KR101319734B1 - Novel hybrid organic compounds and organic electroluminescence device comprising the same - Google Patents

Abstract

The hybrid compound represented by Chemical Formula 1 according to the present invention is an andrasene derivative, and part of the core of the core in which an anthracene moiety having excellent device characteristics and a moiety such as fluorene having excellent fluorescence properties are bonded to each other At the same time, a substituent (electron transporting group) having an electron transporting capacity and a substituent (hole transporting group) having a hole transporting capacity are simultaneously substituted, wherein the electron transporting group and the hole transporting group are each independently an element selected from the group consisting of N, O and S It is characterized by being a C ₂ ~ C ₄₀ heteroaryl group containing. By using this andrasene derivative as an electron transporting material and / or a host material of the organic electroluminescent device, the organic electroluminescent device can be improved in luminous efficiency, brightness, thermal stability, driving voltage, and lifetime.

Description

Novel hybrid organic compound and organic electroluminescent device using same {NOVEL HYBRID ORGANIC COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE SAME}

The present invention relates to a novel hybrid organic compound and an organic electroluminescent device comprising the same.

Generally, an organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. When the voltage is applied between the two electrodes in the structure of the organic EL device, holes are injected into the organic material layer in the anode and electrons in the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground, they shine.

In order to increase the efficiency and stability of the organic EL device, an organic material layer interposed between the anode and the cathode is often manufactured in a multilayer structure composed of different materials instead of a single layer. In 1987, Tang presented an organic electroluminescent device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer, and most organic electroluminescent devices currently used are hole injections that receive holes as a substrate, an anode, and an anode. It consists of a layer, a hole transport layer for transferring holes, a light emitting layer for recombining holes and electrons to emit light, an electron transport layer for transferring electrons, an electron injection layer for receiving electrons from the cathode, and a cathode.

Since the organic electroluminescent device is manufactured in a multi-layered manner, the movement speeds of the holes and the electrons are different. Therefore, if the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer are properly made, holes and electrons can be effectively transferred. As a result, a balance between holes and electrons in the device may be achieved to improve light emission efficiency.

The first material developed as an electron transport material is an oxadiazole derivative (PBD). Thereafter, it was known that triazole derivatives (TAZ) and phenanthroline derivatives (BCP) exhibit electron transport properties. In addition to these materials, the electron transporting material is an organic monomolecular material, and organic metal complexes having excellent electron stability and electron transfer speed are appropriate, and Alq 3 having high stability and electron affinity is most suitable. This is the most widely used at present.

In addition, organic monomolecular materials having an imidazole group, an oxazole group, or a thiazole group are known as materials for the electron injection layer and the electron transport layer.

For example, TPBI known from Kodak Corporation in 1996 is known as a representative electron transport layer material having an imidazole group. The structure of the TPBI contains three N-phenyl benzimidazole groups at 1,3,5 substituted positions of benzene and functionally blocks electrons from the light emitting layer as well as the ability to transfer electrons. However, the TPBI has a problem of low thermal stability when applied to actual devices.

Further, the electron transporting materials disclosed in Japanese Patent Laid-Open No. 11-345686 contain oxazole groups and thiazole groups, and these materials are known to be applicable to the light emitting layer. However, the electron transporting materials have not been put to practical use in terms of driving voltage, brightness and lifetime of the device.

In order to overcome the problems of the prior art and to further improve the characteristics of the organic EL device, it is necessary to develop a more stable and efficient material that can be used as the material for the electron transport layer in the organic EL device.

The present invention is to solve the above problems, to provide a novel hybrid organic compound and a organic electroluminescent device comprising the same, a low driving voltage, which can improve the luminous efficiency, brightness, thermal stability and device life.

The present invention provides a novel hybrid compound represented by the following formula (1).

In Formula 1, L is a substituted or unsubstituted indenoanthracene, anthrabenzosilol, naphthocarbazole or anthrabenzofuran,

Ar ¹ and Ar ² are each independently a C ₂ to C ₄₀ heteroaryl group including one or more elements selected from the group consisting of N, O, and S.

The present invention also provides an organic electroluminescent 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 at least one organic layer One provides an organic electroluminescent device characterized in that it comprises a novel hybrid compound represented by the above formula (1).

According to the present invention, when using the novel hybrid compound represented by Chemical Formula 1 as an electron transporting material and / or a host material of an organic electroluminescent device, a hybrid compound in which a hole transporter and an electron transporter are simultaneously introduced into the compound controls carrier transporting. This improves recombination efficiency by controlling fast hole transportability and improving charge balance, thereby improving luminous efficiency, luminance, thermal stability, driving voltage, and lifetime characteristics of organic EL devices compared with conventional electron transport materials and / or host materials. Can be.

Hereinafter, the present invention will be described in detail.

The novel hybrid compound represented by Chemical Formula 1 according to the present invention is an andracene derivative, and part of a core in which an anthracene moiety having excellent device characteristics and a moiety such as fluorene having excellent fluorescence properties are bonded to each other. In the carbon, a substituent (electron transport group) having an electron transporting capacity and a substituent (hole transporter) having a hole transporting capacity are simultaneously substituted, wherein the electron transporting group and the hole transporting group are each independently selected from the group consisting of N, O and S. it is characterized by a heteroaryl group of C ₂ ~ C ₄₀ containing the element. By using such a hybrid compound as an electron transporting material and / or a host material of the organic electroluminescent device, the organic electroluminescent device can have improved luminous efficiency, brightness, thermal stability, driving voltage, and lifetime characteristics.

The hybrid compound represented by Chemical Formula 1 according to the present invention may be a compound represented by the following Chemical Formula 2.

In Formula 2,

X is selected from the group consisting of CR ⁶ R ⁷ , NR ⁶ , O, S, S (= 0), S (= 0) ₂ , and SiR ⁶ R ⁷ ,

Wherein R ¹ to R ⁷ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ Cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ arylalkyl group, C ₁ ~ C ₄₀ alkyloxy group, C ₅ ~ C ₄₀ aryloxy group, C ₅ ~ C ₄₀ aryl Group and C ₅ ~ C ₄₀ heteroaryl group; Or adjacent groups to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring.

Further, the cycloalkyl group of the R ¹ to R ⁷ wherein the C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of the, C ₃ ~ C ₄₀ Heterocycloalkyl group, C ₆ ~ C ₄₀ arylalkyl group, C ₁ ~ C ₄₀ alkyloxy group, C ₅ ~ C ₄₀ aryloxy group, C ₅ ~ C ₄₀ aryl group and C ₅ ~ C ₄₀ hetero The aryl groups are each independently deuterium, halogen, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ amino group, C It may be unsubstituted or substituted with one or more selected from the group consisting of ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₅ to C ₄₀ heteroaryl group have.

However, two or more of R ¹ to R ⁴ are each independently a C ₂ to C ₄₀ heteroaryl group including one or more elements selected from the group consisting of N, O, and S.

According to one embodiment of the invention, the R ¹ to R ⁴ of R ¹ and R ² are each independently selected from N, O and can heteroaryl date of C ₂ ~ C ₄₀ comprising at least one element selected from the group consisting of S have.

Examples of C ₂ to C ₄₀ heteroaryl groups including one or more elements selected from the group consisting of N, O and S include functional groups represented by the following Chemical Formulas 3 to 39, but are not limited thereto:

In Chemical Formulas 3 to 39,

L, m, n, o and p are each independently integers ranging from 1 to 5;

A plurality of Q ¹ is the same or different from each other, a plurality of Q ² is the same or different from each other, a plurality of Q ³ is the same or different from each other, a plurality of Q ⁴ is the same or different from each other, a plurality of Q ⁵ is each other Same or different;

Q ¹ , Q ² , Q ³ , Q ⁴ and Q ⁵ are the same as or different from each other, and are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ Alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₁ to C ₄₀ amino group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₅ Or a heteroaryl group of -C ₄₀ ; Or a group forming a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group, or a linking group. In this case, in Formulas 3 to 39, _one carbon or nitrogen selected from carbon or nitrogen bondable to Q ₁ , Q ₂ , Q ₃ , Q ₄ or Q ₅ is connected to L of Formula 1, in which case Formula 1 There is no substituent on the carbon or nitrogen of Formula 3 to 39 connected to L of. In addition, in Formulas 3 to 39, _one carbon or nitrogen selected from carbon or nitrogen bondable to Q ₁ , Q ₂ , Q ₃ , Q _4, or Q ₅ may be R ¹ , R ² , R ^3, or R of Formula 2 ^Is connected to one carbon selected from carbons that can be bonded with ⁴ , in this case carbon or nitrogen of formula 3 to 39 is connected to the carbon of formula (2) does not have a substituent, it is connected to carbon or nitrogen of the formula 3 to 39 There is no substituent on the carbon of the formula (2).

Representative examples of the hybrid compound represented by Formula 1 according to the present invention include, but are not limited to:

[Formula 1-001]

;

;

[Formula 1-002]

;

;

[Formula 1-003]

;

;

[Formula 1-004]

;

;

[Formula 1-005]

;

;

[Formula 1-006]

;

;

[Formula 1-007]

;

;

[Formula 1-008]

;

;

[Formula 1-009]

;(여기서, Me는 메틸기임)

Where Me is a methyl group

[Formula 1-010]

;

;

[Formula 1-011]

;

;

[Formula 1-012]

;

;

[Formula 1-013]

;

;

[Formula 1-014]

;

;

[Formula 1-015]

;

;

[Formula 1-016]

;

;

[Formula 2-001]

;

;

[Formula 2-002]

;

;

[Formula 2-003]

;

;

[Formula 2-004]

;

;

[Formula 2-005]

;

;

[Formula 2-006]

;

;

[Formula 2-007]

;

;

[Formula 2-008]

;

;

[Formula 2-009]

;(여기서, Me는 메틸기임)

Where Me is a methyl group

[Formula 2-010]

;

;

[Formula 2-011]

;

;

[Formula 2-012]

;

;

[Formula 2-013]

;

;

[Formula 2-014]

;

;

[Formula 2-015]

;

;

[Formula 2-016]

;

;

[Formula 3-001]

;

;

[Formula 3-002]

;

;

[Formula 3-003]

;

;

[Formula 3-004]

;

;

[Formula 3-005]

;

;

[Formula 3-006]

;

;

[Formula 3-007]

;

;

[Formula 3-008]

;

;

[Formula 3-009]

;

;

[Formula 3-010]

;

;

[Formula 3-011]

;

;

[Formula 3-012]

;

;

[Formula 3-013]

;

;

[Formula 3-014]

;

;

[Formula 4-001]

;

;

[Formula 4-002]

;

;

[Formula 4-003]

;

;

[Formula 4-004]

;

;

[Formula 4-005]

;

;

[Formula 4-006]

;

;

[Formula 4-007]

;

;

[Formula 4-008]

;

;

[Formula 4-009]

; 및

; And

[Formula 4-010]

On the other hand, the present invention provides an organic electroluminescent device comprising a hybrid compound represented by the above formula (1).

The organic electroluminescent device according to the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, wherein the one layer At least one of the organic layer is characterized in that it comprises a hybrid compound represented by the formula (1).

In the organic electroluminescent device according to the present invention, the organic material layer including the compound represented by Formula 1 may be a layer selected from the group consisting of an electron transport layer, a light emitting layer, and a combination thereof.

When the hybrid compound represented by Chemical Formula 1 is included in the electron transport layer, it may be used alone, or may be used in combination with a conventional electron transport material known in the art. Non-limiting examples of such conventional electron transport materials include Alq3 [aluminum tris (8-hydroxyquinoline)], Liq [8-quinolinollithium], PBD [2- (biphenyl-4-yl) -5- (4-tert-butylphenyl ) -1,3,4-oxadiazole], TAZ [3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1,2,4-triazole], Bphen [ 4,7-diphenyl-1,10-phenanthroline], TPBI [1,3,5-tris (1-phenyl-1H-benzo [d] imidazol-2-yl) benzene].

In addition, when the hybrid compound represented by Chemical Formula 1 is included in the light emitting layer, it may be used as a host material capable of bonding with a dopant.

On the other hand, in the organic electroluminescent device according to the present invention, the organic material layer other than the organic material layer containing the compound represented by Formula 1 of the present invention may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and / or an electron injection layer.

As a non-limiting example of the organic electroluminescent device structure according to the present invention, a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked, wherein the electron transport layer and the light emitting layer At least one is to include a hybrid compound represented by the formula (1). An electron injection layer may be disposed on the electron transport layer.

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 the electrode and the organic material layer.

In the organic electroluminescent device according to the present invention, the organic material layer including the hybrid compound represented by Chemical 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 electroluminescent device according to the present invention is an organic material layer using any material and method known in the art, except that at least one layer of at least one organic material layer is formed to include the hybrid compound represented by the formula (1) of the present invention and It can be produced by forming an electrode.

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

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

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

In addition, materials such as a hole injection layer, a hole transport layer, and an electron injection 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 for illustrative purposes only and are not intended to limit the scope of the present invention.

Example 1-1 Synthesis of Compound Represented by Chemical Formula 1-001

Synthesis Example 1-1 Preparation of the Compound Represented by Chemical Formula 1-3

[Reaction Scheme 1-1]

20 g of the compound represented by Chemical Formula 1-1 (9,9-dimethylfluorene) and 23 g of the compound represented by Chemical Formula 1-2 (phthalic anhydride) are added thereto at room temperature by adding 700 mL of dichloromethane (DCM). While stirring, 20.5 g of aluminum chloride (AlCl ₃ ) was slowly added at 0 ° C. After the reaction was stabilized, the reaction mixture was stirred at room temperature for 6 hours, and after completion of the reaction, distilled water was slowly added to the reaction product at 0 ° C., extracted with excess dichloromethane, and washed with distilled water several times. The concentrate was purified by column chromatography, dissolved in dichloromethane (DCM), precipitated in n-hexane, and the resulting solid was filtered. The solid obtained by filtration was dried under reduced pressure to obtain 27 g of a compound represented by Chemical Formula 1-3 (yield: 76%).

1 H NMR: 8.44 (t, 2H), 8.23 (d, 1H), 7.96 (m, 5H), 7.72 (m, 5H), 7.55 (t, 1H), 1.67 (s, 6H)

Synthesis Example 1-2 Preparation of Compound Expressed by Chemical Formula 1-4

[Reaction Scheme 1-2]

27 g of the compound represented by Chemical Formula 1-3 obtained in Synthesis Example 1-1 was added to 50 mL of polyphosphoric acid (H ₃ PO ₄ ). The reaction was heated and stirred at a temperature of 130 ° C. for 3 hours, and then cooled to room temperature. 400 mL of ice water was added thereto, and the resulting solid was filtered and washed several times with methanol. The solid obtained by the filtration was dried under a reduced pressure to obtain 19 g of a compound represented by Chemical Formula 1-4 (yield: 74%).

1 H NMR: 8.29 (t, 3 H), 8.09 (s, 2 H), 7.85 (d, 2 H), 7.72 (m, 2 H), 1.67 (s, 6 H)

Synthesis Example 1-3 Preparation of Compound Represented by Chemical Formula 1-5

[Reaction 1 - 3]

64 g of the compound represented by Chemical Formula 1-4 obtained in Synthesis Example 1-2 was added to 2 L of methanol (MeOH) and then dispersed. To the reaction solution 30 g of sodium borohydride (NaBH ₄ ) was added slowly in three portions under 0 ° C. Thereafter, the reaction solution was stirred at 0 ° C. for 3 hours, and then 3 L of water was added thereto, and the resulting solid was filtered. The solid obtained by filtration was washed several times with excess water and naturally dried to obtain 115 g of a compound represented by Chemical Formula 1-5.

Synthesis Example 1-4 Preparation of the compound represented by Chemical Formula 1-6 in Scheme 1-4

Scheme 1-4

115 g of the compound represented by Chemical Formula 1-5 obtained in Synthesis Example 1-3 was dispersed in 300 mL of 5 N HCl, and then stirred at reflux for 20 hours. After cooling to room temperature, water was added to the reaction solution to form a solid, and the resulting solid was filtered. Thereafter, the solid obtained by filtration was sufficiently washed with excess water and dried under reduced pressure to obtain 60.3 g (yield: 98.5%) of the compound represented by Chemical Formula 1-6.

Synthesis Example 1-5 Preparation of the Compound Represented by Chemical Formula 1-7

Scheme 1-5

60.3 g of the compound represented by Chemical Formula 1-6 obtained in Synthesis Example 1-4 was dispersed in 1.5 L of isopropanol, and then 36.7 g of sodium borohydride was added. The reaction solution was stirred under reflux for 22 hours, cooled to room temperature, and the resulting red colored reaction was added to 2 L of water and stirred. After the resulting solid was filtered, the solid obtained by filtration was sufficiently washed with excess water to obtain an ocher solid. The resulting ocher solid was purified through column chromatography to obtain 27.9 g (yield: 48.7%) of the compound represented by Chemical Formula 1-7 as a light yellow green solid.

1H NMR (500MHz, THF-d8) 8.49 (s, 1H), 8.43 (s, 1H), 8.34 (s, 1H), 8.03 (s, 1H), 7.98 (dd, 2H), 7.95 (m, 1H) , 7.50 (m, 1H), 7.40 (m, 2H), 7.35 (m, 2H), 1.60 (s, 6H)

Mass: [M + 1] + 294

Synthesis Example 1-6 Preparation of the Compound Represented by Chemical Formula 1-8

Scheme 1-6

To the solution obtained by dissolving 27.9 g of the compound represented by Chemical Formula 1-7 obtained in Synthesis Example 1-5 in 400 mL of dimethylformamide (DMF), 18.5 g of N-bromosuccinimide (NBS) was added to the reaction solution. Got it. Thereafter, the reaction solution was stirred at room temperature for 1 hour, and then poured into 1 L of water to obtain a solid, and the resulting solid was filtered. The filtered solid was sufficiently washed with water and methanol, and then dried under reduced pressure to obtain 33.3 g (yield: 94.2%) of the compound represented by Chemical Formula 1-8 as a pale yellow solid.

1H NMR (500MHz, THF-d8) 8.83 (s, 1H), 8.53 (s, 1H), 8.48 (d, 1H), 8.08 (s, 1H), 8.06 (t, 1H), 8.03 (d, 1H) , 7.59 (m, 1H), 7.53 (m, 1H), 7.49 (m, 1H), 7.40 (m, 2H), 1.62 (s, 6H)

Mass: [M + 1] + 372

Synthesis Example 1-7 Preparation of the compound represented by Chemical Formula 1-13 of Scheme 1

[Reaction Scheme 1-7]

13 mL of 2-bromopyridine and 25.2 g of 4-chlorophenylboronic acid were dissolved in 1 L of toluene, followed by 4.7 g of tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] and 2 N of potassium carbonate (K). ₂ CO ₃ ) 300 mL was added. The reaction was stirred at reflux for 22 hours, cooled to room temperature, and separated into an organic layer and a water layer. The organic layer was then washed with water and saturated sodium chloride solution, then dried over anhydrous sodium sulfate and concentrated, then column chromatography (n-hexane; n-hexane / dichloromethane = 9/1; and n-hexane / Purification through ethyl acetate = 10/1) and drying yielded 19.6 g (yield: 77.0%) of the compound represented by Chemical Formula 1-13 as a white solid.

1 H NMR (500 MHz, THF-d8) 8.62 (d, 1H), 8.11 (dd, 2H), 7.86 (d, 1H), 7.77 (td, 1H), 7.44 (dd, 2H), 7.23 (m, 1H)

Mass: [M + 1] + 189

Synthesis Example 1-8 Preparation of the compound represented by Chemical Formula 1-9

[Reaction Scheme 1-8]

15.3 g of the compound represented by Chemical Formula 1-13 obtained in Synthesis Example 1-7 was dispersed in 400 mL of 1,4-dioxane (1,4-dioxane) together with 24.6 g of bis (pinacolato) diboron, followed by 2.8 g of bis (dibenzylideneacetone) palladium (0) [Pd (dba) ₂ ], 5.4 g of tricyclohexylphosphine (PCy ₃ ) and 23.8 g of potassium acetate (KOAc) were added thereto, followed by stirring under reflux to obtain a reaction solution. After cooling to room temperature, 400 mL of distilled water was added to the reaction solution, followed by stirring. Then, 400 mL of dichloromethane was added to separate the organic layer and the water layer. The organic layer separated from the water layer was washed with excess saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated, and then purified by column chromatography (n-hexane; n-hexane / ethyl acetate = 10/1). 13.2 g (yield: 58.1%) of the compound represented by Chemical Formula 1-9 were obtained as a pale yellow solid.

1 H NMR (500 MHz, THF-d8) 8.63 (dt, 1H), 8.10 (d, 2H), 7.89 (d, 1H), 7.82 (d, 2H), 7.76 (td, 1H), 7.22 (m, 1H)

Mass: [M + 1] + 281

Synthesis Example 1-9 Preparation of the compound represented by Chemical Formula 1-10

[Reaction Scheme 1-9]

14.5 g of the compound represented by Formula 1-8 obtained in Synthesis Example 1-6 and 13.1 g of the compound represented by Formula 1-9 obtained in Synthesis Example 1-8 were dissolved in 400 mL of toluene, followed by tetrakis 1.4 g of (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ], 100 mL of 2 N sodium carbonate (Na ₂ CO ₃ ) and 1.8 mL of aliquat 336 were added to the reaction product. The reaction was stirred at reflux for 22 hours and then cooled to room temperature to separate the organic layer and the water layer. The organic layer separated from the water layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The concentrate was then purified via column chromatography (n-hexane; n-hexane / ethyl acetate = 10/1), then dissolved in dichloromethane, a pale yellow solid, and then solidified in methanol to give a pale yellow color. 13.3 g (yield: 76.5%) of the compound represented by Chemical Formula 1-10 was obtained.

1H NMR (500MHz, THF-d8) 8.73 (d, 1H), 8.55 (s, 1H), 8.44 (d, 2H), 8.07 (m, 4H), 7.87 (td, 1H), 7.66 (dd, 2H) , 7.58 (d, 2H), 7.48 (d, 1H), 7.42 (t, 1H), 7.31 (m, 3H), 7.22 (t, 1H), 1.65 (s, 6H)

Mass: [M + 1] + 448

Synthesis Example 1-10 Preparation of the Compound Represented by Chemical Formula 1-11

[Reaction Scheme 1-10]

13.3 g of the compound represented by Chemical Formula 1-11 obtained in Synthesis Example 1-9 was dispersed in 150 mL of dimethylformamide (DMF), and dissolved at a temperature of 80 ° C., and then 5.8 g of N-bromosuccinimide was heated at 40 ° C. Was added to afford the reaction. Thereafter, the reaction mixture was stirred at room temperature for 1 hour and then poured into 300 mL of water to stir again to obtain a solid, and the resulting solid was filtered. The obtained solid was extracted with excess dichloromethane, washed with saturated aqueous sodium thiosulfate solution and saturated sodium chloride solution, and then dried over anhydrous sodium sulfate and concentrated. The concentrate was dissolved in dichloromethane and then solidified in methanol and dried to obtain 13.9 g (yield: 88.7%) of the compound represented by Chemical Formula 1-11 as a mustard solid.

1H NMR (500MHz, THF-d8) 8.74 (d, 1H), 8.66 (s, 1H), 8.60 (d, 1H), 8.46 (d, 2H), 8.09 (d, 1H), 8.02 (s, 1H) , 7.88 (td, 1H), 7.71 (d, 1H), 7.65 (d, 1H), 7.58 (m, 3H), 7.51 (d, 1H), 7.39 (t, 1H), 7.32 (m, 2H), 7.24 (t, 1 H), 1.65 (s, 6 H)

Mass: [M] + 525

Synthesis Example 1-11 Preparation of a compound represented by Chemical Formula 1-14

Scheme 1-11

40 g of carbazole and 81.2 g of 1-bromo-4-iodobenzene were dissolved in toluene, followed by 6.6 g of tris (dibenzylideneacetone) dipalladium (0) [Pd ₂ (dba) ₃ ], 50 wt% of tri-soluble in hexane. 12 mL of -tert-butylphosphine [P (t-Bu) ₃ ] and 57.5 g of sodium tert-butoxide [NaO (t-Bu)] were added, followed by stirring under reflux. The reaction was cooled to room temperature and then filtered using celite 545, then washed sufficiently with excess dichloromethane, and the filtrate was concentrated. The concentrate was purified by column chromatography (n-hexane; n-hexane / dichloromethane = 9/1) to obtain 33.4 g (yield: 43.3%) of the compound represented by Chemical Formula 1-14 as a shiny white solid. Got it.

1 H NMR (500 MHz, THF-d8) 8.13 (d, 2H), 7.80 (dd, 2H), 7.55 (dd, 2H), 7.37 (m, 4H), 7.24 (m, 2H)

Mass: [M] + 321

Synthesis Example 1-12 Preparation of the Compound Represented by Chemical Formula 1-12

Scheme 1-12

33.4 g of the compound represented by Chemical Formula 1-14 and 31.6 g of bis (pinacolato) diboron obtained in Synthesis Example 1-11 were dispersed in 400 mL of 1,4-dioxane, and [1,1′-bis (diphenylphosphino) ) ferrocene] dichloropalladium (II) [Pd (dppf) Cl ₂ ] 2.3 g and potassium acetate 30.5 g were added, followed by stirring under reflux. 400 mL of distilled water was added to the reaction mixture, which was cooled to room temperature, followed by stirring. Then, 400 mL of dichloromethane was added thereto, and the organic layer and the water layer were separated. The organic layer separated from the water layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated, and then purified by column chromatography (n-hexane; n-hexane / dichloromethane = 9/1 to 4/1). To give 32.4 g (yield: 84.5%) of the compound represented by Chemical Formula 1-12 as a white solid.

1H NMR (500MHz, THF-d8) 8.13 (d, 2H), 8.02 (d, 2H), 7.61 (d, 2H), 7.42 (d, 2H), 7.36 (td, 2H), 7.23 (td, 2H) , 1.38 (s, 12 H)

Mass: [M + 1] + 369

Synthesis Example 1-13 Preparation of the Compound Represented by Chemical Formula 1-001

Scheme 1-13

13.9 g of the compound represented by Formula 1-11 obtained in Synthesis Example 1-11 and 11.7 g represented by Formula 1-12 obtained in Synthesis Example 1-12 were dissolved in 200 mL of toluene, followed by tetrakis (triphenylphosphine ) palladium (0) [Pd (PPh ₃ ) ₄ ] 0.9 g, 2 N sodium carbonate 60 mL, and aliquat 336 1.2 mL were added and stirred under reflux for 13 hours. The reactant cooled to room temperature was separated into an organic layer and a water layer, and then the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The concentrate was purified via column chromatography (n-hexane; n-hexane / dichloromethane = 9/1; n-hexane / ethyl acetate = 10/1; chloroform), then precipitated from n-hexane and filtered to give a pale yellow color. 11.8 g (yield: 64.9%) of the compound represented by Chemical Formula 1-001 was obtained.

1H NMR (500MHz, THF-d8) 8.75 (d, 1H), 8.49 (d, 2H), 8.22 (d, 2H), 8.11 (d, 2H), 7.96 (d, 2H), 7.86 (m, 6H) , 7.77 (d, 2H), 7.72 (d, 2H), 7.67 (d, 2H), 7.48 (m, 3H), 7.39 (m, 2H), 7.30 (m, 4H), 7.23 (t, 1H), 1.51 (s, 6H)

Mass: 689

Elemental Analysis: C, 90.67; H, 5. 27; N, 4.07

Example 1-2 Preparation of Compound represented by Chemical Formula 1-002

Instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, 81.2 g of 1-bromo-3-iodobenzene was used, and the compound obtained at this time was used in Chemical Formula 1-14. Except for using in place of the compound represented by, in the same manner as in Example 1-1 to give a compound 12.4 g (yield: 68.2%) represented by the following formula 1-002 as a pale yellow solid.

[Formula 1-002]

1H NMR (500MHz, THF-d8) 8.74 (d, 1H), 8.47 (m, 2H), 8.15 (d, 2H), 8.09 (m, 2H), 7.98 (t, 1H), 7.89 (m, 3H) , 7.82 (m, 2H), 7.75 (d, 1H), 7.66 (m, 5H), 7.61 (d, 1H), 7.47 (d, 1H), 7.38 (t, 3H), 7.31 (m, 3H), 7.24 (m, 3H), 1.58 (s, 3H), 1.52 (s, 3H)

Mass: 689

Elemental Analysis: C, 90.67; H, 5. 27; N, 4.07

<Example 1-3> Preparation of a compound represented by Chemical Formula 1-003

Instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, 101.1 g of 2,7-dibromo-9,9-dimethylfluorene was used, and the obtained compound was used in Synthesis Example 1-12. 9.1 g of a compound represented by the following Chemical Formula 1-003 which is a pale yellow solid, except that the compound represented by Chemical Formula 1-14 is used instead of the compound represented by Chemical Formula 1-14 (yield: 43.2%) Got.

[Formula 1-003]

Mass: 805

Elemental Analysis: C, 91.01; H, 5.51; N, 3.48

Example 1-4 Preparation of a Compound Represented by Chemical Formula 1-004

Instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, 82.1 g of 1,4-dibromonaphthalene was used, and the obtained compound was represented by Chemical Formula 1-14 used in Synthesis Example 1-12. 11.9 g (yield: 61.1%) of a compound represented by the following Chemical Formula 1-004 was obtained as a pale yellow solid, except that the compound was used instead of the compound.

[Formula 1-004]

Mass: 739

Elemental Analysis: C, 91.03; H, 5.18; N, 3.79

Example 1-5 Preparation of the Compound Represented by Chemical Formula 1-005

Instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, 37.7 g of 1,3,5-tribromobenzene was used, and the compound obtained at this time was used in Chemical Formula 1-14. Except for using in place of the compound represented by, in the same manner as in Example 1-1 to obtain a compound of the light yellow solid of the compound represented by Formula 1-005 (yield: 37.9%) of 1-005.

[Formula 1-005]

Mass: 854

Elemental Analysis: C, 90.01; H, 5.07; N, 4.92

Example 1-6 Preparation of a Compound Represented by Chemical Formula 1-006

46.8 g of 3,4 ′, 5-tribromobiphenyl was used instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, and the obtained compound was obtained by Chemical Formula 1- used in Synthesis Example 1-12. Except for using the compound represented by 14, 6.9 g (yield: 28.4%) of the compound represented by the following Chemical Formula 1-006 was obtained as a pale yellow solid, in the same manner as in Example 1-1.

[Formula 1-006]

Mass: 930

Elemental Analysis: C, 90.39; H, 5.09; N, 4.52

Example 1-7 Preparation of a Compound Represented by Chemical Formula 1-007

66.8 g of 3,6-di-tert-butyl-9H-carbazole was used instead of 40 g of Carbazole used in Synthesis Example 1-11, and the obtained compound was used in Chemical Formula 1-14. Except for using in place of the compound represented by, in the same manner as in Example 1-1 to give a compound 14.6 g (yield: 69.1%) represented by the following formula 1-007 as a pale yellow solid.

[Formula 1-007]

Mass: 801

Elemental Analysis: C, 89.96; H, 6.54; N, 3.50

Example 1-8 Preparation of a Compound Represented by Chemical Formula 1-008

46.7 g of 3,6-dimethyl-9H-carbazole was used in place of 40 g of Carbazole used in Synthesis Example 1-11, and the obtained compound was represented by Chemical Formula 1-14 used in Synthesis Example 1-12. Except for using it, the same procedure as in Example 1-1 was carried out to obtain 13.3 g (yield: 70.4%) of a compound represented by the following Chemical Formula 1-008 as a pale yellow solid.

[Formula 1-008]

Mass: 717

Elemental Analysis: C, 90.47; H, 5.62; N, 3.91

Example 1-9 Preparation of a Compound Represented by Chemical Formula 1-009

Instead of 40 g of Carbazole used in Synthesis Example 1-11, 54.4 g of 3,6-dimethoxy-9H-carbazole was used, and the obtained compound was represented by Chemical Formula 1-14 used in Synthesis Example 1-12. Except for using it, the same procedure as in Example 1-1 was carried out to obtain 11.6 g (yield: 58.9%) of a compound represented by the following Chemical Formula 1-009 as a pale yellow solid (Formula 1-009 In which Me is a methyl group.

[Formula 1-009]

Mass: 749

Elemental Analysis: C, 86.60; H, 5. 38; N, 3.74; O, 4.27

Example 1-10 Preparation of a Compound Represented by Chemical Formula 1-010

Example 1-1, except that 33.4 g of 3-bromo-9-phenyl-9H-carbazole is used instead of the compound represented by Formula 1-14 used in Synthesis Example 1-12 9.7 g (yield: 53.5%) of a compound represented by the following Chemical Formula 1-010 as a light yellow solid was obtained.

[Formula 1-010]

Mass: 689

Elemental Analysis: C, 90.67; H, 5. 27; N, 4.07

Example 1-11 Preparation of a Compound Represented by Chemical Formula 1-011

The same procedure as in Example 1-1 was carried out except for using 26.7 g of 3-bromo-9-methyl-9H-carbazole instead of the compound represented by Formula 1-14 used in Synthesis Example 1-12. This yielded 7.8 g (yield: 47.2%) of the compound represented by the following Chemical Formula 1-011 as a pale yellow solid.

[Formula 1-011]

Mass: 627

Elemental Analysis: C, 90.06; H, 5.47; N, 4.47

Example 1-12 Preparation of a Compound Represented by Chemical Formula 1-012

Example 1-1, except that 33.5 g of 4- (3-bromophenyl) dibenzo [b, d] furan was used instead of the compound represented by Chemical Formula 1-14 used in Synthesis Example 1-12. 12.9 g (yield: 71.2%) of a compound represented by the following Chemical Formula 1-012 was obtained as a light yellow solid.

[Formula 1-012]

Mass: 690

Elemental Analysis: C, 90.54; H, 5.11; N, 2.03; O, 2.32

Example 1-13 Preparation of a compound represented by Chemical Formula 1-013

Example 1-1, except that 33.5 g of 4- (4-bromophenyl) dibenzo [b, d] furan was used instead of the compound represented by Chemical Formula 1-14 used in Synthesis Example 1-12. 11.1 g (yield: 61.2%) of the compound represented by the following Chemical Formula 1-013 was obtained as a light yellow solid.

[Formula 1-013]

Mass: 690

Elemental Analysis: C, 90.54; H, 5.11; N, 2.03; O, 2.32

Example 1-14 Preparation of a Compound Represented by Chemical Formula 1-014

Example 1-1, except that 35.2 g of 4- (3-bromophenyl) dibenzo [b, d] thiophene was used instead of the compound represented by Chemical Formula 1-14 used in Synthesis Example 1-12. 10.9 g (yield: 59.2%) of the compound represented by the following Chemical Formula 1-014 was obtained as a light yellow solid.

[Formula 1-014]

Mass: 706

Elemental Analysis: C, 88.48; H, 5.00; N, 1.98; S, 4.54

Example 1-15 Preparation of a Compound Represented by Chemical Formula 1-008

Example 1-1, except that 35.2 g of 4- (4-bromophenyl) dibenzo [b, d] thiophene was used instead of the compound represented by Formula 1-14 used in Synthesis Example 1-12. 10.5 g (yield: 56.3%) of the compound represented by the following Chemical Formula 1-015 as a light yellow solid was obtained by the method.

[Formula 1-015]

Mass: 706

Elemental Analysis: C, 88.48; H, 5.00; N, 1.98; S, 4.54

Example 1-16 Preparation of a Compound Represented by Chemical Formula 1-016

129.2 g of 1,6-dibromopyrene was used instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, and the obtained compound was represented by Chemical Formula 1-14 used in Synthesis Example 1-12. 9.2 g (yield: 43.1%) of a compound represented by the following Chemical Formula 1-016 which was a pale yellow solid was obtained by the same method as Example 1-1, except that the compound was used instead of the compound.

[Formula 1-016]

Mass: 813

Elemental Analysis: C, 91.60; H, 4.96; N, 3.45

Example 2-1 Preparation of a Compound Represented by Chemical Formula 2-001

Instead of 25.2 g of 4-chlorophenylboronic acid used in Synthesis Example 1-7, 25.2 g of 3-chlorophenylboronic acid was used, and the obtained compound was used instead of the compound represented by Formula 1-13 used in Synthesis Example 1-8. Except for using, the same procedure as in Example 1-1 was carried out to obtain 13.9 g (yield: 76.4%) of a compound represented by the following Chemical Formula 2-001 as a pale yellow solid.

[Formula 2-001]

Mass: 689

Elemental Analysis: C, 90.67; H, 5. 27; N, 4.07

Example 2-2 Preparation of a Compound Represented by Chemical Formula 2-002

12.1 g (yield: 66.5%) of a compound represented by the following Chemical Formula 2-002 was obtained as a pale yellow solid.

[Formula 2-002]

Mass: 689

Elemental Analysis: C, 90.67; H, 5. 27; N, 4.07

Example 2-3 Preparation of a Compound Represented by Chemical Formula 2-003

10.4 g (yield: 49.2%) of the compound represented by the following Chemical Formula 2-003 was obtained as a pale yellow solid.

[Formula 2-003]

Mass: 805

Elemental Analysis: C, 91.01; H, 5.51; N, 3.48

Example 2-4 Preparation of a Compound Represented by Chemical Formula 2-004

11 g (yield: 56.4%) of the compound represented by the following Chemical Formula 2-004 was obtained as a pale yellow solid.

[Formula 2-004]

Mass: 739

Elemental Analysis: C, 91.03; H, 5.18; N, 3.79

Example 2-5 Preparation of a Compound Represented by Chemical Formula 2-005

9.5 g (yield: 42.2%) of a compound represented by the following Chemical Formula 2-005 was obtained as a pale yellow solid by the same method as in Example 1.

[Formula 2-005]

Mass: 854

Elemental Analysis: C, 90.01; H, 5.07; N, 4.92

Example 2-6 Preparation of a Compound Represented by Chemical Formula 2-006

6.1 g (yield: 25.1%) of the compound represented by the following Chemical Formula 2-006 was obtained as a pale yellow solid by the same method as in Example 1.

[Formula 2-006]

Mass: 930

Elemental Analysis: C, 90.39; H, 5.09; N, 4.52

Example 2-7 Preparation of a Compound Represented by Chemical Formula 2-007

12.7 g (yield: 60.1%) of the compound represented by the following Chemical Formula 2-007 was obtained as a pale yellow solid.

[Formula 2-007]

Mass: 801

Elemental Analysis: C, 89.96; H, 6.54; N, 3.50

Example 2-8 Preparation of a Compound Represented by Chemical Formula 2-008

12.3 g (yield: 65.3%) of a compound represented by the following Chemical Formula 2-008 which was a pale yellow solid was obtained in the same manner as in Example 1.

[Formula 2-008]

Mass: 717

Elemental Analysis: C, 90.47; H, 5.62; N, 3.91

Example 2-9 Preparation of a Compound Represented by Chemical Formula 2-009

In the same manner as in Example 1, 12.3 g (yield: 62.7%) of a compound represented by the following Chemical Formula 2-009, which was a pale yellow solid, was obtained (In Chemical Formula 2-009, Me is a methyl group).

[Formula 2-009]

Mass: 749

Elemental Analysis: C, 86.60; H, 5. 38; N, 3.74; O, 4.27

Example 2-10 Preparation of a Compound Represented by Chemical Formula 2-010

11.9 g (yield: 65.6%) of the compound represented by the following Chemical Formula 2-010 as a pale yellow solid was obtained in the same manner as in Example 1.

[Formula 2-010]

Mass: 689

Elemental Analysis: C, 90.67; H, 5. 27; N, 4.07

Example 2-11 Preparation of a Compound Represented by Chemical Formula 2-011

In the same manner as in Example 1, 8.5 g (yield: 51.4%) of a compound represented by Chemical Formula 2-011, which was a pale yellow solid, was obtained.

[Formula 2-011]

Mass: 627

Elemental Analysis: C, 90.06; H, 5.47; N, 4.47

Example 2-12 Preparation of a Compound Represented by Chemical Formula 2-012

10.7 g (yield: 59.1%) of the compound represented by the following Chemical Formula 2-012 was obtained as a pale yellow solid.

[Formula 2-012]

Mass: 690

Elemental Analysis: C, 90.54; H, 5.11; N, 2.03; O, 2.32

Example 2-13 Preparation of a compound represented by Chemical Formula 2-013

7.4 g (yield: 40.8%) of the compound represented by the following Chemical Formula 2-013 was obtained as a pale yellow solid by the same method as in Example 1.

[Formula 2-013]

Mass: 690

Elemental Analysis: C, 90.54; H, 5.11; N, 2.03; O, 2.32

Example 2-14 Preparation of a Compound Represented by Chemical Formula 2-014

11.7 g (yield: 63.5%) of a compound represented by the following Chemical Formula 2-014 was obtained as a pale yellow solid by the same method as in Example 1.

[Formula 2-014]

Mass: 706

Elemental Analysis: C, 88.48; H, 5.00; N, 1.98; S, 4.54

Example 2-15 Preparation of a Compound Represented by Chemical Formula 2-015

13.1 g (yield: 70.2%) of a compound represented by the following Chemical Formula 2-015 as a pale yellow solid was obtained in the same manner as in Example 1.

[Formula 2-015]

Mass: 706

Elemental Analysis: C, 88.48; H, 5.00; N, 1.98; S, 4.54

Example 2-16 Preparation of a Compound Represented by Chemical Formula 2-016

11.9 g (yield: 55.7%) of the compound represented by the following Chemical Formula 2-016 which was a pale yellow solid were obtained in the same manner as in Example 1.

[Formula 2-016]

Mass: 813

Elemental Analysis: C, 91.60; H, 4.96; N, 3.45

Example 3-1 Preparation of a Compound Represented by Chemical Formula 3-001

Instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, 31.8 g of 2,5-dibromopyridine was used, and 35.8 g of phenanthren-9-ylboronic acid was used instead of 25.2 g of 4-chlorophenylboronic acid to obtain a compound. See Scheme 1-14), except that the obtained compound was used in place of the compound represented by Chemical Formula 1-13 used in Synthesis Example 1-8, 15.6 g (yield: 75.3%) of a compound represented by the following Chemical Formula 3-001 was obtained as a yellow solid.

Scheme 1-14

[Formula 3-001]

Mass: 789

Elemental Analysis: C, 91.34; H, 5.11; N, 3.55

Example 3-2 Preparation of a Compound Represented by Chemical Formula 3-002

31.8 g of 2,6-dibromopyridine was used instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, and 35.8 g of phenanthren-9-ylboronic acid was used instead of 25.2 g of 4-chlorophenylboronic acid. Except for using in place of the compound represented by the formula (1-13) used in Synthesis Example 1-8, the compound represented by the following formula 3-002 which is a pale yellow solid in the same manner as in Example 1-1 12.3 g (yield: 59.3%) were obtained.

[Formula 3-002]

Mass: 789

Elemental Analysis: C, 91.34; H, 5.11; N, 3.55

Example 3-3 Preparation of a Compound Represented by Chemical Formula 3-003

31.8 g of 2,5-dibromopyridine was used instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, and 43.9 g of triphenylen-2-ylboronic acid was used instead of 25.2 g of 4-chlorophenylboronic acid. Except for using instead of the compound represented by the formula (1) -13 used in Synthesis Example 1-8, the compound represented by the following formula 3-003 which is a pale yellow solid in the same manner as in Example 1-1 10.9 g (yield: 49.6%) was obtained.

[Formula 3-003]

Mass: 838,

Elemental Analysis: C, 91.62; H, 5.05; N, 3.34

Example 3-4 Preparation of a Compound Represented by Chemical Formula 3-004

31.8 g of 2,6-dibromopyridine was used instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, and 43.9 g of triphenylen-2-ylboronic acid was used instead of 25.2 g of 4-chlorophenylboronic acid. Except for using in place of the compound represented by the formula (1-13) used in Synthesis Example 1-8, the compound represented by the following formula 3-004 as a pale yellow solid in the same manner as in Example 1-1 11.9 g (yield: 54.2%) were obtained.

[Formula 3-004]

Mass: 838,

Elemental Analysis: C, 91.62; H, 5.05; N, 3.34

Example 3-5 Preparation of Compound Represented by Formula 3-001

Instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, 42.3 g of 1,3,5-tribromobenzene was used, and 87 mL of 2- (tributylstannyl) pyridine was used instead of 25.2 g of 4-chlorophenylboronic acid. To tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] using 9.4 g instead of 4.7 g, the compound obtained without adding 300 mL of 2 N potassium carbonate was used in Synthesis Example 1-8. 12.7 g of a compound represented by the following formula 3-005 as a pale yellow solid, except that the compound represented by the formula 1-13 was used instead of the compound represented by the formula 1-13 (yield: 63.1%) Got.

[Formula 3-005]

Exact Mass: 766,

Elemental Analysis: C, 89.38; H, 5.13; N, 5.49

Example 3-6 Preparation of a Compound Represented by Chemical Formula 3-006

Instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, 38 g of 1-bromo-4-iodobenzene was used, and 23.2 g of 3-quinolineboronic acid was used instead of 25.2 g of 4-chlorophenylboronic acid. Except for using in place of the compound represented by the formula (1-13) used in Synthesis Example 1-8, the compound represented by the following formula 3-006 which is a pale yellow solid in the same manner as in Example 1-1 13.3 g (yield: 68.2%) were obtained.

[Formula 3-006]

Mass: 739

Elemental Analysis: C, 91.03; H, 5.18; N, 3.79

Example 3-7 Preparation of a Compound Represented by Chemical Formula 3-007

Instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, 38 g of 1-bromo-4-iodobenzene was used and 23.2 g of 8-quinolineboronic acid was used instead of 25.2 g of 4-chlorophenylboronic acid. A compound represented by the following Chemical Formula 3-007, which was a pale yellow solid, carried out in the same manner as Example 1-1, except that the compound represented by Chemical Formula 1-13 used in Synthesis Example 1-8 was used. 15.1 g (yield 77.4%) were obtained.

[Formula 3-007]

Mass: 739

Elemental Analysis: C, 91.03; H, 5.18; N, 3.79

Example 3-8 Preparation of a Compound Represented by Chemical Formula 3-008

Instead of 13 mL of 2-bromopyridine used in Synthesis Example 1-7, 38 g of 1-bromo-4-iodobenzene was used, and 23.2 g of 4-isoquinolineboronic acid was used instead of 25.2 g of 4-chlorophenylboronic acid. Except for using in place of the compound represented by the formula (1-13) used in Synthesis Example 1-8, the compound represented by the following formula 3-008 which is a pale yellow solid in the same manner as in Example 1-1 13.5 g (yield: 69.2%) were obtained.

[Formula 3-008]

Mass: 739

Elemental Analysis: C, 91.03; H, 5.18; N, 3.79

Example 3-9 Preparation of a Compound Represented by Chemical Formula 3-009

The compound obtained using 9.3 g of 2,2'-bipyridin-5-ylboronic acid instead of 13.1 g of compound 1-9 used in Synthesis Example 1-9 was obtained by Chemical Formula 1-10 used in Synthesis Example 1-10. Except for using it instead of the compound shown, 8.5 g (yield: 47.1%) of the compound represented by following formula 3-009 which was a pale yellow solid was obtained by the same method as Example 1-1.

[Formula 3-009]

Mass: 690

Elemental Analysis: C, 88.79; H, 5.11; N, 6.09

Example 3-10 Preparation of a Compound Represented by Chemical Formula 3-010

The compound obtained using 9.3 g of 2,2'-bipyridin-6-ylboronic acid instead of 13.1 g of compound 1-9 used in Synthesis Example 1-9 was obtained by Chemical Formula 1-10 used in Synthesis Example 1-10. 9.6 g (yield: 53.2%) of the compound represented by the following Chemical Formula 3-010 was obtained as a pale yellow solid, except that it was used instead of the compound represented.

[Formula 3-010]

Mass: 690

Elemental Analysis: C, 88.79; H, 5.11; N, 6.09

Example 3-11 Preparation of a Compound Represented by Chemical Formula 3-011

The compound obtained using 9.3 g of 2,2'-bipyridin-5-ylboronic acid instead of 13.1 g of compound 1-9 used in Synthesis Example 1-9 was obtained by Chemical Formula 1-10 used in Synthesis Example 1-10. A compound obtained by using instead of the compound represented and by using 81.2 g of 1-bromo-3-iodobenzene instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, was prepared in Synthesis Example 1-12 12.2 g of a compound represented by the following Chemical Formula 3-011, which was a pale yellow solid, except that the compound represented by Chemical Formula 1-14 was used instead of the compound represented by Chemical Formula 1-14. 67.6%).

[Formula 3-011]

Mass: 690

Elemental Analysis: C, 88.79; H, 5.11; N, 6.09

Example 3-12 Preparation of a Compound Represented by Chemical Formula 3-012

The compound obtained using 9.3 g of 2,2'-bipyridin-6-ylboronic acid instead of 13.1 g of compound 1-9 used in Synthesis Example 1-9 was obtained by Chemical Formula 1-10 used in Synthesis Example 1-10. A compound obtained by using instead of the compound represented and by using 81.2 g of 1-bromo-3-iodobenzene instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11, was prepared in Synthesis Example 1-12 11.6 g of a compound represented by the following Chemical Formula 3-012, which is a pale yellow solid, except that the compound represented by Chemical Formula 1-14 was used instead of the compound represented by Chemical Formula 1-14. 64.3%).

[Formula 3-012]

Mass: 690

Elemental Analysis: C, 88.79; H, 5.11; N, 6.09

<Example 3-13> Preparation of a compound represented by Chemical Formula 3-013

Compound obtained by using 38.9 g of pyrene-1,6-diyldiboronic acid instead of 25.2 g of 4-chlorophenylboronic acid used in Synthesis Example 1-7 was represented by Chemical Formula 1-9 used in Synthesis Example 1-9 Except for using it, the same procedure as in Example 1-1 was carried out to obtain 10.8 g (yield: 50.5%) of a compound represented by the following Chemical Formula 3-013 as a pale yellow solid.

[Formula 3-013]

Mass: 813

Elemental Analysis: C, 91.60; H, 4.96; N, 3.45

Example 3-14 Preparation of a Compound Represented by Chemical Formula 3-014

Compound obtained by using 38.9 g of pyrene-1,6-diyldiboronic acid instead of 25.2 g of 4-chlorophenylboronic acid used in Synthesis Example 1-7 was represented by Chemical Formula 1-9 used in Synthesis Example 1-9 Compounds obtained by using instead of 81.2 g of 1-bromo-4-iodobenzene instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11 were used in Synthesis Example 1-12. 9.1 g (yield: 42.6%) of a compound represented by the following Chemical Formula 3-014 as a pale yellow solid, except that the compound represented by Chemical Formula 1-14 was used instead of the compound represented by Chemical Formula 1-14. Got.

[Formula 3-014]

Mass: 813

Elemental Analysis: C, 91.60; H, 4.96; N, 3.45

Example 4-1 Preparation of a Compound Represented by Chemical Formula 4-001

Synthesis Example 4-1 Preparation of the compound represented by Chemical Formula 2-1

[Reaction Scheme 2-1]

30 g of the compound represented by Chemical Formula 1-7 obtained in Synthesis Example 1-5 was added to 500 mL of dimethylformamide (DMF), and the resulting solution was completely dissolved by heating to 60 ° C., followed by N-bromosuccinimide ( 41.7 g of NBS) were added and stirred for one day. The reaction was poured into 1 L of water to obtain a solid, and the resulting solid was filtered. The filtered solid was sufficiently washed with water and methanol and dried under reduced pressure to obtain 38.1 g (yield: 82.7%) of the compound represented by the formula (2-1) as a pale yellow solid.

Synthesis Example 4-2 Preparation of the Compound Represented by Chemical Formula 2-2

[Reaction Scheme 2-2]

66 g of 4-bromobenzaldehyde and N-phenyl-1,2-phenylene-diamine 65.7 were reacted according to Scheme 2-2 to 4- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid , 19.5 g of the compound represented by the formula (2-2) were obtained.

Synthesis Example 4-3 Preparation of Compound Represented by Chemical Formula 2-3

Scheme 2-3

28 g of the compound represented by Formula 2-1 obtained in Synthesis Example 2-1 and 19.5 g of the compound represented by Formula 2-2 were dissolved in 600 mL of toluene and 200 mL of ethyl alcohol (EtOH), followed by 50 g of tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] 2.1 g, 6 N sodium carbonate (Na ₂ CO ₃ ) was added to the reaction product. The reaction was stirred under reflux for 13 hours and then cooled to room temperature to separate the organic layer and the water layer. The organic layer separated from the water layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The concentrate was then purified by column chromatography (n-hexane; n-hexane / ethyl acetate = 8/1 to 2/1), then dissolved in dichloromethane, a pale yellow solid, and then solidified in methanol. To give 24.6 g (yield: 61.8%) of the compound represented by Chemical Formula 2-3 as a light yellow solid.

Synthesis Example 4-4 Preparation of the Compound Represented by Chemical Formula 4-001

Scheme 2-4

24.5 g of the compound represented by Formula 2-3 obtained in Synthesis Example 4-3 and 16.9 g represented by Formula 1-12 obtained in Synthesis Example 1-12 were dissolved in 300 mL of toluene, followed by tetrakis (triphenylphosphine ) palladium (0) [Pd (PPh ₃ ) ₄ ] 2 g, 100 mL of 2 N sodium carbonate, and 1.7 mL of aliquat 336 were added followed by reflux stirring for 2 days. The reactant cooled to room temperature was separated into an organic layer and a water layer, and then the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The concentrate was purified via column chromatography (n-hexane; n-hexane / dichloromethane = 9/1; n-hexane / ethyl acetate = 6/1), then precipitated from n-hexane and filtered to give a pale yellow solid. 22.1 g (yield: 72.0%) of a compound represented by the above formula 4-001 was obtained.

Mass: 804

Elemental Analysis: C, 89.63; H, 5.14; N, 5.23

Example 4-2 Preparation of a Compound Represented by Chemical Formula 4-002

In the same manner as in Synthesis Example 1-11, except that 81.2 g of 1-bromo-3-iodobenzene was used instead of 81.2 g of 1-bromo-4-iodobenzene used in Synthesis Example 1-11. Compound A was obtained. Thereafter, except that Compound A was used instead of the compound represented by Formula 1-14 used in Synthesis Example 1-12, Compound B was obtained by the same method as Synthesis Example 1-12, and then A compound 19.6 represented by the following Chemical Formula 4-002 was carried out in the same manner as in Synthetic Example 4-4, except that Compound B was used instead of the compound represented by Chemical Formula 1-12 used in Synthesis Example 4-4. g (yield: 63.8%) was obtained.

[Formula 4-002]

Mass: 804

Elemental Analysis: C, 89.63; H, 5.14; N, 5.23

Example 4-3 Preparation of a Compound Represented by Chemical Formula 4-003

In the same manner as in Synthesis Example 1-12, except that 33.4 g of 3-bromo-9-phenyl-9H-carbazole was used instead of the compound represented by Formula 1-14 used in Synthesis Example 1-12. Except for using the compound obtained by performing in place of the compound represented by Formula 1-12 used in Synthesis Example 4-4, the compound represented by the following formula 4-003 23.9 g (yield: 77.9%) of compound was obtained.

[Formula 4-003]

Mass: 804

Elemental Analysis: C, 89.63; H, 5.14; N, 5.23

Example 4-4 Preparation of a Compound Represented by Chemical Formula 4-004

Synthesis Example 1- except that 49.2 g of 9- (4-bromophenyl) -3,6-diphenyl-9H-carbazole was used instead of the compound represented by Formula 1-14 used in Synthesis Example 1-12. A compound obtained by performing the same method as 12 was used in the same manner as in Synthesis Example 4-4, except that the compound represented by Formula 1-12 used in Synthesis Example 4-4 was used. 18.9 g (yield: 51.8%) of the compound represented by -004 was obtained.

[Formula 4-004]

Mass: 956

Elemental Analysis: C, 90.44; H, 5.17; N, 4.39

Example 4-5 Preparation of a Compound Represented by Chemical Formula 4-005

Except for using 19.5 g of 3- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid instead of 19.5 g of the compound represented by Formula 2-2 used in Synthesis Example 4-3 Is the same as in Synthesis Example 4-4 except for using the compound obtained by performing the same manner as in Synthesis Example 4-3 instead of the compound represented by Formula 2-3 used in Synthesis Example 4-4. 20.6 g (yield: 67.1%) of the compound represented by Chemical Formula 4-005 was obtained.

[Formula 4-005]

Mass: 804

Elemental Analysis: C, 89.63; H, 5.14; N, 5.23

Example 4-6 Preparation of a Compound Represented by Chemical Formula 4-006

Except for using 19.5 g of 3- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid instead of 19.5 g of the compound represented by Formula 2-2 used in Synthesis Example 4-3 Is used in place of the compound represented by Chemical Formula 2-3 used in Synthesis Example 4-4, and the compound obtained in the same manner as in Synthesis Example 4-3, and 1- used in Synthesis Example 1-11. A compound obtained by the same method as in Synthesis Example 1-11, except that 81.2 g of 1-bromo-3-iodobenzene was used instead of 81.2 g of bromo-4-iodobenzene, was used instead of the compound represented by Formula 1-12. Except for using, the same procedure as in Synthesis Example 4-4 was carried out to obtain 23.5 g (yield: 76.5%) of the compound represented by the following Chemical Formula 4-006.

[Formula 4-006]

Mass: 804

Elemental Analysis: C, 89.63; H, 5.14; N, 5.23

Example 4-7 Preparation of a Compound Represented by Chemical Formula 4-007

Except for using 19.5 g of 3- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid instead of the compound represented by Formula 2-2 used in Synthesis Example 4-3, Using the compound obtained in the same manner as in Synthesis Example 4-3 instead of the compound represented by Formula 2-3 used in Synthesis Example 4-4, and in Formula 1-14 used in Synthesis Example 1-12 A compound obtained by the same method as Synthesis Example 1-12 was used in Synthesis Example 4-4, except that 33.4 g of 3-bromo-9-phenyl-9H-carbazole was used instead of the compound represented by 24.8 g (yield: 80.6%) of the compound represented by Chemical Formula 4-007 was obtained in the same manner as in Synthesis Example 4-4, except that the compound represented by Chemical Formula 1-12 was used instead of the compound represented by Chemical Formula 1-12.

[Formula 4-007]

Mass: 804

Elemental Analysis: C, 89.63; H, 5.14; N, 5.23

Example 4-8 Preparation of a Compound Represented by Chemical Formula 4-008

Except for using 19.5 g of 3- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid instead of the compound represented by Formula 2-2 used in Synthesis Example 4-3, Using the compound obtained in the same manner as in Synthesis Example 4-3 instead of the compound represented by Formula 2-3 used in Synthesis Example 4-4, and in Formula 1-14 used in Synthesis Example 1-12 Synthesis of the compound obtained in the same manner as in Synthesis Example 1-12, except that 49.2 g of 9- (4-bromophenyl) -3,6-diphenyl-9H-carbazole was used instead of the compound represented by Except for using instead of the compound represented by the formula (1-12) used in Example 4-4, in the same manner as in Synthesis Example 4-4 17.7 g of a compound represented by the following formula 4-008 (yield: 48.5 %) Was obtained.

[Formula 4-008]

Mass: 956

Elemental Analysis: C, 90.44; H, 5.17; N, 4.39

Example 4-9 Preparation of a Compound Represented by Chemical Formula 4-009

Except for using 27.2 g of 4- (3,6-diphenyl-9H-carbazol-9-yl) phenylboronic acid instead of the compound represented by Formula 2-2 used in Synthesis Example 4-3, Using the compound obtained in the same manner as in Example 4-3 instead of the compound represented by Formula 2-3 used in Synthesis Example 4-4, and represented by Formula 1-12 used in Synthesis Example 4-4 Except for using 3- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid instead of the compound to be the same as in Synthesis Example 4-4 to the general formula 4-009 14.8 g (yield: 40.5%) of the compound was obtained.

[Formula 4-009]

Mass: 956

Elemental Analysis: C, 90.44; H, 5.17; N, 4.39

Example 4-10 Preparation of a Compound Represented by Chemical Formula 4-010

Except for using 19.5 g of 3- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenylboronic acid instead of the compound represented by Formula 2-2 used in Synthesis Example 4-3, Using the compound obtained in the same manner as in Synthesis Example 4-3 instead of the compound represented by Formula 2-3 used in Synthesis Example 4-4, and in Formula 1-12 used in Synthesis Example 4-4 Except for using 3- (dibenzo [b, d] thiophen-4-yl) phenylboronic acid instead of the compound represented by: 18.3 g (yield: 36.0%) of compound was obtained.

[Formula 4-010]

Mass: 821,

Elemental Analysis: C, 87.77; H, 4.91; N, 3.41; S, 3.91

Example 5-1 Fabrication of Organic Light-Emitting Device

An organic light emitting device was manufactured by the following method.

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the washing of distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.

The product name DS-205 (Doosan Co., Ltd.) was vacuum deposited to a thickness of 800 kPa on the prepared ITO transparent electrode (anode) to form a hole injection layer. Thereafter, a hole transporting material was formed on the hole injection layer by vacuum evaporation of NPB ( N , N- di (naphthalene-1-yl) -N , N- diphenylbenzidine) having a thickness of 150 kPa.

On top of that, ADN (9,10-di (naphthalen-2-yl) anthracene) is used as a host material, and a dopant material is doped with 5% of DS-405 (Doosan) to form a light emitting layer by depositing 300 ㅕ thick. It was. The compound represented by Chemical Formula 1-001 synthesized in Example 1-1, which is an electron transporting material, was deposited on the emission layer to a thickness of 250 GPa to form an electron transporting layer. Thereafter, LiF, which is an electron injection material, was deposited on the electron transport layer to a thickness of 10 ㅕ to form an electron injection layer, and then aluminum (Al) was deposited on the thickness of 2,000 ㅕ to form a cathode.

<Example 5-2> to <Example 5-15>

In the formation of the electron transport layer, instead of the compound represented by the formula (1-001) (Example 1-1) as the electron transport material, the compound represented by the formula (1-002) (Example 1-2), represented by the formula (1-003) Compound (Example 1-3), compound represented by Formula 1-008 (Example 1-8), compound represented by Formula 1-010 (Example 1-10), compound represented by Formula 2-001 ( Example 2-1), a compound represented by Formula 2-002 (Example 2-1), a compound represented by Formula 2-013 (Example 2-13), a compound represented by Formula 2-016 (Example 2-16), the compound represented by the formula 3-001 (Example 3-1), the compound represented by the formula 3-004 (Example 3-4), the compound represented by the formula 4-002 (Example 4- 2), the compound represented by the general formula 4-007 (Example 4-7), the compound represented by the general formula 4-009 (Example 4-9), and the compound represented by the general formula 4-010 (Example 4-10) Except that each is used, An organic light emitting device was manufactured in the same manner as in Example 5-1.

Comparative Example 1 Fabrication of Organic Light-Emitting Element

Example 5-1 was the same except that Alq3 (aluminum tris (8-hydroxyquinoline)) was used instead of the compound represented by Formula 1-001 (Example 1-1) as the electron transporting material in the formation of the electron transporting layer. An organic light emitting device was manufactured by the method.

<Experimental Example>

The light emitting efficiency at the current density of 10 mA / cm 2 was measured for the organic light emitting diodes manufactured in Examples 5-1 to 5-15 and Comparative Example 1, and the results are shown in Table 1 below.

division Electron transport material The driving voltage (V) Luminous Efficiency (cd / A) Example 5-1 Formula 1-001 4.9 8.3 Example 5-2 Formula 1-002 4.6 6.4 Example 5-3 Formula 1-003 5.5 6.8 Examples 5-4 Formula 1-008 5.2 7.1 Example 5-5 Formula 1-010 5.2 7.5 Example 5-6 Formula 2-001 4.8 6.8 Example 5-7 Formula 2-002 5.1 6.7 Examples 5-8 Formula 2-013 5.6 6.5 Example 5-9 Formula 2-016 4.9 6.6 Examples 5-10 Formula 3-001 5.4 6.6 Example 5-11 Formula 3-004 5.3 7.1 Example 5-12 Formula 4-002 4.8 6.6 Examples 5-13 Formula 4-007 4.6 7.8 Example 5-14 Formula 4-009 5.1 5.8 Example 5-15 Formula 4-010 5.2 7.9 Comparative Example 1 Alq3 5.7 6

As can be seen from Table 1, the organic light emitting device (Examples 5-1 to 5-15) using the compound according to the present invention as an electron transporting material is an organic light emitting device using a conventional Alq3 (Comparative Example 1) The driving voltage and luminous efficiency were much better, and it was confirmed that the high efficiency blue device can be driven.

Example 6-1 Fabrication of Organic Light-Emitting Device

An organic light emitting device was manufactured by the following method.

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the washing of distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.

The product name DS-205 (Doosan Co., Ltd.) was vacuum-deposited to a thickness of 800 위에 on the prepared ITO transparent electrode (anode) to form a hole injection layer, and NPB ( N , N -di (naphthalene-1), a hole transport material thereon -yl) -N and N -diphenylbenzidine) were deposited to a thickness of 150 mm 3 to form a hole transport layer.

Using the compound represented by Chemical Formula 1-001 synthesized in Example 1-1 as a phosphorescent host material thereon, 10% of Ir (ppy) ₃ as a dopant material was deposited to 300 ㅕ thickness to form a light emitting layer. . BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was deposited on the emission layer to a thickness of 100 ㅕ to form a hole blocking layer, and Alq3 (aluminum tris) as an electron transporting material. (8-hydroxyquinoline)) was deposited to a thickness of 200 mm 3 to form an electron transport layer. LiF, an electron injection material, was deposited on the electron transport layer to a thickness of 10 kW to form an electron injection layer, and then Al was deposited on the electron transport layer to a thickness of 2,000 kW to form a cathode.

Example 6-2 Fabrication of Organic Light-Emitting Device

Except for using the compound represented by Formula 1-002 (Example 1-2) instead of the compound represented by Formula 1-001 (Example 1-1) as the phosphorescent host material in forming the emission layer An organic light emitting device was manufactured in the same manner as in 6-1.

Comparative Example 2 Fabrication of Organic Light-Emitting Element

Except for using CBP (4,4'-di (9H-carbazol-9-yl) biphenyl) instead of the compound represented by the formula (1-001) as a phosphorescent host material in the formation of the light emitting layer (Example 1-1) Was manufactured in the same manner as in Example 6-1.

<Experimental Example 2>

The light emission efficiency at the current density of 10 mA / cm 2 was measured for the organic light emitting diodes manufactured in Examples 6-1 and 6-2 and Comparative Example 1, and the results are shown in Table 2 below.

division Phosphorescent host material The driving voltage (V) Luminous Efficiency (cd / A) Example 6-1 Formula 1-001 6.2 42.1 Example 6-2 Formula 1-002 5.9 39.7 Comparative Example 2 CBP 6.9 35.2

As can be seen in Table 2, the organic light emitting device (Example 6-1 and Example 6-2) using the compound according to the present invention as a host material than the organic light emitting device (Comparative Example 2) using the conventional CBP It was confirmed that the driving voltage and the luminous efficiency were excellent.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, and that various changes and modifications may be made without departing from the scope of the invention. It is natural to belong.

Claims (9)

Formulas 1-001 to 1-003, 1-008, 1-010, 2-001, 2-002, 2-013, 2-016, 3-001, 3-004, 4-002, 4-007, Hybrid compound represented by any one selected from 4-009 and 4-010:
[Formula 1-001]

;
[Formula 1-002]

;
[Formula 1-003]

;
[Formula 1-008]

;
[Formula 1-010]

;
[Formula 2-001]

;
[Formula 2-002]

;
[Formula 2-013]

;
[Formula 2-016]

;
[Formula 3-001]

;
[Formula 3-004]

;
[Formula 4-002]

;
[Formula 4-007]

;
[Formula 4-009]

; And
[Formula 4-010]

. Hybrid compound represented by the formula (2):
(2)

In Formula 2,
X is selected from the group consisting of CR ⁶ R ⁷ , NR ⁶ , O, S, S (= 0), S (= 0) ₂ , and SiR ⁶ R ⁷ ,
Wherein R ¹ to R ⁷ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ Cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ arylalkyl group, C ₁ ~ C ₄₀ alkyloxy group, C ₅ ~ C ₄₀ aryloxy group, C ₅ ~ C ₄₀ aryl Group and C ₅ ~ C ₄₀ heteroaryl group; Or a group forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group,
Wherein R ¹ to R ⁷ wherein C alkyl group of ₁ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, C of ₃ ~ C ₄₀ heteroaryl A cycloalkyl group, a C ₆ -C ₄₀ arylalkyl group, a C ₁ -C ₄₀ alkyloxy group, a C ₅ -C ₄₀ aryloxy group, a C ₅ -C ₄₀ aryl group and a C ₅ -C ₄₀ heteroaryl group Deuterium, halogen, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ amino group, C ₃ ~ Unsubstituted or substituted with one or more selected from the group consisting of a C ₄₀ cycloalkyl group, a C ₃ -C ₄₀ heterocycloalkyl group, a C ₆ -C ₄₀ aryl group, and a C ₅ -C ₄₀ heteroaryl group,
Wherein R ¹ to R ⁷ in R ¹ has the formula 18, 22, 23, 31, and the heteroaryl group represented by any one selected from the group consisting of 32 and 34 ~ 38, R ² is the formula 3 to 7, and 13 Heteroaryl group represented by any one selected from the group consisting of to 16.
(3)

;
[Chemical Formula 4]

;
[Chemical Formula 5]

;
[Chemical Formula 6]

;
(7)

;
[Chemical Formula 13]

;
[Chemical Formula 14]

;
[Chemical Formula 15]

;
[Chemical Formula 16]

;
[Chemical Formula 18]

;
[Chemical Formula 22]

;
(23)

;
(31)

;
(32)

;
(34)

;
(35)

;
(36)

;
(37)

;
(38)

(In Chemical Formulas 3 to 7, 13 to 16, 18, 22, 23, 31, 32, 34 to 38,
L, m, n, o and p are each independently integers ranging from 1 to 5;
A plurality of Q ¹ is the same or different from each other, a plurality of Q ² is the same or different from each other, a plurality of Q ³ is the same or different from each other, a plurality of Q ⁴ is the same or different from each other, a plurality of Q ⁵ is each other Same or different;
Q ¹ , Q ² , Q ³ , Q ⁴ and Q ⁵ are the same as or different from each other, and are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ Alkenyl group, C ₁ to C ₄₀ alkoxy group, C ₁ to C ₄₀ amino group, C ₃ to C ₄₀ cycloalkyl group, C ₃ to C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and C ₅ Or a heteroaryl group of -C ₄₀ ; Or a group forming a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group, or a linking group,
Wherein at least one carbon selected from carbon or nitrogen which may be combined with Q ₁ , Q ₂ , Q ₃ , Q ₄ or Q _{5 in} Formulas 3 to 7, 13 to 16, 18, 22, 23, 31, 32, 34 to 38 Or nitrogen is connected to one carbon selected from carbons bondable to R ¹ or R ² in formula (2), in which case it is linked to carbon of formula (2) in formulas 3 to 7, 13 to 16, 18, 22, 23, 31 , 32, 34 to 38 of the carbon or nitrogen does not have a substituent, the formula 3 of the formula 3 to 7, 13 to 16, 18, 22, 23, 31, 32, 34 to 38 of the carbon or nitrogen Carbon has no substituents). delete delete An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,
At least one of the one or more organic material layers comprises the hybrid compound according to claim 1 or 2. The organic electroluminescent device according to claim 5, wherein the organic material layer including the hybrid compound is an electron transport layer, a light emitting layer, or both. The organic electroluminescent device according to claim 6, wherein the hybrid compound is used as a host in the light emitting layer. The organic electroluminescent device according to claim 6, wherein the hybrid compound is used as a phosphorescent host in the light emitting layer. delete