KR101805913B1 - Anthracene derivative and organic electroluminescence device using the same - Google Patents

Abstract

The present invention relates to a novel anthracene derivative and an organic electroluminescent device using the same. More specifically, the present invention relates to a novel anthracene derivative and an organic electroluminescent device using the same, wherein the anthracene moiety having excellent device characteristics and the fluorine For example, an anthracene derivative having an indenoanthracene core and substituted with an aryl group in the core, and an organic electroluminescent device having improved properties such as efficiency, driving voltage and lifetime by using the anthracene derivative.

Description

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

The present invention relates to a novel anthracene derivative and an organic electroluminescent device using the same. More specifically, the present invention relates to a novel anthracene derivative and an organic electroluminescent device using the same, wherein the anthracene moiety having excellent device characteristics and the fluorine For example, an anthracene derivative having an indenoanthracene core and substituted with an aryl group in the core, and an organic electroluminescent device having improved properties such as efficiency, driving voltage and lifetime by using the anthracene derivative.

Background Art [0002] An organic electronic device is an electronic device using an organic semiconductor material, and requires the exchange of holes and / or electrons between the electrode and the organic semiconductor material. The organic electronic device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Is an electronic device. 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 the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor. These devices include an electron / hole injecting material, an electron / hole extracting material, Materials or luminescent materials. Hereinafter, the organic light emitting device will be described in detail, but in the organic electronic devices, the electron / hole injecting material, the electron / hole extracting material, the electron / hole transporting material, or the light emitting material all have a similar principle.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. 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. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

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.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

The light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained according to the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device described above, a material constituting the organic material layer in the device, that is, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, However, the development of a stable and efficient organic material layer material for an organic light emitting device has not yet been sufficiently achieved, and therefore, the development of new materials has been continuously required.

In order to solve the above problems, the present invention provides a novel luminescent material capable of improving luminescence efficiency, brightness, power efficiency, thermal stability, and device lifetime and an organic electroluminescent device using the same.

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

In Formula 1, X is ^{CR 6 R 7, NR 6,} O, S, S (= O), S (= O) 2 and is selected from the group consisting of SiR ⁶ R ^7;

R ¹ to R ⁷ are the same or different and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₅ to C ₄₀ An aryl group, a C ₅ to C ₄₀ heteroaryl group, a C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₅ to C ₄₀ arylamino group, a C ₅ to C ₄₀ diaryl An amino group, a C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, and a C ₃ to C ₄₀ heterocycloalkyl group; Or a group forming a fused aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring adjacent to each other,

Wherein R ¹ to R ⁷ of the C ₁ ~ C ₄₀ in the alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₅ ~ C ₄₀ aryl group, a heteroaryl of C ₅ ~ C ₄₀ An aryl group, a C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₅ to C ₄₀ arylamino group, a C ₅ to C ₄₀ diarylamino group, a C ₆ to C ₄₀ arylalkyl group , The C ₃ to C ₄₀ cycloalkyl group and the C ₃ to C ₄₀ heterocycloalkyl group are each independently selected from the group consisting of deuterium, halogen, nitrile group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, A C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₅ to C ₄₀ A heteroaryl group of 1 to 5 carbon atoms;

Two or more of R ¹ to R ⁴ are each independently a C ₅ to C ₄₀ aryl group.

The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,

Wherein at least one of the one or more organic material layers is an organic material layer including a compound represented by the general formula (1) of the present invention.

In the organic electroluminescent device, the organic compound layer including the compound represented by Formula 1 is preferably a light emitting layer.

When the compound represented by the formula (1) of the present invention is employed as a light emitting layer material of an organic electroluminescent device, color purity and efficiency can be increased as compared with a conventional light emitting material. Accordingly, the organic electroluminescent device according to the present invention exhibits excellent characteristics in terms of luminous efficiency, luminance, power efficiency, driving voltage and lifetime, and thus has a great effect on maximizing the performance and lifetime of a full-color organic EL panel.

The compound represented by the formula (1) of the present invention is an anthracene derivative, which is a core in which an anthracene moiety having excellent device characteristics and a fluorine moiety having excellent fluorescence properties are bonded to each other, for example, indenoanthracene Having a core, and having an aryl group substituted on the core.

In the compound represented by the general formula (I) of the present invention, R ¹ to R ⁷ are the same or different, each independently represent hydrogen, deuterium, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C _A C ₅ to C ₄₀ aryl group, a C ₅ to C ₄₀ heteroaryl group, a C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₅ to C ₄₀ arylamino group, C ₅ ~ C ₄₀ of the diarylamino group, C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ heterocycloalkyl selected from the group consisting of an alkyl group or a; Or adjacent groups to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring.

In addition, the R ¹ to R ⁷ wherein C alkyl group of ₁ ~ C ₄₀ of the, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₅ ~ C ₄₀ aryl group, C ₅ ~ a heteroaryl group of C _40, C ₅ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₅ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ of the diarylamino group, C ₆ ~ C _A C ₃ to C ₄₀ cycloalkyl group and a C ₃ to C ₄₀ heterocycloalkyl group are each independently selected from the group consisting of deuterium, a halogen, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ A C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C A heteroaryl group having ₅ to ₄₀ carbon atoms, or a substituted or unsubstituted heteroaryl group having ₅ to ₄₀ carbon atoms.

The aryl 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 ₅ ~ C ₄₀ of the, C ₅ ~ C ₄₀ A C ₅ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₅ to C ₄₀ arylamino group, a C ₅ to C ₄₀ diarylamino group, a C ₆ to C ₄₀ the arylalkyl group, C ₃ ~ C ₄₀ cycloalkyl group and C ₃ ~ C ₄₀ heterocycloalkyl from the substituent to be introduced is substituted on an alkyl group C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, a group heteroaryl C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a C ₅ ~ C ₄₀ of, each independently represent a deuterium, a halogen, a nitrile group, a nitro group, C ₁ ~ C ₄₀ Al kilgi, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ of the amino group, C ₃ - of C ₄₀ cycloalkyl group, a C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ of A group and a C ₅ ~ at least one second substituent selected from the group consisting of C ₄₀ heteroaryl substituted or additional; Or adjacent fused condensed aliphatic rings, condensed aromatic rings, fused heteroaliphatic rings or fused heteroaromatic rings, or spiro bonds.

In the compound represented by the formula (1) of the present invention, at least two of R ¹ to R ⁴ are each independently a C ₅ to C ₄₀ aryl group, and preferably two or more of R ¹ to R ⁴ are each independently to an aryl group of C ₅ ~ C ₄₀ selected from the group consisting of structural formulas of the general formula (2). Non-limiting examples, wherein R ¹ to R ⁴ of R ¹ and R ^2; Or R ³ and R ⁴ ; Or R ¹ , R ² and R ³ ; Or R ¹ , R ² and R ⁴ ; Or R ¹ , R ² , R ³ and R ⁴ are each independently a C ₅ to C ₄₀ aryl group selected from the group consisting of the following structural formula (2).

In this formula,

k, l, m and n are each independently an integer ranging from 1 to 5;

A plurality of Q ^{1 s} are the same or different from each other, a plurality of Q ^{2 s} are the same or different from each other, a plurality of Q ^{3 s} are the same or different from each other, and the plurality of Q ^{4 s} are the same or different from each other;

Q ¹ , Q ² , Q ³ and Q ⁴ are the same or different and each independently represents hydrogen, deuterium, halogen, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, A C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₅ to C ₄₀ Lt; / RTI >; Or adjacent groups to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring.

Further, the Q ¹ to Q ⁴ alkoxy group of C ₁ ~ a C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of the in, C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ A C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₅ to C ₄₀ heteroaryl group are each independently selected from the group consisting of deuterium, a halogen, a nitrile group, a nitro group, a C ₁ to C ₄₀ the alkyl group, C an alkenyl group of _{2 ~ C 40, C 1 ~} C 40 alkoxy group, C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ of the ~ C ₄₀ aryl group and the addition of a C ₅ ~ one or more third substituent selected from the group consisting of C ₄₀ heteroaryl group may be substituted or unsubstituted.

As a non-limiting example, the C ₅ -C ₄₀ aryl group selected from the group consisting of the structural formula (2) may be phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, An aryl group selected from the group consisting of phenanthryl, pyrenyl, fluorenyl, fluoranthenyl and perylenyl, each of these aryl groups being independently selected from the group consisting of 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 of the amino group, C of ₃ ~ C ₄₀ cycloalkyl An alkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₅ to C ₄₀ heteroaryl group; Or adjacent fused condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings or condensed heteroaromatic rings or spiro bonds.

The following compounds are representative examples of the compound represented by the formula (1) of the present invention, but the compounds represented by the formula (1) of the present invention are not limited thereto.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a compound represented by Formula 1, wherein the organic electroluminescent device comprises a compound represented by Formula 1, .

Specifically, 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 layers sandwiched between the anode and the cathode,

At least one of the one or more organic layers is an organic layer including a compound represented by the general formula (1).

The organic compound layer containing 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 an organic electroluminescent device as a light emitting layer material. In this case, the organic electroluminescent device may have improved luminous efficiency, brightness, power efficiency, thermal stability, and device life. More preferably, the compound represented by Formula 1 may be included in an organic electroluminescent device as a light emitting layer material of green or blue. Therefore, it is preferable that the organic material layer including the compound represented by the formula (1) is a light emitting layer.

In the organic electroluminescent device according to the present invention, the organic material layer other than the organic material layer including the compound represented by the formula (1) of the present invention may be a hole injection layer, a hole transport layer, a light emitting layer, and / or an electron transport layer.

The organic electroluminescent device according to the present invention may have a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and a cathode are sequentially laminated, And the like. An electron injection layer may be disposed on the electron transport layer.

In addition, the organic electroluminescent device according to the present invention may have an insulating layer or an adhesive layer interposed between the electrode and the organic layer, as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

In the organic electroluminescent device according to the present invention, the organic material layer containing the compound represented by Formula 1 may be formed by a vacuum evaporation 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 may be formed by forming a layer of an organic material 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 contain the compound represented by Formula 1 of the present invention ≪ / RTI >

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.

The hole injecting layer, the hole transporting layer and the electron transporting layer are not particularly limited, and ordinary materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[Reaction Scheme 1]

Synthesis Example 1-1 Preparation of Bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) -benzoic acid of Reaction Scheme 1

40 g (1 eq, 0.146 mol) of Bromo-9,9-dimethyl-9H-fluorene and 36.5 g (1.1 eq, 0.161 mol) of 2-bromo phthalic anhydride were placed in a reaction vessel and 1.5 L of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was washed and placed in a Hexane 2 liter container. The solution was filtered and dried to obtain 59.8 g of a bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) ≪ / RTI >

^{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] Synthesis of 9-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H)

20 g (1 eq, 0.0399 mol) of Bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) -benzoic acid was placed in a flask and 50 ml of polyphosphoric acid was added. Followed by heating and stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of 9-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) %).

^{1 H-NMR: 8.29 (t} , 3H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H).

Synthesis Example 1-3 Synthesis of 9-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H-indeno [1,2- b] anthracene -6,11-diol

4.96 g (2.2 eq, 0.054 mol) of 2-bromonaphthrene was added to the flask, and 200 ml of THF was added to dissolve. 38.4 ml (2.5 eq, 0.06 mol) of n-BuLi was slowly added dropwise at -78 deg. After stirring for 1 hour, 11.8 g (1 eq, 0.024 mol) of 9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracene-6,11 (13H) -dione was added. And the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was extracted with washing water and ethyl acetate using distilled water and then subjected to column chromatography to obtain 9-dibromo-13,13-dimethyl-6,11-di (naphthalen- 1,2-b] anthracene-6,11-diol (yield = 78%).

^{1 H-NMR: 8.02 (d} , 3H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 9H), 7.46 (s, 2H), 7.19 (d, 2H), 1.67 (s , 6H).

Synthesis Example 1-4 Synthesis of 9-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H-indeno [1,2- b] anthracene (EMI- Produce

9-dibromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- 21.58g (10eq, 0.13mol) of Potasuumiodide and 19.61g (16.5eq, 0.223mol) of sodium hypophosphite were placed in a flask and 500ml of Acetic acid was added. Followed by heating and stirring for 5 hours. After reaction, the reaction solution was added to an excess amount of distilled water to form a solid, washed and then filtered and subjected to column chromatography to obtain 9-dibromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) [1,2-b] anthracene (EMI 1) (yield = 76%).

^{1 H-NMR: 8.11 (d} , 3H), 8.02 (d, 2H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 4H), 7.46 (s, 2H), 7.19 (d , ≪ / RTI > 2H), 1.67 (s, 6H).

[Reaction Scheme 2]

[Synthesis Example 1-5] Preparation of EMI 2 of Reaction Scheme 2

In Synthesis Example 1-3, EMI 2 could be obtained using 2-bromo-9,9-dimethyl-9H-fluorene instead of 2-bromonaphthrene.

Elemental Analysis: C, 84.00; H, 5.45; Br, 10.54 / HRMS [M] < ⁺ & gt ^; : 758.

[Reaction Scheme 3]

[Synthesis Example 1-6] Preparation of EMI 3 in Reaction Scheme 3

In Synthesis Example 1-3, EMI3 was obtained using 4-bromobiphenyl instead of 2-bromonaphthrene.

Elemental Analysis: C, 83.3; H, 4.91, Br, 11.79 / HRMS [M] < ⁺ & gt ^; : 678.

[Reaction Scheme 4]

[Synthesis Example 1-7] Preparation of EMI 4 in Reaction Scheme 4

In Synthesis Example 1-3, EMI4 was obtained using 3-bromofluoranthene instead of 2-bromonaphthrene.

Elemental Analysis: C, 85.37; H, 4.30, Br, 10.33 / HRMS [M] < ⁺ & gt ^; : 774.

[Synthesis Example 1-8] Preparation of Compound Inv 1-1

10 g (1 eq, 0.016) of 9-dibromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H- indeno [1,2- b] anthracene mol) and naphthalen-2-ylboronic acid 3.2g ( 1.2eq, 0.019mol), Pd (PPh 3) 4 0.65g (0.03eq, 5.7mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution and 15ml Toluene 150ml put After dissolving, the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction mixture was filtered through Celite and then extracted with MC to obtain final compound Inv 1-1 (13,13-dimethyl-6,9,11-tri (naphthalen-2-yl) 13H-indeno [1,2-b] anthracene) (yield = 88.7%).

Inv 1-1: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] < ⁺ & gt ^; : 672.

[Synthesis Examples 1-9 to 1-27] Preparation of Compound Inv 1-2 to Compound Inv 1-20

Synthesis was carried out using the same method as the preparation of compound Inv 1-1 of Synthesis Example 1-8, and it was obtained as a pale yellow solid.

Inv 1-2: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] < ⁺ & gt ^; : 672.

Inv 1-3: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 772

Inv 1-4: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 722

Inv 1-5: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 1-6: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 1-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 1-8: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] < ⁺ & gt ^; : 738

Inv 1-9: Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] < ⁺ & gt ^; : 860

Inv 1-10: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 1-11: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 1-12: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 1-13: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 798

Inv 1-14: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] < ⁺ & gt ^; : 848

Inv 1-15: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 799

Inv 1-16: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 1-17: Elemental Analysis: C, 94.87; H, 5.13, HRMS [M] < ⁺ & gt ^; : 746

Inv 1-18: Elemental Analysis: C, 94.94; H, 5.06 / HRMS [M] < ⁺ & gt ^; : 796

Inv 1-19: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 1-20: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

[Synthesis Example 1-28] Preparation of compound Inv 1-21

(9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2-b] anthracene (1.2 eq, 0.016 mol) of naphthalen-2-ylboronic acid and 0.6 g (0.03 eq, 5.1 mmol) of Pd (PPh ₃ ) ₄ were placed in a flask, and 2M K ₂ CO ₃ saturated aqueous solution (15 ml) and toluene (150 ml), and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of the final compound Inv 1-21 through column chromatography.

Inv 1-21: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

[Synthesis Example 1-29 to Synthesis Example 1-47] Synthesis of Compound Inv 1-22 to Compound Inv 1-40

Synthesis was carried out using the same method as that of the compound Inv 1-21 of Synthesis Example 1-28, and it was obtained as a pale yellow solid.

Inv 1-22: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

Inv 1-23: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] < ⁺ & gt ^; : 854

Inv 1-24: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] < ⁺ & gt ^; : 854

Inv 1-25: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 1-26: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 1-27: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 1-28: Elemental Analysis: C, 93.75; H, 6.25 / HRMS [M] < ⁺ & gt ^; : 870

Inv 1-29: Elemental Analysis: C, 94.32; H, 5.68 / HRMS [M] < ⁺ & gt ^; : 992

Inv 1-30: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 1-31: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 1-32: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 1-33: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] < ⁺ & gt ^; : 930

Inv 1-34: Elemental Analysis: C, 94.25; H, 5.75 / HRMS [M] < ⁺ & gt ^; : 980

Inv 1-35: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] < ⁺ & gt ^; : 930

Inv 1-36: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 1-37: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] < ⁺ & gt ^; : 878

Inv 1-38: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 928

Inv 1-39: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 1-40: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

[Synthesis Example 1-48] Preparation of compound Inv 1-41

(9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2-b] anthracene 3.0 g (1.2 eq, 0.016 mol) of naphthalen-2-ylboronic acid and 0.6 g (0.03 eq, 5.1 mmol) of Pd (PPh ₃ ) ₄ were placed in a flask, and 2M K ₂ CO ₃ saturated aqueous solution and 150 ml of toluene, and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of final compound Inv 1-41 through column chromatography.

Inv 1-41: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

[Synthesis Examples 1-49 to 1-57] Preparation of compound Inv 1-42 to compound Inv 1-50

Synthesis was carried out using the same method as the preparation of compound Inv 1-41 of Synthesis Example 1-48, and it was obtained as a pale yellow solid.

Inv 1-42: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

Inv 1-43: Elemental Analysis: C, 94.54; H, 5.46 / HRMS [M] < ⁺ & gt ^; : 774

Inv 1-44: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 1-45: Elemental Analysis: C, 94.14; H, 5.86 / HRMS [M] < ⁺ & gt ^; : 790

Inv 1-46: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 1-47: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 912

Inv 1-48: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] < ⁺ & gt ^; : 800

Inv 1-49: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 799

Inv 1-50: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] < ⁺ & gt ^; : 848

[Synthesis Example 1-58] Preparation of compound Inv 1-51

10 g (1 eq, 0.012 mol) of the 9-bromo-6,11-di (fluoranthen-3-yl) -13,13-dimethyl-13H- indeno [1,2- b] anthracene mol) and naphthalen-2-ylboronic acid 2.9g ( 1.2eq, 0.015mol), Pd (PPh 3) 4 0.52g (0.03eq, 4.6mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution and 15ml Toluene 150ml And the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction mixture was filtered through Celite and then extracted with MC to obtain 7.8 g (yield: 80%) of final compound Inv 1-51 through column chromatography.

Inv 1-51: Elemental Analysis: C, 95.09; H, 4.91 / HRMS [M] < ⁺ & gt ^; : 820

[Synthesis Example 1-59 to Synthesis Example 1-67] Synthesis of Compound Inv 1-52 to Compound Inv 1-60

Synthesis was carried out using the same method as the preparation of Compound Inv 1-51 of Synthesis Example 1-58, and it was obtained as a pale yellow solid.

Inv 1-52: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] < ⁺ & gt ^; : 848

Inv 1-53: Elemental Analysis: C, 95.14; H, 4.86 / HRMS [M] < ⁺ & gt ^; : 870

Inv 1-54: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] < ⁺ & gt ^; : 846

Inv 1-55: Elemental Analysis: C, 94.77; H, 5.23 / HRMS [M] < ⁺ & gt ^; : 886

Inv 1-56: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] < ⁺ & gt ^; : 846

Inv 1-57: Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] < ⁺ & gt ^; : 1008

Inv 1-58: Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] < ⁺ & gt ^; : 896

Inv 1-59: Elemental Analysis: C, 95.27; H, 4.73 / HRMS [M] < ⁺ & gt ^; : 894

Inv 1-60: Elemental Analysis: C, 95.31; H, 4.69 / HRMS [M] < ⁺ & gt ^; : 944

[Reaction Scheme 5]

[Synthesis Example 2-1] Preparation of 2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid in Reaction Scheme 5

40 g (1 eq, 0.146 mol) of 2-bromo-9,9-dimethyl-9H-fluorene and 23.8 g (1.1 eq, 0.161 mol) of phthalic anhydride were placed in a reaction vessel and 1 liter of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was washed in a Hexane 2 liter container, and then filtered and dried to obtain 50.4 g of 2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid in a yield of 82%.

¹ H-NMR: 8.44 (t, IH), 8.23 (d, IH), 7.96 (m, 6H), 7.72 (m, 5H), 7.55 (t,

Synthesis Example 2-2 Synthesis of 2-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H)

20 g (1 eq, mol) of 2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid was added to the flask and 50 ml of polyphosphoric acid was added. And heated at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 16.6 g of 2-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) 81%).

^{1 H-NMR: 8.29 (t} , 2H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 3H), 1.67 (s, 6H).

Synthesis Example 2-3 Synthesis of 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H-indeno [1,2- b] anthracene -6,11-diol

2-Bromonaphthrene 4.96 g (2.2 eq, 0.054 mol) was added to the flask and dissolved in 200 ml THF. 38.4 ml (2.5 eq, 0.06 mol) of n-BuLi was slowly added dropwise at -78 deg. After stirring for 1 hour, 2-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) -dione, 10 g (1 eq, 0.024 mol) was added. And the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and extracted with ethyl acetate. Then, 2-bromo-13,13-dimethyl-6,11-di- 1,2-b] anthracene-6,11-diol (yield = 72%).

^{1 H-NMR: 8.02 (d} , 2H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 10H), 7.46 (s, 2H), 7.19 (d, 2H), 1.67 (s , 6H).

Synthesis Example 2-4 Synthesis of 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H-indeno [1,2- b] anthracene (EMI- Produce

2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- (10eq, 0.075mol) and 6g (5eq, 0.037mol) of sodium hypophosphite were placed in a flask and 200ml of acetic acid was added. Followed by heating and stirring for 5 hours. After the reaction, the reaction mixture was added to an excess amount of distilled water to form a solid, washed, and then filtered and subjected to column chromatography to obtain 3.56 g (yield = 76%).

^{1 H-NMR: 8.11 (d} , 2H), 8.02 (d, 2H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 5H), 7.46 (s, 2H), 7.19 (d , ≪ / RTI > 2H), 1.67 (s, 6H).

[Reaction Scheme 6]

[Synthesis Example 2-5] Preparation of EMI 6 in Reaction Scheme 6

In Synthesis Example 2-3, EMI6 was obtained using 2-bromo-9,9-dimethyl-9H-fluorene instead of 2-bromonaphthrene.

Elemental Analysis: C, 84.00; H, 5.45; Br, 10.54 / HRMS [M] < ⁺ & gt ^; : 758.

[Reaction Scheme 7]

[Synthesis Example 2-6] Preparation of EMI7 of Reaction Scheme 7

In Synthesis Example 2-3, EMI7 was obtained by using 4-bromobiphenyl instead of 2-bromonaphthrene.

Elemental Analysis: C, 83.3; H, 4.91, Br, 11.79 / HRMS [M] < ⁺ & gt ^; : 678.

[Reaction Scheme 8]

[Synthesis Example 2-7] Preparation of EMI 8 of Reaction Scheme 8

In Synthesis Example 2-3, EMI 8 could be obtained using 3-bromofluoranthene instead of 2-bromonaphthrene.

Elemental Analysis: C, 85.37; H, 4.30, Br, 10.33 / HRMS [M] < ⁺ & gt ^; : 774.

[Synthesis Example 2-8] Preparation of compound Inv 2-1

10 g (1 eq, 0.014) of 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H- indeno [1,2- b] anthracene mol) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g (0.03eq, 5.1mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution and 15ml Toluene 150ml put After dissolving, the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of final compound Inv 2-1 through column chromatography.

¹ H-NMR: 8.11 (d, 3H), 8.02 (d, 3H), 7.95 (m, 3H), 7.61 (m, 5H) , ≪ / RTI > 2H), 1.67 (s, 6H).

Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] < ⁺ & gt ^; : 672.

[Synthesis Example 2-9] Preparation of compound Inv 2-2

10 g (1 eq, 0.014) of 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H- indeno [1,2- b] anthracene mol) and 10- (naphthalen-2-yl) anthracen-9-ylboronic acid 6.5g (1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g ( placed in the flask a 0.03eq, 5.1mmol) 2M K ₂ CO ₃ saturated aqueous solution (15 ml) and toluene (150 ml), and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 10.4 g (yield: 82%) of the final compound Inv 2-2 through column chromatography.

¹ H-NMR: 8.11 (m, 6H), 7.95 (m, 6H), 7.61 (m, 4H), 7.64 , 6H).

Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] < ⁺ & gt ^; : 672.

[Synthesis Example 2-10] Preparation of compound Inv 2-3

10 g (1 eq, 0.014) of 2-bromo-13,13-dimethyl-6,11-di-13H-indeno [1,2- b] anthracene (EMI5) obtained in Synthetic Example 2-4 mol) and 3- (naphthalen-2-yl) phenylboronic acid 4.7g (1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g (0.03eq, 5.1mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution And 150 ml of toluene, and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.9 g (yield: 88%) of the final compound Inv 2-3 by column chromatography.

¹ H-NMR: 8.11 (m, 6H), 7.95 (m, 6H), 7.61 (m, 4H), 7.64 , ≪ / RTI > 4H), 1.67 (s, 6H).

Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 772

[Synthesis Examples 2-11 to 2-19] Preparation of compound Inv 2-4 to compound Inv 2-12

Synthesis was performed using the same method as the preparation of Compound Inv 2- 1 of Synthesis Example 2-8, and it was obtained as a pale yellow solid.

Inv 2-4: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 2-5: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 2-6: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 2-7: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] < ⁺ & gt ^; : 738

Inv 2-8: Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] < ⁺ & gt ^; : 860

Inv 2-9: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 746

Inv 2-10: Elemental Analysis: C, 94.87; H, 5.13 / HRMS [M] < ⁺ & gt ^; : 746

Inv 2-11: Elemental Analysis: C, 94.94; H, 5.06 / HRMS [M] < ⁺ & gt ^; : 796

Inv 2-12: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

[Synthesis Example 2-20] Preparation of compound Inv 2-13

10 g of 6,11-bis (9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2- b] anthracene (EMI6) obtained in Synthetic Example 2-5 (1eq, 0.014mol) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g into the flask (0.03eq, 5.1mmol) 2M K2CO3 saturated aqueous solution 15ml and 150ml Toluene And the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of the final compound Inv 1-21 through column chromatography.

Inv 2-13: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

[Synthesis Examples 2-21 to 2-31] Preparation of the compounds Inv 2-14 to Inv 2-24

Synthesis was carried out using the same method as the preparation of Compound Inv 2- 13 of Synthesis Example 2-20, and it was obtained as a pale yellow solid.

Inv 2-14: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

Inv 2-15: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] < ⁺ & gt ^; : 854

Inv 2-16: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 2-17: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 2-18: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 2-19: Elemental Analysis: C, 93.75; H, 6.25 / HRMS [M] < ⁺ & gt ^; : 870

Inv 2-20: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] < ⁺ & gt ^; : 992

Inv 2-21: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 879

Inv 2-22: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] < ⁺ & gt ^; : 878

Inv 2-23: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 928

Inv 2-24: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

[Synthesis Example 2-32] Preparation of compound Inv 2-25

(9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2-b] anthracene EMI 7) 10g (1eq, 0.014mol ) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g (0.03eq, 5.1mmol) were placed in the flask 2M K2CO3 saturated aqueous solution And 150 ml of toluene, and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite, and then extracted with MC to obtain 9.3 g (yield: 83%) of final compound Inv 2-25 through column chromatography.

Inv 2-25: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

[Synthesis Example 2-33 to Synthesis Example 2-43] Preparation of compound Inv 2-26 to compound Inv 2-36

Synthesis was performed using the same method as the preparation of Compound Inv 2-25 of Synthesis Example 2-32, and it was obtained as a pale yellow solid.

Inv 2-26: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

Inv 2-27: Elemental Analysis: C, 94.54; H, 5.46 / HRMS [M] < ⁺ & gt ^; : 774

Inv 2-28: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 2-29: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 2-30: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 2-31: Elemental Analysis: C, 94.14; H, 5.86 / HRMS [M] < ⁺ & gt ^; : 790

Inv 2-32: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 912

Inv 2-33: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] < ⁺ & gt ^; : 800

Inv 2-34: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 799

Inv 2-35: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] < ⁺ & gt ^; : 848

Inv 2-36: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] < ⁺ & gt ^; : 800

[Synthesis Example 2-44] Preparation of compound Inv 2-37

10 g (1 eq, 0.012 mol) of 9-bromo-6,11-di (fluoranthen-3-yl) -13,13-dimethyl-13H- indeno [1,2- b] anthracene mol) and naphthalen-2-ylboronic acid 2.9g ( 1.2eq, 0.015mol), Pd (PPh 3) 4 0.52g (0.03eq, 4.6mmol) were placed in the flask was dissolved into saturated aqueous 2M K2CO3 and 15ml Toluene 150ml 12 Lt; / RTI > After completion of the reaction, the reaction mixture was filtered through Celite and then extracted with MC to obtain 7.8 g (yield: 80%) of the final compound Inv 2-37 through column chromatography.

Inv 2-37: Elemental Analysis: C, 95.09; H, 4.91 / HRMS [M] < ⁺ & gt ^; : 820

[Synthesis Example 2-45 to Synthesis Example 2-55] Preparation of compound Inv 2-38 to compound Inv 2-48

Synthesis was carried out using the same method as the preparation of Compound Inv 2-37 of Synthesis Example 2-44, and it was obtained as a pale yellow solid.

Inv 2-38: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] < ⁺ & gt ^; : 848

Inv 2-39: Elemental Analysis: C, 95.14; H, 4.86 / HRMS [M] < ⁺ & gt ^; : 870

Inv 2-40: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] < ⁺ & gt ^; : 846

Inv 2-41: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] < ⁺ & gt ^; : 846

Inv 2-42: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] < ⁺ & gt ^; : 846

Inv 2-43: Elemental Analysis: C, 94.77; H, 5.23 / HRMS [M] < ⁺ & gt ^; : 886

Inv 2-44: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] < ⁺ & gt ^; : 846

Inv 2-45: Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] < ⁺ & gt ^; : 1008

Inv 2-46: Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] < ⁺ & gt ^; : 896

Inv 2-47: Elemental Analysis: C, 95.27; H, 4.73 / HRMS [M] < ⁺ & gt ^; : 894

Inv 2-48: Elemental Analysis: C, 95.31; H, 4.69 / HRMS [M] < ⁺ & gt ^; : 944

[Reaction Scheme 9]

[Synthesis Example 3-1] Preparation of 2- (9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid of Reaction Scheme 9

40 g (1 eq, 0.146 mol) of 9,9-dimethyl-9H-fluorene and 36.5 g (1.1 eq, 0.161 mol) of phthalic anhydride were placed in a reaction vessel and 1.5 liter of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was placed in a 2-liter Hexane container, washed and then filtered and dried to obtain 59.8 g of 2- (9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid in a yield of 82%.

^{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 3-2] Preparation of 13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) -dione (EMI9)

20 g (1 eq, 0.0399 mol) of 2- (9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid was added to the flask and 50 ml of polyphosphoric acid was added. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of 13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) -dione (EMI- 78%).

^{1 H-NMR: 8.29 (t} , 3H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H).

[Reaction Scheme 10]

[Synthesis Example 3-3] Preparation of 2- (9,9'-spirobi [fluorene] -2-ylcarbonyl) benzoic acid of Reaction Scheme 10

10 g (1 eq, 0.06 mol) of spirofluorene and 10.2 g (1.1 eq, 0.069 mol) of phthalic anhydride were placed in a reaction vessel and 1 liter of dichloromethane was added. 13.8 g (1.5 eq, 0.1 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was placed in a 2-liter Hexane container, washed, and then filtered and dried to obtain 22 g of 2- (9,9'-spirobi [fluorene] -2-ylcarbonyl) benzoic acid in a yield of 82%.

^{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 3-4 Preparation of spiro [fluorene-9,13'-indeno [1,2-b] anthracene] -6 ', 11'-dione (EMI10)

20 g (1 eq, 0.04 mol) of 2- (9,9'-spirobi [fluorene] -2-ylcarbonyl) benzoic acid were placed in a flask and 50 ml of polyphosphoric acid was added. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of spiro [fluorene-9,13'-indeno [1,2-b] anthracene] -6 ', 11'-dione (EMI- = 78%).

^{1 H-NMR: 8.29 (t} , 3H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H).

[Synthesis Example 3-5] Preparation of compound Inv 3-1

2-Bromonaphthrene (5.3 g, 2.2 eq, 0.067 mol) was added to the flask, and 200 ml of THF was added to dissolve the solution. 45.3 ml (2.5 eq, 0.075 mol) of n-BuLi was slowly added dropwise at -78 ° C. 10 g (1 eq, 0.03 mol) of 13,13-dimethyl-13H-indeno [1,2-b] anthracene-6,11-dione (EMI-9) obtained in Synthesis Example 3-2 , And the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was extracted with washing and ethyl acetate as distilled water, and then subjected to column chromatography to obtain 13,13-dimethyl-6,11-di (naphthalen-2-yl) b] anthracene-6,11-diol (yield = 72%).

5 g (1 eq, 0.0075 mol) of 13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- 12.45g (10eq, 0.075mol) of potassium iodide and 6g (5eq, 0.037mol) of sodium hypophosphite were placed in a flask, and 200ml of acetic acid was added thereto, followed by heating and stirring for 5 hours. After the reaction, the reaction solution was added to an excess amount of distilled water to form a solid and washed, and then filtered and subjected to column chromatography to obtain the final compound 13,13-dimethyl-6,11-di (naphthalen-2-yl) , 2-b] anthracene (yield = 76%).

Inv 3-1: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] < ⁺ & gt ^; : 546

[Synthesis Examples 3-6 to 3-33] Preparation of compound Inv 3-2 to compound Inv 3-29

It was synthesized using the same method as the preparation of compound Inv 3-1 of Synthesis Example 3-5, and it was obtained as a pale yellow solid.

Inv 3-2: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] < ⁺ & gt ^; : 598

Inv 3-3: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] < ⁺ & gt ^; : 678

Inv 3-4: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] < ⁺ & gt ^; : 598

Inv 3-5: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 646

Inv 3-6: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 646

Inv 3-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 3-8: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] < ⁺ & gt ^; : 546

Inv 3-9: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] < ⁺ & gt ^; : 694

Inv 3-10: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 3-11: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] < ⁺ & gt ^; : 794

Inv 3-12: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 646

Inv 3-13: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 3-14: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] < ⁺ & gt ^; : 922

Inv 3-15: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] < ⁺ & gt ^; : 668

Inv 3-16: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] < ⁺ & gt ^; : 720

Inv 3-17: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] < ⁺ & gt ^; : 800

Inv 3-18: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] < ⁺ & gt ^; : 720

Inv 3-19: Elemental Analysis: C, 95.28; H, 4.72 / HRMS [M] < ⁺ & gt ^; : 768

Inv 3-20: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] < ⁺ & gt ^; : 694

Inv 3-21: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 3-22: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] < ⁺ & gt ^; : 794

Inv 3-23: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 646

Inv 3-24: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 3-25: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] < ⁺ & gt ^; : 922

Inv 3-26: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] < ⁺ & gt ^; : 668

Inv 3-27: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] < ⁺ & gt ^; : 720

Inv 3-28: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] < ⁺ & gt ^; : 800

Inv 3-29: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] < ⁺ & gt ^; : 720

[Reaction Scheme 11]

Synthesis Example 4-1 Preparation of 4-bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) -benzoic acid in Reaction Scheme 11

40 g (1 eq, 0.146 mol) of 2-bromo-9,9-dimethyl-9H-fluorene and 36.5 g (1.1 eq, 0.161 mol) of 2-bromo phthalic anhydride were placed in a reaction vessel and 1.5 liter of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was washed in a Hexane 2 liter container and then filtered and dried to obtain 59.8 g of 4-bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) 82%.

^{1 H-NMR: 8.44 (t} , 1H), 8.23 (d, 1H), 7.96 (m, 5H), 7.72 (m, 5H), 7.55 (t, 1H), 1.67 (s, 6H).

[Synthesis Example 4-2] Synthesis of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H)

Polyphosphoric acid (50 ml) was added to 20 g (1 eq, 0.0399 mol) of 4-bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) -benzoic acid. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) = 78%).

^{1 H-NMR: 8.29 (t} , 2H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H).

[Synthesis Example 4-3] Synthesis of 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H-indeno [1,2-b] anthracene-6,11-

20 g (1 eq, 0.041 mol) of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracene-6,11 (13H) -dione was placed in a flask and 150 ml of MeOH was added. 6.2 g (4 eq, 0.164 mol) of sodium borohydride was added slowly at 0 ° C. After stirring for 5 hours, add ice-water slowly. MC and then Hex recrystallized to obtain 15 g (yield: 78%) of 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H- indeno [1,2- b] anthracene-6,11- .

HRMS [M] ⁺ : calcd 486.6, found 485.97.

[Synthesis Example 4-4] Synthesis of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2-b] anthracen-11 (13H)

(1 eq, 0.003 mol) of 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H-indeno [1,2- b] anthracene-6,11-diol and 100 ml of 5N HCl . After stirring for 5 hours, the resulting solid was filtered and washed several times with distilled water. And dried naturally to obtain 13.2 g (yield: 92%) of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracen-11 (13H) -one.

HRMS [M] ⁺ : calcd 468.18, found 465.9

[Synthesis Example 4-5] Preparation of 2,9-dibromo-13,13-dimethyl-13H-indeno [1,2-b] anthracene (EMI11)

13 g (1 eq, 0.027 mol) of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracen-11 (13H) -one were placed in a flask and 200 ml of IPA was added. 3.1 g (3 eq, 0.081 mol) of sodium borohydride was slowly added at 0 ° C, and the mixture was heated and stirred at 100 ° C. After stirring for 24 to 36 hours, the mixture was cooled to room temperature and then ice-water was slowly added thereto. The resulting solid was filtered, washed several times with distilled water, and then dried. 8.5 g (yield: 70%) of 2,9-dibromo-13,13-dimethyl-13H-indeno [l, 2-b] anthracene (EMI11) was obtained through column chromatography.

HRMS [M] < ⁺ >: calcd 452.1 found 449.9.

[Reaction Scheme 12]

[Synthesis Example 4-6] Synthesis of 2,9-dibromo-6,11,13,13-tetramethyl-11,13-dihydro-6H-indeno [1,2- b] anthracene-6,11-diol Produce

(1 eq, 0.02 mol), and 200 ml of THF was added to the flask. The flask was charged with 10 g (1 eq, 0.02 mol) of 2,9-dibromo-13,13-dimethyl-6H- indeno [1,2- b] anthracene-6,11 1 g (2.2 eq, 0.045 mol) of methyllithium was slowly added at 0 ° C, and the mixture was heated and stirred at 60 ° C. After stirring for 12 hours, the mixture was cooled to room temperature, and then ice-water was slowly added thereto. MC and then rinsed several times with distilled water. After removing the solvent, 2.5 g of 2,9-dibromo-6,11,13,13-tetramethyl-11,13-dihydro-6H-indeno [1,2-b] anthracene-6,11- Yield = 25%).

Elemental Analysis: C, 58.39; H, 4.31; Br, 31.08, 0. 6.22 / HRMS [M] < ⁺ & gt ^; : 514.

[Synthesis Example 4-7] Preparation of 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2-b] anthracene (EMI12)

2.5 g of 2,9-dibromo-6,11,13,13-tetramethyl-11,13-dihydro-6H-indeno [1,2-b] anthracene-6,11- Was used to obtain 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2-b] anthracene (EMI12).

Elemental Analysis: C, 62.53; H, 4.20; Br, 33.28 / HRMS [M] < ⁺ & gt ^; : 477.

[Reaction Scheme 13]

Synthesis Example 4-8 Synthesis of 2,9-dibromo-6,11-di-tert-butyl-13,13-dimethyl-11,13-dihydro-6H-indeno [1,2- b] anthracene- Preparation of 6,11-diol

Synthesis of 2,9-dibromo-6,11-di-tert-butyl-13,13-dimethyl-11,13-dihydro-6H-indeno [1,2- b] anthracene -6,11-diol (yield = 20%).

Elemental Analysis: C, 62.22; H, 5.73; Br, 27.71; O, 5.35 / HRMS [M] < ⁺ & gt ^; : 598.

[Synthesis Example 4-9] Preparation of 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2-b] anthracene (EMI13)

2 g (yield = 77%) of 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2-b] anthracene was synthesized using the same method as in Synthesis Example 4-8 .

Elemental Analysis: C, 65.97; H, 5.71; Br, 28.31 / HRMS [M] < ⁺ & gt ^; : 564.

[Synthesis Example 4-10] Preparation of compound Inv 4-1

10 g (1 eq, 0.022 mol) of 2,9-dibromo-13,13-dimethyl-13H-indeno [1,2-b] anthracene (EMI11) obtained in Synthetic Example 4-5 and 6.2 g of naphthalen- (2.2 eq, 0.048 mol) and 0.76 g (0.03 eq, 6.61 mmol) of Pd (PPh ₃ ) ₄ were placed in a flask, and 20 ml of a saturated aqueous solution of 2M K ₂ CO ₃ and 300 ml of toluene were added and dissolved. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.96 g (yield: 83%) of final compound Inv 4-1 by column chromatography

Inv 4-1: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] < ⁺ & gt ^; : 546

[Synthesis Examples 4-11 to 4-39] Preparation of compound Inv 4-2 to compound Inv 4-30

Synthesis was carried out using the same method as the preparation of compound Inv 4-1 of Synthesis Example 4-10, and it was obtained as a pale yellow solid.

Inv 4-2: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] < ⁺ & gt ^; : 546

Inv 4-3: Elemental Analysis: C, 94.79; H, 5.21 / HRMS [M] < ⁺ & gt ^; : 696

Inv 4-4: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] < ⁺ & gt ^; : 698

Inv 4-5: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] < ⁺ & gt ^; : 698

Inv 4-6: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 4-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 4-8: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] < ⁺ & gt ^; : 694

Inv 4-9: Elemental Analysis: C, 93.76; H, 6.24 / HRMS [M] < ⁺ & gt ^; : 678

Inv 4-10: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] < ⁺ & gt ^; : 923

Inv 4-11: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] < ⁺ >: 574

Inv 4-12: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] < ⁺ >: 574

Inv 4-13: Elemental Analysis: C, 94.44; H, 5.56 / HRMS [M] < ⁺ & gt ^; : 724

Inv 4-14: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] < ⁺ & gt ^; : 626

Inv 4-15: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] < ⁺ & gt ^; : 626

Inv 4-16: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 778

Inv 4-17: Elemental Analysis: C, 94.18; H, 5.82 / HRMS [M] < ⁺ & gt ^; : 726

Inv 4-18: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 722

Inv 4-19: Elemental Analysis: C, 93.44; H, 6.56 / HRMS [M] < ⁺ & gt ^; : 706

Inv 4-20: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 951

Inv 4-21: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 4-22: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 4-23: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] < ⁺ & gt ^; : 694

Inv 4-24: Elemental Analysis: C, 93.76; H, 6.24 / HRMS [M] < ⁺ & gt ^; : 678

Inv 4-25: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] < ⁺ & gt ^; : 923

Inv 4-26: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] < ⁺ >: 574

Inv 4-27: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] < ⁺ >: 574

Inv 4-28: Elemental Analysis: C, 94.44; H, 5.56 / HRMS [M] < ⁺ & gt ^; : 724

Inv 4-29: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] < ⁺ & gt ^; : 626

Inv 4-30: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] < ⁺ & gt ^; : 626

[Reaction Scheme 14]

[Synthesis Example 5-1] Preparation of 2,2'-dibromobiphenyl of Reaction Scheme 14

1,2-dibromobenzene 10 g (1 eq, 0.042 mol) was placed in a flask and 150 ml of THF was added. After slowly adding 14.2 ml (0.5 eq, 0.021 mol) of n-buthyllithium at -78 ° C, the temperature was raised to room temperature. After stirring for 1 hour, distilled water was added and stirred for 1 minute. After extracting hexane and removing the solvent, 5 g (yield: 65%) of 2,2'-dibromobiphenyl was obtained by column chromatography.

Elemental Analysis: C, 46.20; H, 2.58; Br, 51.22 / HRMS [M] < ⁺ & gt ^; : 312.

[Synthesis Example 5-2] Synthesis of 5,5-dimethyl-5H-dibenzo [b, d] silole of Reaction Scheme 14

1,2-dibromobiphenyl were placed in a 10 g (1 eq, 0.032 mol) flask and 150 ml of THF was added. Add slowly 24.1 ml (1.2eq, 0.038mol) of n-buthyllithium at -78 ° C, stir for 30 minutes and add 4.1g (1.2eq, 0.038mol) of chlorotrimethylsilane. After stirring for 4 hours, distilled water was added and stirred for about 10 minutes. After extraction with hexane and solvent removal, 5.17 g (yield = 77%) of 5,5-dimethyl-5H-dibenzo [b, d] silole was obtained by column chromatography.

Elemental Analysis: C, 79.94; H, 6.71; Si, 13.35 / HRMS [M] < ⁺ & gt ^; : 210.

[Synthesis Example 5-3] Synthesis of 4-bromo-2- (5,5-dimethyl-5H-dibenzo [b, d] silole-3-carbonyl) benzoic acid

5 g (1 eq, 0.023 mol) of 5,5-dimethyl-5H-dibenzo [b, d] silole and 5.7 g (1.1 eq, 0.025 mol) of 2-bromo phthalic anhydride were placed in a flask and 200 ml of dichloromethane was added. 4.5 g (1.5 eq, 0.0345 mol) of aluminum chloride was gradually added at 0 ° C, then the temperature was raised to room temperature, and the mixture was stirred for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was placed in a 500 ml Hexane container, washed, and then filtered and dried to obtain 6.5 g of 4-bromo-2- (5,5-dimethyl-5H-dibenzo [b, d] silole-3-carbonyl) benzoic acid (Yield = 65%).

Elemental Analysis: C, 60.42; H, 3.92; Br, 18.27; O, 10.97; Si, 6.42

HRMS [M] < ⁺ & gt ^; : 436.

Synthesis Example 5-4 Preparation of 9-bromo-5,5-dimethyl-5H-anthra [2,3-b] benzo [d] silole-7,12-dione (EMI14)

5 g (1 eq, 0.011 mol) of 4-bromo-2- (5,5-dimethyl-5H-dibenzo [b, d] silole-3-carbonyl) benzoic acid and 50 ml of polyphosphoric acid were added. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 9-bromo-5,5-dimethyl-5H-anthra [2,3-b] benzo [d] silole-7,12- 4.5 g (Yield = 72%) was obtained.

Elemental Analysis: C, 63.01; H, 3.61; Br, 19.05; O, 7.63; Si, 6.70

HRMS [M] < ⁺ & gt ^; : 418

[Synthesis Example 5-5] Preparation of compound Inv 5-1

3.2 g (1.2 eq, 0.019 mol) of naphthalen-2-ylboronic acid and 0.65 g (0.03 eq, 5.7 mmol) of Pd (PPh ₃ ) _{4 were} added to 10 g (1 eq, 0.016 mol) of EM- 15 ml of 2M K ₂ CO ₃ saturated aqueous solution and 150 ml of toluene were added to the flask, and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain final compound Inv 5-1 (13,13-dimethyl-6,9,11-tri (naphthalen-2-yl) 13H-indeno [1,2-b] anthracene (yield: 88.7%).

Inv 5-1: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] < ⁺ & gt ^; : 672.

[Synthesis Example 5-6 to Synthesis Example 5-51] Preparation of compound Inv 5-2 to compound Inv 5-47

Synthesis was carried out using the same method as the preparation of compound Inv 5-1 of Synthesis Example 5-5, and it was obtained as a pale yellow solid.

Inv 5-2: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] < ⁺ & gt ^; : 672.

Inv 5-3: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 772

Inv 5-4: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 722

Inv 5-5: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 5-6: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 5-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] < ⁺ & gt ^; : 698

Inv 5-8: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] < ⁺ & gt ^; : 738

Inv 5-9: Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] < ⁺ & gt ^; : 860

Inv 5-10: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 5-11: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 5-12: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 5-13: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 798

Inv 5-14: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] < ⁺ & gt ^; : 848

Inv 5-15: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 799

Inv 5-16: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 5-17: Elemental Analysis: C, 94.87; H, 5.13 / HRMS [M] < ⁺ & gt ^; : 746

Inv 5-18: Elemental Analysis: C, 94.94; H, 5.06 / HRMS [M] < ⁺ & gt ^; : 796

Inv 5-19: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 5-20: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] < ⁺ & gt ^; : 748

Inv 5-21: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

Inv 5-22: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

Inv 5-23: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] < ⁺ & gt ^; : 854

Inv 5-24: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] < ⁺ & gt ^; : 854

Inv 5-25: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 5-26: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 5-27: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] < ⁺ & gt ^; : 830

Inv 5-28: Elemental Analysis: C, 93.75; H, 6.25 / HRMS [M] < ⁺ & gt ^; : 870

Inv 5-29: Elemental Analysis: C, 94.32; H, 5.68 / HRMS [M] < ⁺ & gt ^; : 992

Inv 5-30: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 5-31: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 5-32: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 5-33: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] < ⁺ & gt ^; : 930

Inv 5-34: Elemental Analysis: C, 94.25; H, 5.75 / HRMS [M] < ⁺ & gt ^; : 980

Inv 5-35: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] < ⁺ & gt ^; : 930

Inv 5-36: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 5-37: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] < ⁺ & gt ^; : 878

Inv 5-38: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 928

Inv 5-39: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 5-40: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 5-41: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] < ⁺ & gt ^; : 880

Inv 5-42: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] < ⁺ & gt ^; : 804

Inv 5-43: Elemental Analysis: C, 94.54; H, 5.46 / HRMS [M] < ⁺ & gt ^; : 774

Inv 5-44: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 5-45: Elemental Analysis: C, 94.14; H, 5.86 / HRMS [M] < ⁺ & gt ^; : 790

Inv 5-46: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] < ⁺ & gt ^; : 750

Inv 5-47: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] < ⁺ & gt ^; : 912

[ Synthetic example  6-1] Compound Inv  Manufacturing of 6-1

[Reaction Scheme 15]

≪ Step 1 > 2- (9,9- dimethyl -9H- 불소 -2- carbonyl ) benzoic acid  (Compound 1-3)

Dimethylfluorene (20 g, compound 1-1) and phthalic anhydride (23 g, compound 1-2) were dissolved in dichloromethane and stirred at room temperature, followed by slowly adding 20.5 g of aluminum chloride at 0 ° C.

When the reaction mixture stabilized, it was stirred at reflux for 6 hours at 40 ° C, concentrated and purified by column chromatography. Thereafter, the solution was dissolved in dichloromethane, precipitated in n-hexane and filtered, and the obtained solid was dried under reduced pressure to give the title compound (27 g, yield 76%).

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

≪ Step 2 > 13, 13- dimethyl -6H- indeno [1,2-b] anthracene-6,11 (13H) - dione  (Compound 1-4) Synthesis of

50 ml of polyphosphoric acid was added to the compound (27 g) obtained in <Step 1>, and the mixture was heated and stirred at 130 ° C for 3 hours. Then, 400 ml of ice water was added at room temperature, and the solid was filtered, washed with methanol, and dried under reduced pressure to obtain the title compound (19 g, yield 74%).

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

<Step 3> 13, 13- dimethyl -11,13- dihydro -6H- indeno [1,2-b] anthracene-6,11-diol (Compound 1-5)

The compound (64 g) obtained by repeating the process of <Step 2> several times was dispersed in 2 L of methanol, and sodium borohydride (30 g) was added in three portions at 0 ° C. slowly. After stirring at 0 ° C for 3 hours, 3 L of water was added and the mixture was filtered. The obtained solid was thoroughly washed with water and then dried naturally.

<Step 4> 13, 13- dimethyl -6H- indeno [1,2-b] anthracene-11 (13H) - one (Compound 1-6) Synthesis of

The product obtained in Step 3 was dispersed in 300 ml of 5N HCl and refluxed with stirring for 20 hours. After cooling to room temperature, the mixture was filtered using 300 ml of water.

The obtained solid was sufficiently washed with water and dried under reduced pressure to give the title compound (60.3 g, yield 98.5%).

<Step 5> 13, 13- dimethyl -13H-indeno [1,2-b] anthracene (Compound 1-7) Synthesis of

The compound (60.3 g) obtained in <Step 4> was dispersed in 1.5 L of isopropanol and 36.7 g of sodium borohydride was added. The reaction mixture was refluxed for 22 hours and then cooled to room temperature. The red reaction product was poured into 2 L of water and stirred. The solid was filtered and washed with water sufficiently to obtain an ocher-colored solid.

Water was removed and the residue was purified by column chromatography to give the title compound (27.9 g, yield 48.7%) as a light green solid.

^{1 H 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, IH), 7.40 (m, 2H), 7.35

Mass: [M + 1] &lt; + &gt; 294

&Lt; Step 6 > bromo -13,13- dimethyl -13H-indeno [1,2-b] anthracene (Compound 1-8) Synthesis of

The compound (27.9 g) obtained in Step 5 was dissolved in 400 ml of dimethylformamide, and 18.5 g of N-bromosuccinimide was added.

The reaction mixture was stirred at room temperature for 1 hour, poured into 1 L of water and the solid was filtered. The solid was sufficiently washed with water and methanol, and dried under reduced pressure to give the title compound (33.3 g, yield 94.2%) as a pale yellow solid.

^{1 H 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, IH), 7.53 (m, IH), 7.49

Mass: [M + 1] &lt; + &gt; 372

<Step 7> 13, 13- dimethyl -11- phenyl -13H-indeno [1,2-b] anthracene (Compound 1-10)

The compound (33.3 g) obtained in Step 6 and phenylboronic acid (Compound 1-9, 13 g) were dissolved in 450 ml of toluene, 3 g of tetrakis (triphenylphosphine) palladium (0) and 150 ml of 2N sodium carbonate were added and stirred under reflux.

The reaction mixture was cooled to room temperature and the organic and aqueous layers were separated, washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated.

Purification by column chromatography (n-hexane to n-hexane / dichloromethane = 9/1) followed by precipitation in n-hexane and filtration afforded the title compound (32.3 g, 97.8%) as a yellow solid.

^{1 H NMR (500MHz, THF-} d8) 8.54 (s, 1H), 8.49 (s, 1H), 8.37 (d, 1H), 7.86 (m, 2H), 7.80 (m, 2H), 7.71 (s, 1H ), 7.64 (m, 3H), 7.54 (m, 3H)

Mass: [M + 1] &lt; + &gt; 370

<Step 8> 6- bromo -13,13- dimethyl -11- phenyl -13H-indeno [1,2-b] anthracene (Compound 1-11) Synthesis of

The compound (32.3 g) obtained in Step 7 was dissolved in 400 ml of dimethylformamide and 17.1 g of N-bromosuccinimide was added.

The reaction mixture was stirred at room temperature for 1 hour and then poured into 1 liter of water. The resulting solid was filtered, washed sufficiently with water and methanol, and dried under reduced pressure to give the title compound (38.2 g, yield 97.5%) as a pale yellow solid.

^{1 H NMR (500MHz, THF-} d8) 8.64 (s, 1H), 8.58 (d, 1H), 7.92 (s, 1H), 7.62 (m, 6H), 7.51 (d, 1H), 7.47 (dd, 2H ), 7.36 (m, 2H), 7.26 (t, IH), 1.65 (s, 6H)

Mass: [M + 1] &lt; + &gt; 448

<Step 9> pyrene -One- boronic acid (Compound 1-13) Synthesis of

1-Bromophenylene (Compound 1-12, 30 g) was dissolved in 500 ml of tetrahydrofuran and cooled to -78 ° C. N-butyllithium solution (1.6N, 80 mL) was slowly added dropwise while stirring for 1 hour and 30 mL of triisopropylborate was added.

The reaction solution was stirred at room temperature for 15 hours while gradually raising the temperature. 250 ml of 1N HCl was slowly added, and the aqueous layer was removed. The organic layer was washed with saturated ammonium chloride solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. After boiling in n-hexane and recrystallization, the title compound (15.7 g, 60.0%) was obtained as an off-white solid.

<Step 10> 13, 13- dimethyl -11- phenyl -6- ( pyren -One- yl ) -13H-indeno [1,2-b] anthracene (Compound Inv  6-1)

20 g of the compound obtained in Step 8 and 11.8 g of the compound obtained in Step 9 were dissolved in 200 ml of toluene and then 1.4 g of tetrakis (triphenylphosphine) palladium (0) and 60 ml of a 2N sodium carbonate aqueous solution were added thereto, Lt; / RTI &gt;

After the reaction solution was cooled to room temperature and the organic layer and the water layer were separated, the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated.

Purification by column chromatography (n-hexane to n-hexane / dichloromethane = 9/1) followed by precipitation in n-hexane and filtration afforded the title compound (5.75 g, 25.2%) as a pale yellow solid .

^{1 H NMR (500MHz, THF-} d8) 8.48 (d, 1H), 8.31 (m, 2H), 8.26 (m, 1H), 8.17 (dd, 1H), 8.13 (dd, 1H), 8.08 (s, 1H 1H), 7.44 (d, 1H), 7.34 (m, 1H), 8.04 (d, , 7.26 (m, 4 H), 7.12 (m, 1 H), 1.28 (s, 3 H), 1.14

Mass: [M] + 546

[ Synthetic example  6-2] Compound Inv  Manufacturing of 6-2

20 g of the compound obtained in Step 8 of Synthesis Example 6-1 and 14.6 g of 4,4,5,5-tetramethyl-2- (phenanthren-9-yl) -1,3,2-dioxaborolane were dissolved in toluene , 1.4 g of tetrakis (triphenylphosphine) palladium (0), 60 ml of 2N sodium carbonate and 1.8 ml of aliquat 336 were added and stirred under reflux for 21 hours.

The reaction solution was cooled to room temperature, and the organic layer and the water layer were separated. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated.

Purification by column chromatography (n-hexane to n-hexane / dichloromethane = 9/1) followed by precipitation in n-hexane and filtration afforded the title compound (12.7 g, 58.0%) as a pale yellow solid .

^{1 H NMR (500MHz, THF-} d8) 8.98 (m, 2H), 8.04 (s, 1H), 7.99 (d, 1H), 7.94 (s, 1H), 7.79 (m, 1H), 7.68 (m, 4H ), 7.61 (m, 5H), 7.58 (d, IH), 7.46 (d, IH), 7.35 , 1.18 (s, 3H)

Mass: [M] &lt; + &gt; 570

[ Synthetic example  6-3] Compound Inv  Manufacture of 6-3

(20 g) obtained in Step 8 of Synthesis Example 6-1 and 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborolane (17 g) were dissolved in toluene 200 1.4 g of tetrakis (triphenylphosphine) palladium (0), 60 ml of 2N sodium carbonate and 1.8 ml of aliquat 336 were added and stirred under reflux for 21 hours.

The reaction solution was cooled to room temperature, and the organic layer and the water layer were separated. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated.

Purification by column chromatography (n-hexane to n-hexane / dichloromethane = 9/1) followed by precipitation in n-hexane and filtration afforded the title compound (11.5 g, 48.2%) as a pale yellow solid .

^{1 H NMR (500MHz, THF-} d8) 9.15 (s, 1H), 8.93 (d, 2H), 8.21 (m, 2H), 8.10 (d, 2H), 8.06 (m, 2H), 7.91 (d, 2H ), 7.78 (s, 1H), 7.67 (m, 4H), 7.44 (m, 4H), 7.28 (dd, 2H) , 1.14 (s, 3H)

Mass: [M] &lt; + &gt; 596

[ Example  1] Organic Field  Manufacturing of light emitting device

An organic electroluminescent device was fabricated in the following manner.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine. Thereafter, an organic electroluminescent device having the structure shown in Table 1 was fabricated.

Specifically, DS-HIL (Doosan) was thermally vacuum-deposited on the prepared ITO (anode) to form a hole injecting layer. On the hole injecting layer, a hole transporting material a-NPB ( N , N - di (naphthalene-1-yl) -N , N- diphenylbenzidine) was vacuum deposited to a thickness of 150 Å to form a hole transport layer.

Compound Inv 1-1 and DS-Dopant (Doosan) manufactured by Synthetic Example were vacuum deposited to a thickness of 300 Å to form a light emitting layer. Alq3, an electron transporting material, was vacuum deposited on the light emitting layer to a thickness of 250 Å To form an electron transporting layer. Thereafter, LiF as an electron injecting material was deposited to a thickness of 10 Å to form an electron injecting layer, and aluminum was vacuum deposited thereon to a thickness of 2000 Å to form a cathode.

[ Example  2 ~ 214] Organic Field  Manufacturing of light emitting device

The compounds Inv 1-2 to Inv 1-60, the compounds Inv 2-1 to Inv 2-48, the compounds Inv 3-1 to Inv 3-29, the compounds Inv 4-1 to Inv 4 -30, and the compounds Inv 5-1 to Inv 5-47, respectively, were used in place of the compounds Inv 5-1 to Inv 5-47.

[ Example  215 ~ 217] Organic Field  Manufacturing of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that each of the compounds Inv 6-1 to Inv 6-3 was used instead of the compound Inv 1-1 in forming the light emitting layer and C-545T was used as a dopant .

[Comparative Example 1] Production of organic electroluminescent device

Except that the compounds Inv 1-1 and DS-Dopant (Doosan) manufactured in the synthesis example at the time of forming the light emitting layer were replaced with Alq3 and C-545T represented by Green elements, A light emitting device was fabricated.

Hole injection layer
(HIL) Hole transport layer
(HTL) The organic light-
(EML) Electron transport layer
(ETL) Electron injection layer
(EIL) cathode
(cathode) Examples 1-214 DS-HIL a-NPB Inv 1-1 to 5-47 + DS-dopant Alq3 LiF Al Examples 215-217 DS-HIL a-NPB Inv 6-1 to 6-3 + C-545T Alq3 LiF Al Comparative Example 1 DS-HIL a-NPB Alq3 + C-545T Alq3 LiF Al

[ Experimental Example ]

Each of the organic electroluminescent devices manufactured in Examples 1 to 217 and Comparative Example 1 was measured for luminous efficiency at a current density of 10 mA / cm 2, and the results are shown in Tables 2 to 7 below.

As described above, according to the present invention, the efficiency can be increased by about 40% or more in comparison with the case of using the conventional light emitting material. This result can be regarded as a result of the fact that the energy transfer from the host to the dopant is facilitated by the combination of the materials of the present invention rather than the host and dopant system of the conventional Alq3 and C-545T. This has a great effect on maximizing the performance of a full-color organic EL panel.

Compound The driving voltage (V) The luminous efficiency (cd / A) Inv 6-1 4.9 19.9 Inv 6-2 5.1 21.2 Inv 6-3 5.3 22.1

Table 7 shows that the organic electroluminescent device using the compound according to the present invention as a host material is superior in terms of voltage and efficiency to organic electroluminescent devices using conventional Alq3, and the lifetime is particularly improved.

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 (8)

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

(1) X is CR ⁶ R ^7, and; R ¹ and R ² are different from each other and each independently represents a C ₆ to C ₄₀ aryl group selected from the group consisting of structural formulas of the following formula (2), provided that any one of R ¹ and R ²

, R &lt; ¹ &gt; and R &lt; ² &

, And when R &lt; ¹ &gt; and R &lt; ² &

Is excluded; R ³ and R ⁴ are hydrogen; R ⁵ to R ⁷ are the same or different and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ An aryl group, a C ₅ to C ₄₀ heteroaryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diaryl An amino group, an arylalkyl group having ₇ to ₄₀ carbon atoms, a cycloalkyl group having ₃ to ₄₀ carbon atoms, and a heterocycloalkyl group having ₃ to ₄₀ carbon atoms, Wherein R ⁵ to R ⁷ of the C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, a heteroaryl of C ₅ ~ C ₄₀ An aryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, a C ₇ to C ₄₀ arylalkyl group , The C ₃ to C ₄₀ cycloalkyl group and the C ₃ to C ₄₀ heterocycloalkyl group are each independently selected from the group consisting of deuterium, halogen, nitrile group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, A C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₅ to C ₄₀ A heteroaryl group of 1 to 5 carbon atoms; (2)

In Formula 2, k, l, m and n are each independently an integer ranging from 1 to 5; A plurality of Q ^{1 s} are the same or different from each other, a plurality of Q ^{2 s} are the same or different from each other, a plurality of Q ^{3 s} are the same or different from each other, and the plurality of Q ^{4 s} are the same or different from each other; Q ¹ , Q ² , Q ³ and Q ⁴ are the same or different and each independently represents hydrogen, deuterium, halogen, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, A C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₅ to C ₄₀ &Lt; / RTI &gt; delete 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode, Wherein at least one of the one or more organic compound layers is an organic compound layer containing a compound represented by the general formula (1) according to claim 4. The organic electroluminescent device according to claim 6, wherein the organic compound layer including the compound represented by Formula 1 is a light emitting layer. 5. The compound according to claim 4, wherein the compound selected from the group consisting of the compounds Inv 6-1 to Inv 6-18: