WO2013100603A1 - Organic light emitting compound and organic light emitting diode using same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound, and an organic light emitting diode which has improved luminous efficiency, brightness, thermal stability, operating voltage, lifespan and the like by containing the organic light emitting compound in at least one organic material layer - particularly in a light emitting layer.

Description

Organic light emitting compound and organic electroluminescent device using same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifetime by including the same in one or more organic material layers, in particular in the light emitting layer.

An organic electroluminescent device (hereinafter referred to as an organic EL device) generally has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic EL device, for example, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) ), An electron injection layer (EIL), and the like.

When voltage is applied between the two electrodes of the organic EL device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet, and the excitons are in the ground state. When it falls, it glows.

The light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors. In addition, in order to increase luminous efficiency through increasing color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

Generally, a carbazole compound such as CBP (4,4-dicarbazolybiphenyl) is used as the phosphorescent host material, and a metal complex compound containing heavy atoms such as Ir and Pt is widely used as the phosphorescent dopant material. have.

However, CBP, which is currently used phosphorescent host material, has a low glass transition temperature (Tg) of about 110 ° C., and crystallization in the device is easy, resulting in a very short lifespan of about 150 hours.

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic light emitting compound having better thermal stability and an organic EL device having improved characteristics such as luminous efficiency, brightness, power efficiency, driving voltage, and lifespan.

The present invention to achieve the above object provides a compound represented by the following formula (1).

Formula 1

Where

X ₁ and X ₂ are each independently selected from the group consisting of CR ₁ R ₂ , O, S, NR ₃ and SiR ₄ R ₅ ;

Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, Substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, and a substituted or unsubstituted silyl group;

R ₁ to R ₅ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, Substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₆₀ aryl group and a substituted or unsubstituted amine selected from the group consisting of unsubstituted silyl, and adjacent groups combine with each other to form a condensed ring;

n and m are each independently an integer from 1 to 4;

At least one Ar ₃ is the same or different from each other, at least one Ar ₄ is the same or different from each other, and each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ Alkynyl group, substituted or unsubstituted C ₆ ~ C ₆₀ Aryl group, substituted or unsubstituted nuclear atoms of 5 to 60 Heteroaryl group, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, substituted or unsubstituted It is selected from the group consisting of a ring heteronuclear alkyl group having 3 to 60 ring atoms, a substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, and a substituted or unsubstituted silyl group.

The present invention also provides an organic EL device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers is It provides an organic EL device comprising a compound represented by the formula (1). Preferably, the compound of the present invention can be used as a phosphorescent host material of the light emitting layer.

The compound represented by Chemical Formula 1 of the present invention has excellent thermal stability, light emitting performance, and the like, and the organic EL device including the same may significantly improve characteristics such as light emission performance, driving voltage, and lifetime, so that a full color display panel may be effectively used. Can be applied.

The compound of the present invention is a phenothiazine (phenoazine) (Formula 1 is one of X ₁ and X ₂ is NH and the other S is), phenoxazine (phenoxazine) (Formula 1 of X ₁ and X ₂ Is NH and the other is O), acridine (compound 1 in which X ₁ and X ₂ are NH and the other is CH ₂ ), phenazasiline (in Formula 1) A compound having one of X ₁ and X ₂ as NH and the other as SiH ₂ ), etc., as a central moiety, which facilitates the introduction of various substituents and stabilizes triplet energy levels by the substituents. The energy level is controlled to improve the characteristics of the device as a host of blue to red light emitting materials and at the same time improve the electron and / or hole transport capacity, luminous efficiency, driving voltage and lifetime characteristics. Can be. Therefore, it can be applied to not only the light emitting layer but also a hole transport layer, an electron transport layer, and the like.

The compound of the present invention has a structure represented by the following formula (1).

<Formula 1>

Wherein X ₁ and X ₂ are each independently selected from the group consisting of CR ₁ R ₂ , O, S, NR ₃ and SiR ₄ R ₅ . Preferably, in consideration of light emitting capability, voltage / current efficiency and the like, X ₁ and X ₂ are each independently CR ₁ R ₂ or SiR ₄ R ₅ .

R ₁ to R ₅ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, Substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted It is selected from the group consisting of a C ₆ ~ C ₆₀ arylamine group, and a substituted or unsubstituted silyl group, adjacent groups may combine with each other to form a condensed ring. Preferably, R ₁ to R ₅ are each independently a substituted or unsubstituted C ₁ to C ₆₀ alkyl group or a substituted or unsubstituted C ₆ to C ₆₀ aryl group.

R ₁ to R ₅ are each independently halogen, cyano, C ₁ to C ₆₀ alkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₆₀ alkoxy group , C aryloxy of ₆ ~ C _60, C ₃ ~ C ₆₀ cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.

Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, Substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, and a substituted or unsubstituted silyl group.

Ar ₁ and Ar ₂ are each independently halogen, cyano, C ₁ to C ₆₀ alkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₆₀ alkoxy group , C aryloxy of ₆ ~ C _60, C ₃ ~ C ₆₀ cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.

According to an embodiment of the present invention, the aryl groups of Ar ₁ and Ar ₂ are each independently an unsubstituted C ₆ ~ C ₆₀ aryl group or C ₆ ~ C ₆₀ aryl group, a nuclear atom of 5 to 60 hetero A C ₆ to C ₆₀ aryl group substituted with an aryl group or an amino group, and the heteroaryl groups of Ar ₁ and Ar ₂ are each independently an unsubstituted heteroaryl group having 5 to 60 nuclear atoms or a C ₆ to C _{60 group} ; It may be an aryl group, a heteroaryl group having 5 to 60 nuclear atoms or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group.

More specifically, the unsubstituted aryl groups of Ar ₁ and Ar ₂ are each independently phenyl, biphenyl, naphthalene, phenanthrene, anthracene, pyrene ), Fluorine (fluorine) and the like, and the unsubstituted heteroaryl groups of Ar ₁ and Ar ₂ are each independently pyridine, pyrimidine, pyridazine, pyrazine, Triazine, benzimidazole, quinoline, isoquinoline, isoquinoline, quinoxaline, carbazole, dibenzofuran, dibenzothiophene , Phenanthroline, acridine, phenothiazine, and the like.

In particular, when Ar ₁ and Ar ₂ are the substituents described above, the molecular weight is significantly increased compared to conventional organic light emitting materials (eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)), thereby improving glass transition temperature and thereby high thermal stability. Can have Therefore, the device including the compound of the present invention can be improved in characteristics such as durability and lifespan. In particular, the improvement of device life has a great effect on maximizing performance in full color organic light emitting panel.

In addition to such thermal stability, in consideration of light emitting ability, voltage / current efficiency, etc., Ar ₁ and Ar ₂ are each independently an unsubstituted C ₆ ~ C ₆₀ aryl group; C ₆ -C ₆₀ aryl group substituted with a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms or an amino group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C ₆ -C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group. More specifically, Ar ₁ is an unsubstituted C ₆ ~ C ₆₀ aryl group; Or a heteroaryl group of 5 to 60 nuclear atoms substituted with an aryl group of C ₆ to C ₆₀ , and Ar ₂ is substituted with an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms or an amino group C ₆ ~ C ₆₀ Aryl group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms substituted with a heteroaryl group having 5 to 60 nuclear atoms.

In Formula 1, n and m are each independently an integer of 1-4. Preferably, n and m are each one.

At least one Ar ₃ is the same or different from each other, and at least one Ar ₄ is the same or different from each other. Ar ₃ and Ar ₄ may each independently be hydrogen or any substituent, which may include deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₆₀ alkyl group, substituted or unsubstituted C ₂ to C ₆₀ alkenyl group, substituted or unsubstituted C ₂ to C ₆₀ alkynyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted Or an unsubstituted C ₁ to C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted nuclear atom 3 to 60 heterocycloalkyl groups, substituted or unsubstituted C ₆ to C ₆₀ arylamine groups, substituted or unsubstituted silyl groups, and the like.

Ar ₃ and Ar ₄ are each independently halogen, cyano, C ₁ ~ C ₆₀ alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₆₀ alkoxy group , C aryloxy of ₆ ~ C _60, C ₃ ~ C ₆₀ cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.

In the present invention, the aryl groups, heteroaryl groups and arylamine groups of Ar ₁ to Ar ₄ , R ₁ to R ₅ may each independently have a structure described below, but are not limited thereto.

The following compounds are representative examples of the compound of formula 1 of the present invention, but the compound of formula 1 of the present invention is not limited to those illustrated below.

In the above formula, Ar ₁ to Ar ₄ , R ₃ to R ₅ are as described above.

Compound of the present invention can be synthesized according to a general synthesis method, the detailed synthesis process for the compound of the present invention will be described in detail in the synthesis examples described below.

The present invention also provides for (i) an anode; (ii) a cathode; And (iii) one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers comprises a compound represented by the formula (1). To provide. In this case, the compound represented by Formula 1 may include one kind or two or more kinds.

Preferably, the organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer, preferably a light emitting layer.

Preferably, the compounds of the present invention may be included in the light emitting layer as blue, green and / or red phosphorescent host and / or fluorescent host materials, particularly preferably phosphorescent host materials. In the present invention, the light emitting layer may include a phosphorescent guest material or a fluorescent guest material.

The organic EL device structure of the present invention is a structure in which one or two or more organic material layers are laminated between electrodes, and for example, (i) an anode, a light emitting layer, a cathode, (ii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron The structure of a transport layer, an electron injection layer, a cathode, (iii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode is mentioned.

In addition, as described above, the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between an electrode and an organic material layer.

In the organic EL device according to the present invention, the organic material layer including the compound represented by Formula 1 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 organic EL device according to the present invention forms an organic material layer and an electrode by using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Formula 1 of the present invention. Can be prepared.

For example, a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet may be used as the substrate.

The anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

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

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

Preparation Example 1 Synthesis of Compound Mat 1-A

Step 1 Synthesis of 9,9-dimethyl-10-phenyl-9,10-dihydroacridine

9,9-dimethyl-9,10-dihydroacridine (3.14 g, 15 mmol), bromobenzene (2.35 g, 1 equiv), sodium tert-butoxide (4.27 g, 3 equiv), tris (dibenzylideneacetone) in a 250 mL round flask under nitrogen ) dipalladium) (0.255 g, 3 mol%) and 1,1'-bis (diphenylphosphino) ferrocene (0.25 g, 3 mol%) were added, followed by stirring under reflux overnight at 75 ml of toluene.

After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to obtain 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3.4g, yield 80%).

<Step 2> Synthesis of 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine

9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3 g, 10.5 mmol) and n-bromosuccinimide (1.9 g, 1 equivalent) obtained in <Step 1> together with 50 ml carbon tetrachloride in a 250 ml round flask The mixture was stirred for 3 hours under a nitrogen atmosphere.

After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to give 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2.3g, yield 60%).

Step 3 Synthesis of Mat 1-A

9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2g, 5.5mmol), bis (pinacolato) diboron (1.7g, 1.2 equivalents) obtained in <Step 2>, [1,1'-bis ( diphenylphosphino) ferrocene] dichloropalladium (II) (0.12 g, 3 mol%), potassium acetate (1.6 g, 3 equiv) and 1,4-dioxane (30 mL) were stirred under reflux overnight under a nitrogen atmosphere in a 100 mL round flask.

After put to complete the reaction of H ₂ O, by the addition of methylene chloride to separate the H ₂ O layer and an organic layer. After heating up under reduced pressure to remove the solvent, the residue was purified by column chromatography to obtain Mat 1-A (1.8 g, 80%).

GC-Mass: 410

Preparation Example 2 Synthesis of Compound Mat 1-B

Step 1 Synthesis of 10- (4,6-diphenylpyridin-2-yl) -9,9-dimethyl-9,10-dihydroacridine

9,9-dimethyl-9,10-dihydroacridine (3.14 g, 15 mmol), 2-bromo-4,6-diphenylpyridine (4.65 g, 1 equiv) and sodium tert-butoxide (4.27 g) in a 250 ml round flask under nitrogen , 3 equivalents), tris (dibenzylideneacetone) dipalladium) (0.255 g, 3 mol%) and 1,1'-bis (diphenylphosphino) ferrocene (0.25 g, 3 mol%), then refluxed overnight in toluene (75 mL) Stirred.

After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to obtain 10- (4,6-diphenylpyridin-2-yl) -9,9-dimethyl-9,10-dihydroacridine (6.2g, yield 80% )

<Step 2> Synthesis of Mat 1-B

In a 250 ml round flask, 10- (4,6-diphenylpyridin-2-yl) -9,9-dimethyl-9,10-dihydroacridine (4.6 g, 10.5 mmol) and n-bromosuccin imide ( 1.9 g, 1 equiv) was stirred with 50 mL carbon tetrachloride under nitrogen atmosphere for 3 hours.

After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to give Mat 1-B (3.26g, yield 60%).

GC-Mass: 516

Synthesis Example 1 Synthesis of Compound Mat 1

Mat 1-A (5 g, 12.2 mmol) synthesized in Preparation Example 1, Mat 1-B (6.3 g, 1 equivalent) synthesized in Preparation Example 2, tetrakis (triphenylphosphine) palladium (0) (0.7 g, 5 mol%) ) And potassium carbonate (5 g, 3 equiv) were added to a 250 mL round flask with 1,4-dioxane (61 mL) and H ₂ O (18 mL) and stirred under reflux for 3 hours under a nitrogen atmosphere.

After completion of the reaction, the reaction solution was filtered through celite and purified by column chromatography to give Mat 1 (7g, 80% yield).

Elemental Analysis: C, 88.18; H, 6.00; N, 5.82 / GC-Mass: 720

Synthesis Example 2 Synthesis of Compound Mat 2

<Step 1> Synthesis of Mat 2-B

Mat 2-B (3.3 g, yield 60%) was synthesized in the same manner as in Preparation Example 2, using 2-bromo-4,6-diphenylpyrimidine instead of 2-Bromo-4,6-diphenylpyridine.

GC-Mass: 517

<Step 2> Synthesis of Mat 2

Using Mat 2-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 2 (6g, yield 68%).

Elemental Analysis: C, 86.39; H, 5.86; N, 7.75 / GC-Mass: 721

Synthesis Example 3 Synthesis of Compound Mat 3

<Step 1> Synthesis of Mat 3-B

Instead of 2-Bromo-4,6-diphenylpyridine, 2-bromo-4,6-diphenyl-1,3,5-triazine was used to prepare Mat 3-B (3.2 g, yield 60). %) Was obtained.

Elemental Analysis: C, 69.37; H, 4. 46; Br, 15.38; N, 10.79 / GC-Mass: 518

<Step 2> Synthesis of Mat 3

Using Mat 3-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 3 (5.8g, 66% yield).

Elemental Analysis: C, 84.62; H, 5.71; N, 9.67 / GC-Mass : 722

Synthesis Example 4 Synthesis of Compound Mat 4

<Step 1> Synthesis of Mat 4-B

Instead of 2-Bromo-4,6-diphenylpyridine, using the 2-bromo-5-phenylpyridine was carried out in the same manner as in Preparation Example 2 to obtain Mat 4-B (3.5g, 62% yield).

GC-Mass: 440

<Step 2> Synthesis of Mat 4

Using Mat 4-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 4 (5.2g, yield 67%).

Elemental Analysis: C, 87.41; H, 6.09; N, 6.51 / GC-Mass: 644

Synthesis Example 5 Synthesis of Compound Mat 5

<Step 1> Synthesis of Mat 5-B

Instead of 2-Bromo-4,6-diphenylpyridine, using the 2-bromo-5-phenylpyrimidine was carried out in the same manner as in Preparation Example 2 to obtain Mat 5-B (3.3g, 61% yield).

GC-Mass: 421

<Step 2> Synthesis of Mat 5

Using Mat 5-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 5 (4.8g, 62% yield).

Elemental Analysis: C, 85.42; H, 5.92; N, 8.66 / GC-Mass: 645

Synthesis Example 6 Synthesis of Compound Mat 6

<Step 1> Synthesis of Mat 6-B

Mat 6-B (4g, 73% yield) was obtained by the same procedure as Preparation Example 2, using 2- (4-bromophenyl) naphthalene instead of 2-Bromo-4,6-diphenylpyridine.

GC-Mass: 489

<Step 2> Synthesis of Mat 6

Using Mat 6-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 6 (5.1g, 61% yield).

Elemental Analysis: C, 89.88; H, 6.09; N, 4.03 / GC-Mass: 693

Synthesis Example 7 Synthesis of Compound Mat 7

<Step 1> Synthesis of Mat 7-B

Instead of 2-Bromo-4,6-diphenylpyridine, 3,3 '-(5-bromo-1,3-phenylene) dipyridine was used to carry out Mat 7-B (3.6 g, yield 66). %) Was obtained.

GC-Mass: 517

<Step 2> Synthesis of Mat 7

Using Mat 7-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 7 (3.2g, yield 37%).

Elemental Analysis: C, 86.39; H, 5.86; N, 7.75 / GC-Mass: 721

Synthesis Example 8 Synthesis of Compound Mat 8

<Step 1> Synthesis of Mat 8-B

Instead of 2-Bromo-4,6-diphenylpyridine, using 4-bromo-2,6-diphenylpyridine was carried out in the same manner as in Preparation Example 2 to obtain Mat 8-B (3.6g, 66% yield).

GC-Mass: 516

<Step 2> Synthesis of Mat 8

Using Mat 8-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 8 (3.6g, yield 41%).

Elemental Analysis: C, 88.18; H, 6.00; N, 5.82 / GC-Mass: 720

Synthesis Example 9 Synthesis of Compound Mat 9

<Step 1> Synthesis of Mat 9-B

In Preparation Example 2, instead of 2-bromo-4,6-diphenylpyridine, 4-bromo-N, N-diphenylaniline was used to obtain Mat 9-B (4 g, 74% yield).

GC-Mass: 530

<Step 2> Synthesis of Mat 9

Mat 9-B was used in place of Mat 1-B to obtain Mat 9 (5.5 g, yield 62%).

Elemental Analysis: C, 88.13; H, 6. 16; N, 5.71 / GC-Mass: 734

Synthesis Example 10 Synthesis of Compound Mat 10

<Step 1> Synthesis of Mat 10-B

Instead of 2-Bromo-4,6-diphenylpyridine, using 4-bromodibenzo [b, d] thiophene was carried out in the same manner as in Preparation Example 2 to obtain Mat 10-B (3g, 54% yield).

GC-Mass: 469

<Step 2> Synthesis of Mat 10

Using Mat 10-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 10 (4.9g, yield 60%).

Elemental Analysis: C, 85.42; H, 5.68; N, 4.15; S, 4.75 / GC-Mass: 673

Synthesis Example 11 Synthesis of Compound Mat 11

Step 1 Synthesis of Mat 11-A

Mat 11-A (1.6g, 73% yield) was obtained by performing the same procedure as Preparation Example 1 using 2-bromo-4,6-diphenylpyridine instead of bromobenzene.

GC-Mass: 563

<Step 2> Synthesis of Mat 11

Using Mat 11-A instead of Mat 1-A was carried out in the same manner as in Synthesis Example 1 to obtain Mat 11 (5g, yield 57%).

Elemental Analysis: C, 87.84; H, 5. 76; N, 6.40 / GC-Mass: 874

Synthesis Example 12 Synthesis of Compound Mat 12

Step 1 Synthesis of Mat 12-A

Mat 12-A (1.8 g, yield 80%) was obtained by performing the same procedure as Preparation Example 1 using 2 2-bromonaphthalene instead of bromobenzene.

GC-Mass: 460

<Step 2> Synthesis of Mat 12

Using Mat 12-A instead of Mat 1-A was carried out in the same manner as in Synthesis Example 1 to obtain Mat 12 (5.6g yield 72%).

Elemental Analysis: C, 88.68; H, 5.88; N, 5.44 / GC-Mass: 770

Synthesis Example 13 Synthesis of Compound Mat 13

Mat 12-A was used instead of Mat 1-A and Mat 2-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis example 1 to obtain Mat 13 (4.2 g, yield 60%).

Elemental Analysis: C, 87.01; H, 5. 74; N, 7.25 / GC-Mass: 771

Synthesis Example 14 Synthesis of Compound Mat 14

Step 1 Synthesis of Mat 14-B

Instead of 2-Bromo-4,6-diphenylpyridine, 3-bromo-9- (4,6-diphenylpyridin-2-yl) -9H-carbazole was used to carry out Mat 14-B (2.3 g, yield 44%).

GC-Mass: 681

Step 2 Synthesis of Mat 14

Using Mat 14-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 14 (3.9g, yield 36%).

Elemental Analysis: C, 88.00; H, 5.68; N, 6.32 / GC-Mass: 885

Synthesis Example 15 Synthesis of Compound Mat 15

Step 1 Synthesis of Mat 15-B

Mat 15-B (3.5 g, yield 65%) was obtained by the same procedure as Preparation Example 2 using 2- (4-bromophenyl) -4,6-diphenylpyridine instead of 2-Bromo-4,6-diphenylpyridine. .

GC-Mass: 592

Step 2 Synthesis of Mat 15

Using Mat 15-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 15 (4.8g, yield 50%).

Elemental Analysis: C, 88.80; H, 5.94; N, 5.27 / GC-Mass: 796

Synthesis Example 16 Synthesis of Compound Mat 16

<Step 1> Synthesis of Mat 16-A, Mat 16-B

10H-phenothiazine was used instead of 9,9-Dimethyl-9,10-dihydroacridine to carry out the same procedure as in Preparation Example 1 to obtain Mat 16-A (1.5 g, yield 66%), 2-bromo-4,6 Mat 16-B (3.8g, yield: 67%) was obtained by performing the same procedure as Preparation Example 2 using 2- (4-bromophenyl) pyridine instead of -diphenylpyridine.

GC-Mass: 400 (Mat 16-A)

GC-Mass: 440 (Mat 16-B)

<Step 2> Synthesis of Mat 16

Mat 16-A was used instead of Mat 1-A and Mat 16-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis Example 1, thereby obtaining Mat 16 (3.4 g, yield 63%).

Elemental Analysis: C, 83.12; H, 5. 23; N, 6.61; S, 5.04 / GC-Mass: 634

Synthesis Example 17 Synthesis of Compound Mat 17

Step 1 Synthesis of Mat 17-B

Mat 17-B (4.2 g, yield 73%) was obtained by the same procedure as Preparation Example 2 using 2-methylquinoline instead of 2-Bromo-4,6-diphenylpyridine.

GC-Mass: 414

Step 2 Synthesis of Mat 17

Mat 16-A was used instead of Mat 1-A, and Mat 17-B was used instead of Mat 1-B to carry out the same procedure as Synthesis Example 1, thereby obtaining Mat 17 (3.2 g, yield 63%).

Elemental Analysis: C, 82.73; H, 5. 12; N, 6.89; S, 5.26 / GC-Mass: 608

Synthesis Example 18 Synthesis of Compound Mat 18

Step 1 Synthesis of Mat 18-B

10H-phenothiazine instead of 9,9-Dimethyl-9,10-dihydroacridine and 3-bromo-9-phenyl-9H-carbazole instead of 2-bromo-4,6-diphenylpyridine The procedure was carried out to obtain Mat 18-B (2.1 g, 38% yield).

GC-Mass: 518

Step 2 Synthesis of Mat 18

Mat 16-A was used instead of Mat 1-A, and Mat 18-B was used instead of Mat 1-B, and Mat 18 (3.6 g, yield 58%) was obtained in the same manner as in Synthesis example 1.

Elemental Analysis: C, 80.75; H, 4.38; N, 5.89; S, 8.98 / GC-Mass: 712

Synthesis Example 19 Synthesis of Compound Mat 19

Step 1 Synthesis of Mat 19-A

Mat 19-A (1.1 g, yield 50%) was obtained in the same manner as in Preparation Example 1, using 9,9-diphenyl-9,10-dihydroacridine instead of 9,9-Dimethyl-9,10-dihydroacridine. .

GC-Mass: 534

Step 2 Synthesis of Mat 19

Using Mat 19-A instead of Mat 1-A was carried out the same procedure as in Synthesis Example 1 to obtain Mat 19 (2.3g, 41% yield).

Elemental Analysis: C, 89.43; H, 5. 60; N, 4.97 / GC-Mass: 845

Synthesis Example 20 Synthesis of Compound Mat 20

<Step 1> Synthesis of Mat 20-A, 20-B

10H-phenothiazine instead of 9,9-Dimethyl-9,10-dihydroacridine and 2-bromonaphthalene instead of bromobenzene were used to carry out Mat 20-A (1.3 g, yield 45%). Synthesis was carried out in the same manner as in Preparation Example 2 using 10H-phenothiazine instead of 9,9-dimethyl-9,10-dihydroacridine and 2- (4-bromophenyl) pyridine instead of 2-bromo-4,6-diphenylpyridine Mat 20-B (1 g, yield 40%) was synthesized.

GC-Mass: 584 (Mat 20-A)

GC-Mass: 564 (Mat 20-B)

<Step 2> Synthesis of Mat 20

Using Mat 20-A instead of Mat 1-A and Mat 20-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 20 (2.1 g, yield 32%).

Elemental Analysis: C, 90.32; H, 5. 23; N, 4.45 / GC-Mass: 943

Synthesis Example 21 Synthesis of Compound Mat 21

Step 1 Synthesis of Mat 21-B

Mat 21-B (4.2 g, yield 76%) was obtained in the same manner as in Preparation Example 2, using 10H-phenoxazine instead of 9,9-Dimethyl-9,10-dihydroacridine.

GC-Mass: 491

Step 2 Synthesis of Mat 21

Mat 21-B was used in place of Mat 1-B to obtain Mat 21 (4.6 g, 55% yield).

Elemental Analysis: C, 84.46; H, 5. 21; N, 8.04; O, 2.30 / GC-Mass: 695

Synthesis Example 22 Synthesis of Compound Mat 22

Step 1 Synthesis of Mat 22-A

Mat 22-A (1.3 g, yield 45%) was obtained by the same procedure as in Preparation Example 1, using 5,10-dihydrophenazine instead of 9,9-dimethyl-9,10-dihydroacridine and using 2 equivalents of bromobenzene. .

GC-Mass: 459

Step 2 Synthesis of Mat 22

Mat 22-A was used instead of Mat 1-A and Mat 2-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis Example 1 to obtain Mat 22 (4.6 g, yield 55%).

Elemental Analysis: C, 85.57; H, 5. 35; N, 9.07 / GC-Mass: 770

Examples 1 to 22 Fabrication of Green Organic EL Devices

After a high purity sublimation tablet of Compounds Mat1 to Mat22 synthesized in Synthesis Example 1-22 by a commonly known method, a green organic EL device was manufactured according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / Compound Compounds of Synthesis Examples 1 to 22 + 10% Ir (ppy) ₃ (300nm) / BCP (10 nm) / Alq on the thus prepared ITO transparent electrode _An organic EL device was fabricated by stacking ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

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

Comparative Example 1 Fabrication of Green Organic EL Device

An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound of the present invention as a light emitting host material in forming the emission layer.

The structure of CBP is as follows.

[Evaluation Example 1]

For each organic EL device produced in Example 1-22 and Comparative Example 1, the driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

Table 1

Sample	Host	Drive voltage (V)	EL peak (nm)	Current efficiency (cd / A)
Example 1	Mat1	5.70	517	42.8
Example 2	Mat2	5.81	516	41.7
Example 3	Mat3	5.80	519	40.9
Example 4	Mat4	5.81	515	41.5
Example 5	Mat5	5.81	517	40.9
Example 6	Mat6	5.73	516	42.5
Example 7	Mat7	5.78	518	41.8
Example 8	Mat8	5.70	514	40.9
Example 9	Mat9	5.79	518	41.5
Example 10	Mat10	5.75	516	40.9
Example 11	Mat11	5.77	515	42.1
Example 12	Mat12	5.79	518	41.5
Example 13	Mat13	5.80	517	40.9
Example 14	Mat14	5.84	518	40.9
Example 15	Mat15	5.81	516	41.4
Example 16	Mat16	5.79	516	41.5
Example 17	Mat17	5.80	517	40.4
Example 18	Mat18	5.86	515	40.6
Example 19	Mat19	5.89	516	39.3
Example 20	Mat20	5.84	517	39.8
Example 21	Mat21	6.06	518	39.2
Example 22	Mat22	6.12	518	39.5
Comparative Example 1	CBP	6.93	516	38.2

As shown in Table 1 above, when the compound according to the present invention was used as the light emitting layer of the organic EL device (Examples 1 to 22), the voltage and efficiency in comparison with the organic EL device using the conventional CBP (Comparative Example 1) It can be seen that the better performance in the.

Claims (7)

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

   <Formula 1>

   

   Where

   X ₁ and X ₂ are each independently selected from the group consisting of CR ₁ R ₂ , O, S, NR ₃ and SiR ₄ R ₅ ;

   Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, Substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, and a substituted or unsubstituted silyl group;

   R ₁ to R ₅ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ to C ₆₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, Substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₆₀ aryl group and a substituted or unsubstituted amine selected from the group consisting of unsubstituted silyl, and adjacent groups combine with each other to form a condensed ring;

   n and m are each independently an integer from 1 to 4;

   At least one Ar ₃ is the same or different from each other, at least one Ar ₄ is the same or different from each other, and each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₆₀ Alkynyl group, substituted or unsubstituted C ₆ ~ C ₆₀ Aryl group, substituted or unsubstituted nuclear atoms of 5 to 60 Heteroaryl group, substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, substituted or unsubstituted It is selected from the group consisting of a ring heteronuclear alkyl group having 3 to 60 ring atoms, a substituted or unsubstituted C ₆ ~ C ₆₀ arylamine group, and a substituted or unsubstituted silyl group.
2. The method of claim 1,

   The aryl groups of Ar ₁ and Ar ₂ are each independently unsubstituted C ₆ ~ C ₆₀ aryl group or C ₆ ~ C ₆₀ aryl group, C ₆ ~ ₆₀ heteroaryl group or C ₆ substituted with an amino group An aryl group of ~ C ₆₀ , and each of the heteroaryl groups of Ar ₁ and Ar ₂ is independently an unsubstituted heteroaryl group having 5 to 60 nuclear atoms, or an aryl group having ₆ to C ₆₀ atoms, and 5 to 60 nuclear atoms. A heteroaryl group or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group.
3. The method of claim 1,

   Ar ₁ and Ar ₂ are each independently an unsubstituted C ₆ ~ C ₆₀ aryl group; C ₆ -C ₆₀ aryl group substituted with a C ₆ ~ C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms or an amino group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C ₆ -C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group.
4. The method of claim 1,

   Ar ₁ is an unsubstituted C ₆ ~ C ₆₀ aryl group; Or a heteroaryl group of 5 to 60 nuclear atoms substituted with an aryl group of C ₆ to C ₆₀ , and Ar ₂ is substituted with an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms or an amino group C ₆ ~ C ₆₀ Aryl group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C ₆ to C ₆₀ aryl group or a heteroaryl group having 5 to 60 nuclear atoms substituted with a heteroaryl group having 5 to 60 nuclear atoms.
5. The method of claim 1,

   And X ₁ and X ₂ are each independently CR ₁ R ₂ or SiR ₄ R ₅ .
6. An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,

   At least one of the organic layer is an organic electroluminescent device comprising a compound according to any one of claims 1 to 5.
7. The method of claim 6,

   The compound is an organic electroluminescent device, characterized in that contained in the light emitting layer.