - [1,1'- Biphenyl ] -3-yl) -2-phenylpyrimidine

Except that 2 - ([1,1'-biphenyl] -4-yl) -4- (3,5-dibromophenyl) -6-phenyl-1,3,5-triazine was used as a reactant Was carried out in the same manner as in [Preparation Example 4] to obtain 29 g of the target compound; HRMS [M] < + >: 615.55

[ Preparation Example  10]

2- (3- (6 - ([1,1'- Biphenyl ] -4-yl) -2- Phenylpyrimidine Yl) -5- Bromophenyl ) -1,10-phenanthroline Synthesis

Except that 2 - ([1,1'-biphenyl] -4-yl) -4- (3,5-dibromophenyl) -6-phenyl-1,3,5-triazine was used as a reactant Was subjected to the same procedure as in [Preparation Example 5] to obtain 28 g of the desired compound; HRMS [M] < + >: 640.56

[ Synthetic example  1] Synthesis of Mat 1

(9.25 mmol) of 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- 250 mL of 1,4-dioxane was added to 1.24 g (10.17 mmol) of boronic acid. _{Pd (PPh 3) 4 0.53g (} 0.46mmol), K 2 CO 3 was added to 3.19g (23.1mol) was heated to reflux at 120 for 24 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of an aqueous ammonium chloride solution. The mixture was extracted with 200 mL of MC and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.37 g (yield 88%) of the desired compound. (S, 3H), 7.85 (m, 2H), 7.75 (m, 2H), 8.24 (s, m, 2H); 7.51-7.41 (m, 10H), HRMS [M] < ⁺ & gt ^; : 537.67

[ Synthetic example  2] Synthesis of Mat 2

The same procedure as in [Synthesis Example 1] was repeated except that naphthalene-2-ylboronic acid was used as a reactant, to obtain 5.1 g of the desired compound; HRMS [M] < + >: 587.73

[ Synthetic example  3] Synthesis of Mat 3

The same procedure as in [Synthesis Example 1] was carried out except that naphthalene-1-ylboronic acid was used as a reactant, to obtain 4.8 g of the desired compound; HRMS [M] < + >: 587.73

[ Synthetic example  4] Synthesis of Mat 4

The same procedure as in [Synthesis Example 1] was conducted except that phenanthrene-9-ylboronic acid was used as a reactant, to obtain 5.6 g of the desired compound; HRMS [M] < + >: 637.79

[ Synthetic example  5] Synthesis of Mat 5

The same procedure as in [Synthesis Example 1] was conducted except that an anthracene-9-ylboronic acid was used as a reactant, to obtain 5.5 g of the desired compound; HRMS [M] < + >: 637.79

[ Synthetic example  6] Synthesis of Mat 6

The procedure of Synthesis Example 1 was repeated except that (10-phenylanthracene-9-yl) boronic acid was used as a reactant, to obtain 6.9 g of the title compound; HRMS [M] < + >: 713.88

[ Synthetic example  7] Synthesis of Mat 7

The same procedure as in [Synthesis Example 1] was conducted except that triphenylene-2-ylboronic acid was used as a reactant, to obtain 5.4 g of the title compound; HRMS [M] < + >: 687.85

[ Synthetic example  8] Synthesis of Mat 8

The same procedure as in [Synthesis Example 1] was repeated but using (3a1,6-dihydropyren-1-yl) boronic acid as a reactant, 6.0 g of the target compound was obtained; HRMS [M] < + >: 661.81

[ Synthetic example  9] Synthesis of Mat 9

The same procedure as in [Synthesis Example 1] was repeated except for using (9,9-dimethyl-9H-flowen-3-yl) boronic acid as a reactant, to obtain 5.8 g of the desired compound; HRMS [M] < + >: 653.83

[ Synthetic example  10] Synthesis of Mat 10

The same procedure as in [Synthesis Example 1] was repeated, except that (9-phenyl-9H-carbazol-3-yl) boronic acid was used as a reaction product to obtain 7 g of the target compound; HRMS [M] < + >: 702.86

[ Synthetic example  11] Synthesis of Mat 11

The same procedure as in [Synthesis Example 1] was conducted except that dibenzo [b, d] furan-2-ylboronic acid was used as a reactant, to obtain 5.6 g of the desired compound; HRMS [M] < + >: 627.75

[ Synthetic example  12] Synthesis of Mat 12

(9.25 mmol) of 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- To 1.7 g (10.17 mmol) of the sol was added 250 mL of xylene. 0.42 g (0.46 mmol) of Pd ₂ (dba) ₃ , 0.44 g (0.92 mmol) of Xphos and 2.2 g (23.1 mol) of NaOtBu were added and the mixture was refluxed at 120 to 24 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of an aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.46 g (yield 77%) of the desired compound. (M, 4H), 7.50-7.16 (m, 12H (m, 2H), 7.42 ); HRMS [M] < ⁺ & gt ^; : 626.76

[ Synthetic example  13] Synthesis of Mat 13

The same procedure as in [Synthesis Example 12] was conducted except that 3-phenyl-9H-carbazole was used as a reactant, to obtain 5.9 g of the title compound; HRMS [M] < + >: 702.86

[ Synthetic example  14] Synthesis of Mat 14

(Dibenzo [b, e] [1,4] dioxin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used as a reactant , The same procedure as in [Synthesis Example 1] was conducted to obtain 6.1 g of the desired compound; HRMS [M] < + >: 643.75

[ Synthetic example  15] Synthesis of Mat 15

The same procedure as in [Synthesis Example 12] was conducted except that 10H-phenoxazine was used as a reactant, to obtain 5.2 g of the target compound; HRMS [M] < + >: 642.76

[ Synthetic example  16] Synthesis of Mat 16

Except that 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,10-phenanthroline was used as a reactant in Synthesis Example 1 ] To obtain the desired compound (4.3 g); HRMS [M] < + >: 639.76

[ Synthetic example  17] Synthesis of Mat 17

The same procedure as in [Synthesis Example 1] was repeated except that quinolin-8-ylboronic acid was used as a reactant, to obtain 5.0 g of the target compound; HRMS [M] < + >: 588.71

[ Synthetic example  18] Synthesis of Mat 18

The same procedure as in [Synthesis Example 1] was conducted except that 4- (pyridin-3-yl) phenyl) boronic acid was used as a reactant to obtain 6.5 g of the desired compound; HRMS [M] < + >: 614.75

[ Synthetic example  19] Synthesis of Mat 19

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 1] to obtain 3.2 g of the target compound; HRMS [M] < + >: 537.67

[ Synthetic example  20] Synthesis of Mat 20

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 2] to obtain 2.8 g of the desired compound; HRMS [M] < + >: 587.73

[ Synthetic example  21] Synthesis of Mat 21

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 3] to obtain 3.2 g of the desired compound; HRMS [M] < + >: 587.73

[ Synthetic example  22] Synthesis of Mat 22

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 4] to obtain 3.0 g of the target compound; HRMS [M] < + >: 637.79

[ Synthetic example  23] Synthesis of Mat 23

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 5] to obtain 4.2 g of the target compound; HRMS [M] < + >: 637.79

[ Synthetic example  24] Synthesis of Mat 24

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 6] to obtain 5.2 g of the desired compound; HRMS [M] < + >: 713.88

[ Synthetic example  25] Synthesis of Mat 25

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 7] to obtain 4.8 g of the desired compound; HRMS [M] < + >: 687.85

[ Synthetic example  26] Synthesis of Mat 26

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 8] to obtain 3.3 g of the target compound; HRMS [M] < + >: 661.81

[ Synthetic example  27] Synthesis of Mat 27

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 9] to obtain 4.6 g of the desired compound; HRMS [M] < + >: 653.83

[ Synthetic example  28] Synthesis of Mat 28

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 10] to obtain 4.3 g of the target compound; HRMS [M] < + >: 702.86

[ Synthetic example  29] Synthesis of Mat 29

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 11] to obtain 3.3 g of the target compound; HRMS [M] < + >: 627.75

[ Synthetic example  30] Synthesis of Mat 30

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 12] to obtain 2.5 g of the desired compound; HRMS [M] < + >: 626.76

[ Synthetic example  31] Synthesis of Mat 31

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was carried out in the same manner as in [Synthesis Example 13] to obtain the objective compound (2.8 g); HRMS [M] < + >: 702.86

[ Synthetic example  32] Synthesis of Mat 32

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 14] to obtain 2.1 g of the desired compound; HRMS [M] < + >: 643.75

[ Synthetic example  33] Synthesis of Mat 33

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 15] to obtain 1.6 g of the desired compound; HRMS [M] < + >: 642.76

[ Synthetic example  34] Synthesis of Mat 34

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 16] to obtain 3.0 g of the target compound; HRMS [M] < + >: 639.76

[ Synthetic example  35] Synthesis of Mat 35

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 17] to obtain 3.6 g of the desired compound; HRMS [M] < + >: 588.71

[ Synthetic example  36] Synthesis of Mat 36

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-4-yl) phenyl) -2- phenylpyrimidine was used as a reactant Was obtained in the same manner as in [Synthesis Example 18], 3.7 g of the desired compound; HRMS [M] < + >: 614.75

[ Synthetic example  37] Synthesis of Mat 37

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 1] was conducted to obtain 4.5 g of the target compound; HRMS [M] < + >: 587.73

[ Synthetic example  38] Synthesis of Mat 38

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 2] was conducted to obtain 4.3 g of the objective compound; HRMS [M] < + >: 637.79

[ Synthetic example  39] Synthesis of Mat 39

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 3] was conducted to obtain 3.8 g of the target compound; HRMS [M] < + >: 637.79

[ Synthetic example  40] Synthesis of Mat 40

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant [Synthesis Example 4] was carried out to obtain 4.9 g of the desired compound; HRMS [M] < + >: 687.85

[ Synthetic example  41] Synthesis of Mat 41

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant [Synthesis Example 5] was carried out to obtain 4.8 g of the target compound; HRMS [M] < + >: 687.85

[ Synthetic example  42] Synthesis of Mat 42

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 6] was conducted to obtain the desired compound (5.1 g; HRMS [M] < + >: 763.94

[ Synthetic example  43] Synthesis of Mat 43

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant [Synthesis Example 7] was carried out to obtain 4.7 g of the target compound; HRMS [M] < + >: 737.91

[ Synthetic example  44] Synthesis of Mat 44

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant [Synthesis Example 8] was carried out to obtain 6.0 g of the target compound; HRMS [M] < + >: 711.87

[ Synthetic example  45] Synthesis of Mat 45

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant [Synthesis Example 9] was carried out to obtain 5.3 g of the target compound; HRMS [M] < + >: 703.89

[ Synthetic example  46] Synthesis of Mat 46

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant [Synthesis Example 10] was carried out to obtain 4.9 g of the desired compound; HRMS [M] < + >: 752.92

[ Synthetic example  47] Synthesis of Mat 47

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 11] was conducted to obtain 3.8 g of the objective compound; HRMS [M] < + >: 677.81

[ Synthetic example  48] Synthesis of Mat 48

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 12] was conducted to obtain 3.6 g of the target compound; HRMS [M] < + >: 676.82

[ Synthetic example  49 Synthesis of Mat 49

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 13] was conducted to obtain 4.0 g of the target compound; HRMS [M] < + >: 752.92

[ Synthetic example  50] Synthesis of Mat 50

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 14] was conducted to obtain 3.2 g of the target compound; HRMS [M] < + >: 693.81

[ Synthetic example  51] Synthesis of Mat 51

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The same procedure as in [Synthesis Example 15] was conducted to obtain 2.7 g of the target compound; HRMS [M] < + >: 692.82

[ Synthetic example  52] Synthesis of Mat 52

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The procedure of Synthesis Example 16 was repeated to obtain 3.0 g of the target compound; HRMS [M] < + >: 689.82

[ Synthetic example  53] Synthesis of Mat 53

Except that 8- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) quinoline was used as a reactant The procedure of Synthesis Example 18 was followed to obtain 3.1 g of the target compound; HRMS [M] < + >: 664.81

[ Synthetic example  54] Synthesis of Mat 54

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-bromo-4-methylpyridine, 5.5 g of the title compound was obtained by carrying out the same processes as in [Synthesis Example 1]; HRMS [M] < + >: 613.76

[ Synthetic example  55] Synthesis of Mat 55

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde, the procedure of Synthetic Example 2 was repeated to give the desired compound (5.8 g; HRMS [M] < + >: 663.82

[ Synthetic example  56] Synthesis of Mat 56

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' - yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde, the procedure of Synthesis Example 3 was repeated to obtain the desired compound (5.1 g; HRMS [M] < + >: 663.82

[ Synthetic example  57] Synthesis of Mat 57

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' - yl) -2-phenylpyrimidine was used in place of 2-chloro-4-methoxybenzaldehyde, the procedure of Synthetic Example 4 was repeated to give the desired compound (6.7 g; HRMS [M] < + >: 713.88

[ Synthetic example  58] Synthesis of Mat 58

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-bromo-2-methylpyridine, 6.1 g of the title compound was obtained by carrying out the same processes as in [Synthesis Example 5]; HRMS [M] < + >: 713.88

[ Synthetic example  59] Synthesis of Mat 59

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzyl chloride, the procedure of Synthesis Example 6 was repeated to obtain 6.6 g of the desired compound; HRMS [M] < + >: 789.98

[ Synthetic example  60] Synthesis of Mat 60

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-bromo-2-methylpyridine, the procedure of Synthesis Example 7 was repeated to obtain 6.0 g of the target compound; HRMS [M] < + >: 763.94

[ Synthetic example  61] Synthesis of Mat 61

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' - yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde, the procedure of Synthetic Example 8 was repeated to give the desired compound (5.7 g; HRMS [M] < + >: 737.91

[ Synthetic example  62] Synthesis of Mat 62

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzyl chloride, the procedure of Synthetic Example 9 was repeated to give the desired compound (4.6 g; HRMS [M] < + >: 729.93

[ Synthetic example  63] Synthesis of Mat 63

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-methylpyridine, the procedure of Synthetic Example 10 was repeated to give the desired compound (4.7 g); HRMS [M] < + >: 778.96

[ Synthetic example  64] Synthesis of Mat 64

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzyl chloride in the same manner as in [Synthesis Example 11], 5.1 g of the desired compound was obtained; HRMS [M] < + >: 703.85

[ Synthetic example  65] Synthesis of Mat 65

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' - yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde to obtain the desired compound (4.2 g); HRMS [M] < + >: 702.86

[ Synthetic example  66] Synthesis of Mat 66

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde, the procedure of Synthetic Example 13 was repeated to give the desired compound (4.7 g); HRMS [M] < + >: 778.96

[ Synthetic example  67] Synthesis of Mat 67

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde, the procedure of Synthetic Example 14 was repeated to give the desired compound (3.8 g; HRMS [M] < + >: 719.84

[ Synthetic example  68] Synthesis of Mat 68

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' - yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde to obtain the title compound (4.5 g); HRMS [M] < + >: 718.86

[ Synthetic example  69] Synthesis of Mat 69

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-bromo-4-methylpyridine, 5.5 g of the title compound was obtained by carrying out the same processes as in [Synthesis Example 16]; HRMS [M] < + >: 715.86

[ Synthetic example  70] Synthesis of Mat 70

The reaction was carried out using 4 - ([1,1'-biphenyl] -4-yl) -6- (5-bromo-4 ' -Yl) -2-phenylpyrimidine was used in place of 2-chloro-4-fluorobenzaldehyde, the procedure of Synthetic Example 17 was repeated to give the desired compound (4.9 g; HRMS [M] < + >: 664.81

[ Synthetic example  71] Synthesis of Mat 71

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 1] was carried out except for using phosphorus to obtain 6.4 g of the desired compound; HRMS [M] < + >: 637.77

[ Synthetic example  72] Synthesis of Mat 72

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 2] was carried out except for using phosphorus to obtain 5.9 g of the desired compound; HRMS [M] < + >: 688.26

[ Synthetic example  73] Synthesis of Mat 73

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 3] was carried out except that phosphorus was used to obtain 5.2 g of the target compound; HRMS [M] < + >: 688.83

[ Synthetic example  74] Synthesis of Mat 74

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 4] was carried out except that phosphorus was used to obtain 6.8 g of the desired compound; HRMS [M] < + >: 738.89

[ Synthetic example  75] Synthesis of Mat 75

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 5] was carried out except for using phosphorus to obtain 7.6 g of the desired compound; HRMS [M] < + >: 738.89

[ Synthetic example  76] Synthesis of Mat 76

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 6] was conducted except that phosphorus was used to obtain 7.9 g of the desired compound; HRMS [M] < + >: 814.99

[ Synthetic example  77] Synthesis of Mat 77

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 7] was conducted except that phosphorus was used to obtain 8.3 g of the target compound; HRMS [M] < + >: 788.95

[ Synthetic example  78] Synthesis of Mat 78

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 8] was conducted except that phosphorus was used to obtain 4.3 g of the target compound; HRMS [M] < + >: 762.92

[ Synthetic example  79] Synthesis of Mat 79

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 9] was conducted except that phosphorus was used to obtain 3.6 g of the target compound; HRMS [M] < + >: 754.94

[ Synthetic example  80] Synthesis of Mat 80

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The procedure of Synthesis Example 10 was followed except that phosphorus was used to obtain 4.1 g of the desired compound; HRMS [M] < + >: 803.97

[ Synthetic example  81] Synthesis of Mat 81

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 11] was conducted except that phosphorus was used to obtain 3.5 g of the desired compound; HRMS [M] < + >: 728.26

[ Synthetic example  82] Synthesis of Mat 82

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 12] was carried out except that phosphorus was used to obtain 2.9 g of the desired compound; HRMS [M] < + >: 727.87

[ Synthetic example  83] Synthesis of Mat 83

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 13] was conducted except that phosphorus was used to obtain 3.1 g of the target compound; HRMS [M] < + >: 803.97

[ Synthetic example  84] Synthesis of Mat 84

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 14] was conducted except that phosphorus was used to obtain 3.3 g of the desired compound; HRMS [M] < + >: 744.85

[ Synthetic example  85] Synthesis of Mat 85

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 15] was conducted except that phosphorus was used to obtain 2.4 g of the target compound; HRMS [M] < + >: 743.87

[ Synthetic example  86] Synthesis of Mat 86

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 17] was carried out except for using phosphorus to obtain 4.6 g of the desired compound; HRMS [M] < + >: 689.82

[ Synthetic example  87] Synthesis of Mat 87

The reaction was carried out using 2- (3- (6 - ([1,1'-biphenyl] -4-yl) -2-phenylpyrimidin-4-yl) -5-bromophenyl) -1,10- The same procedure as in [Synthesis Example 18] was conducted except that phosphorus was used to obtain 3.9 g of the desired compound; HRMS [M] < + >: 715.86

[ Synthetic example  88] Synthesis of Mat 88

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 1] was carried out except that triazine was used to obtain 4.1 g of the desired compound; HRMS [M] < + >: 538.65

[ Synthetic example  89] Synthesis of Mat 89

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 4] was conducted except that triazine was used to obtain 3.8 g of the target compound; HRMS [M] < + >: 638.78

[ Synthetic example  90] Synthesis of Mat 90

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 5] was carried out except that triazine was used to obtain 2.9 g of the title compound; HRMS [M] < + >: 638.77

[ Synthetic example  91] Synthesis of Mat 91

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 7] was conducted except that triazine was used to obtain 4.0 g of the desired compound; HRMS [M] < + >: 688.83

[ Synthetic example  92] Synthesis of Mat 92

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 9] was conducted except that triazine was used to obtain 3.1 g of the target compound; HRMS [M] < + >: 654.82

[ Synthetic example  93] Synthesis of Mat 93

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 10] was conducted except that triazine was used to obtain 4.4 g of the desired compound; HRMS [M] < + >: 703.85

[ Synthetic example  94] Synthesis of Mat 94

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 12] was conducted except that triazine was used to obtain 2.5 g of the desired compound; HRMS [M] < + >: 627.75

[ Synthetic example  95] Synthesis of Mat 95

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 15] was conducted except that triazine was used to obtain 2.1 g of the desired compound; HRMS [M] < + >: 643.75

[ Synthetic example  96] Synthesis of Mat 96

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 16] was conducted except that triazine was used to obtain 2.6 g of the target compound; HRMS [M] < + >: 640.75

[ Synthetic example  97] Synthesis of Mat 97

4- (3-bromo-5- (pyridin-3-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 17] was conducted except that triazine was used to obtain 2.9 g of the title compound; HRMS [M] < + >: 589.70

[ Synthetic example  98] Synthesis of Mat 98

Except that 4 - ([1,1'-biphenyl] -4-yl) -6- (3-bromo-5- (pyridin-3- yl) phenyl) -2-phenylpyrimidine was used as a reactant Was subjected to the same procedure as in [Synthesis Example 18] to obtain 3.8 g of the desired compound; HRMS [M] < + >: 614.72

[ Synthetic example  99] Synthesis of Mat 99

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 22] was conducted except that triazine was used to obtain 3.6 g of the desired compound; HRMS [M] < + >: 638.77

[ Synthetic example  100] Synthesis of Mat 100

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 23] was conducted except that triazine was used to obtain 3.0 g of the objective compound; HRMS [M] < + >: 638.77

[ Synthetic example  101] Synthesis of Mat 101

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 25] was conducted except that triazine was used to obtain 3.2 g of the desired compound; HRMS [M] < + >: 688.83

[ Synthetic example  102] Synthesis of Mat 102

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 27] was conducted except that triazine was used to obtain 2.9 g of the title compound; HRMS [M] < + >: 654.82

[ Synthetic example  103] Synthesis of Mat 103

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 30] was conducted except that triazine was used to obtain 2.1 g of the desired compound; HRMS [M] < + >: 627.75

[ Synthetic example  104] Synthesis of Mat 104

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 34] was conducted except that triazine was used to obtain 2.8 g of the desired compound; HRMS [M] < + >: 640.75

[ Synthetic example  105] Synthesis of Mat 105

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 35] was conducted except that triazine was used to obtain 2.3 g of the target compound; HRMS [M] < + >: 589.70

[ Synthetic example  106] Synthesis of Mat 106

4- (3-bromo-5- (pyridin-4-yl) phenyl) -6-phenyl-1,3,5- The same procedure as in [Synthesis Example 36] was conducted except that triazine was used to obtain 2.8 g of the desired compound; HRMS [M] < + >: 615.74

[ Synthetic example  107] Synthesis of Mat 107

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline, the same procedure as in [Synthesis Example 1] was conducted to obtain 2.0 g of the target compound; HRMS [M] < + >: 588.71

[ Synthetic example  108] Synthesis of Mat 108

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline, the procedure of Synthesis Example 3 was repeated to obtain 2.9 g of the desired compound; HRMS [M] < + >: 638.77

[ Synthetic example  109] Synthesis of Mat 109

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline, the same procedure as in [Synthesis Example 4] was conducted to obtain 3.3 g of the objective compound; HRMS [M] < + >: 688.83

[ Synthetic example  110] Synthesis of Mat 110

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline, the procedure of Synthesis Example 7 was repeated to obtain the desired compound (3.7 g); HRMS [M] < + >: 738.89

[ Synthetic example  111] Synthesis of Mat 111

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline, the procedure of Synthesis Example 9 was carried out to obtain 2.6 g of the target compound; HRMS [M] < + >: 704.88

[ Synthetic example  112] Synthesis of Mat 112

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline, the procedure of Synthesis Example 12 was carried out to obtain 2.0 g of the target compound; HRMS [M] < + >: 677.81

[ Synthetic example  113] Synthesis of Mat 113

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline, the procedure of Synthesis Example 12 was carried out to obtain the desired compound (3.4 g); HRMS [M] < + >: 677.81

[ Synthetic example  114] Synthesis of Mat 114

As a reaction product, 8- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- Quinoline [Synthetic Example 53] By the same procedure as above, 2.9 g of the desired compound was obtained; HRMS [M] < + >: 665.80

[ Synthetic example  115] Synthesis of Mat 115

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of [ HRMS [M] < + >: 614.75

[ Synthetic example  116] Synthesis of Mat 116

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-bromo-6-phenyl-1,3,5-triazine to obtain 2.5 g of the title compound. HRMS [M] < + >: 664.81

[ Synthetic example  117] Synthesis of Mat 117

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-6-phenyl-1,3,5-triazine to obtain the desired compound (3.3 g); HRMS [M] < + >: 714.87

[ Synthetic example  118] Synthesis of Mat 118

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-6-phenyl-1,3,5-triazine to obtain the desired compound (3.0 g); HRMS [M] < + >: 714.87

[ Synthetic example  119] Synthesis of Mat 119

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-6-phenyl-1,3,5-triazine to obtain 3.8 g of the title compound. HRMS [M] < + >: 764.93

[ Synthetic example  120] Synthesis of Mat 120

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-6-phenyl-1,3,5-triazine, 2.7 g of the title compound was obtained by carrying out the same procedure as in [Synthesis Example 62]; HRMS [M] < + >: 730.92

[ Synthetic example  121] Synthesis of Mat 121

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-bromo-6-phenyl-1,3,5-triazine to obtain 2.0 g of the desired compound. HRMS [M] < + >: 703.85

[ Synthetic example  122] Synthesis of Mat 122

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-6-phenyl-1,3,5-triazine. HRMS [M] < + >: 716.85

[ Synthetic example  123] Synthesis of Mat 123

The reaction was carried out using 2 - ([1,1'-biphenyl] -4-yl) -4- (5-bromo-4 ' -Yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-6-phenyl-1,3,5-triazine to obtain 3.8 g of the title compound. HRMS [M] < + >: 664.81

[ Synthetic example  124] Synthesis of Mat 124

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline, the procedure of Synthesis Example 71 was repeated to obtain 3.0 g of the target compound; HRMS [M] < + >: 639.76

[ Synthetic example  125] Synthesis of Mat 125

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline, the procedure of Synthesis Example 72 was repeated to obtain the desired compound (3.4 g); HRMS [M] < + >: 689.82

[ Synthetic example  126] Synthesis of Mat 126

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline was used in place of 4-fluorobenzyl bromide to obtain 4.1 g of the target compound; HRMS [M] < + >: 739.88

[ Synthetic example  127] Synthesis of Mat 127

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline, the procedure of Synthesis Example 77 was followed to obtain the desired compound (4.6 g); HRMS [M] < + >: 789.94

[ Synthetic example  128] Synthesis of Mat 128

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline, the procedure of Synthesis Example 79 was repeated to give the object compound (3.8 g); HRMS [M] < + >: 755.93

[ Synthetic example  129] Synthesis of Mat 129

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline, the procedure of Synthesis Example 82 was repeated to obtain 2.6 g of the target compound; HRMS [M] < + >: 728.86

[ Synthetic example  130] Synthesis of Mat 130

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline was used in place of 2-chloro-2-fluoroaniline to obtain 2.0 g of the target compound; HRMS [M] < + >: 744.86

[ Synthetic example  131] Synthesis of Mat 131

The reaction was carried out using 2- (3- (4 - ([1,1'-biphenyl] -4-yl) -6- -1,10-phenanthroline was used in place of 4-fluorobenzyl chloride, the procedure of Synthesis Example 87 was repeated to obtain 4.0 g of the target compound; HRMS [M] < + >: 716.85

[ Example  1] Blue organic Field  Manufacturing of light emitting device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was produced as follows.

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

(30 nm) / LiF (1 nm) of Synthesis Example 1 of Synthesis Example 1 was added to the ITO transparent electrode prepared as described above, DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS- ) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.

The structures of NPB, ADN and Alq ₃ used in this case are as follows.

[ Comparative Example 1] blue  abandonment Field  Manufacturing of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the lifetime improving layer was not included and the electron transport layer material Alq ₃ was deposited at 30 nm.

[ Evaluation example  One]

The driving voltage, current efficiency and emission wavelength at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 1 to 62 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

Sample Electron transport layer Driving voltage
(V) Current efficiency
(cd / A) Emission peak
(nm) Example 1 One 4.0 5.9 458 Example 2 2 4.2 5.8 458 Example 3 3 4.3 5.9 459 Example 4 4 4.1 5.8 458 Example 5 5 4.5 5.9 458 Example 6 6 4.0 6.0 458 Example 7 7 4.1 6.0 458 Example 8 8 4.1 6.1 459 Example 9 9 4.2 5.8 457 Example 10 10 4.6 5.8 458 Example 11 11 4.5 5.9 458 Example 12 12 4.4 5.9 458 Example 13 13 4.1 5.7 458 Example 14 14 4.1 5.9 459 Example 15 15 4.0 5.9 458 Example 16 16 4.2 6.0 458 Example 17 17 4.3 6.0 458 Example 18 18 4.1 6.1 458 Example 19 19 4.5 5.8 459 Example 20 20 4.0 5.8 458 Example 21 21 4.2 5.9 458 Example 22 22 4.3 5.9 459 Example 23 23 4.1 5.9 458 Example 24 24 4.5 5.8 458 Example 25 25 4.0 5.9 458 Example 26 26 4.3 6.0 458 Example 27 27 4.5 6.0 459 Example 28 28 4.4 6.1 457 Example 29 29 4.1 5.8 458 Example 30 30 4.1 5.8 458 Example 31 31 4.0 5.9 458 Example 32 32 4.1 5.9 458 Example 33 33 4.3 5.7 458 Example 34 52 4.3 5.9 458 Example 35 54 4.2 5.8 458 Example 36 55 4.0 5.9 459 Example 37 56 4.2 6.0 458 Example 38 59 4.3 5.9 458 Example 39 60 4.1 6.0 458 Example 40 61 4.5 6.0 458 Example 41 63 4.0 6.1 458 Example 42 64 4.0 5.8 459 Example 43 65 4.2 5.8 458 Example 44 66 4.3 5.9 458 Example 45 67 4.1 5.9 458 Example 46 70 4.5 5.7 458 Example 47 71 4.0 5.9 459 Example 48 72 4.1 5.8 457 Example 49 73 4.1 5.9 458 Example 50 75 4.2 6.0 458 Example 51 76 4.1 6.1 458 Example 52 77 4.1 5.8 459 Example 53 78 4.0 5.8 457 Example 54 79 4.1 5.9 458 Example 55 80 4.2 5.9 458 Example 56 82 4.4 5.7 458 Example 57 83 4.4 5.9 458 Example 58 84 4.5 5.8 459 Example 59 88 4.2 5.9 458 Example 60 90 4.1 5.9 458 Example 61 100 4.5 5.9 457 Example 62 101 4.2 5.7 458 Comparative Example 1 Alq ₃ 4.7 5.6 458

As shown in Table 1, the organic EL devices of Examples 1 to 62 using the compound represented by Formula 1 of the present invention as the electron transport layer exhibited higher current efficiency than the organic EL device of Comparative Example 1 using Alq ₃ as the electron transport layer And the driving voltage.

Claims (10)

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

here,
L ₁ and L ₂ are the same or different and each is a single bond, a C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nuclear atoms,
R ₁ and R ₂ are the same or different and are each independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms;
Ar ₁ and Ar ₂ are different from each other and are each independently a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms,
X ₁ , X ₂ and X ₃ are the same or different and are each independently N or C (R ₃ ), and at least two are N;
R ₃ 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, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 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 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, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of is selected from the group consisting of,
L ₁ and The arylene group and the heteroarylene group of L _{2 and} the aryl group and heteroaryl group of R ₁ to R ₃ and Ar ₁ to Ar ₂ are each independently a lower alkyl group, a cyano group, a halogen, a C ₁ to C ₄₀ alkyl group, a C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to the a heteroaryl group of 60, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C of ₄₀ groups of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ from the group consisting of an aryl amine of the C ₆₀ And when they are substituted with a plurality of substituents, they may be the same or different from each other. The method according to claim 1,
Wherein Ar ₁ and Ar ₂ are different from each other, and each independently is a C ₆ to C ₆₀ aryl group. The method according to claim 1,
X ₁ and X ₂ are each independently N,
It said X ₃ is selected from N or C (R _3),
Wherein Ar ₁ and Ar ₂ are different from each other and are each independently selected from phenyl or biphenyl. The method according to claim 1,
Wherein R ₁ and R ₂ are the same or different and are each independently selected from a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms. The method according to claim 1,
The compound will be at least one of the R ₁ or R ₂ is selected from the group consisting of substituents of Formulas 2 to 5:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

here,
* Represents a moiety bonded to Formula 1;
X ₄ to X ₂₆ are the same or different and are each independently N or C (R ₅ )
R ₅ 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, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 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 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, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group of an amine of is selected from the group consisting of,
R ₅ is an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, The oxides and arylamine groups are each independently selected from the group consisting of 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, 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 ₆ heteroaryl group, ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C aryl phosphine oxide group and a C ₆ ~ ₆₀ may be substituted with at least one member selected from the group consisting of an aryl amine of the C _60, the case be substituted with a plurality of substituents, they same or another It may be different. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

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 represented by Formula 1 according to Claim 1. 8. The method of claim 7,
Wherein the organic material layer is selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, and an electron injecting layer. 8. The method of claim 7,
Wherein the organic material layer is selected from the group consisting of a light emitting layer, a hole transporting layer, and an electron transporting layer. 8. The method of claim 7,
Wherein the organic material layer is an electron transporting layer.