KR20130010633A - Anthracene derivative and organic electroluminescent device using the same - Google Patents

Abstract

PURPOSE: A compound is provided to have excellent electron transferring performance, hole transferring performance, and a light emitting performance, thereby providing an organic electroluminescence device with improved light emitting efficiency, thermal stability, driving voltage and lifetime. CONSTITUTION: A compound is indicated in chemical formula 1. In chemical formula 1, each of X1-X6 is hydrogen, deuterium or halogen, each of R1-R4 is selected from hydrogen, deuterium, a C1-40 alkyl group, a C2-40 alkenyl group, a C5-40 aryl group, a C5-40 heteroaryl group, a C5-40 aryloxy group, a C1-40 alkyloxy group, an amino group, a C3-40 cycloalkyl group, and a C3-40 heterocycloalkyl group, or a group which can form a fused aliphatic ring, aromatic ring, heteroaliphatic ring or heteroaromatic ring with a neighboring group.

Description

Anthracene derivative and organic electroluminescent device using the same {ANTHRACENE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel anthracene derivative having excellent electron transporting ability, hole transporting ability and light emitting ability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, and lifetime by including the same in at least one organic material layer. .

An organic electronic device is an electronic device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material. Organic electronic devices can be divided into two types according to the principle of operation. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form. The second type is an electronic device that injects holes and / or electrons into an organic semiconductor material layer that interfaces with the electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of organic electronic devices include organic light emitting devices, organic solar cells, organic photoconductor (OPC) drums, and organic transistors, all of which are electron / hole injection materials, electron / hole extraction materials, and electron / hole transport materials for driving the devices. Materials or luminescent materials are required. Hereinafter, the organic light emitting device will be described in detail. However, in other organic electronic devices, an electron / hole injection material, an electron / hole extraction material, an electron / hole transport material, or a light emitting material may all operate on a similar principle.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic layer between them. The organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML), electron transport layer (ETL) ), An electron injection layer (EIL), and the like.

When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected into the anode, electrons are injected into the organic layer, electrons are injected into the organic layer, excitons are formed when injected holes and electrons meet, When it falls to a state, it becomes a light.

The material used as the organic material layer in the organic light emitting device may be classified into a light emitting material, a charge transport material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

The light emitting material 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 present 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 produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order to fully exhibit the excellent characteristics of the above-described organic light emitting device, the material constituting the organic material layer in the device, that is, the hole injection material, the hole transport material, the light emitting material, the electron transport material, the electron injection material, etc. is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been sufficiently achieved, and therefore, the development of new materials is continuously required.

Republic of Korea Patent Publication No. 10-2011-0024695 (2011. 03. 09)

An object of the present invention is to include an anthracene derivative compound having excellent electron transporting ability, hole transporting ability and light emitting ability, and organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifetime by including the same in at least one organic material layer. To provide.

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

Where

X ₁ to X ₆ Are each independently hydrogen, deuterium or halogen;

R ₁ to R ₄ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ of the Aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ Heterocycloalkyl group; A group which forms 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 ₄ One or more of the each independently represent a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C aryl group of ₅ ~ C _40, C ₅ ~ heteroaryl of C ₄₀ A group, a C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, an amino group, a C ₃ to C ₄₀ cycloalkyl group and a C ₃ to C ₄₀ heterocycloalkyl group; A group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group.

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 organic layer is It provides an organic electroluminescent device comprising a compound represented by the formula (1).

The compound represented by Formula 1 of the present invention has excellent electron transporting ability, hole transporting ability, and light emitting ability, and the organic electroluminescent device including the same can be greatly improved in terms of light emitting performance, driving voltage, lifetime, and the like. It can be effectively applied to a color display panel and the like.

The compound represented by Formula 1 of the present invention is an anthracene derivative in which one or more substituents are optionally present at positions 1,4,5,8 of the anthracene core having excellent device properties. For example, it is a compound in which aryl, heteroaryl, an alkyl group, etc. are substituted in the 1, 1, 4, 1, 5, 1, 8 positions of anthracene.

In the compound of formula 1 of the present invention, X ₁ to X ₆ Are each independently hydrogen, deuterium or halogen.

R ₁ to R ₄ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ of the Aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ Or a group which forms 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 ₄ At least one is a substituent other than hydrogen or deuterium, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₅ ~ C ₄₀ Aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ heterocycloalkyl group Selected from; A group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group.

Preferably, one functional group selected from R ₁ to R ₄ may be a substituent other than hydrogen or deuterium, two functional groups selected from R ₁ to R ₄ may be a substituent other than hydrogen or deuterium, and R ₁ to R ₄ The three functional groups selected from among them may be substituents other than hydrogen or deuterium, and all of R ₁ to R ₄ may be substituents other than hydrogen or deuterium. Here, substituents other than hydrogen or deuterium may be selected from a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₅ to C ₄₀ aryl group, and C ₅ to C ₄₀ Heteroaryl group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ heterocycloalkyl group or , the adjacent groups condensed (fused) an aliphatic ring, a condensed aromatic ring, a condensed may date to form a heterocyclic aliphatic ring or a fused heteroaromatic ring, preferably a C ₅ ~ C ₄₀ aryl group, C ₅ ~ heteroaryl of C ₄₀ It may be an aryl group, a group which forms a fused aromatic ring or a condensed heteroaromatic ring with an adjacent group.

R ₁ to the R ₄ a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ of the aryl group, C ₅ ~ C ₄₀ heteroaryl group , C ₅ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, amino group, C ₃ to C ₄₀ cycloalkyl group and C ₃ to C ₄₀ heterocycloalkyl group are each independently deuterium, halogen, nitrile Group, nitro group, cyano group, silyl group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, may be substituted with one or more substituents selected from the group consisting of C ₅ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ heteroaryl group for.

In addition, these substituents 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, amino group, C ₃ ~ C ₄₀ Is further substituted with one or more substituents selected from the group consisting of a cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₅ to C ₄₀ aryl group, and a C ₅ to C ₄₀ heteroaryl group; Condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, or condensed heteroaromatic rings can be formed or spiro bonds with adjacent groups.

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.

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 Chemical Formula 1. Provided is a light emitting device. In this case, the compound represented by Formula 1 may include one kind or two or more kinds.

The organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. Preferably, the compound represented by Formula 1 may be included in the organic electroluminescent device as a light emitting layer, a hole transport layer and / or an electron transport layer material. For example, when the organic light emitting device is included as an emission layer material, the organic light emitting device may improve luminous efficiency, brightness, power efficiency, thermal stability, and device life.

For example, a substrate, an anode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode may be sequentially stacked, and the light emitting layer may be represented by Formula 1 according to the present invention. It may include a compound represented by. An electron injection layer may be positioned 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 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 electroluminescent device according to the present invention forms an organic material layer and an electrode 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. It can be manufactured by.

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, 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 examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Reaction Scheme 1]

< Preparation  1> 1- of Scheme 1 iodoanthracene  Produce

<Step 1> 1- iodoanthracene -9,10 (4 aH , 9 aH ) - dione  Produce

47g (210mmol) of 1-aminoanthracene-9,10 (4aH, 9aH) -dione was added to 200 ml of cooled 95% sulfuric acid and left for 30 minutes, and 40g (580mmol) of sodium nitrite was added thereto. After stirring for 3 hours at room temperature, the mixture was poured into 2.5LH ₂ O and stirred for further 30 minutes. The filtered solution was stored and the filtered purple solid was placed in 2.5 LH ₂ O again for 15 minutes. The mixture was filtered again and the previous solution was combined and 100 g of KI was added. The precipitated orange solid was filtered, washed with H ₂ O until sulfuric acid was completely removed, and dried to give 57.9 g (yield 82%) of the title compound.

HRMS [M] ⁺ : 335.

<Step 2> 1- iodoanthracene  Produce

5 g (14.88 mmol) of 1-iodoanthracene-9,10 (4aH, 9aH) -dione obtained in step 1 was added to 50 ml of 2-propanol and 50 ml of tetrahydrofuran and stirred at 0 ° C. After adding 1 g of NaBH _{4, the} mixed solution obtained after 30 minutes was further stirred at room temperature for 30 minutes, and the precipitated solid was filtered by adding H ₂ O to filter 1-iodo-4a, 9,9a, 10-tetrahydroanthracene-9,10- diol was obtained. The solid was added to glacial acetic acid (50 ml) with 3 ml (30.6 mmol) of phenylhydrazine and stirred at 80 to 95 ° C. for 7 hours. The obtained mixed solution was cooled and diluted with H ₂ O, and then filtered to dry the brown solid. The solid was passed through a silica gel using hexane to increase the purity, evaporated, dissolved in THF, and recrystallized with EtOH to give 0.81 g (yield 18%) of the title compound.

HRMS [M] ⁺ : 303

Scheme 2

< Preparation  2> 1,5- in Scheme 2 diiodoanthracene  Produce

<Step 1> 1,5- diaminoanthracene -9,10 (4 aH , 9 aH ) - dione  Produce

The same procedure as in Step 1 of Preparation Example 1 was repeated except that 1,5-diaminoanthracene-9,10 (4aH, 9aH) -dione was used instead of 1-aminoanthracene-9,10 (4aH, 9aH) -dione. 1,5-diaminoanthracene-9,10 (4aH, 9aH) -dione &Lt; / RTI &gt;

HRMS [M] ⁺ : 461

<Step 2> 1,5- diiodoanthracene  Produce

The same procedure as in Step 2 of Preparation Example 1 was repeated except that 1,5-diaminoanthracene-9,10 (4aH, 9aH) -dione was used instead of 1-iodoanthracene-9,10 (4aH, 9aH) -dione. 1,5-diiodoanthracene was obtained.

¹ H NMR (CDCl 3) 7.21 (t, 2H), 8.12 (t, 4H), 8.61 (s, 2H), HRMS [M] ⁺ : 429

Scheme 3

< Preparation  3> 1,8- of Scheme 3 diiodoanthracene  Produce

<Step 1> 1, 8- diiodoanthracene -9,10 (4 aH , 9 aH ) - dione  Produce

11.5 g (41.8 mmol) of 1,8-dichloroanthracene-9,10 (4aH, 9aH) -dione, 25.05 g (167.1 mmol) of sodium iodide, and 0.8 g of copper-bronze were added to 40 ml of nitrobenzene and stirred under reflux for 16 hours. It was. The mixed solution was evaporated and recrystallized with chlorobenzene to give 6.34 g (yield 33%) of the title compound.

HRMS [M] ⁺ : 461

<Step 2> 1,8- diiodoanthracene  Produce

1,8-diiodoanthracene-9,10 (4aH, 9aH) -dione instead of 1-iodoanthracene-9,10 (4aH, 9aH) -dione Except for using the same procedure as in Step 2 of Preparation Example 1 to obtain a 1,8-diiodoanthracene.

[M] ⁺ : 429

[Reaction Scheme 4]

< Preparation  4> 1,4- in Scheme 4 diiodoanthracene  Produce

<Step 1> 1,4- diiodoanthracene -9,10 (4 aH , 9 aH ) - dione  Produce

The same procedure as in Step 1 of Preparation Example 1 was performed except that 1,4-diaminoanthracene-9,10 (4aH, 9aH) -dione was used instead of 1-aminoanthracene-9,10 (4aH, 9aH) -dione. 1,4-diiodoanthracene-9,10 (4aH, 9aH) -dione was obtained.

HRMS [M] ⁺ : 461

<Step 2> 1,4- diiodoanthracene  Produce

The same procedure as in Step 2 of Preparation Example 1 was repeated except that 1,4-diiodoanthracene-9,10 (4aH, 9aH) -dione was used instead of 1-iodoanthracene-9,10 (4aH, 9aH) -dione. 1,4-diiodoanthracene was obtained.

[M] ⁺ : 429

< Synthetic example  1> Compound Mat  Manufacture of 1-1

7 g (23 mmol) of 1-iodoanthracene, 3.4 g (27 mmol) of phenylboronic acid, and 0.8 g (0.69 mmol) of Pd (PPh ₃ ) ₄ obtained in Preparation Example 1 were placed in a flask, and 26 ml of a saturated aqueous solution of 2M K ₂ CO ₃ and 80 ml of toluene were added. After melting, the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite, and then column chromatography was performed to prepare 4.6 g (yield 80%) of compound Mat 1-1 (1-phenylanthracene).

Elemental Analysis: C, 94.45; H, 5.55 / HRMS [M] ⁺ : 253

< Synthetic example  2> compound Mat  Manufacture of 1-5

Compound Mat 1-5 was prepared in the same manner as in Synthesis Example 1 except for using phenanthren-1-yl boronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.88; H, 5.12 / HRMS [M] ⁺ : 353

< Synthetic example  3> Compound Mat  Manufacture of 1-8

Compound Mat 1-8 was prepared in the same manner as in Synthesis Example 1 except for using triphenylen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 95.02; H, 4.98 / HRMS [M] ⁺ : 403

< Synthetic example  4> Compound Mat  Manufacture of 1-10

Compound Mat 1-10 was prepared in the same manner as in Synthesis Example 1 except for using 1H-phenalen-5-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] ⁺ : 341

< Synthetic example  5> Compound Mat  Manufacture of 1-11

Compound Mat 1-11 was prepared in the same manner as in Synthesis Example 1 except for using 9,12a-dihydroperylen-3-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] ⁺ 429

< Synthetic example  6> Compound Mat  Manufacture of 1-12

Except for using pyren-1-ylboronic acid instead of phenylboronic acid, the compound Mat 1-12 was prepared in the same manner as in Synthesis Example 1.

Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] ⁺ 377

< Synthetic example  7> Compound Mat  Manufacture of 1-14

Compound Mat 1-14 was prepared in the same manner as in Synthesis Example 1 except for using biphenyl-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.51; H, 5.49 / HRMS [M] ⁺ : 329

< Synthetic example  8> Compound Mat  Manufacture of 1-17

Compound Mat 1-17 was prepared in the same manner as in Synthesis Example 1 except for using 9,9-dimethyl-9H-fluoren-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.01; H, 5.99 / HRMS [M] ⁺ : 369

< Synthetic example  9> Compound Mat  Manufacture of 1-18

Compound Mat 1-18 was prepared in the same manner as in Synthesis Example 1 except for using 4- (naphthalen-2-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] ⁺ : 379

< Synthetic example  10> Compound Mat  Manufacture of 1-19

Compound Mat 1-19 was prepared in the same manner as in Synthesis Example 1 except for using 4- (naphthalen-1-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] ⁺ : 379

< Synthetic example  11> Compound Mat  Preparation of 1-21

Compound Mat 1-21 was prepared in the same manner as in Synthesis Example 1 except for using 4- (9,9-dimethyl-9H-fluoren-2-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.13; H, 5.87 / HRMS [M] ⁺ : 445

< Synthetic example  12> Compound Mat  Manufacture of 1-26

Compound Mat 1-26 was prepared by the same procedure as in Synthesis Example 1, except that dibenzo [b, d] thiophen-4-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 86.63; H, 4.47; S, 8.90 / HRMS [M] ⁺ : 359

< Synthetic example  13> Compound Mat  Preparation of 1-28

Compound Mat 1-28 was prepared in the same manner as in Synthesis Example 1 except for using 4- (dibenzo [b, d] thiophen-4-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 88.04; H, 4. 62; S, 7.34 / HRMS [M] ⁺ : 435

< Synthetic example  14> Compound Mat  Manufacture of 1-30

Compound Mat 1-30 was prepared in the same manner as in Synthesis Example 1 except for using 4- (diphenylamino) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 91.18; H, 5.50; N, 3.32 / HRMS [M] ⁺ : 420

< Synthetic example  15> Compound Mat  Manufacture of 1-34

Compound Mat 1-34 was prepared in the same manner as in Synthesis Example 1 except for using 4- (pyridin-2-yl) -D4-phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 89.52; H, 6. 31; N, 4.18 / HRMS [M] ⁺ : 334

< Synthetic example  16> Compound Mat  Manufacture of 1-40

Compound Mat 1-40 was prepared in the same manner as in Synthesis Example 1 except for using 4- (thieno [3,2-b] thiophen-2-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 79.55; H, 4.11; S, 16.34 / HRMS [M] ⁺ : 391

< Synthetic example  17> Compound Mat  Manufacture of 1-43

Compound Mat 1-43 was prepared in the same manner as in Synthesis Example 1 except for using 2'-fluorobiphenyl-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 89.63; H, 4.92; F, 5.45 / HRMS [M] ⁺ : 347

< Synthetic example  18> Compound Mat  Preparation of 1-44

Compound Mat 1-44 was prepared in the same manner as in Synthesis Example 1 except for using 6- (naphthalen-2-yl) pyridin-3-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 91.31; H, 5.02; N, 3.67 / HRMS [M] ⁺ : 380

< Synthetic example  19> Compound Mat  Manufacture of 1-61

Compound Mat 1-61 was prepared in the same manner as in Synthesis Example 1 except for using 4- (1,3,5-triazin-2-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 82.86; H, 4.54; N, 12.60 / HRMS [M] ⁺ : 332

< Synthetic example  20> compound Mat  Manufacture of 1-67

A compound Mat 1-67 was prepared in the same manner as in Synthesis Example 1 except for using 7- (pyrimidin-2-yl) naphthalen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 87.93; H, 4. 74; N, 7.32 / HRMS [M] ⁺ : 381

< Synthetic example  21> Compound Mat  Manufacture of 1-68

Compound Mat 1-68 was prepared in the same manner as in Synthesis Example 1 except for using 7- (1,3,5-triazin-2-yl) naphthalen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 84.57; H, 4.47; N, 10.96 / HRMS [M] ⁺ : 382

< Synthetic example  22> compound Mat  Manufacture of 1-71

Compound Mat 1-71 was prepared in the same manner as in Synthesis Example 1 except for using 5- (naphthalen-2-yl) thiophen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 87.01; H, 4.69; S, 8.30 / HRMS [M] ⁺ : 385

< Synthetic example  23> compound Mat  Manufacture of 1-81

Compound Mat 1-81 was prepared in the same manner as in Synthesis Example 1 except for using 4aH-phenothiazin-8-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 83.17; H, 4.56; N, 3.73; S, 8.54 / HRMS [M] ⁺ : 374

< Synthetic example  24> Compound Mat  Manufacture of 1-85

Compound Mat 1-85 was prepared in the same manner as in Synthesis Example 1 except for using 1,10-phenanthrolin-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 87.62; H, 4.52; N, 7.86 / HRMS [M] ⁺ : 355

< Synthetic example  25> Compound Mat  Manufacture of 2-1

A compound Mat was prepared in the same manner as in Synthesis Example 1, except that 1,5-diiodoanthracene of Preparation Example 2 was used instead of 1-iodoanthracene of Preparation Example 1, and 2 equivalents of phenylboronic acid and Pd (PPh ₃ ) ₄ were added. 2-1 was prepared.

Elemental Analysis: C, 94.51; H, 5.49 / HRMS [M] ⁺ : 329

< Synthetic example  26> compound Mat  Manufacture of 2-2

Compound Mat 2-2 was prepared in the same manner as in Synthesis Example 25, except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] ⁺ 429

< Synthetic example  27> Compound Mat  Manufacture of 2-5

Compound Mat 2-5 was prepared in the same manner as in Synthesis Example 25, except that phenanthren-1-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] ⁺ 529

< Synthetic example  28> Compound Mat  Manufacture of 2-7

Compound Mat 2-7 was prepared in the same manner as in Synthesis Example 25, except that anthracen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] ⁺ : 529

< Synthetic example  29> Compound Mat  Manufacture of 2-8

Compound Mat 2-8 was prepared in the same manner as in Synthesis Example 25, except that triphenylen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] ⁺ 629

< Synthetic example  30> Compound Mat  Manufacture of 2-10

Compound Mat 2-10 was prepared in the same manner as in Synthesis Example 25, except that 1H-phenalen-5-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.83; H, 5.17 / HRMS [M] ⁺ : 505

< Synthetic example  31> Compound Mat  Manufacture of 2-12

Compound Mat 2-12 was prepared in the same manner as in Synthesis Example 25, except that pyren-1-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 95.47; H, 4.53 / HRMS [M] ⁺ 577

< Synthetic example  32> Compound Mat  Manufacture of 2-14

Compound Mat 2-14 was prepared in the same manner as in Synthesis Example 25, except that biphenyl-4-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.57; H, 5.43 / HRMS [M] ⁺ 481

< Synthetic example  33> Compound Mat  Preparation of 2-17

Compound Mat 2-17 was prepared in the same manner as in Synthesis Example 25 except for using 9,9-dimethyl-9H-fluoren-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 93.91; H, 6.09 / HRMS [M] ⁺ : 561

< Synthetic example  34> Compound Mat  Manufacture of 2-18

Compound Mat 2-18 was prepared in the same manner as in Synthesis Example 25, except that 4- (naphthalen-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  35> Compound Mat  Preparation of 2-19

Except for using 4- (naphthalen-1-yl) phenylboronic acid instead of phenylboronic acid to prepare a compound Mat 2-19 in the same manner as in Synthesis Example 25.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  36> Compound Mat  Preparation of 2-21

Compound Mat 2-21 was prepared in the same manner as in Synthesis Example 25, except that 4- (9,9-dimethyl-9H-fluoren-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.08; H, 5.92 / HRMS [M] ⁺ : 713

< Synthetic example  37> Compound Mat  Preparation of 2-22

Compound Mat 2-22 was prepared in the same manner as in Synthesis Example 25, except that 4-phenylnaphthalen-1-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  38> Compound Mat  Preparation of 2-26

Compound Mat 2-26 was prepared in the same manner as in Synthesis Example 25, except that dibenzo [b, d] thiophen-4-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 84.10; H, 4.09; S, 11.82 / HRMS [M] ⁺ : 541

< Synthetic example  39> Compound Mat  Preparation of 2-28

Compound Mat 2-28 was prepared in the same manner as in Synthesis Example 25 except for using 4- (dibenzo [b, d] thiophen-4-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 86.42; H, 4. 35; S, 9.23 / HRMS [M] ⁺ : 693

< Synthetic example  40> Compound Mat  Preparation of 2-29

1,5-diiodoanthracene 10g (23mmol) and diphenylamine 3.9g (23mmol) obtained in Preparation Example 2, Pd ₂ (dba) ₃ 0.63g (0.69mmol), p (t-bu) ₃ 0.47g (2.3mmol), NaO 5.5 g (57.5 mmol) of (t-bu) was added to the flask, and 200 ml of Toluene was dissolved therein, followed by heating and stirring for 24 hours. After the reaction was completed, the reaction solution was filtered through Celite, and then subjected to column chromatography, to obtain compound Mat 2-29 7g (yield 60%).

Elemental Analysis: C, 89.03; H, 5.51; N, 5.46 / HRMS [M] ⁺ : 511

< Synthetic example  41> Compound Mat  Manufacture of 2-30

Compound Mat 2-30 was prepared in the same manner as in Synthesis Example 25, except that 4- (diphenylamino) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 90.33; H, 5.46; N, 4.21 / HRMS [M] ⁺ : 663

< Synthetic example  42> Compound Mat  Manufacture of 2-34

Compound Mat 2-34 was prepared in the same manner as in Synthesis Example 25, except that 4- (pyridin-2-yl) -D4-phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 87.77; H, 6. 54; N, 5.69 / HRMS [M] ⁺ : 491

< Synthetic example  43> Compound Mat  Preparation of 2-35

Compound Mat 2-35 was prepared in the same manner as in Synthesis Example 25, except that 4-hexylthiophen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 79.95; H, 7. 50; S, 12.55 / HRMS [M] ⁺ : 509

< Synthetic example  44> Compound Mat  Manufacture of 2-43

Compound Mat 2-43 was prepared in the same manner as in Synthesis Example 25 except for using 2'-fluorobiphenyl-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 88.01; H, 4. 66; F, 7.33 / HRMS [M] ⁺ : 517

< Synthetic example  45> Compound Mat  Preparation of 2-44

Compound Mat 2-44 was prepared in the same manner as in Synthesis Example 25, except that 6- (naphthalen-2-yl) pyridin-3-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  46> Compound Mat  Preparation of 2-53

Compound Mat 2-53 was prepared in the same manner as in Synthesis Example 25 except for using 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  47> Compound Mat  Preparation of 2-58

Compound Mat 2-58 was prepared in the same manner as in Synthesis Example 25, except that 4- (pyrimidin-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 83.93; H, 4.56; N, 11.51 / HRMS [M] ⁺ : 485

< Synthetic example  48> Compound Mat  Preparation of 2-60

Except for using 2- (pyrimidin-2-yl) phenylboronic acid in place of phenylboronic acid, the compound Mat 2-60 was prepared in the same manner as in Synthesis Example 25.

Elemental Analysis: C, 83.93; H, 4.56; N, 11.51 / HRMS [M] ⁺ : 485

< Synthetic example  49> Compound Mat  Preparation of 2-61

Compound Mat 2-61 was prepared in the same manner as in Synthesis Example 25, except that 4- (1,3,5-triazin-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 78.67; H, 4.13; N, 17.20 / HRMS [M] ⁺ : 487

< Synthetic example  50> Compound Mat  Preparation of 2-64

Compound Mat 2-64 was prepared in the same manner as in Synthesis Example 25 except for using 7- (pyridin-2-yl) naphthalen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  51> compound Mat  Preparation of 2-68

Compound Mat 2-68 was prepared in the same manner as in Synthesis Example 25, except that 7- (1,3,5-triazin-2-yl) naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 81.61; H, 4.11; N, 14.28 / HRMS [M] ⁺ : 587

< Synthetic example  52> Compound Mat  Preparation of 2-71

Compound Mat 2-71 was prepared in the same manner as in Synthesis Example 25, except that 5- (naphthalen-2-yl) thiophen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 84.81; H, 4.41; S, 10.78 / HRMS [M] ⁺ : 593

< Synthetic example  53> Compound Mat  Preparation of 2-78

Compound Mat 2-78 was prepared in the same manner as in Synthesis Example 25, except that 4- (bis (4-tert-butylphenyl) amino) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 89.14; H, 7.71; N, 3.15 / HRMS [M] ⁺ : 888

< Synthetic example  54> Compound Mat  Preparation of 2-81

Compound Mat 2-81 was prepared in the same manner as in Synthesis Example 25, except that 4aH-phenothiazin-8-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 79.69; H, 4. 22; N, 4.89; S, 11.20 / HRMS [M] ⁺ : 571

< Synthetic example  55> Compound Mat  Preparation of 2-85

Compound Mat 2-85 was prepared in the same manner as in Synthesis Example 25, except that 1,10-phenanthrolin-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 85.37; H, 4.15; N, 10.48 / HRMS [M] ⁺ : 533

< Synthetic example  56> Compound Mat  Manufacture of 3-1

A compound Mat was prepared in the same manner as in Synthesis Example 1, except that 1,8-diiodoanthracene of Preparation Example 3 was used instead of 1-iodoanthracene of Preparation Example 1, and 2 equivalents of phenylboronic acid and Pd (PPh ₃ ) ₄ were added. 3-1 was prepared.

Elemental Analysis: C, 94.51; H, 5.49 / HRMS [M] ⁺ : 329

< Synthetic example  57> Compound Mat  Manufacture of 3-2

Compound Mat 3-2 was prepared in the same manner as in Synthesis Example 56, except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] ⁺ 429

< Synthetic example  58> Compound Mat  Manufacture of 3-5

Compound Mat 3-5 was prepared in the same manner as in Synthesis Example 56, except that phenanthren-1-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] ⁺ 529

< Synthetic example  59> compound Mat  Manufacture of 3-7

Compound Mat 3-7 was prepared in the same manner as in Synthesis Example 56 except for using anthracen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] ⁺ : 529

< Synthetic example  60> compound Mat  Manufacture of 3-8

Compound Mat 3-8 was prepared in the same manner as in Synthesis Example 56, except that triphenylen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] ⁺ 629

< Synthetic example  61> compound Mat  Manufacture of 3-10

Compound Mat 3-10 was prepared in the same manner as in Synthesis Example 56, except that 1H-phenalen-5-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.83; H, 5.17 / HRMS [M] ⁺ : 505

< Synthetic example  62> Compound Mat  Manufacture of 3-12

Compound Mat 3-12 was prepared in the same manner as in Synthesis Example 56, except that pyren-1-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 95.47; H, 4.53 / HRMS [M] ⁺ 577

< Synthetic example  63> Compound Mat  Manufacture of 3-14

Compound Mat 3-14 was prepared in the same manner as in Synthesis Example 56 except for using biphenyl-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.57; H, 5.43 / HRMS [M] ⁺ 481

< Synthetic example  64> Compound Mat  Preparation of 3-17

Compound Mat 3-17 was prepared in the same manner as in Synthesis Example 56 except for using 9,9-dimethyl-9H-fluoren-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 93.91; H, 6.09 / HRMS [M] ⁺ : 561

< Synthetic example  65> Compound Mat  Manufacture of 3-18

Compound Mat 3-18 was prepared in the same manner as in Synthesis Example 56, except that 4- (naphthalen-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  66> Compound Mat  Preparation of 3-19

Compound Mat 3-19 was prepared in the same manner as in Synthesis Example 56, except that 4- (naphthalen-1-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  67> Compound Mat  Preparation of 3-21

Compound Mat 3-21 was prepared in the same manner as in Synthesis Example 56, except that 4- (9,9-dimethyl-9H-fluoren-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.08; H, 5.92 / HRMS [M] ⁺ : 713

< Synthetic example  68> compound Mat  Preparation of 3-22

Compound Mat 3-22 was prepared by the same procedure as in Synthesis Example 56 except for using 4-phenylnaphthalen-1-ylboronic acid instead of phenylboronic acid.

< Synthetic example  69> compound Mat  Preparation of 3-26

Compound Mat 3-26 was prepared in the same manner as in Synthesis Example 56 except for using dibenzo [b, d] thiophen-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 84.10; H, 4.09; S, 11.82 / HRMS [M] ⁺ : 541

< Synthetic example  70> Compound Mat  Preparation of 3-28

Compound Mat 3-28 was prepared in the same manner as in Synthesis Example 56 except for using 4- (dibenzo [b, d] thiophen-4-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 86.42; H, 4. 35; S, 9.23 / HRMS [M] ⁺ : 693

< Synthetic example  71> Compound Mat  Preparation of 3-29

Compound Mat 3-29 was prepared in the same manner as in Synthesis Example 40 except for using 1,8-diiodoanthracene instead of 1,5-diiodoanthracene.

Elemental Analysis: C, 89.03; H, 5.51; N, 5.46 / HRMS [M] ⁺ : 511

< Synthetic example  72> compound Mat  Manufacture of 3-30

Compound Mat 3-30 was prepared in the same manner as in Synthesis Example 56 except for using 4- (diphenylamino) phenylboronic acid) instead of phenylboronic acid.

Elemental Analysis: C, 90.33; H, 5.46; N, 4.21 / HRMS [M] ⁺ : 663

< Synthetic example  73> compound Mat  Preparation of 3-34

Compound Mat 3-34 was prepared in the same manner as in Synthesis Example 56 except for using 4- (pyridin-2-yl) -D4-phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 87.77; H, 6. 54; N, 5.69 / HRMS [M] ⁺ : 491

< Synthetic example  74> Compound Mat  Preparation of 3-35

Except that 4-hexylthiophen-2-ylboronic acid is used instead of phenylboronic acid, Compound Mat 3-35 was prepared by the same procedure as in Synthesis Example 56.

Elemental Analysis: C, 79.95; H, 7. 50; S, 12.55 / HRMS [M] ⁺ : 509

< Synthetic example  75> compound Mat  Preparation of 3-43

Compound Mat 3-43 was prepared in the same manner as in Synthesis Example 56 except for using 2'-fluorobiphenyl-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 88.01; H, 4. 66; F, 7.33 / HRMS [M] ⁺ : 517

< Synthetic example  76> Compound Mat  Preparation of 3-44

Compound Mat 3-44 was prepared in the same manner as in Synthesis Example 56, except that 6- (naphthalen-2-yl) pyridin-3-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  77> compound Mat  Manufacture of 3-53

Compound Mat 3-53 was prepared in the same manner as in Synthesis Example 56 except for using 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  78> Compound Mat  Preparation of 3-58

Compound Mat 3-58 was prepared in the same manner as in Synthesis Example 56, except that 4- (pyrimidin-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 83.93; H, 4.56; N, 11.51 / HRMS [M] ⁺ : 485

< Synthetic example  79> Compound Mat  Preparation of 3-60

Compound Mat 3-60 was prepared in the same manner as in Synthesis Example 56, except that 2- (pyrimidin-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 83.93; H, 4.56; N, 11.51 / HRMS [M] ⁺ : 485

< Synthetic example  80> compound Mat  Preparation of 3-61

Compound Mat 3-61 was prepared in the same manner as in Synthesis Example 56, except that 4- (1,3,5-triazin-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 78.67; H, 4.13; N, 17.20 / HRMS [M] ⁺ : 487

< Synthetic example  81> Compound Mat  Preparation of 3-64

Compound Mat 3-64 was prepared in the same manner as in Synthesis Example 56 except for using 7- (pyridin-2-yl) naphthalen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  82> Compound Mat  Preparation of 3-68

Compound Mat 3-68 was prepared in the same manner as in Synthesis Example 56, except that 7- (1,3,5-triazin-2-yl) naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 81.61; H, 4.11; N, 14.28 / HRMS [M] ⁺ : 587

< Synthetic example  83> Compound Mat  Preparation of 3-71

Compound Mat 3-71 was prepared in the same manner as in Synthesis Example 56 except for using 5- (naphthalen-2-yl) thiophen-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 84.81; H, 4.41; S, 10.78 / HRMS [M] ⁺ : 593

< Synthetic example  84> compound Mat  Preparation of 3-78

Compound Mat 3-78 was prepared in the same manner as in Synthesis Example 56 except for using 4- (bis (4-tert-butylphenyl) amino) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 89.14; H, 7.71; N, 3.15 / HRMS [M] ⁺ : 888

< Synthetic example  85> Compound Mat  Preparation of 3-81

Compound Mat 3-81 was prepared in the same manner as in Synthesis Example 56 except for using 4aH-phenothiazin-8-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 79.69; H, 4. 22; N, 4.89; S, 11.20 / HRMS [M] ⁺ : 571

< Synthetic example  86> Compound Mat  Preparation of 3-85

Compound Mat 3-85 was prepared in the same manner as in Synthesis Example 56 except for using 1,10-phenanthrolin-2-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 85.37; H, 4.15; N, 10.48 / HRMS [M] ⁺ : 533

< Synthetic example  87> Compound Mat  Manufacture of 4-1

Compound Mat was prepared by the same procedure as in Synthesis Example 1, except that 1,4-diiodoanthracene of Preparation Example 4 was used instead of 1-iodoanthracene of Preparation Example 1 and 2 equivalents of phenylboronic acid and Pd (PPh ₃ ) ₄ were added. 4-1 was prepared.

Elemental Analysis: C, 94.51; H, 5.49 / HRMS [M] ⁺ : 329

< Synthetic example  88> compound Mat  Manufacture of 4-2

Compound Mat 4-2 was prepared in the same manner as in Synthesis Example 87, except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] ⁺ 429

< Synthetic example  89> Compound Mat  Manufacture of 4-5

Except for using phenanthren-1-ylboronic acid instead of phenylboronic acid, the compound Mat 4-5 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] ⁺ 529

< Synthetic example  90> Compound Mat  4-7 manufacturing

Except for using anthracen-2-ylboronic acid in place of phenylboronic acid, the compound Mat 4-7 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] ⁺ : 529

< Synthetic example  91> Compound Mat  Manufacture of 4-8

Except for using triphenylen-2-ylboronic acid in place of phenylboronic acid, the compound Mat 4-8 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] ⁺ 629

< Synthetic example  92> Compound Mat  Manufacture of 4-10

A compound Mat 4-10 was prepared in the same manner as in Synthesis Example 87, except that 1H-phenalen-5-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.83; H, 5.17 / HRMS [M] ⁺ : 505

< Synthetic example  93> compound Mat  Manufacture of 4-12

Except for using pyren-1-ylboronic acid instead of phenylboronic acid, the compound Mat 4-12 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 95.47; H, 4.53 / HRMS [M] ⁺ 577

< Synthetic example  94> Compound Mat  Manufacture of 4-14

Compound Mat 4-14 was prepared in the same manner as in Synthesis Example 87, except for using biphenyl-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 94.57; H, 5.43 / HRMS [M] ⁺ 481

< Synthetic example  95> Compound Mat  Preparation of 4-17

Compound Mat 4-17 was prepared in the same manner as in Synthesis Example 87, except that 9,9-dimethyl-9H-fluoren-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 93.91; H, 6.09 / HRMS [M] ⁺ : 561

< Synthetic example  96> Compound Mat  Manufacture of 4-18

Except for using 4- (naphthalen-2-yl) phenylboronic acid in place of phenylboronic acid, the compound Mat 4-18 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  97> Compound Mat  Preparation of 4-19

Except for using 4- (naphthalen-1-yl) phenylboronic acid instead of phenylboronic acid to prepare a compound Mat 4-19 in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  98> Compound Mat  Manufacture of 4-21

Compound Mat 4-21 was prepared in the same manner as in Synthesis Example 87, except that 4- (9,9-dimethyl-9H-fluoren-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 94.08; H, 5.92 / HRMS [M] ⁺ : 713

< Synthetic example  99> Compound Mat  Manufacture of 4-22

Except for using 4-phenylnaphthalen-1-ylboronic acid in place of phenylboronic acid, the compound Mat 4-22 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 94.81; H, 5.19 / HRMS [M] ⁺ : 581

< Synthetic example  100> Compound Mat  Manufacture of 4-26

Compound Mat 4-26 was prepared in the same manner as in Synthesis Example 87 except for using dibenzo [b, d] thiophen-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 84.10; H, 4.09; S, 11.82 / HRMS [M] ⁺ : 541

< Synthetic example  101> Compound Mat  Preparation of 4-28

Compound Mat 4-28 was prepared in the same manner as in Synthesis Example 87 except for using 4- (dibenzo [b, d] thiophen-4-yl) phenylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 86.42; H, 4. 35; S, 9.23 / HRMS [M] ⁺ : 693

< Synthetic example  102> Compound Mat  Manufacture of 4-29

Compound Mat 4-29 was prepared in the same manner as in Synthesis Example 40 except for using 1,4-diiodoanthracene instead of 1,5-diiodoanthracene.

Elemental Analysis: C, 89.03; H, 5.51; N, 5.46 / HRMS [M] ⁺ : 511

< Synthetic example  103> Compound Mat  Manufacture of 4-30

Except for using 4- (diphenylamino) phenylboronic acid instead of phenylboronic acid to prepare a compound Mat 4-30 in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 90.33; H, 5.46; N, 4.21 / HRMS [M] ⁺ : 663

< Synthetic example  104> Compound Mat  Preparation of 4-34

Compound Mat 4-34 was prepared in the same manner as in Synthesis Example 87, except that 4- (pyridin-2-yl) -D4-phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 87.77; H, 6. 54; N, 5.69 / HRMS [M] ⁺ : 491

< Synthetic example  105> Compound Mat  Manufacture of 4-35

Except for using 4-hexylthiophen-2-ylboronic acid instead of phenylboronic acid, the compound Mat 4-35 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 79.95; H, 7. 50; S, 12.55 / HRMS [M] ⁺ : 509

< Synthetic example  106> Compound Mat  Manufacture of 4-43

Compound Mat 4-43 was prepared in the same manner as in Synthesis Example 87 except for using 2'-fluorobiphenyl-4-ylboronic acid instead of phenylboronic acid.

Elemental Analysis: C, 88.01; H, 4. 66; F, 7.33 / HRMS [M] ⁺ : 517

< Synthetic example  107> Compound Mat  Preparation of 4-44

Compound Mat 4-44 was prepared in the same manner as in Synthesis Example 87, except that 6- (naphthalen-2-yl) pyridin-3-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  108> compound Mat  Preparation of 4-53

Compound Mat 4-53 was prepared in the same manner as in Synthesis Example 87, except that 4- (pyridin-2-yl) naphthalen-1-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  109> compound Mat  Preparation of 4-58

Except for using 4- (pyrimidin-2-yl) phenylboronic acid instead of phenylboronic acid to prepare a compound Mat 4-58 in the same manner as in Synthesis Example 87.

< Synthetic example  110> Compound Mat  Manufacture of 4-60

Except for using 2- (pyrimidin-2-yl) phenylboronic acid instead of phenylboronic acid was prepared in the same manner as in Synthesis Example 87 to prepare a compound Mat 4-60.

Elemental Analysis: C, 83.93; H, 4.56; N, 11.51 / HRMS [M] ⁺ : 485

< Synthetic example  111> Compound Mat  Manufacture of 4-61

Compound Mat 4-61 was prepared in the same manner as in Synthesis Example 87, except that 4- (1,3,5-triazin-2-yl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 78.67; H, 4.13; N, 17.20 / HRMS [M] ⁺ : 487

< Synthetic example  112> Compound Mat  Manufacture of 4-64

Compound Mat 4-64 was prepared in the same manner as in Synthesis Example 87, except that 7- (pyridin-2-yl) naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 90.38; H, 4.83; N, 4.79 / HRMS [M] ⁺ : 583

< Synthetic example  113> Compound Mat  Preparation of 4-68

Compound Mat 4-68 was prepared in the same manner as in Synthesis Example 87, except that 7- (1,3,5-triazin-2-yl) naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 81.61; H, 4.11; N, 14.28 / HRMS [M] ⁺ : 587

< Synthetic example  114> Compound Mat  Preparation of 4-71

Except for using 5- (naphthalen-2-yl) thiophen-2-ylboronic acid instead of phenylboronic acid, the compound Mat 4-71 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 84.81; H, 4.41; S, 10.78 / HRMS [M] ⁺ : 593

< Synthetic example  115> Compound Mat  Preparation of 4-78

Compound Mat 4-78 was prepared in the same manner as in Synthesis Example 87, except that 4- (bis (4-tert-butylphenyl) amino) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 89.14; H, 7.71; N, 3.15 / HRMS [M] ⁺ : 888

< Synthetic example  116> Compound Mat  Manufacture of 4-81

Except for using 4aH-phenothiazin-8-ylboronic acid in place of phenylboronic acid, Compound Mat 4-81 was prepared in the same manner as in Synthesis Example 87.

Elemental Analysis: C, 79.69; H, 4. 22; N, 4.89; S, 11.20 / HRMS [M] ⁺ : 571

< Synthetic example  117> Compound Mat  Preparation of 4-85

Compound Mat 4-85 was prepared in the same manner as in Synthesis Example 87, except that 1,10-phenanthrolin-2-ylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 85.37; H, 4.15; N, 10.48 / HRMS [M] ⁺ : 533

< Synthetic example  118> Compound Mat  Manufacture of 5-1

10 g (23 mmol) of 1,5-diiodoanthracene, 2.3 g (11.5 mmol) of 4- (pyridin-2-yl) phenylboronic acid, and 0.8 g (0.69 mmol) of Pd (PPh ₃ ) ₄ obtained in Preparation Example 2 were placed in a flask. 26 ml of saturated aqueous K ₂ CO ₃ solution and 80 ml of toluene were added thereto, and the mixture was heated and stirred for 12 hours. After the reaction was completed, the reaction solution was filtered through Celite, and then subjected to column chromatography, obtaining 5.2 g of compound 2- (4- (5-iodoanthracen-1-yl) phenyl) pyridine (yield 50%).

5.2 g (11.5 mmol) of 2- (4- (5-iodoanthracen-1-yl) phenyl) pyridine and 2.9 g (11.5 mmol) of 4- (pyridin-2-yl) naphthalen-1-ylboronic acid, Pd (PPh _{3 4} ) 0.4g (0.34mmol) was added to the flask, and 13 ml of a 2M K ₂ CO ₃ saturated aqueous solution and 40 ml of Toluene were dissolved, followed by heating and stirring for 12 hours. After the reaction was completed, the reaction solution was filtered through Celite, and then column chromatography was performed to prepare 5 g (80%) of Mat 5-1.

Elemental Analysis: C, 89.86; H, 4.90; N, 5.24 / HRMS [M] ⁺ : 533

< Synthetic example  119> Compound Mat  Manufacture of 5-2

Dibenzo [b, d] thiophen-2-ylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-2 was prepared by following the same procedure as in Synthesis Example 118 except for using 9,9-dimethyl-9H-fluoren-3-ylboronic acid instead.

Elemental Analysis: C, 89.09; H, 5.11; S, 5.80 / HRMS [M] ⁺ : 551

< Synthetic example  120> Compound Mat  Manufacture of 5-3

4-D5-phenylnaphthalen-1-ylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-3 was prepared by following the same procedure as in Synthesis Example 118 except for using naphthalen-2-ylboronic acid instead.

Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] ⁺ : 510

< Synthetic example  121> Compound Mat  5-4 manufacturing

4- (diphenylamino) phenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid Instead of using the 4- (bis (4-tert-butylphenyl) amino) phenylboronic acid was carried out in the same manner as in Synthesis Example 118 to prepare a compound Mat 5-4.

Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] ⁺ : 775

< Synthetic example  122> compound Mat  5-5 manufacturing

3,5-dicyclohexylphenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-5 was prepared by following the same procedure as in Synthesis Example 118 except for using phenanthren-9-ylboronic acid instead.

Elemental Analysis: C, 92.88; H, 7. 12 / HRMS [M] ⁺ : 593

< Synthetic example  123> compound Mat  5-6 manufacturing

2-fluorophenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-6 was prepared by following the same procedure as in Synthesis Example 118 except for using phenylboronic acid-D5 instead.

Elemental Analysis: C, 88.35; H, 6. 27; F, 5.38 / HRMS [M] ⁺ : 352

< Synthetic example  124> Compound Mat  5-7 manufacturing

Compound Mat 5-7 was prepared in the same manner as in Synthesis Example 25, except that 4- (triphenylsilyl) phenylboronic acid was used instead of phenylboronic acid.

Elemental Analysis: C, 87.90; H, 5.47; Si, 6.63 / HRMS [M] ⁺ : 846

< Synthetic example  125> compound Mat  5-8 manufacturing

4-tert-butylphenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-8 was prepared by following the same procedure as in Synthesis Example 118 except for using 4-tritylphenylboronic acid instead.

Elemental Analysis: C, 93.59; H, 6.41 / HRMS [M] ⁺ : 627

< Synthetic example  126> Compound Mat  Manufacture of 5-9

4- (dicyclohexylamino) phenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-9 was prepared by following the same procedure as in Synthesis Example 118 except for using 4- (diphenylamino) phenylboronic acid instead.

Elemental Analysis: C, 88.71; H, 7. 15; N, 4.14 / HRMS [M] ⁺ : 675

< Synthetic example  127> compounds Mat  5-10 manufacturing

Compound Mat 5-10 was prepared in the same manner as in Synthesis Example 118 except for using 1,8-diiodoanthracene instead of 1,5-diiodoanthracene.

Elemental Analysis: C, 89.86; H, 4.90; N, 5.24 / HRMS [M] ⁺ : 533

< Synthetic example  128> Compound Mat  5-11 Manufacturing

1,8-diiodoanthracene instead of 1,5-diiodoanthracene, dibenzo [b, d] thiophen-2-ylboronic acid, 4- (pyridin-2-yl) naphthalen- instead of 4- (pyridin-2-yl) phenylboronic acid 1-ylboronic acid Instead of 9,9-dimethyl-9H-fluoren-3-ylboronic acid was used in the same manner as in Synthesis Example 118 to prepare a compound Mat 5-11.

Elemental Analysis: C, 89.09; H, 5.11; S, 5.80 / HRMS [M] ⁺ : 551

< Synthetic example  129> Compound Mat  5-12 manufacturing

1,8-diiodoanthracene instead of 1,5-diiodoanthracene, 4-D5-phenylnaphthalen-1-ylboronic acid, 4- (pyridin-2-yl) naphthalen-1- instead of 4- (pyridin-2-yl) phenylboronic acid ylboronic acid A compound Mat 5-12 was prepared by following the same procedure as in Synthesis Example 118 except for using naphthalen-2-ylboronic acid instead.

Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] ⁺ : 510

< Synthetic example  130> Compound Mat  Preparation of 5-13

1,8-diiodoanthracene instead of 1,5-diiodoanthracene, 4- (diphenylamino) phenylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid A compound Mat 5-13 was prepared by following the same procedure as in Synthesis Example 118 except for using 4- (bis (4-tert-butylphenyl) amino) phenylboronic acid instead.

Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] ⁺ : 775

< Synthetic example  131> compound Mat  Manufacture of 5-14

1,8-diiodoanthracene, instead of 1,5-diiodoanthracene, 3,5-dicyclohexylphenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-14 was prepared by following the same procedure as in Synthesis Example 118 except for using phenanthren-9-ylboronic acid instead.

Elemental Analysis: C, 92.88; H, 7. 12 / HRMS [M] ⁺ : 593

< Synthetic example  132> Compound Mat  5-15 manufacturing

1,8-diiodoanthracene instead of 1,5-diiodoanthracene, 2-fluorophenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-15 was prepared by following the same procedure as in Synthesis Example 118 except for using phenylboronic acid-D5 instead.

Elemental Analysis: C, 88.35; H, 6. 27; F, 5.38 / HRMS [M] ⁺ : 352

< Synthetic example  133> compound Mat  Preparation of 5-17

1,8-diiodoanthracene instead of 1,5-diiodoanthracene, 4-tert-butylphenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-17 was prepared by following the same procedure as in Synthesis Example 118 except for using 4-tritylphenylboronic acid instead.

Elemental Analysis: C, 93.59; H, 6.41 / HRMS [M] ⁺ : 627

< Synthetic example  134> Compound Mat  Manufacture of 5-18

1,8-diiodoanthracene instead of 1,5-diiodoanthracene, 4- (dicyclohexylamino) phenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-18 was prepared by following the same procedure as in Synthesis Example 118 except for using 4- (diphenylamino) phenylboronic acid instead.

Elemental Analysis: C, 88.71; H, 7. 15; N, 4.14 / HRMS [M] ⁺ : 675

< Synthetic example  135> Compound Mat  Preparation of 5-19

Compound Mat 5-19 was prepared in the same manner as in Synthesis Example 118 except for using 1,4-diiodoanthracene instead of 1,5-diiodoanthracene.

Elemental Analysis: C, 89.86; H, 4.90; N, 5.24 / HRMS [M] ⁺ : 533

< Synthetic example  136> Compound Mat  5-20 manufacturing

1,4-diiodoanthracene instead of 1,5-diiodoanthracene, dibenzo [b, d] thiophen-2-ylboronic acid, 4- (pyridin-2-yl) naphthalen- instead of 4- (pyridin-2-yl) phenylboronic acid 1-ylboronic acid A compound Mat 5-20 was prepared by following the same procedure as in Synthesis Example 118 except for using 9,9-dimethyl-9H-fluoren-3-ylboronic acid instead.

Elemental Analysis: C, 89.09; H, 5.11; S, 5.80 / HRMS [M] ⁺ : 551

< Synthetic example  137> Compound Mat  Preparation of 5-21

1,4-diiodoanthracene, instead of 1,5-diiodoanthracene, 4-D5-phenylnaphthalen-1-ylboronic acid, 4- (pyridin-2-yl) naphthalen-1- instead of 4- (pyridin-2-yl) phenylboronic acid ylboronic acid A compound Mat 5-21 was prepared by following the same procedure as in Synthesis Example 118 except for using naphthalen-2-ylboronic acid instead.

Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] ⁺ : 510

< Synthetic example  138> Compound Mat  Preparation of 5-22

1,4-diiodoanthracene instead of 1,5-diiodoanthracene, 4- (diphenylamino) phenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid Instead of using the 4- (bis (4-tert-butylphenyl) amino) phenylboronic acid was carried out in the same manner as in Synthesis Example 118 to prepare a compound Mat 5-22.

Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] ⁺ : 775

< Synthetic example  139> Compound Mat  Preparation of 5-23

1,4-diiodoanthracene instead of 1,5-diiodoanthracene, 3,5-dicyclohexylphenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-23 was prepared by following the same procedure as in Synthesis Example 118 except for using phenanthren-9-ylboronic acid instead.

Elemental Analysis: C, 92.88; H, 7. 12 / HRMS [M] ⁺ : 593

< Synthetic example  140> Compound Mat  Preparation of 5-24

1,4-diiodoanthracene instead of 1,5-diiodoanthracene, 2-fluorophenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-24 was prepared by following the same procedure as in Synthesis Example 118 except for using phenylboronic acid-D5 instead.

Elemental Analysis: C, 88.35; H, 6. 27; F, 5.38 / HRMS [M] ⁺ : 352

< Synthetic example  141> Compound Mat  Preparation of 5-26

1,4-diiodoanthracene instead of 1,5-diiodoanthracene, 4-tert-butylphenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-26 was prepared by following the same procedure as in Synthesis Example 118 except for using 4-tritylphenylboronic acid instead.

Elemental Analysis: C, 93.59; H, 6.41 / HRMS [M] ⁺ : 627

< Synthetic example  142> Compound Mat  Preparation of 5-27

1,4-diiodoanthracene instead of 1,5-diiodoanthracene, 4- (dicyclohexylamino) phenylboronic acid, 4- (pyridin-2-yl) naphthalen-1-ylboronic acid instead of 4- (pyridin-2-yl) phenylboronic acid A compound Mat 5-27 was prepared by following the same procedure as in Synthesis Example 118 except for using 4- (diphenylamino) phenylboronic acid instead.

Elemental Analysis: C, 88.71; H, 7. 15; N, 4.14 / HRMS [M] ⁺ : 675

< Example  1> organic Field  Manufacture of light emitting device

An organic electroluminescent device was manufactured by the following method.

The glass substrate coated with ITO (Indium tin oxide) to 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 and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and the substrate was transferred to a vacuum depositor.

DS-205 (Doosan Co., Ltd.) was thermally vacuum deposited to 800 Å on the ITO (anode) thus prepared to form a hole injection layer, and α-NPB (N, N - di ( naphthalene-1-yl) -N, N - diphenylbenzidine) was vacuum deposited to a thickness of 150 kPa to form a hole transport layer.

Using the compound Mat 1-8 prepared in Synthesis Example 3 as a blue host material and doped with DS-405 (Doosan Co., Ltd.) 5% as a dopant to form a light emitting layer by vacuum deposition to a thickness of 300 kPa, to form a light emitting layer, Alq3, an electron transporting material, was vacuum deposited to a thickness of 250 kPa to form an electron transporting layer. Thereafter, LiF, which is an electron injection material, was deposited to a thickness of 10 kW to form an electron injection layer, and aluminum was vacuum deposited to a thickness of 2000 kW thereon to form a cathode to fabricate an organic EL device.

< Example  2 ~ 21> organic Field  Manufacture of light emitting device

When forming the light emitting layer, instead of compound Mat 1-8, compound Mat 1-11, Mat 1-12, Mat 1-17, Mat 1-18, Mat 1-21, Mat 1-28, Mat 1-40, Mat 1-44 , Mat 1-67, Mat 1-68, Mat 1-71, Mat 2-2, Mat 2-8, Mat 2-17, Mat 3-2, Mat 3-8, Mat 3-17, Mat 4-2 An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Mat 4-8 and Mat 4-17 were used.

< Comparative example  1> organic Field  Manufacture of light emitting device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that ADN (9,10-di (naphthalene-2-yl) anthracene) was used instead of the compound Mat 1-8.

< Example  22 ~ 69> Organic Field  Manufacture of light emitting device

As a green host material instead of the compound Mat 1-8 which is a blue host when forming the emission layer, the compound Mat 2-7, Mat 2-12, Mat 2-18, Mat 2-21, Mat 2-22, Mat 2-26, Mat 2- 28, Mat 2-34, Mat 2-35, Mat 2-53, Mat 2-58, Mat 2-64,, Mat 2-71, Mat 3-7, Mat 3-12, Mat 3-18, Mat 3 -21, Mat 3-22, Mat 3-26, Mat 3-28, Mat 3-34, Mat 3-35, Mat 3-53, Mat 3-58, Mat 3-64, Mat 3-71, Mat 4 -7, Mat 4-12, Mat 4-18, Mat 4-21, Mat 4-22, Mat 4-26, Mat 4-28, Mat 4-34, Mat 4-35, Mat 4-53, Mat 4 -58, Mat 4-64, Mat 4-71, Mat 5-1, Mat 5-2, Mat 5-3, Mat 5-10, Mat 5-11, Mat 5-12, Mat 5-18, Mat 5 An organic electroluminescent device was manufactured in the same manner as in Example 1, except for using -19, Mat 5-20 and C-545T instead of DS-405 as a dopant material.

< Comparative example  2> organic Field  Manufacture of light emitting device

An organic electroluminescent device was manufactured in the same manner as in Example 22, except that Alq3 (aluminum tris (8-hydroxyquinoline)) was used as the host material.

< Example  70 ~ 79> Organic Field  Manufacture of light emitting device

Instead of the compound α-NPB used as the hole transporting material, Mat 2-29, Mat 2-30, Mat 2-78, Mat 3-29, Mat 3-30, Mat 3-78, Mat 4-29, Mat 4- An organic electroluminescent device was manufactured in the same manner as in Comparative Example 2, except that 30, Mat 4-78, and Mat 5-9 were used.

< Example  80 ~ 82> Organic Field  Manufacture of light emitting device

An organic electroluminescent device was manufactured in the same manner as in Comparative Example 2, except that Mat 2-60, Mat 3-60, Mat 4-60 were used instead of the compound Alq3 used as the electron transporting material.

Hole injection layer
(HIL) Hole transport layer
(HTL) Organic light emitting layer
(EML) Electron transport layer
(ETL) Electron injection layer
(EIL) cathode
(cathode) Example 1-21 DS-205 a-NPB Compounds of Examples 1-21 + DS-405 Alq3 LiF Al Example 22-69 DS-205 a-NPB Compounds of Examples 22-69 + C-545T Alq3 LiF Al Example 70-79 DS-205 Compounds of Examples 70-79 Alq3 + C-545T Alq3 LiF Al Example 80-82 DS-205 a-NPB Alq3 + C-545T Compounds of Examples 80-82 LiF Al Comparative Example 1 DS-205 a-NPB ADN + DS405 Alq3 LiF Al Comparative Example 2 DS-205 a-NPB Alq3 + C-545T Alq3 LiF Al

< Experimental Example >

For each organic electroluminescent device manufactured in Examples 1 to 82 and Comparative Examples 1 and 2, the luminous efficiency and driving voltage at a current density of 10 mA / cm 2 were measured, and the results are shown in Tables 2 to 5 below. .

compound Voltage
(V) efficiency
(cd / A) compound Voltage
(V) efficiency
(cd / A) Mat 1-8 (Example 1) 5.3 6.0 Mat 1-71 (Example 12) 5.6 6.4 Mat 1-11 (Example 2) 5.9 6.5 Mat 2-2 (Example 13) 5.2 7.0 Mat 1-12 (Example 3) 6.5 6.4 Mat 2-8 (Example 14) 5.1 7.4 Mat 1-17 (Example 4) 6.4 6.8 Mat 2-17 (Example 15) 4.9 8.0 Mat 1-18 (Example 5) 5.6 7.0 Mat 3-2 (Example 16) 5.3 7.2 Mat 1-21 (Example 6) 5.3 6.8 Mat 3-8 (Example 17) 5.5 7.6 Mat 1-28 (Example 7) 5.8 8.1 Mat 3-17 (Example 18) 4.9 8.2 Mat 1-40 (Example 8) 4.9 8.5 Mat 4-2 (Example 19) 5.1 7.2 Mat 1-44 (Example 9) 6 7.2 Mat 4-8 (Example 20) 5.6 7.2 Mat 1-67 (Example 10) 6.2 6.2 Mat 4-17 (Example 21) 5.1 7.9 Mat 1-68 (Example 11) 5.9 7.0 Comparative Example 1 5.7 6

compound Voltage
(V) efficiency
(cd / A) compound Voltage
(V) efficiency
(cd / A) Mat 2-7 (Example 22) 4.9 13.5 Mat 3-71 (Example 47) 4.0 13.8 Mat 2-12 (Example 23) 4.8 13.6 Mat 4-7 (Example 48) 4.9 13.4 Mat 2-18 (Example 24) 5.2 13.7 Mat 4-12 (Example 49) 4.9 13.6 Mat 2-21 (Example 25) 5.1 12.5 Mat 4-18 (Example 50) 5.5 13.7 Mat 2-22 (Example 26) 4.6 12.1 Mat 4-21 (Example 51) 5.6 12.5 Mat 2-26 (Example 27) 4.5 13.8 Mat 4-22 (Example 52) 4.9 12.1 Mat 2-28 (Example 28) 5.0 14.5 Mat 4-26 (Example 53) 4.8 13.5 Mat 2-34 (Example 29) 5.1 13.1 Mat 4-28 (Example 54) 5.5 14.6 Mat 2-35 (Example 30) 4.8 11.3 Mat 4-34 (Example 55) 5.2 13.8 Mat 2-53 (Example 31) 5.3 14.5 Mat 4-35 (Example 56) 4.8 11.9 Mat 2-58 (Example 32) 5.9 14.3 Mat 4-53 (Example 57) 5.4 14.7 Mat 2-64 (Example 33) 4.1 13.9 Mat 4-58 (Example 58) 5.9 14.4 Mat 2-71 (Example 34) 3.9 13.7 Mat 4-64 (Example 59) 4.2 13.5 Mat 3-7 (Example 35) 4.8 13.6 Mat 4-71 (Example 60) 4.3 13.5 Mat 3-12 (Example 36) 4.8 13.5 Mat 5-1 (Example 61) 5.2 14.5 Mat 3-18 (Example 37) 5.5 13.7 Mat 5-2 (Example 62) 5.3 15.8 Mat 3-21 (Example 38) 5.3 12.6 Mat 5-3 (Example 63) 4.7 16.1 Mat 3-22 (Example 39) 4.7 12.8 Mat 5-10 (Example 64) 4.7 13.5 Mat 3-26 (Example 40) 4.3 13.7 Mat 5-11 (Example 65) 5.1 14.2 Mat 3-28 (Example 41) 5.1 14.3 Mat 5-12 (Example 66) 4.9 14.3 Mat 3-34 (Example 42) 5.1 13.5 Mat 5-18 (Example 67) 4.5 15.2 Mat 3-35 (Example 43) 4.8 11.4 Mat 5-19 (Example 68) 4.8 14.2 Mat 3-53 (Example 44) 5.5 14.6 Mat 5-20 (Example 69) 4.9 12.5 Mat 3-58 (Example 45) 5.4 14.7 Comparative Example 2 4.7 11.7 Mat 3-64 (Example 46) 4.2 13.5

compound Voltage (V) Efficiency (cd / A) Mat 2-29 (Example 70) 4.1 11.5 Mat 2-30 (Example 71) 4.0 11.7 Mat 2-78 (Example 72) 4.2 12.0 Mat 3-29 (Example 73) 4.2 12.3 Mat 3-30 (Example 74) 4.1 12.1 Mat 3-78 (Example 75) 4.0 11.4 Mat 4-29 (Example 76) 4.3 11.0 Mat 4-30 (Example 77) 4.2 12.9 Mat 4-78 (Example 78) 4.3 13.1 Mat 5-9 (Example 79) 4.0 12.1 Comparative Example 2 4.7 11.7

compound Voltage (V) Efficiency (cd / A) Mat 2-60 (Example 80) 4 11.5 Mat 3-60 (Example 81) 4.2 11.7 Mat 4-60 (Example 82) 4.3 11.9 Comparative Example 2 4.7 11.7

As shown in the table, it can be seen that the organic electroluminescent device adopting the compound according to the present invention as a light emitting material, a hole transporting material or an electron transporting material exhibits excellent performance in terms of driving voltage and efficiency.

Claims (8)

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

In this formula,
X ₁ to X ₆ Are each independently hydrogen, deuterium or halogen;
R ₁ to R ₄ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₅ ~ C ₄₀ of the Aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ Heterocycloalkyl group; A group which forms 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 ₄ One or more of the each independently represent a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C aryl group of ₅ ~ C _40, C ₅ ~ heteroaryl of C ₄₀ A group, a C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, an amino group, a C ₃ to C ₄₀ cycloalkyl group and a C ₃ to C ₄₀ heterocycloalkyl group; A group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. The method of claim 1, wherein, R ₁ to R ₄ of the C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₅ ~ of C ₄₀ heteroaryl group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ heterocycloalkyl group are each independently Deuterium, halogen, nitrile group, nitro group, cyano group, silyl group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, amino group, C ₃ ~ C ₄₀ Compound which is substituted or unsubstituted with one or more substituents selected from the group consisting of a cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₅ ~ C ₄₀ aryl group and C ₅ ~ C ₄₀ heteroaryl group . According to claim 1, one functional group selected from R ₁ to R ₄ C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₅ ~ C ₄₀ Aryl C ₅ to C ₄₀ heteroaryl group, C ₅ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, amino group, C ₃ to C ₄₀ cycloalkyl group and C ₃ to C ₄₀ hetero Selected from the group consisting of cycloalkyl groups; A compound characterized by forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. According to claim ₁ , R ₁ to R ₄ Two functional groups each independently selected from C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₅ to C ₄₀ aryl group, C ₅ to C ₄₀ hetero An aryl group, a C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, an amino group, a C ₃ to C ₄₀ cycloalkyl group and a C ₃ to C ₄₀ heterocycloalkyl group; A compound characterized by forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. According to claim ₁ , the three functional groups selected from R ₁ to R ₄ are each independently C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₅ ~ C ₄₀ Aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₅ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ Heterocycloalkyl group; A compound characterized by forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. According to claim 1, R ₁ to R ₄ The Each independently a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₅ to C ₄₀ aryl group, C ₅ to C ₄₀ heteroaryl group, C ₅ ~ aryloxy C _40, C ₁ ~ C ₄₀ of the alkyloxy group, amino group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ selected from the group consisting of C ₄₀ heterocycloalkyl group, or; A compound characterized by forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
At least one of the organic layer comprises an compound according to any one of claims 1 to 6 characterized in that the organic electroluminescent device. The organic electroluminescent device according to claim 7, wherein the organic material layer is selected from the group consisting of a light emitting layer, a hole transporting layer and an electron transporting layer.