KR20110083442A - Organic light device and organic light compound for the same - Google Patents

Abstract

PURPOSE: An organic light device and an organic light compound for the same are provided to obtain excellent generation efficiency when applied to a light device and light compound for solar power generation, thereby enabling the use as OLED materials. CONSTITUTION: An organic light device comprises first and second electrodes and a monolayered organic film. The monolayered organic film is formed between the first electrode and the second electrode. A derivative is independently hydrogen, substituted or unsubstituted C6-C50 aryl group, substituted or unsubstituted C2-C50 heteroaryl group, substituted or unsubstituted C2-C50 cycloalkyl group, substituted or unsubstituted C2-C50 heterocycloalkyl group, or substituted or unsubstituted saturated or unsaturated hydrocarbon.

Description

ORGANIC LIGHT DEVICE AND ORGANIC LIGHT COMPOUND FOR THE SAME}

The present invention relates to an organic optical device and an organic optical compound used therein,

More particularly, the present invention relates to an organic light emitting device capable of realizing excellent luminous efficiency, luminous brightness, color purity, and luminous lifetime, an organic light emitting compound or an optical device for photovoltaic power generation, and an optical compound used therefor.

As the information age rapidly enters, the importance of a display, which serves as an interface between the electronic information device and the human being, is increasing. In particular, there is an urgent need to develop a display that can be conveniently used anytime and anywhere, and provides a vivid screen with a sense of reality. Further research is being conducted to develop thinner, lighter, unbreakable flexible displays by fabricating displays on flexible substrates such as plastic instead of glass substrates. Organic light emitting diode (OLED) displays are attracting great attention as next generation flat panel display technologies that are best suited for such applications.

Electroluminescence in organic semiconductors was first discovered in anthracene crystals in 1963 by Pope, Kallmann and Magnate [M. Pope, HP Kallmamm and P. Magnae, J. Chem. Phys. 38 , 2042 (1963), followed by W. Helfrich [W. Helfrich and WG Schneider, Phys. Rev. Lett. 14 , 229 (1965)]. However, the high purity anthracene crystal is an insulator with an electric conductivity of 10 ^-20 s / cm or less. Therefore, electrons and holes are injected and light emission efficiency is very low when a high voltage of several hundred volts is applied. In addition, there was a big problem in terms of practical use of highly reactive alkali metals as electrodes. Since 1982, Vincett et al. Succeeded in forming an amorphous anthracene thin film and fabricating an organic light emitting diode by vacuum deposition. The luminous efficiency of this device was very low at about 0.05%, but this method has been used as a typical OLED manufacturing method to date.

In 1987 the light-emitting layer and a charge transport layer, such as Kodak's Tang each Alq ₃ The development of low molecular OLED displays has been rapid since the formation of green light emitting phenomena with improved efficiency and stability by forming a double-layer low molecular organic thin film called and TPD. In this device structure, electrons and holes accumulate at the diamine / Alq ₃ interface due to the difference in the electron energy levels of the hole transporting material and the electron transporting material, thereby increasing the probability of electron-hole recombination. As a result, the device showed a luminance of 1000 cd / m ² or higher and a high luminous efficiency of 1.5 lm / W at a driving voltage of 10V or lower. This result shows the possibility of developing a high-brightness, high-efficiency display using an organic thin-film light emitting diode, so it played a big role in activating OLED research worldwide.

In the late 1980s, the structure of the low molecular OLED device started with a simple structure of an anode (ITO), a hole transfer layer (HTL) emission layer (EML), and a cathode (Mg: Ag). Later, in the case of a fluorescent device, a hole injection layer (HIL) such as CuPc was introduced, and the structure became complicated as Al: Li was developed as a cathode and an electron injection layer material, and a material such as LiF was developed. Accordingly, the efficiency and driving voltage of the electro-optical characteristics have been improved.

The light emitting device is a self-luminous device, and has a wide viewing angle, excellent contrast, and fast response time. The light emitting device is classified into an inorganic light emitting device using an inorganic compound as an emitting layer and an organic light emitting device using an organic compound. Compared with inorganic light emitting devices, organic photoelectric devices have been studied in many ways in that they have excellent physical properties such as high luminance, low driving voltage, and short response speed, and are capable of multicoloring. The organic optical devices are generally used as anodes, organic light emitting layers, and cathodes. It has a laminated structure, such as anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode or anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode It can have various structures.

On the other hand, high-performance organic optical compounds are important in order to implement organic optical devices having high luminous efficiency and long operating life.

 In order to manufacture a panel having a large size and low power consumption, the organic photochemical compounds must further improve luminous efficiency, luminous luminance, and the like, and especially life characteristics.

In addition, the development of alternative energy of fossil fuel is urgently needed, such organic light emitting devices and organic light emitting compounds can be applied to organic photoelectric devices and photo compounds for photovoltaic power generation through the conversion of ideas.

The first technical problem to be achieved by the present invention is to provide an organic optical device having improved luminous efficiency, luminous brightness, color purity and luminous lifetime.

The second technical problem to be achieved by the present invention is to provide a new organic photochemical compound.

In addition, an object of the present invention is to provide an organic light emitting device and an organic light emitting compound, or an organic optical device and a photo compound for photovoltaic power generation.

An organic optical device according to the first aspect of the present invention, the first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic photo compound of formula A:

<Formula A>

Wherein A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 are each independently or related to hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 hetero An aryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon,

X1, X2, X3, X4 are each 0 (zero), Si, S, Se, O, C or N,

If one of X1 and X2 is zero, the other is not zero.

If one of X3 and X4 is zero, the other is not zero.

If X1, X2, X3 or X4 is zero, the corresponding C2, C1, A1d or A1c is zero

Rings containing X1 and X2 are either resonance or non-resonant.

In order to achieve another object of the present invention, there is provided an organic photo compound represented by the formula (A).

The organic optical device according to the present invention provides high luminous efficiency, high luminous brightness, high color purity and significantly improved luminous lifetime,

In addition, the present invention provides an organic light emitting device and an organic light emitting compound, or an organic optical device and a photo compound for photovoltaic power generation.

Hereinafter, the present invention will be described in detail with reference to Examples.

The present invention may be modified in various ways and may have various forms, and thus embodiments (or embodiments) will be described in detail in the text. However, this is not intended to limit the present invention to the specific form disclosed, it should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.

The terminology used herein is for the purpose of describing particular embodiments (suns, aspects, and embodiments) (or embodiments) only and is not intended to be limiting of the invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms “comprises” or “consists” are intended to indicate that there is a feature, number, step, action, component, part, or combination thereof described on the specification, but one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art. Terms such as those defined in the commonly used dictionaries should be construed as having meanings consistent with the meanings in the context of the related art and shall not be construed in ideal or excessively formal meanings unless expressly defined in this application. Do not.

In the present specification, an organic photochemical compound is a compound used in an organic optical device, and is not necessarily limited to a compound capable of emitting light, and its application range is not limited to an organic light emitting layer, and an organic photonic compound such as a charge injection layer and a charge transport layer It can be used in any layer that constitutes the ruler.

In the present specification, the terms "photochemical compound" and "optical device" are intended to be encompassed in consideration of the case where the present invention is applied to both an organic light emitting device and a device for photovoltaic power generation regardless of a dictionary or customary definition. The selected term.

An organic optical device according to the first aspect of the present invention, the first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic photo compound of formula A:

<Formula A>

In the formula for the derivative, A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 are each independently or related to hydrogen, including deuterium, a substituted or unsubstituted C6-C50 aryl group. , A substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon,

X1, X2, X3, X4 are each 0 (zero), Si, S, Se, O, C or N,

If one of X1 and X2 is zero, the other is not zero.

If one of X3 and X4 is zero, the other is not zero.

If X1, X2, X3 or X4 is zero, the corresponding C2, C1, A1d or A1c is zero

Rings containing X1 and X2 are either resonance or non-resonant.

The inventors of the present invention have developed a variety of specific derivatives, in which A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 and X1, X2, X3 and X4 are selected from the substituents of the compound represented by Formula A. To develop an organic optical compound that can be used as various organic films between the first electrode and the second electrode, such as an electron transport layer (ETM), an emission layer (EML), a hole transport layer (HTM), and an organic optical device using the same

When used as an organic light emitting device, it has been found that performance improvement such as increased efficiency and driving voltage can be improved, and the ability as an OLED material can be maximized, and in particular, the light emission life is significantly improved.

If this is applied to photovoltaic devices and photochemical fields for photovoltaic power generation, it is expected to obtain excellent power generation efficiency.

Hereinafter, the compound represented by Formula A will be described with reference to the organic light emitting device, but the present invention should not be construed as a limitation.

The compound represented by Chemical Formula A is suitable as a material forming an organic film interposed between the first electrode and the second electrode of the organic optical device. The compound represented by the formula (A) is suitable for use in an organic film, particularly a hole transport layer, a hole injection layer or a light emitting layer of an organic light emitting device, and is used as a dopant material as well as a host material. The compound represented by Formula A provides a color of blue to green and is suitable for use in a white light emitting device.

A1a and A1b, A1a and A1c, A1b and A1d, B1 and C1, B2 and C2, and some of A2a and A2b may be related groups,

This functional group is a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group ,

Moreover, it is preferable that at least one of said A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 is a phenyl group.

The aryl group is a monovalent group having an aromatic ring system, and may include two or more ring systems, and the two or more ring systems may exist in a bonded or fused form with each other. The heteroaryl group refers to a group in which at least one carbon of the aryl group is substituted with at least one selected from the group consisting of N, O, S, P, Si, and Se.

Meanwhile, a cycloalkyl group refers to an alkyl group having a ring system, and the heterocycloalkyl group refers to a group in which at least one carbon of the cycloalkyl group is substituted with at least one selected from the group consisting of N, O, S, P, Si, and Se. .

When one or more hydrogen of the aryl group and heteroaryl group is substituted, their substituents are C1-C50 alkyl group; C1-C50 alkoxy group; C 6 -C 50 aryl groups which are unsubstituted or substituted with C 1 -C 50 alkyl groups or C 1 -C 50 alkoxy groups; C2-C50 heteroaryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; C5-C50 cycloalkyl group substituted with an unsubstituted or C1-C50 alkyl group or a C1-C50 alkoxy group and a group represented by a C5-C50 heterocycloalkyl group substituted with an unsubstituted or C1-C20 alkyl group or a C1-C20 alkoxy group, or a silane group It may be one or more selected from the group consisting of.

More specifically, A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 independently or independently of each other, hydrogen, phenyl group, tolyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group , Biphenylenyl group, anthracenyl group, benzoanthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, creie Cenyl group, pisenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentaxenyl group, tetraphenylenyl group, hexaphenyl group, hexasenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group , Heptacenyl group, fluorenyl group, pyrantrenyl group, obarenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, thiophenyl group, indolyl group, furinyl group, benzimidazolyl group, quinolinyl group, Benzothiophenyl group, parathiazinyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, Imidazolinyl, oxazolyl, thiazolyl, triazolyl, tetrazolyl, oxdiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, thianthrenyl, Cyclopentyl group, cyclohexyl group, oxiranyl group, pyrrolidinyl group, pyrazolidinyl group, imidazolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, di (C6-C50 aryl) amino group, Silane groups and derivatives thereof.

In the present specification, the term "derivative" refers to a group in which at least one hydrogen of the groups listed above is substituted with a substituent as described above.

Preferably, the A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 independently or independently of each other, hydrogen, phenyl group, biphenyl group, tolyl group, naphthyl group, naphthalenylphenyl group, Dimethylbenzyl, pyrenyl, phenanthrenyl, benzo [de] anthracenyl, benzo [a] anthracenyl, benzo [b] anthracenyl, benzo [c] anthracenyl, 11,11-dimethylbenzo [ de] anthracenyl group, 11, 11-diethyl benzo [de] anthracenyl group, 11, 11- dimethyl benzo [a] anthracenyl group, 11, 11- dimethyl benzo [b] anthracenyl group, 11, 11- Dimethylbenzo [c] anthracenyl group, bifluorenyl group, 6,6,12,12-tetramethyl-indeno [1,2-b] fluorenyl group, N-phenylcarbazolyl group, N-ethylcarr Bazolyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, imidazolinyl group, indolyl group, quinolinyl group, diphenylamino group, dibiphenylamino group, di (tert-butylbenzyl) amino group, (tolyl (Phenyl) amino group, (phenyl) (ratio Phenyl) amino group, (phenyl) (naphthyl) amino group, di (bifetyl) amino group, difluorenylamino group, di-p-tolylamino group, silane group and derivatives thereof.

In more detail, in accordance with an embodiment of the present invention, the organic photochemical compound used in the organic photoelectric device of the present invention may have a structure of the formula 1 to 185 (in the present specification, the formula is omitted, not described). But not limited to:

The organic photochemical compound according to the present invention represented by Chemical Formula A may be synthesized using a conventional synthesis method, and for more detailed synthesis route of the compound, see Schemes 1 to 185 of the following Synthesis Example. The compound of formula (A) is suitable for use in organic membranes of organic optical devices, in particular hole transport layers, hole injection layers or light emitting layers. The structure of the organic light emitting device according to the present invention is very diverse. One or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer and an electron injection layer may be further included between the first electrode and the second electrode.

More specifically, embodiments of the organic light emitting device according to the present invention

First, the organic light emitting device may have a structure consisting of a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode,

In addition, the organic light emitting device may have a structure consisting of a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode,

Furthermore, the organic light emitting device may have a structure of a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode.

In this case, at least one of the electron transport layer, the light emitting layer, or the hole transport layer may include a compound according to the present invention.

The light emitting layer of the organic optical device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm. The compounds according to the invention can also be used as fluorescent dopants in light emitting layers.

Hereinafter, a method of manufacturing an organic optical device according to the present invention will be described with reference to an organic optical device. First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Herein, a substrate used in a conventional organic optical device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 ^-5 to 10 ^-3 torr, a deposition rate of 0.01 to 100 Pa / sec, and a film thickness are appropriately selected in the range of usually 100 Pa to 1 µm.

In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. After the coating, the heat treatment temperature for removing the solvent is preferably selected from a temperature range of about 80 ° C to 200 ° C.

The hole injection layer material may be a compound having Formula A as described above.

Or phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or the starburst type amine derivatives described in Advanced Material, 6, p.677 (1994), for example, TCTA, m-MTDATA, m-. MTDAPB, 2-TNATA (4,4,4-tris (N- (2-naphtyl) -N-phenylamino) triphenylamine: 4,4,4-tris (N- (naphthyl) -N-phenylamino) triphenyl Amines), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3, 4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonicacid: polyaniline / camphorsulfonic acid) or PANI / PSS

Known hole injection materials such as (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)) and the like can be used.

The hole injection layer may have a thickness of about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.

Alternatively, the hole injection layer may be formed by vacuum vapor deposition. Although specific deposition conditions depend on the compound used, they are selected from the range of conditions substantially the same as the formation of a general hole injection layer. For example, DNTPD (N, N-bis- [4- (di-m-tolylamino) phenyl] -N, N-diphenylbiphenyl-4,4-diamine) may be used.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. When the hole transport layer is formed by the vacuum deposition method or the spinning method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from a range of conditions almost the same as that of the formation of the hole injection layer.

The hole transport layer material may include a compound of formula A as described above. Or, for example, carbazole derivatives, such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'- diphenyl- [1,1-biphenyl] Conventional amine derivatives having aromatic condensed rings such as -4,4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (? -NPD), and the like The same well-known hole transport material may be used. The hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be degraded, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.

Next, the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like. When the light emitting layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The light emitting layer may include a compound of formula A according to the present invention as described above. At this time, the compound of formula A may be used with a suitable known host material or may be used with a known dopant material.

It is also possible to use the compound of formula A alone. For host materials, for example, Alq3 (tris (8-hydroxy-quinolatealuminium) or CBP (4,4'-N, N'-dicarbazole-biphenyl), or PVK (poly (n-vinylcarbazole) ) Can be used.

In the case of the dopant material, IDE102, IDE105, and C545T, available from Hayashibara Corp., can be used as fluorescent dopants, and red phosphorescent dopants PtOEP, RD61 from UDC, green phosphorescent dopants Ir, etc. can be used. (PPy) 3 (PPy = 2-phenylpyridine), F2Irpic which is a blue phosphorescent dopant, red phosphorescent dopant RD 61 by UDC, etc. can be used. MQD (N-methylquinacridone), coumarin (Coumarine) derivative, etc. can also be used.

The doping concentration is not particularly limited, but the content of the dopant is generally 0.01 to 15 parts by weight based on 100 parts by weight of the host. The thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa.

This is because, when the thickness of the light emitting layer is less than 100 kW, the light emission characteristics may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.

When a light emitting compound is used with a phosphorescent dopant in the light emitting layer, a method such as vacuum deposition, spin coating, cast method, LB method, etc. is used on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer. The hole blocking layer HBL can be formed. In the case of forming the hole blocking layer by vacuum deposition or spin coating, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer. Known hole blocking materials that can be used include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and BCP.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated, and when the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase. The hole blocking layer may be omitted. In this case, an organic light emitting device having the structure shown in FIG. 1B is obtained.

Next, the electron transport layer (ETL) is formed using various methods such as vacuum deposition, spin coating, and casting.

When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer. The electron transport layer material functions to stably transport electrons injected from an electron injection electrode (Cathode), and a quinoline derivative, particularly tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, PBD and the like are known. Materials may also be used.

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, which does not particularly limit the material.

As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from the range of conditions almost the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 50 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method.

The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic electroluminescent compound according to another embodiment of the present invention may be represented by Chemical Formula A, and more specifically, may be represented by Chemical Formulas 1 to 185. Details of the compounds are the same as those described for the above-mentioned organic feet and devices.

Hereinafter, the synthesis examples and examples of the present invention will be specifically illustrated, but the present invention is not limited to the following synthesis examples and examples. In the following synthesis, the intermediate compound is indicated by adding the serial number to the number of the final product. For example, compound 1 is represented by compound [1], and the intermediate compound of the said compound is described by [1-1] etc. In the present specification, the chemical number is indicated as the chemical formula number. For example, the compound represented by the formula (1) is represented by compound 1.

Synthesis Example 1 Synthesis of Compound [1]

In a 2 L round flask, 50.0 g (0.337 mol) of phthalic anhydride and 112 g (0.843 mol) of aluminum chloride are stirred with 500 mL of dichloromethane. 37.0 g (0.337 mol) of 1,1-dimethyl-1H-silol is dissolved in 300 mL of dichloromethane and added dropwise to the reaction solution at room temperature. After stirring for 6 hours at room temperature, the reaction solution is poured into 2L of purified water. The organic layer is separated and washed with 1 L of saturated brine. The organic layer is separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and recrystallized with dichloromethane and normal-hexane to give 51.0 g (59%) of the intermediate compound [1-1] as a white solid.

50.0 g (0.194 mol) of the intermediate compound [1-1] were added to the flask, and stirred with 300 mL of polyphosphoric acid at 150 ° C. for 3 hours. The reaction solution is poured into 3L of purified water and solidified. The yellow solid was washed with methanol to yield 42.0 g (90%) of the intermediate compound [1-2] .

10.0 g (41.61 mmol) of the intermediate compound [1-2] were dissolved in 200 mL of anhydrous tetrahydrofuran, and 7.9 g (0.208 mol) of lithium aluminum hydride was added slowly at 0 ° C. in a flask. The temperature was raised to reflux for 12 hours and cooled to room temperature. The reaction solution is poured slowly into ethanol to solidify. The solid was filtered and recrystallized with dichloromethane and methanol to give 6.5g (74%) of the target compound [1] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 6H), 5.54 (d, 1H), 7.00 (d, 1H), 7.60 (m, 3H), 7.85 (s, 1H), 7.99 (m , 2H)

MS / FAB: 210 (M ⁺ )

Synthesis Example 2 Synthesis of Compound [2]

Dissolve 8.17 g (52.01 mmol) of bromobenzene in 100 mL of anhydrous tetrahydrofuran in a flask. 20.8 mL (52.01 mmol) of normal butyllithium (2.5 mol) solution was slowly added dropwise at 78 ° C. At the same temperature, 5.0 g (20.80 mol) of an intermediate compound [1-2] were added, and the temperature was raised to room temperature for 8 hours. Pour the reaction solution into 200 mL of saturated aqueous ammonium solution. The organic layer is separated and washed with saturated brine. The organic layer is separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure in a 500 mL flask and stirred with 200 mL of acetic acid. 22.0 g (0.208 mol) of sodium phosphate monohydrate and 17.3 g (0.104 mol) of potassium iodide were added and stirred under reflux for 12 hours. Cool to room temperature and filter the resulting solid. Washing with 100 mL of methanol gave 3.9 g (51%) of the title compound [2] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.64 (s, 6H), 5.51 (d, 1H), 7.00 ~ 7.10 (m, 3H), 7.40 ~ 7.60 (m, 10H), 8.45 (m, 2H)

MS / FAB: 362 (M ⁺ )

Synthesis Example 3 Synthesis of Compound [3]

In the same manner as in Synthesis Examples 1 and 2 , target compound [3] was obtained using 1,1-dimethyl-1H-silol, naphtho [2,3-c] furan-1,3-dione and bromobenzene. .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.61 (s, 6H), 5.49 (d, 1H), 6.99 ~ 7.09 (m, 3H), 7.39 ~ 7.59 (m, 10H), 8.05 (m, 2H) , 8.35 (s, 2H)

MS / FAB: 412 (M ⁺ )

Synthesis Example 4 Synthesis of Compound [4]

In the same manner as in Synthesis Examples 1 and 2 , 1,1-dimethyl-1H-silol, naphtho [1,2-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [4] . .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.61 (s, 6H), 5.55 (d, 1H), 6.98 ~ 7.05 (m, 3H), 7.39 ~ 7.55 (m, 8H), 7.75 ~ 7.95 (m, 4H), 8.05 (m, 1 H), 8.80 (m, 1 H)

MS / FAB: 412 (M ⁺ )

Synthesis Example 5 Synthesis of Compound [5]

In the same manner as in Synthesis Examples 1 and 2 , 1,1-dimethyl-1H-silol, puro [3,4-b] pyrazine-5,7-dione, and bromobenzene were used to obtain the target compound [5] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 6H), 5.50 (d, 1H), 6.99 (d, 1H), 7.40 ~ 7.59 (m, 10H), 8.50 (m, 2H)

MS / FAB: 364 (M ⁺ )

Synthesis Example 6 Synthesis of Compound [6]

Synthesis Example 1 , the desired compound [6] was obtained by using 1,1-dimethyl-1H-benzo [b] silol and futal anhydride in the same manner.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 6H), 7.35 (m, 1H), 7.50 ~ 7.60 (m, 4H), 7.95 ~ 8.05 (m, 4H), 8.41 (s, 1H)

MS / FAB: 260 (M ⁺ )

Synthesis Example 7 Synthesis of Compound [7]

In the same manner as in Synthesis Examples 1 and 2 , target compound [7] was obtained using 1,1-dimethyl-1H-benzo [b] silol, phthalic anhydride, and bromobenzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 6H), 7.30 ~ 7.55 (m, 15H), 7.90 (m, 1H), 8.49 (m, 2H)

MS / FAB: 412 (M ⁺ )

Synthesis Example 8 Synthesis of Compound [8]

Synthesis Example 1 1,1-dimethyl-benzo -1H- the second vortex same way [b] silole, using naphtho [2,3-c] furan-1,3-dione, bromobenzene desired compound [8 ] Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.63 (s, 6H), 7.31 ~ 7.63 (m, 15H), 7.90 (m, 3H), 8.30 (s, 2H)

MS / FAB: 462 (M ⁺ )

Synthesis Example 9 Synthesis of Compound [9]

Synthesis Example 1, the same way 1,1-dimethyl-2 vortex -1H- benzo [b] silole, using naphtho [1,2-c] furan-1,3-dione, bromobenzene target compound [10 ] Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 6H), 7.30 ~ 7.61 (m, 13H), 7.70 ~ 7.85 (m, 5H), 8.05 (m, 1H), 8.80 (m, 1H)

MS / FAB: 462 (M ⁺ )

Synthesis Example 10 Synthesis of Compound [10]

In the same manner as in Synthesis Examples 1 and 2 , 1,1-dimethyl-1H-benzo [b] silol, puro [3,4-b] pyrazine-5,7-dione, and bromobenzene were used as target compounds [10] Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 6H), 7.31 ~ 7.60 (m, 13H), 7.89 (m, 1H), 8.70 (m, 2H)

MS / FAB: 414 (M ⁺ )

Synthesis Example 11 Synthesis of Compound [11]

In the same manner as in Synthesis Example 1 , target compound [11] was obtained using 5,5,10,10-tetramethyl-5,10-dihydrosilanelene and maleic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 12H), 7.45 ~ 7.60 (m, 6H), 7.95 ~ 8.05 (m, 4H)

MS / FAB: 318 (M ⁺ )

Synthesis Example 12 Synthesis of Compound [12]

In the same manner as in Synthesis Example 1 , the target compound [12] was obtained using 5,5,10,10-tetramethyl-5,10-dihydrosilanelene and fuphthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.35 ~ 7.60 (m, 6H), 7.90 (m, 2H), 8.25 ~ 8.35 (m, 4H)

MS / FAB: 368 (M ⁺ )

Synthesis Example 13 Synthesis of Compound [13]

In the same manner as in Synthesis Examples 1 and 2 , the target compound [13] was obtained using 5,5,10,10-tetramethyl-5,10-dihydrosilanelene, anhydrous phthalic anhydride and bromobenzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 12H), 7.35 ~ 7.59 (m, 16H), 7.91 (m, 2H), 8.25 (s, 2H)

MS / FAB: 520 (M ⁺ )

Synthesis Example 14 Synthesis of Compound [14]

5,5,10,10-tetramethyl-5,10-dihydrosilanetrene, naphtho [2,3-c] furan-1,3-dione and bromobenzene in the same manner as in Synthesis Examples 1 and 2 Was used to obtain the target compound [14] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.64 (s, 12H), 7.36 ~ 7.59 (m, 16H), 7.90 (m, 2H), 8.28 ~ 8.32 (m, 4H)

MS / FAB: 570 (M ⁺ )

Synthesis Example 15 Synthesis of Compound [15]

5,5,10,10-tetramethyl-5,10-dihydrosilanetrene, naphtho [1,2-c] furan-1,3-dione and bromobenzene in the same manner as in Synthesis Examples 1 and 2 Was used to obtain the target compound [15] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.35 ~ 7.57 (m, 15H), 7.85 ~ 7.91 (m, 3H), 8.15 (m, 1H), 8.30 (s, 2H) , 8.81 (m, 1 H)

MS / FAB: 570 (M ⁺ )

Synthesis Example 16 Synthesis of Compound [16]

5,5,10,10-tetramethyl-5,10-dihydrosilanerene, furo [3,4-b] pyridine-5,7-dione and bromobenzene were used in the same manner as in Synthesis Examples 1 and 2. The desired compound [16] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 12H), 7.40 ~ 7.61 (m, 15H), 8.05 (s, 2H), 8.30 (m, 1H), 8.79 (m, 1H)

MS / FAB: 521 (M ⁺ )

Synthesis Example 17 Synthesis of Compound [17]

5,5,10,10-tetramethyl-5,10-dihydrosilanetrene, puro [3,4-b] pyrazine-5,7-dione and bromobenzene were used in the same manner as in Synthesis Examples 1 and 2. The target compound [17] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.39 ~ 7.60 (m, 14H), 8.00 (s, 2H), 8.69 (d, 2H)

MS / FAB: 522 (M ⁺ )

Synthesis Example 18 Synthesis of Compound [18]

50 g (0.120 mol) of an intermediate compound [18-1] prepared by using 5,5,10,10-tetramethyl-5,10-dihydrosilanelene and anhydrous phthalic anhydride in the same manner as in Synthesis Example 1 78.5 g (1.20 mol) of zinc and 48.0 g (1.20 mol) of sodium hydroxide were added thereto, and 1.0 L of diethylene glycol was added thereto, followed by stirring at 150 ° C. for 12 hours. Cool to room temperature and filter the reaction solution using diatomaceous earth. The filtrate is poured into 5 L of purified water and acidified with concentrated hydrochloric acid. The resulting white solid was filtered to give 35.3 g (73%) of an intermediate compound [18-2] .

35 g (86.93 mmol) of the intermediate compound [18-2] were added to the flask and stirred with 300 mL of methanesulfonic acid at room temperature for 5 hours. The reaction solution is poured into 3L of purified water and solidified. The orange solid was washed with methanol to yield 29.0 g (87%) of the intermediate compound [18-3] .

38.9 g (0.188 mol) of 2-bromonaphthalene and 4.57 g (0.188 mol) of magnesium are added to the flask, and the mixture is stirred under reflux with 500 mL of anhydrous tetrahydrofuran to dissolve. After cooling to room temperature, 29 g (75.39 mol) of an intermediate compound [18-3] were added, followed by stirring under reflux for 12 hours. Cool the reaction solution to room temperature and pour the reaction solution into 1 mol aqueous hydrochloric acid. The organic layer is separated and washed with saturated brine. The organic layer is separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the yellow solid obtained was recrystallized from dichloromethane and methanol to obtain 35 g (94%) of an intermediate compound [18-4] as a yellow solid.

In a flask, 35 g (70.74 mmol) of an intermediate compound [18-4] are stirred with 1 L of N, N-dimethylformamide. 13.85 g (77.81 mmol) of N-bromosuccinimide is added at room temperature, followed by stirring for 8 hours. Methanol is added to the reaction solution, and the resulting yellow solid is filtered. The solid was dried in vacuo to yield 38 g (94%) of the intermediate compound [18-5] .

38 g (66.24 mmol) of the intermediate compound [18-5] were dissolved in 1 L of anhydrous tetrahydrofuran, and 31.8 mL (79.48 mmol) of normal butyllithium (2.5 mol) was slowly added dropwise in an argon atmosphere at -78 ° C. Trimethyl borate mL (mmol) was added dropwise at the same temperature and raised to room temperature for 8 hours. Pour the reaction solution into 1 L of 1N aqueous hydrochloric acid solution at room temperature. The organic layer is separated and washed with saturated brine. The organic layer is separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the yellow solid obtained was recrystallized from dichloromethane and hexane to give 30 g (84%) of an intermediate compound [18-6] as an off-white solid.

Intermediate compound [18-6] 5.0 g (9.28 mmol), 1- (3-bromophenyl) naphthalene 2.63 g (9.28 mmol), tetrakis (triphenylphosphine) palladium 214 mg (0.186 mmol) in a 250 mL round bottom flask 10 mL of 2 mol-sodium carbonate solution and 100 mL of 1,4-dioxane are added thereto, followed by stirring under reflux for 10 hours in a nitrogen atmosphere. Methanol is added at room temperature to crystallize. The solid was filtered and recrystallized from dichloromethane and methanol to obtain 3.7 g (57%) of the title compound [18] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.64 (s, 12H), 7.35 ~ 7.75 (m, 17H), 7.90 ~ 8.05 (m, 7H), 8.15 (m, 2H), 8.40 ~ 8.50 (m, 2H)

MS / FAB: 697 (M ⁺ )

Synthesis Example 19 Synthesis of Compound [19]

Intermediate compound prepared using 5,5,10,10-tetramethyl-5,10-dihydrosilanelene, 4-bromophthalic anhydride and bromobenzene in the same manner as in Synthesis Examples 1 and 2 [19-1 ] 3.1g (62%) of the title compound [19] was prepared according to Synthesis Example 18 using 5.0 g (8.34 mmol) and phenylboronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.40 ~ 7.65 (m, 20H), 8.00 (d, 1H), 8.10 (s, 1H), 8.30 (s, 2H)

MS / FAB: 596 (M ⁺ )

Synthesis Example 20 Synthesis of Compound [20]

Intermediate compound prepared using 5,5,10,10-tetramethyl-5,10-dihydrosilanelene, 4-bromophthalic anhydride and bromobenzene in the same manner as in Synthesis Examples 1 and 2 [19-1 ] 3.5g (56%) of the target compound [20] was prepared according to Synthesis Example 18 using 5.8 g (8.34 mmol) and phenylboronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 12H), 7.45 ~ 7.62 (m, 14H), 7.95 ~ 8.10 (m, 11H), 8.25 (s, 2H)

MS / FAB: 746 (M ⁺ )

Synthesis Example 21 Synthesis of Compound [21]

Intermediate compound prepared using 5,5,10,10-tetramethyl-5,10-dihydrosilanelene, 4-bromophthalic anhydride, bromobenzene in the same manner as in Synthesis Examples 1 and 2 [21-1 ] of the desired compound [21] 2.1g (40%) was prepared in accordance with 5.0g (6.42mmol) and phenylboronic acid, synthesized in example 18 using 2-naphthaleneboronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.64 (s, 12H), 7.35 ~ 7.75 (m, 19H), 7.85 ~ 8.10 (m, 13H), 8.25 (m, 2H)

MS / FAB: 823 (M ⁺ )

Synthesis Example 22 Synthesis of Compound [22]

5.0 g (7.14 mmol) of the intermediate compound [19-1], 1.45 g (8.57 mmol) of diphenylamine, and 50 mL of toluene were added to a 100 mL round bottom flask, and 16 mg (0.071 mmol) of palladium acetate (II) and tert-butoxide were added in a nitrogen atmosphere. Sodium seed 1.03 g (10.71 mmol) and dirt butyl phosphine (50% toluene solution) 0.07 mL (0.0.142 mmol) was added and the mixture was stirred under reflux for 10 hours. The reaction solution is cooled to room temperature and methanol is added dropwise. The resulting solid is filtered. Vacuum drying at room temperature gave 2.9 g (51%) of the title compound [22] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 12H), 7.01 ~ 7.25 (m, 12H), 7.44 ~ 7.75 (m, 13H), 7.95 (m, 2H), 8.25 (m, 2H)

MS / FAB: 787 (M ⁺ )

Synthesis Example 23 Synthesis of Compound [23]

In the same manner as in Synthesis Example 22 , 3.5 g (57%) of the target compound [23] was obtained using 5.0 g (6.42 mmol) of an intermediate compound [21-1] and 2.39 g (14.12 mmol) of diphenylamine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.03 ~ 7.35 (m, 25H), 7.55 ~ 7.96 (m, 11H), 8.28 (s, 2H)

MS / FAB: 955 (M ⁺ )

Synthesis Example 24 Synthesis of Compound [24]

3.24 g (9.28 mmol) of intermediate compound [18-6] 5.0 g (9.28 mmol) and 2- (3-bromophenyl) -1-phenyl-1H-benzo [d] imidazole were prepared in the same manner as in Synthesis example 18 . To give 3.0 g (42%) of the title compound [24] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 12H), 7.20 to 7.71 (m, 21H), 7.90 to 8.01 (m, 5H), 8.25 to 8.30 (m, 3H), 8.49 (m, 1H)

MS / FAB: 762 (M ⁺ )

Synthesis Example 25 Synthesis of Compound [25]

In the same manner as in Synthesis Example 18 , 5.0 g (9.28 mmol) of the intermediate compound [18-6] and 4-bromopyridine were used to produce the target compound [25] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.35 ~ 7.75 (m, 10H), 7.95 ~ 8.05 (m, 7H), 8.30 (m, 2H), 8.70 (m, 2H)

MS / FAB: 571 (M ⁺ )

Synthesis Example 26 Synthesis of Compound [26]

In the same manner as in Synthesis Example 18 , 5.0 g (9.28 mmol) of the intermediate compound [18-6] and 6-bromo-2,2'-bipyridine were used to prepare the target compound [26] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.64 (s, 12H), 7.01-7.10 (m, 2H), 7.34-7.71 (m, 12H), 7.90-8.00 (m, 5H), 8.28 (m, 2H), 8.50 (m, 1H), 8.85 (m, 1H), 8.99 (m, 1H)

MS / FAB: 648 (M ⁺ )

Synthesis Example 27 Synthesis of Compound [27]

In the same manner as in Synthesis Example 18 , 5.0 g (9.28 mmol) of an intermediate compound [18-6] and 2-bromoquinoline were used to prepare the target compound [27] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.67 (s, 12H), 7.30 ~ 7.50 (m, 5H), 7.51 ~ 7.60 (m, 6H), 7.70 ~ 8.10 (m, 10H), 8.28 (m, 2H)

MS / FAB: 621 (M ⁺ )

Synthesis Example 28 Synthesis of Compound [28]

In the same manner as in Synthesis Example 1 , target compound [28] was prepared using 5,5-dimethyl-5H-dibenzo [b, d] silol and maleic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 6H), 7.35 ~ 7.62 (m, 5H), 7.79 (m, 1H), 8.00 ~ 8.05 (m, 3H), 8.39 (s, 1H)

MS / FAB: 260 (M ⁺ )

Synthesis Example 29 Synthesis of Compound [29]

In the same manner as in Synthesis Example 1 , the target compound [29] was prepared using 5,5-dimethyl-5H-dibenzo [b, d] silol and futal anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.65 (s, 6H), 7.29 ~ 7.61 (m, 5H), 7.88 ~ 7.95 (m, 3H), 8.21 ~ 8.30 (m, 4H)

MS / FAB: 310 (M ⁺ )

Synthesis Example 30 Synthesis of Compound [30]

In the same manner as in Synthesis Examples 1 and 2 , 5,5-dimethyl-5H-dibenzo [b, d] silol, butyric anhydride, and bromobenzene were used to produce the target compound [30] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.64 (s, 6H), 7.31 ~ 7.63 (m, 15H), 7.90 (m, 3H), 8.25 (m, 2H)

MS / FAB: 462 (M ⁺ )

Synthesis Example 31 Synthesis of Compound [31]

Synthesis Example 1 , 2 in the same manner as 5,5-dimenyl-5H-dibenzo [b, d] silol, puro [3,4-b] pyrazine-5,7-dione, bromobenzene The target compound [31] was obtained as a solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 6H), 7.33 ~ 7.52 (m, 12H), 7.61 (t, 1H), 7.99 (s, 1H), 8.01 (s, 1H), 8.74 (s, 2H), 8.12-8.18 (m, 3H), 8.45 (d, 1H)

MS / FAB: 464 (M ⁺ )

Synthesis Example 32 Synthesis of Compound [32]

Synthesis Example 1 Obtained the desired compound as a yellow solid [1] using 1,1,4,4-tetramethyl-1,4-dihydrosilol [3,2-b] silol and fuphthalic anhydride in the same manner as in Synthesis example 1 It was.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.14 (s, 6H), 0.66 (s, 6H), 5.20 (d, 1H), 6.50 (d, 1H), 7.59 ~ 7.60 (m, 3H), 7.83 (s, 1H), 8.00-8.01 (m, 2H)

MS / FAB: 292 (M ⁺ )

Synthesis Example 33 Synthesis of Compound [33]

Synthesis Example 1 1,1,4,4-tetramethyl-1,4-dihydrosilol [3,2-b] silol and naphtho [2,3-c] furan-1,3-dione in the same manner as in Synthesis example 1 Was obtained to obtain the target compound [33] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.14 (s, 6H), 0.66 (s, 6H), 5.20 (d, 1H), 6.50 (d, 1H), 7.39 ~ 7.40 (m, 2H), 7.90 ~ 8.00 (m, 4H), 8.30 (s, 2H)

MS / FAB: 342 (M ⁺ )

Synthesis Example 34 Synthesis of Compound [34]

1,1,4,4-tetramethyl-1,4-dihydrosilol [3,2-b] silol and naphtho [2,3-c] furan-1,3 in the same manner as in Synthesis Examples 1 and 2 -Dione and bromobenzene were used to obtain the target compound [34] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.14 (s, 6H), 0.66 (s, 6H), 5.20 (d, 1H), 6.50 (d, 1H), 7.15 ~ 7.16 (m, 2H), 7.40 ~ 7.52 (m, 10H), 7.89-7.90 (m, 2H), 8.30 (s, 2H)

MS / FAB: 494 (M ⁺ )

Synthesis Example 35 Synthesis of Compound [35]

In the same manner as in Synthesis Example 1 , compound [35-1] and the desired compound [35] as a yellow solid were obtained using futal anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 5.30 (d, 1H), 6.90 (d, 1H), 7.50 (s, 1H), 7.59 ~ 7.60 (m, 3H), 8.00 ~ 8.01 (m, 3H), 8.44 (s, 1H)

MS / FAB: 342 (M ⁺ )

Synthesis Example 36 Synthesis of Compound [36]

In the same manner as in Synthesis Example 1 , compound [35-1] and naphtho [2,3-c] furan-1,3-dione were used to obtain the target compound [36] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 5.30 (d, 1H), 6.90 (d, 1H), 7.39 ~ 7.40 (m, 2H), 7.50 (s, 1H), 7.60 (s, 1H), 7.90-7.91 (m, 2H), 8.23-8.25 (m, 2H), 8.31 (s, 2H)

MS / FAB: 392 (M ⁺ )

Synthesis Example 37 Synthesis of Compound [37]

Using the compound [35-1] , naphtho [2,3-c] furan-1,3-dione and bromobenzene in the same manner as in Synthesis Examples 1 and 2 , the target compound [37] as a yellow solid was obtained. .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 5.30 (d, 1H), 6.90 (d, 1H), 7.39 ~ 7.41 (m, 4H), 7.50 ~ 7.52 (m, 9H) , 7.60 (s, 1H), 7.91 ~ 7.92 (m, 2H), 8.23 (s, 1H), 8.25 (s, 1H)

MS / FAB: 544 (M ⁺ )

Synthesis Example 38 Synthesis of Compound [38]

In the same manner as in Synthesis Example 1 , compound [38-1] and maleic anhydride were used to obtain the target compound [38] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.33 (t, 1H), 7.52 ~ 7.61 (m, 4H), 7.89 ~ 7.92 (m, 3H), 8.00 ~ 8.01 (m, 3H), 8.44 (s, 1H)

MS / FAB: 392 (M ⁺ )

Synthesis Example 39 Synthesis of Compound [39]

In the same manner as in Synthesis Example 1 , the title compound [39] was obtained as a yellow solid using compound [38-1] , butyric anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.33 ~ 7.39 (m, 3H), 7.52 (d, 1H), 7.61 (t, 1H), 7.89 ~ 7.92 (m, 5H) , 8.23-8.25 (m, 2H), 8.31 (s, 2H)

MS / FAB: 442 (M ⁺ )

Synthesis Example 40 Synthesis of Compound [40]

In the same manner as in Synthesis Examples 1 and 2 , compound [38-1] , objective acid [40] of a yellow solid was obtained using broth benzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.33 ~ 7.41 (m, 5H), 7.41 ~ 7.61 (m, 10H), 7.89 ~ 7.92 (m, 5H), 8.23 (s, 1H), 8.25 (s, 1H)

MS / FAB: 594 (M ⁺ )

Synthesis Example 41 Synthesis of Compound [41]

In the same manner as in Synthesis Examples 1 , 2, and 19 , compound [38-1] , objective acid [41] of a yellow solid was obtained using phthalic anhydride, bromobenzene, and phenylboronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.33 ~ 7.52 (m, 17H), 7.60 ~ 7.61 (m, 2H), 7.89-7.97 (m, 4H), 8.13 (s, 1H), 8.23 (s, 1H), 8.25 (s, 1H)

MS / FAB: 670 (M ⁺ )

Synthesis Example 42 Synthesis of Compound [42]

In the same manner as in Synthesis Examples 1 , 2, and 18 , compound [38-1] , objective acid [42] of a yellow solid was obtained using 2-phthalomonoline and 2-bromoquinoline.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.33-7.41 (m, 5H), 7.51-7.61 (m, 7H), 7.78 (t, 1H), 7.89-7.98 (m, 6H), 8.06-8.10 (m, 2H), 8.23 (s, 1H), 8.25 (s, 1H)

MS / FAB: 645 (M ⁺ )

Synthesis Example 43 Synthesis of Compound [43]

In the same manner as in Synthesis Example 1 , 2, 22 , compound [43-1] , 5- bromophthalic anhydride, bromobenzene, and diphenylamine were used to obtain the target compound [43] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.02 ~ 7.09 (m, 16H), 7.20 ~ 7.24 (m, 8H), 7.41 ~ 7.52 (m, 10H), 7.64 (d, 1H), 7.75 (d, 1H), 7.92 (s, 2H), 8.23 (s, 1H), 8.25 (s, 1H)

MS / FAB: 929 (M ⁺ )

Synthesis Example 44 Synthesis of Compound [44]

Synthesis Example 1 The purpose of the yellow solid using the compound [38-1] , 5-bromo anhydride, bromobenzene, and 2,2'-bipyridin-6-yl boronic acid in the same manner as in Synthesis Example 1 , 2, 19 Compound [44] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.66 (s, 12H), 7.08-7.10 (m, 2H), 7.33-77.7 (m, 15H), 7.89-7.92 (m, 3H), 8.00 (d, 1H), 8.12 (d, 1H), 8.23-8.25 (m, 2H), 8.53 (d, 1H), 8.64 (s, 1H), 8.90 (d, 1H), 9.30 (d, 1H)

MS / FAB: 749 (M ⁺ )

Synthesis Example 45 Synthesis of Compound [45]

Synthesis Example In the same manner as 1 , thiophene and phthalic anhydride were used to obtain the target compound as a yellow solid [45] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.65-7.68 (m, 3H), 7.76-7.78 (m, 2H), 7.86 (s, 1H), 8.15 (d, 2H)

MS / FAB: 184 (M ⁺ )

Synthesis Example 46 Synthesis of Compound [46]

In the same manner as in Synthesis Examples 1 and 2 , thiophene, phthalic anhydride and bromobenzene were used to obtain the target compound as a yellow solid [46] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.42-7.55 (m, 12H), 7.76-7.78 (m, 2H), 8.55 (s, 2H)

MS / FAB: 336 (M ⁺ )

Synthesis Example 47 Synthesis of Compound [47]

In the same manner as in Synthesis Examples 1 and 2 , thiophene, naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [47] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.39-7.52 (m, 12H), 7.76-7.78 (m, 2H), 7.92 (d, 2H), 8.29 (s, 2H)

MS / FAB: 386 (M ⁺ )

Synthesis Example 48 Synthesis of Compound [48]

In the same manner as in Synthesis Examples 1 and 2 , thiophene, naphtho [1,2-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [48] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.41 to 7.52 (m, 10H), 7.71 to 7.82 (m, 6H), 8.10 (d, 1H), 8.92 (d, 1H)

MS / FAB: 386 (M ⁺ )

Synthesis Example 49 Synthesis of Compound [49]

In the same manner as in Synthesis Examples 1 and 2 , thiophene, puro [3,4-b] pyrazine-5,7-dione, and bromobenzene were used to obtain the target compound [49] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.41-7.52 (m, 10H), 7.76-7.78 (m, 2H), 8.73 (d, 2H)

MS / FAB: 338 (M ⁺ )

Synthesis Example 50 Synthesis of Compound [50]

In the same manner as in Synthesis Example 1 , the target compound [50] was obtained as yellow solid using thianthrene and maleic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.40 (s, 2H), 7.59-7.60 (m, 2H), 8.01 (d, 2H)

MS / FAB: 266 (M ⁺ )

Synthesis Example 51 Synthesis of Compound [51]

In the same manner as in Synthesis Example 1 , the target compound [51] was obtained as a yellow solid by using thianthrene and futal anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.38-7.39 (m, 2H), 7.65 (s, 2H), 7.90 (d, 2H) , 8.30 (s, 2H)

MS / FAB: 316 (M ⁺ )

Synthesis Example 52 Synthesis of Compound [52]

In the same manner as in Synthesis Example 2 , the target compound [52] was obtained as a yellow solid using thiansrene, phthalic anhydride, and bromobenzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.39-7.52 (m, 12H), 7.74 (s, 2H), 7.90 (d, 2H)

MS / FAB: 468 (M ⁺ )

Synthesis Example 53 Synthesis of Compound [53]

Synthesis Example 2 The same procedure as in Synthesis Example 2 was used to obtain the target compound [53] as a yellow solid using thianthrene, naphtho [2,3-c] furan-1,3-dione, and bromobenzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.39-7.52 (m, 12H), 7.65 (s, 2H), 7.92 (d, 2H) , 8.30 (s, 2H)

MS / FAB: 518 (M ⁺ )

Synthesis Example 54 Synthesis of Compound [54]

By the same method as in Example 2 using Tian seuren, naphtho [1,2-c] furan-1,3-dione, bromobenzene, to give the desired compound [54] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.39-7.51 (m, 11H), 7.64 (s, 2H), 7.84-7.91 (m, 3H), 8.11 (d, 1H), 8.92 (d, 1H)

MS / FAB: 518 (M ⁺ )

Synthesis Example 55 Synthesis of Compound [55]

Tian the seuren, furo [3,4-b] pyridine-5,7-dione, bromo target compound [55] of the yellow solid using the parent benzene In the same manner as in Synthesis Example 2 was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.41-7.58 (m, 13H), 8.35 (d, 1H), 8.83 (d, 1H)

MS / FAB: 469 (M ⁺ )

Synthesis Example 56 Synthesis of Compound [56]

By the same method as in Example 2 using Tian seuren, furo [3,4-b] pyrazine-5,7-dione, bromobenzene, to give the desired compound [56] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.41-7.52 (m, 12H), 8.73 (d, 2H)

MS / FAB: 470 (M ⁺ )

Synthesis Example 57 Synthesis of Compound [57]

Synthesis Example 18 An intermediate compound [57-1] and 1- (3-bromophenyl) naphthalene, synthesized using thianthrene, phthalic anhydride and 2-bromonaphthalene in the same manner as the target compound of yellow solid. [57] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.39-7.75 (m, 15H), 7.91-8.07 (m, 7H), 8.41 (d, 1H), 8.55 (d, 1H)

MS / FAB: 644 (M ⁺ )

Synthesis Example 58 Synthesis of Compound [58]

Synthesis Example 19 An intermediate compound [58-1] synthesized using thiansrene, 5-bromo anhydride and bromobenzene, and a target compound of yellow solid [58] using phenylboronic acid were obtained in the same manner as in Synthesis Example 19. It was.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21 (d, 2H), 7.41-7.75 (m, 18H), 7.97 (s, 1H), 8.12 (s, 1H)

MS / FAB: 544 (M ⁺ )

Synthesis Example 59 Synthesis of Compound [59]

Synthesis Example 19 The objective of the yellow solid using the intermediate compound [59-1] and naphthalene-2-yl boronic acid synthesize | combined using thian srene, 5-bromo anhydride, and 2-bromonaphthalene by the same method. Compound [59] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.20 (d, 2H), 7.58-7.75 (m, 12H), 7.72-7.73 (m, 3H), 7.92-8.00 ( m, 10H), 8.13 (s, 1H)

MS / FAB: 694 (M ⁺ )

Synthesis Example 60 Synthesis of Compound [60]

Synthesis Example 21 Intermediate compound [60-1] synthesized using 2-bromothiasene, 5-bromophthalic anhydride and 2-bromonaphthalene in the same manner as in Synthesis Example 21 , naphthalene-2-ylboronic acid, phenylborone An acid was used to obtain the title compound [60] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.22-7.33 (m, 3H), 7.41-7.42 (m, 1H), 7.51-7.75 (m, 16H), 7.72-7.73 (m, 3H), 7.93- 8.00 (m, 10H), 8.13 (s, 1H)

MS / FAB: 770 (M ⁺ )

Synthesis Example 61 Synthesis of Compound [61]

In the same manner as in Synthesis Example 22 , the intermediate compound [59-1] and diphenylamine were used to obtain the title compound [61] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 10H), 7.21-7.22 (m, 6H), 7.58-7.74 (m, 8H), 7.73-7.75 (m, 3H), 7.93- 7.98 (m, 6 H)

MS / FAB: 735 (M ⁺ )

Synthesis Example 62 Synthesis of Compound [62]

In the same manner as in Synthesis Example 22 , the intermediate compound [60-1] and diphenylamine were used to obtain the title compound [62] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.21 (m, 25H), 7.58-7.74 (m, 8H), 7.73-7.75 (m, 3H), 7.93-7.98 (m, 6H)

MS / FAB: 902 (M ⁺ )

Synthesis Example 63 Synthesis of Compound [63]

In the same manner as in Synthesis Example 18 , an intermediate compound [57-1] and 2- (3-bromophenyl) -1-phenyl-1H-benzo [d] imidazole were obtained to obtain the target compound as a yellow solid [63] . It was.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.21-7.22 (m, 4H), 7.45-7.75 (m, 17H), 7.91-8.00 (m, 5H), 8.23 ( d, 1H), 8.54 (d, 1H)

MS / FAB: 710 (M ⁺ )

Synthesis Example 64 Synthesis of Compound [64]

In the same manner as in Synthesis Example 18 , the intermediate compound [57-1] and 4-bromopyridine were used to obtain the target compound [64] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99 to 7.20 (m, 2H), 7.21 (d, 2H), 7.37 to 7.38 (m, 2H), 7.58 to 7.73 (m, 6H), 7.91 to 8.00 ( m, 7H), 8.75 (d, 2H)

MS / FAB: 519 (M ⁺ )

Synthesis Example 65 Synthesis of Compound [65]

In the same manner as in Synthesis Example 18 , an intermediate compound [57-1] and 6-bromo-2,2'-bipyridine were used to obtain the target compound [65] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99 to 7.00 (m, 3H), 7.15 to 7.21 (m, 3H), 7.37 to 7.38 (m, 2H), 7.59 to 7.70 (m, 8H), 7.91 to 8.0 (m, 5H), 8.53 (d, 1H), 8.78 (d, 1H), 8.93 (d, 1H)

MS / FAB: 596 (M ⁺ )

Synthesis Example 66 Synthesis of Compound [66]

In the same manner as in Synthesis Example 18 , the intermediate compound [57-1] and 2-bromoquinoline were used to obtain the title compound [66] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99-7.00 (m, 2H), 7.20 (d, H), 7.35-7.38 (m, 3H), 7.59-7.75 (m, 6H), 7.73-7.77 ( m, 2H), 7.91-8.05 (m, 8H)

MS / FAB: 569 (M ⁺ )

Synthesis Example 67 Synthesis of Compound [67]

In the same manner as in Synthesis Example 1 , dibenzo [b, d] thiophene and maleic anhydride were used to obtain the target compound [67] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.51-7.54 (m, 2H), 7.67-7.68 (m, 2H), 7.78 (s, 1H), 7.86 (s, 1H), 7.98 (s, 1H) , 8.15 (d, 2H), 8.43 (d, 1H)

MS / FAB: 234 (M ⁺ )

Synthesis Example 68 Synthesis of Compound [68]

In the same manner as in Synthesis Example 1 , the title compound [68] was obtained using dibenzo [b, d] thiophene and phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.38-7.39 (m, 2H), 7.50-7.52 (m, 2H), 7.91-7.98 (m, 5H), 8.31 (s, 2H), 8.43 (d, 1H)

MS / FAB: 284 (M ⁺ )

Synthesis Example 69 Synthesis of Compound [69]

Using the dibenzo [b, d] thiophene, anhydrous Fu deoxidation, bromobenzene in the same manner as in Synthesis Example 2, to give the desired compound [69] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.39-7.52 (m, 14H), 7.91-7.98 (m, 5H), 8.43 (d, 1H)

MS / FAB: 436 (M ⁺ )

Synthesis Example 70 Synthesis of Compound [70]

Synthesis Example 2 A yellow solid target compound [70] was obtained using dibenzo [b, d] thiophene, puro [3,4-b] pyrazine-5,7-dione and bromobenzene in the same manner as in Synthesis example 2. .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.41-7.52 (m, 12H), 7.78 (s, 1H), 7.86 (s, 1H), 7.98 (d, 1H), 8.43 (d, 1H)

MS / FAB: 438 (M ⁺ )

Synthesis Example 71 Synthesis of Compound [71]

Synthesis Example In the same manner as 1 , thieno [3,2-b] thiophene and phthalic anhydride were used to obtain the target compound [71] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.97 (d, 1H), 7.20 (d, 1H), 7.67-77.6 (m, 2H), 7.78 (s, 1H), 7.85 (s, 1H), 8.16 (d, 2H)

MS / FAB: 240 (M ⁺ )

Synthesis Example 72 Synthesis of Compound [72]

Synthesis Example In the same manner as 1 , thieno [3,2-b] thiophene and naphtho [2,3-c] furan-1,3-dione were used to obtain the target compound [72] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.97 (d, 1H), 7.20 (d, 1H), 7.39 ~ 7.40 (m, 2H), 7.91 ~ 7.92 (m, 4H), 8.31 (s, 2H)

MS / FAB: 290 (M ⁺ )

Synthesis Example 73 Synthesis of Compound [73]

Synthesis Example 2 In the same manner, a target compound of yellow solid was obtained using thieno [3,2-b] thiophene, naphtho [2,3-c] furan-1,3-dione, and bromobenzene [73] . It was.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.97 (d, 1H), 7.20 (d, 1H), 7.40 ~ 7.52 (m, 12H), 7.91 (d, 2H), 8.31 (s, 2H)

MS / FAB: 442 (M ⁺ )

Synthesis Example 74 Synthesis of Compound [74]

Synthesis Example In the same manner as in 1 , benzo [1,2-b: 4,5-b '] dithiophene and phthalic anhydride were used to obtain the target compound [74] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.65-7.76 (m, 3H), 7.78-7.86 (m, 5H), 8.16 (d, 2H)

MS / FAB: 290 (M ⁺ )

Synthesis Example 75 Synthesis of Compound [75]

Synthesis Example 1 In the same manner, the title compound as a yellow solid using benzo [1,2-b: 4,5-b '] dithiophene and naphtho [2,3-c] furan-1,3-dione [75] Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.38-7.39 (m, 2H), 7.65 (d, 1H), 7.78-7.79 (m, 2H), 7.86-7.91 (m, 5H), 8.31 (s, 2H)

MS / FAB: 340 (M ⁺ )

Synthesis Example 76 Synthesis of Compound [76]

Synthesis Example 2 The purpose of the yellow solid using benzo [1,2-b: 4,5-b '] dithiophene, naphtho [2,3-c] furan-1,3-dione and bromobenzene in the same manner Compound [76] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.39 to 7.51 (m, 12H), 7.65 (d, 1H), 7.77 to 7.78 (m, 2H), 7.86 to 7.91 (m, 3H), 8.31 (s, 2H)

MS / FAB: 492 (M ⁺ )

Synthesis Example 77 Synthesis of Compound [77]

Synthesis Example In the same manner as 1 , dibenzo [1,2-b: 4,5-b '] dithiophene and maleic anhydride were used to obtain the title compound [77] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.50-7.52 (m, 2H), 7.66-7.57 (m, 2H), 7.77 (s, 1H), 7.78 (s, 1H), 7.84 (s, 1H) , 7.85 (s, 1H), 7.97 (s, 1H), 8.16 (s, 2H), 8.45 (d, 1H)

MS / FAB: 340 (M ⁺ )

Synthesis Example 78 Synthesis of Compound [78]

Synthesis Example In the same manner as 1 , dibenzo [1,2-b: 4,5-b '] dithiophene and phthalic anhydride were used to obtain the target compound [78] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.38-7.39 (m, 2H), 7.50-7.52 (m, 2H), 7.78 (s, 1H), 7.86 (s, 1H), 7.91-7.98 (m, 5H), 8.31 (s, 2H), 8.45 (d, 1H)

MS / FAB: 390 (M ⁺ )

Synthesis Example 79 Synthesis of Compound [79]

Synthesis Example In the same manner as 2 , dibenzo [1,2-b: 4,5-b '] dithiophene, phthalic anhydride and bromobenzene were used to obtain the title compound [79] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.38-7.51 (m, 14H), 7.78 (s, 1H), 7.86 (s, 1H), 7.91-7.98 (m, 5H), 8.45 (d, 1H)

MS / FAB: 542 (M ⁺ )

Synthesis Example 80 Synthesis of Compound [80]

Synthesis Example 19 Intermediate compound [80-1] and phenylborone synthesized using dibenzo [1,2-b: 4,5-b '] dithiophene, 5-bromophthalic anhydride and bromobenzene in the same manner An acid was used to obtain the title compound [80] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.41-7.51 (m, 17H), 7.61 (d, 1H), 7.78 (s, 1H), 7.86 (s, 1H), 7.90 (s, 1H), 7.90 (s, 1H), 7.91 (s, 1h), 7.97-7.98 (m, 2H), 8.12 (s, 1H), 8.45 (d, 1H)

MS / FAB: 618 (M ⁺ )

Synthesis Example 81 Synthesis of Compound [81]

Synthesis Example 18 In the same manner, the intermediate compound [81-1] and 2-bromoquinoline synthesized using dibenzo [1,2-b: 4,5-b '] dithiophene, anhydrous phthalic anhydride and bromobenzene were synthesized. The desired compound [81] was obtained as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.35-7.60 (m, 11H), 7.77-77.7 (m, 2H), 7.86 (s, 1H), 7.91-7.98 (m, 6H), 8.06-8.09 ( m, 2H), 8.45 (d, 1H)

MS / FAB: 593 (M ⁺ )

Synthesis Example 82 Synthesis of Compound

Synthesis Example In the same manner as the 19 , the intermediate compound [80-1] and 2,2'-bipyridine-6-ylboronic acid were used to obtain the target compound of the yellow solid [82] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.00 (d, 1H), 7.13 ~ 7.14 (m, 1H), 7.41 ~ 7.52 (m, 12H), 7.63 ~ 7.70 (m, 2H), 7.78 (s, 1H), 7.86 (s, 1H), 7.91 (s, 2H), 7.98-8.00 (m, 2H), 8.63 (s, 1H), 8.78 (d, 1H), 8.93 (d, 1H)

MS / FAB: 696 (M ⁺ )

Synthesis Example 83 Synthesis of Compound [83]

Synthesis Example In the same manner as 1 , dithienothiophene and futal anhydride were used to obtain the target compound as a yellow solid [83] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.09 to 7.14 (m, 2H), 7.68 to 7.70 (m, 2H), 7.82 to 7.85 (m, 2H), 8.14 to 8.17 (m, 2H)

MS / FAB: 295 (M ⁺ )

Synthesis Example 84 Synthesis of Compound

In the same manner as in Synthesis Example 1 , dithienothiophene and naphtho [2,3-c] furan-1,3-dione were used to obtain the target compound [84] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.09 ~ 7.14 (m, 2H), 7.37 ~ 7.41 (m, 2H), 7.88 ~ 7.92 (m, 4H), 8.27 ~ 8.30 (m, 2H)

MS / FAB: 345 (M ⁺ )

Synthesis Example 85 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , dithienothiophene, naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [85] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.11-7.15 (m, 2H), 7.38-7.53 (m, 12H), 7.89-7.91 (m, 2H), 8.29-8.32 (m, 2H)

MS / FAB: 498 (M ⁺ )

Synthesis Example 86 Synthesis of Compound

In the same manner as in Synthesis Example 1 , the title compound [86] was obtained using the compound [86-1] and futal anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.06 to 7.09 (m, 2H), 7.65 to 7.68 (m, 2H), 7.82 to 7.85 (m, 2H), 8.15 to 8.19 (m, 2H)

MS / FAB: 351 (M ⁺ )

Synthesis Example 87 Synthesis of Compound [87]

In the same manner as in Synthesis Example 1 , Compound [86-1] and naphtho [2,3-c] furan-1,3-dione were used to obtain the target compound [87] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.07 to 7.10 (m, 2H), 7.38 to 7.41 (m, 2H), 7.88 to 7.72 (m, 4H), 8.29 to 8.32 (m, 2H)

MS / FAB: 401 (M ⁺ )

Synthesis Example 88 Synthesis of Compound [88]

In the same manner as in Synthesis Examples 1 and 2 , compound [86-1] , naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the title compound [88] . .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.06-7.09 (m, 2H), 7.37-7.53 (m, 12H), 7.90-7.83 (m, 2H), 8.30-8.33 (m, 2H)

MS / FAB: 554 (M ⁺ )

Synthesis Example 89 Synthesis of Compound [89]

In the same manner as in Synthesis Example 1 , the compound [89-1] and the desired compound [89] as a yellow solid were obtained using futal anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.64-7.69 (m, 3H), 7.77-7.87 (m, 7H), 8.15-8.19 (m, 2H)

MS / FAB: 340 (M ⁺ )

Synthesis Example 90 Synthesis of Compound

In the same manner as in Synthesis Example 1 , Compound [89-1] and naphtho [2,3-c] furan-1,3-dione were used to obtain the target compound [90] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.38-7.41 (m, 2H), 7.74-7.73 (m, 10H), 8.30-8.35 (m, 2H)

MS / FAB: 390 (M ⁺ )

Synthesis Example 91 Synthesis of Compound [91]

In the same manner as in Synthesis Examples 1 and 2 , Compound [89-1] , Naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the title compound [91] . .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.37 to 7.53 (m, 12H), 7.76 to 7.81 (m, 4H), 7.84 to 7.74 (m, 4H), 8.30 to 8.34 (m, 2H)

MS / FAB: 542 (M ⁺ )

Synthesis Example 92 Synthesis of Compound

Using Selenium nopen anhydride, Fu deoxidized in the same manner as in Synthesis Example 1, to give the desired compound [92] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.08 to 7.71 (m, 2H), 7.57 to 7.70 (m, 3H), 8.01 to 8.05 (m, 3H)

MS / FAB: 231 (M ⁺ )

Synthesis Example 93 Synthesis of Compound [93]

In the same manner as in Synthesis Examples 1 and 2 , selenofene, phthalic anhydride and bromobenzene were used to obtain the target compound as a yellow solid [93] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.05 ~ 7.12 (m, 4H), 7.43 ~ 7.56 (m, 10H), 8.54 ~ 8.57 (m, 2H)

MS / FAB: 384 (M ⁺ )

Synthesis Example 94 Synthesis of Compound [94]

In the same manner as in Synthesis Examples 1 and 2 , selenenophene, naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the title compound [94] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.06 ~ 7.11 (m, 4H), 7.44 ~ 7.53 (m, 10H), 7.90 ~ 7.93 (m, 2H), 8.29 ~ 8.32 (m, 2H)

MS / FAB: 434 (M ⁺ )

Synthesis Example 95 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , selenofene, naphtho [1,2-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [95] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.07 to 7.13 (m, 4H), 7.40 to 7.49 (m, 8H), 7.78 to 7.84 (m, 5H), 8.79 to 8.80 (d, 1H)

MS / FAB: 434 (M ⁺ )

Synthesis Example 96 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , selenenophene, puro [3,4-b] pyrazine-5,7-dione, and bromobenzene were used to obtain the title compound [96] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.06-7.09 (m, 2H), 7.45-7.52 (m, 10H), 8.68-8.70 (m, 2H)

MS / FAB: 386 (M ⁺ )

Synthesis Example 97 Synthesis of Compound [97]

Using the celecoxib not Trenton, maleic anhydride in the same manner as in Synthesis Example 1, to give the desired compound [97] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.35-7.42 (m, 4H), 7.62-7.69 (m, 4H), 7.99-8.02 (m, H)

MS / FAB: 361 (M ⁺ )

Synthesis Example 98 Synthesis of Compound [98]

Using the celecoxib not Transistor anhydride, Fu deoxidized in the same manner as in Synthesis Example 1, to give the desired compound [98] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.28 to 7.31 (m, 2H), 7.42 to 7.47 (m, 4H), 7.91 to 7.97 (m, 4H), 8.29 to 8.33 (m, 2H)

MS / FAB: 411 (M ⁺ )

Synthesis Example 99 Synthesis of Compound [99]

Using the Synthesis Example 1, 2 and celecoxib not Transistor anhydride, Fu deoxidation in the same way, bromobenzene, to give the desired compound [99] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.30-7.73 (m, 2H), 7.41-7.54 (m, 14H), 7.92-7.99 (m, 4H)

MS / FAB: 563 (M ⁺ )

Synthesis Example 100 Synthesis of Compound [100]

In the same manner as in Synthesis Examples 1 and 2 , selenantrene, naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [100] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.29 to 7.33 (m, 2H), 7.42 to 7.55 (m, 14H), 7.88 to 7.91 (m, 4H), 8.30 to 8.33 (m, 2H)

MS / FAB: 614 (M ⁺ )

Synthesis Example 101 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , selenantrene, naphtho [1,2-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [101] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.30-7.73 (m, 2H), 7.40-7.55 (m, 13H), 7.83-7.89 (m, 4H), 8.10-8.14 (m, 2H), 8.92- 8.93 (d, 1 H)

MS / FAB: 614 (M ⁺ )

Synthesis Example 102 Synthesis of Compound [102]

Synthesis Example 18 The intermediate compound [102-1] and 2- (3-bromophenyl) -1-phenyl-1H-benzo [d obtained using selenantrene and 2-bromonaphthalene in the same manner as in Synthesis Example ] Imidazole was used to obtain the target compound [102] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.31 (m, 4H), 7.43-7.59 (m, 15H), 7.70-7.74 (m, 2H), 7.93-8.01 (m, 7H), 8.33- 8.37 (m, 2 H)

MS / FAB: 806 (M ⁺ )

Synthesis Example 103 Synthesis of Compound [103]

In the same manner as in Synthesis Example 18 , the intermediate compound [102-1] and 4-bromopyridine were used to obtain the target compound [103] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.28 to 7.31 (m, 2H), 7.40 to 7.46 (m, 4H), 7.65 to 7.71 (m, 4H), 7.89 to 7.99 (m, 9H), 8.74 to 8.77 (m, 2 H)

MS / FAB: 615 (M ⁺ )

Synthesis Example 104 Synthesis of Compound

In the same manner as in Synthesis Example 18 , the intermediate compound [102-1] and 6-bromo-2,2'-bipyridine were used to obtain the target compound of the yellow solid [104] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.08 ~ 7.12 (m, 2H), 7.36 ~ 7.42 (m, 6H), 7.60 ~ 7.72 (m, 6H), 7.91 ~ 8.03 (m, 7H), 8.52 ~ 8.54 (d, 1H), 8.89-9.91 (d, 1H), 9.30-9.32 (d, 1H),

MS / FAB: 692 (M ⁺ )

Synthesis Example 105 Synthesis of Compound [105]

In the same manner as in Synthesis Example 18 , the intermediate compound [102-1] and 2-bromoquinoline were used to obtain the target compound [105] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.28-7.32 (m, 2H), 7.36-7.43 (m, 5H), 7.57-7.72 (m, 4H), 7.74-7.77 (m, 2H), 7.94- 8.15 (m, 10 H)

MS / FAB: 665 (M ⁺ )

Synthesis Example 106 Synthesis of Compound [106]

A dibenzo [b, d] Selenium nopen, the target compound [106] of the yellow solid using the maleic anhydride in the same manner as in Synthesis Example 1 was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.34 to 7.38 (m, 2H), 7.42 to 7.48 (m, 3H), 7.74 to 7.79 (m, 2H), 8.12 to 8.19 (m, 3H)

MS / FAB: 281 (M ⁺ )

Synthesis Example 107 Synthesis of Compound [107]

In the same manner as in Synthesis Example 1 , dibenzo [b, d] selenophene and fuphthalic anhydride were used to obtain the target compound as a yellow solid [107] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.35-7.44 (m, 5H), 7.84-7.72 (m, 4H), 8.16-8.21 (m, 3H)

MS / FAB: 332 (M ⁺ )

Synthesis Example 108 Synthesis of Compound [108]

A dibenzo [b, d] Selenium nopen anhydride, Fu deoxidation, bromo target compound [108] of the yellow solid using the parent benzene By the same method as in Examples 1 and 2 was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.36-7.52 (m, 15H), 7.79-7.84 (m, 3H), 8.06-8.09 (m, 2H)

MS / FAB: 484 (M ⁺ )

Synthesis Example 109 Synthesis of Compound [109]

Synthesis Example 1, 2 Subjected compound of yellow solid using dibenzo [b, d] selenophene, puro [3,4-b] pyrazine-5,7-dione, bromobenzene in the same manner as in Synthesis Examples 1 and 2. [109] ] Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.37 to 7.54 (m, 12H), 7.78 to 7.85 (m, 3H), 8.73 to 8.77 (m, 2H)

MS / FAB: 486 (M ⁺ )

Synthesis Example 110 Synthesis of Compound [110]

In the same manner as in Synthesis Example 1 , the desired compound [110] as a yellow solid was obtained using 3a, 6a-dihydroselenophene- [3,2-b] selenophene and phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.11-7.13 (d, 1H), 7.64-7.69 (m, 3H), 7.95-8.01 (m, 3H)

MS / FAB: 335 (M ⁺ )

Synthesis Example 111 Synthesis of Compound [111]

Synthesis Example 1 The target compound as a yellow solid using 3a, 6a-dihydroselenophene- [3,2-b] selenophene and naphtho [2,3-c] furan-1,3-dione in the same manner as in Synthesis Example 1. [111] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.12 to 7.14 (d, 1H), 7.42 to 7.46 (m, 2H), 7.92 to 7.99 (m, 5H), 8.31 to 8.36 (m, 2H)

MS / FAB: 385 (M ⁺ )

Synthesis Example 112 Synthesis of Compound [112]

3a, 6a-dihydroselenophene- [3,2-b] selenophene, naphtho [2,3-c] furan-1,3-dione and bromobenzene were used in the same manner as in Synthesis Examples 1 and 2. The desired compound [112] was obtained as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.13-7.18 (d, 1H), 7.42-7.73 (m, 10H), 7.81-7.87 (m, 3H), 8.29-8.32 (m, 2H)

MS / FAB: 537 (M ⁺ )

Synthesis Example 113 Synthesis of Compound [113]

In the same manner as in Synthesis Example 1 , the target compound [113] was obtained as a yellow solid using benzodiselenophene and phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.70-6.71 (d, 1H), 7.18-7.19 (d, 1H), 7.41-7.44 (m, 2H), 7.63-7.69 (m, 3H), 8.16- 8.21 (m, 3H)

MS / FAB: 385 (M ⁺ )

Synthesis Example 114 Synthesis of Compound

In the same manner as in Synthesis Example 1 , the desired compound [114] as a yellow solid was obtained using benzodiselenophene and naphtho [2,3-c] furan-1,3-dione.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69 ~ 6.70 (d, 1H), 7.18 ~ 7.19 (d, 1H), 7.38 ~ 7.45 (m, 4H), 7.95 ~ 8.02 (m, 3H), 8.17 ~ 8.23 (m, 3H)

MS / FAB: 435 (M ⁺ )

Synthesis Example 115 Synthesis of Compound [115]

In the same manner as in Synthesis Example 2 , benzodiselenophene, naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the title compound [115] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.71-6.72 (d, 1H), 7.19-7.20 (d, 1H), 7.45-7.56 (m, 14H), 7.88-7.72 (m, 2H), 8.25- 8.29 (m, 2 H)

MS / FAB: 587 (M ⁺ )

Synthesis Example 116 Synthesis of Compound

In the same manner as in Synthesis Example 1 , compound [116-1] and the target compound [116] were obtained as yellow solid using futal anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69 ~ 6.70 (d, 1H), 7.19 ~ 7.20 (d, 1H), 7.66 ~ 7.73 (m, 5H), 7.89 ~ 7.96 (m, 3H), 8.33 ~ 8.36 (m, 2 H)

MS / FAB: 435 (M ⁺ )

Synthesis Example 117 Synthesis of Compound

In the same manner as in Synthesis Example 1 , compound [116-1] and naphtho [2,3-c] furan-1,3-dione were used to obtain the target compound [117] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.68 ~ 6.70 (d, 1H), 7.18 ~ 7.19 (d, 1H), 7.39 ~ 7.44 (m, 2H), 7.63 ~ 7.68 (m, 2H), 7.88 ~ 7.94 (m, 3H), 7.99-8.03 (m, 2H), 8.29-8.25 (m, 3H)

MS / FAB: 485 (M ⁺ )

Synthesis Example 118 Synthesis of Compound [118]

In the same manner as in Synthesis Examples 1 and 2 , compound [116-1], naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the title compound [118] as a yellow solid. .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69 ~ 6.70 (d, 1H), 7.17 ~ 7.19 (d, 1H), 7.43 ~ 7.56 (m, 12H), 7.65 ~ 7.69 (m, 2H), 7.85 ~ 7.91 (m, 3H), 8.31-8.36 (m, 3H)

MS / FAB: 638 (M ⁺ )

Synthesis Example 119 Synthesis of Compound [119]

In the same manner as in Synthesis Example 1 , compound [119-1] and the desired compound [119] as a yellow solid were obtained using phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.11-7.13 (d, 1H), 7.61-7.68 (m, 3H), 7.82-7.86 (m, 2H), 7.99-8.04 (m, 2H)

MS / FAB: 439 (M ⁺ )

Synthesis Example 120 Synthesis of Compound [120]

Synthesis Example In the same manner as 1 , compound [119-1] and naphtho [2,3-c] furan-1,3-dione were used to obtain the target compound [120] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.12 to 7.14 (d, 1H), 7.40 to 7.45 (m, 2H), 7.91 to 8.01 (m, 5H), 8.30 to 8.34 (m, 2H)

MS / FAB: 489 (M ⁺ )

Synthesis Example 121 Synthesis of Compound [121]

In the same manner as in Synthesis Examples 1 and 2 , compound [119-1], naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [121] as a yellow solid. .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.11 to 7.17 (m, 3H), 7.42 to 7.74 (m, 10H), 7.82 to 7.89 (m, 3H), 8.30 to 8.35 (m, 2H)

MS / FAB: 641 (M ⁺ )

Synthesis Example 122 Synthesis of Compound [122]

Synthesis Example In the same manner as 1 , compound [122-1] and objective compound [122] of yellow solid were obtained using futal anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.11-7.13 (d, 1H), 7.62-7.70 (m, 4H), 7.96-8.02 (m, 3H)

MS / FAB: 543 (M ⁺ )

Synthesis Example 123 Synthesis of Compound [123]

Synthesis Example 1 In the same manner as the compound [122-1] and naphtho [2,3-c] furan-1,3-dione to obtain the target compound [123] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.13-7.15 (d, 1H), 7.40-7.45 (m, 2H), 7.88-7.96 (m, 5H), 8.29-8.33 (m, 2H)

MS / FAB: 593 (M ⁺ )

Synthesis Example 124 Synthesis of Compound [124]

In the same manner as in Synthesis Examples 1 and 2 , Compound [122-1], Naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the title compound [124] . .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.11-7.17 (M, 3H), 7.41-7.55 (m, 10H), 7.86-7.91 (m, 3H), 8.28-8.32 (m, 2H)

MS / FAB: 745 (M ⁺ )

Synthesis Example 125 Synthesis of Compound

Synthesis Example In the same manner as in 1, 1-phenyl-1H-pilol and futal anhydride were used to obtain the target compound [125] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.92 (d, 1H), 7.35 ~ 7.57 (m, 10H), 8.06 (m, 2H)

MS / FAB: 243 (M ⁺ )

Synthesis Example 126 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , 1-phenyl-1H-pilol, naphtho [2,3-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound [126] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.92 (d, 1H), 7.29 ~ 7.50 (m, 18H), 7.81 (m, 2H), 8.11 (s, 2H)

MS / FAB: 446 (M ⁺ )

Synthesis Example 127 Synthesis of Compound [127]

In the same manner as in Synthesis Examples 1 and 2 , the target compound [127] was obtained using 1-phenyl-1H-pilol, naphtho [1,2-c] furan-1,3-dione and bromobenzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.92 (d, 1H), 7.31 ~ 7.50 (m, 16H), 7.61 (d, 2H), 7.72 ~ 7.78 (m, 2H), 8.02 (d, 1H) , 8.33 (d, 1 H)

MS / FAB: 446 (M ⁺ )

Synthesis Example 128 Synthesis of Compound [128]

In the same manner as in Synthesis Examples 1 and 2 , the target compound [128] was obtained using 1-phenyl-1H-pilol, furo [3,4-b] pyrazine-5,7-dione and bromobenzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.92 (d, 1H), 7.31 ~ 7.50 (m, 16H), 8.35 (d, 2H)

MS / FAB: 398 (M ⁺ )

Synthesis Example 129 Synthesis of Compound [129]

Synthesis Example In the same manner as 1 , 5,10-diethyl-5,10-dihytropenazine and maleic anhydride were used to obtain the target compound [129] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.25 (m, 6H), 3.20 (m, 4H), 6.58 (d, 2H), 6.78 (d, 2H), 7.17 (m, 2H), 7.48 (m , 4H)

MS / FAB: 288 (M ⁺ )

Synthesis Example 130 Synthesis of Compound [130]

Synthesis Example In the same manner as in 1 , 5,10-diphenyl-5,10-dihydrophenazine and futal anhydride were used to obtain the target compound [130] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66 ~ 6.73 (m, 6H), 6.91 ~ 6.98 (m, 4H), 7.10 (m, 4H), 7.29 (d, 2H) , 7.81-7.86 (m, 4H)

MS / FAB: 435 (M ⁺ )

Synthesis Example 131 Synthesis of Compound [131]

In the same manner as in Synthesis Examples 1 and 2 , target compound [131] was obtained using 5,10-diphenyl-5,10-dihydrophenazine, anhydrous phthalic anhydride, and bromobenzene.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66-6.73 (m, 6H), 6.91-6.97 (m, 4H), 7.10 (m, 4H), 7.29-7.42 (m, 12H), 7.51 (d, 2H)

MS / FAB: 587 (M ⁺ )

Synthesis Example 132 Synthesis of Compound

5,10-diphenyl-5,10-dihydrophenazine, naphtho [2,3-c] furan-1,3-dione and bromobenzene in the same manner as in Synthesis Examples 1 and 2 [132] obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66-6.73 (m, 6H), 6.91-6.97 (m, 4H), 7.10 (m, 4H), 7.29-7.41 (m, 12H), 7.61 (d, 2H), 8.01 (s, 2H)

MS / FAB: 637 (M ⁺ )

Synthesis Example 133 Synthesis of Compound [133]

Using the Synthesis Examples 1 and 2 worked as a vortex method 5,10- diphenyl -5,10- dihydro-phenazine, furo [3,4-b] pyrazine-5,7-dione, bromobenzene object compound [ 133] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66 ~ 6.74 (m, 8H), 6.91 (t, 2H), 7.10 (m, 4H), 7.31 ~ 7.42 (m, 10H) , 8.33 (d, 2 H)

MS / FAB: 589 (M ⁺ )

Synthesis Example 134 Synthesis of Compound

Intermediate compound synthesized using 5,10-diphenyl-5,10-dihydrophenazine, 5-bromophthalic anhydride and 2-bromonaphthalene in the same manner as in Synthesis Examples 1 and 2 [134-1] Using di-diphenylamine, the target compound [134] was obtained in the same manner as in Synthesis Example 22 .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66-6.73 (m, 10H), 6.91-6.97 (m, 7H), 7.03 (s, 1H), 7.10 (m, 8H) , 7.48 ~ 7.49 (m, 6H), 7.63 ~ 7.65 (m, 3H), 7.82 ~ 7.90 (m, 6H)

MS / FAB: 854 (M ⁺ )

Synthesis Example 135 Synthesis of Compound [135]

Intermediate compounds synthesized using 2-bromo-5,10-diphenyl-5,10-dihydrophenazine, 5-bromophthalic anhydride and 2-bromonaphthalene in the same manner as in Synthesis Examples 1 and 2 [135-1] The target compound [135] was obtained in the same manner as in Synthesis Example 22 using hyperdiphenylamine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.52 (s, 1H), 6.64 (d, 1H), 6.73 (d, 1H), 6.83 (m, 12H), 6.91 ~ 6.97 (m, 9H), 7.03 (s, 1H), 7.10 (m, 12H), 7.48-7.49 (m, 6H), 7.63-7.75 (m, 3H), 7.82-7.90 (m, 6H)

MS / FAB: 1021 (M ⁺ )

Synthesis Example 136 Synthesis of Compound [136]

Synthesis Example 18 Intermediate compounds [136-1] and 2- (3- synthesized using 5,10-diphenyl-5,10-dihydrophenazine, anhydrous phthalic anhydride and 2-bromonaphthalene in the same manner as in Synthesis Example 18 The target compound [136] was obtained using bromophenyl) -1-phenyl-1H-benzo [d] imidazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ

MS / FAB: 829 (M ⁺ )

Synthesis Example 137 Synthesis of Compound

In the same manner as in Synthesis Example 18, the target compound [137] was obtained using the intermediate compound [136-1] and 4-bromopyridine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66-6.73 (m, 6H), 6.91-6.97 (m, 4H), 7.10 (m, 4H), 7.29 (d, 2H) , 7.48-7.49 (m, 3H), 7.63 (d, 1H), 7.81-7.90 (m, 7H), 8.25 (d, 2H)

MS / FAB: 638 (M ⁺ )

Synthesis Example 138 Synthesis of Compound [138]

In the same manner as in Synthesis Example 18, the target compound [138] was obtained using an intermediate compound [136-1] and 6-bromo-2,2'-bipyridine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66-6.73 (m, 6H), 6.91-6.97 (m, 4H), 7.00 (d, 1H), 7.04-7.10 (m, 5H), 7.29 (d, 2H), 7.49 ~ 7.60 (m, 6H), 7.81 ~ 7.90 (m, 5H), 8.14 (d, 1H), 8.26 (d, 1H), 8.50 (d, 1H)

MS / FAB: 715 (M ⁺ )

Synthesis Example 139 Synthesis of Compound

In the same manner as in Synthesis Example 18, the target compound [139] was obtained using an intermediate compound [136-1] and 2- chloroquinoline .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.58 (d, 2H), 6.66-6.73 (m, 6H), 6.91-6.97 (m, 4H), 7.10 (m, 4H), 7.25-7.29 (m, 3H), 7.49-7.50 (m, 4H), 7.63-7.68 (m, 2H), 7.88-7.96 (m, 8H)

MS / FAB: 688 (M ⁺ )

Synthesis Example 140 Synthesis of Compound [140]

Synthesis Example In the same manner as in 1 , 10-phenyl-10H-phenothiazine and maleic anhydride were used to obtain the target compound [140] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.73-6.68 (m, 3H), 6.81 (t, 1H), 7.01-7.07 (m, 2H), 7.16-7.31 (m, 5H), 7.57 (d, 2H), 8.06 (m, 2H)

MS / FAB: 325 (M ⁺ )

Synthesis Example 141 Synthesis of Compound

Synthesis Example In the same manner as 1 , 10-phenyl-10H-phenothiazine and phthalic anhydride were used to obtain the target compound [141] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.73 (m, 2H), 6.91 ~ 6.93 (m, 2H), 7.07 (t, 1H), 7.16 ~ 7.31 (m, 5H), 7.35 (d, 2H) , 7.59 (s, 1H), 7.81 (d, 2H), 7.98 (s, 1H), 8.09 (s, 1H)

MS / FAB: 376 (M ⁺ )

Synthesis Example 142 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , 10-phenyl-10H-phenothiazine, phthalic anhydride, and bromobenzene were used to obtain the target compound [142] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.73 (m, 2H), 6.91 to 6.63 (m, 2H), 7.07 (t, 1H), 7.16 to 7.31 (m, 5H), 7.35 to 7.41 (m, 12H), 7.59 (s, 1H), 7.81 (d, 2H)

MS / FAB: 528 (M ⁺ )

Synthesis Example 143 Synthesis of Compound [143]

Synthesis Example 18 An intermediate compound [143-1] and 4-bromopyridine synthesized using 10-phenyl-10H-phenothiazine, phthalic anhydride, and bromobenzene in the same manner as in Synthesis Example 18 [143] Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.73 (m, 2H), 6.91 to 6.63 (m, 2H), 7.07 (t, 1H), 7.16 to 7.31 (m, 5H), 7.35 to 7.41 (m, 7H), 7.59 (s, 1H), 7.81-7.89 (m, 4H), 8.29 (d, 2H)

MS / FAB: 529 (M ⁺ )

Synthesis Example 144 Synthesis of Compound

Synthesis Example In the same manner as 1 , 10-phenyl-10H-phenoxazine and maleic anhydride were used to obtain the target compound [144] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69 ~ 6.73 (m, 3H), 6.87 ~ 7.02 (m, 4H), 7.10 ~ 7.14 (m, 3H), 7.24 ~ 7.29 (m, 2H), 7.59 ~ 7.64 (m, 3 H)

MS / FAB: 309 (M ⁺ )

Synthesis Example 145 Synthesis of Compound

Synthesis Example In the same manner as in 1 , the target compound [145] was obtained using 10-phenyl-10H-phenoxazine and phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69 ~ 6.73 (m, 3H), 6.87 ~ 7.05 (m, 5H), 7.08 (s, 1H), 7.10 (m, 2H), 7.29 (m, 2H) , 7.81 (d, 2H), 7.94 (d, 2H)

MS / FAB: 359 (M ⁺ )

Synthesis Example 146 Synthesis of Compound [146]

Using the Synthesis Example 1, 2, 10-phenyl -10H- peok pictures, anhydrous Fu deoxidation, bromobenzene with vortex same method to give the desired compound [146].

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69 to 6.73 (m, 3H), 6.87 to 6.61 (m, 2H), 6.99 to 7.05 (m, 3H), 7.08 (s, 1H), 7.10 (m, 2H), 7.29-7.42 (m, 12H), 7.81 (d, 2H)

MS / FAB: 512 (M ⁺ )

Synthesis Example 147 Synthesis of Compound

Synthesis Example 18 An intermediate compound [147-1] synthesized using 10-phenyl-10H-phenoxazine, phthalic anhydride, and bromobenzene in the same manner as in Synthesis Example 18 , and a target compound using 4-bromopyrimidine [147] Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69-6.73 (m, 3H), 6.87-7.05 (m, 5H), 7.08 (s, 1H), 7.10 (m, 2H), 7.29-7.42 (m, 7H), 7.81 (d, 2H), 7.99 (d, 1H), 8.26 (d, 1H), 8.57 (s, 1H)

MS / FAB: 514 (M ⁺ )

Synthesis Example 148 Synthesis of Compound

Synthesis Example In the same manner as 1 , 9-phenyl-9H-carbazole maleic anhydride was used to obtain the target compound [148] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.57 (m, 11H), 7.84 (d, 1H), 8.06 (m, 2H), 8.25 (d, 1H)

MS / FAB: 293 (M ⁺ )

Synthesis Example 149 Synthesis of Compound [149]

Synthesis Example In the same manner as in 1 , 9-phenyl-9H-carbazole and phthalic anhydride were used to obtain the target compound [149] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.48 (m, 9H), 7.81-7.84 (m, 5H), 8.11 (d, 2H), 8.25 (d, 1H)

MS / FAB: 343 (M ⁺ )

Synthesis Example 150 Synthesis of Compound [150]

In the same manner as in Synthesis Examples 1 and 2 , 9-phenyl-9H-carbazole, phthalic anhydride, and bromobenzene were used to obtain the target compound [150] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.48 (m, 19H), 7.81-7.84 (m, 5H), 8.25 (d, 1H)

MS / FAB: 496 (M ⁺ )

Synthesis Example 151 Synthesis of Compound [151]

In the same manner as in Synthesis Examples 1 and 2 , 9-phenyl-9H-carbazole, furo [3,4-b] pyrazine-5,7-dione and bromobenzene were used to obtain the target compound [151] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.48 (m, 19H), 7.84 (d, 1H), 8.25 (d, 1H), 8.54 (s, 2H)

MS / FAB: 498 (M ⁺ )

Synthesis Example 152 Synthesis of Compound [152]

In the same manner as in Synthesis Example 1 , target compound [152] was obtained using 1,5-diphenyl-1,5-dihydropyrrole [2,3-f] indole and phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.62 (d, 1H), 7.30 ~ 7.57 (m, 17H), 8.06 (m, 2H)

MS / FAB: 409 (M ⁺ )

Synthesis Example 153 Synthesis of Compound [153]

Synthesis Example 1 Using 1,5-diphenyl-1,5-dihydropyrrole [2,3-f] indole and naphtho [2,3-c] furan-1,3-dione in the same manner as in Synthesis Example 1 Compound [153] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.62 (d, 1H), 7.30 ~ 7.50 (m, 15H), 7.81 (m, 4H), 8.21 (s, 2H)

MS / FAB: 459 (M ⁺ )

Synthesis Example 154 Synthesis of Compound [154]

In the same manner as in Synthesis Examples 1 and 2 , 1,5-diphenyl-1,5-dihydropyrrole [2,3-f] indole, naphtho [2,3-c] furan-1,3-dione, bro Mobenzene was used to obtain the target compound [154] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.62 (d, 1H), 7.30 ~ 7.50 (m, 25H), 7.81 (m, 2H), 8.21 (s, 2H)

MS / FAB: 611 (M ⁺ )

Synthesis Example 155 Synthesis of Compound [155]

In the same manner as in Synthesis Example 1 , the target compound [155] was obtained using 5,11-diphenyl-5,11-dihydroindole [3,2-b] carbazole and maleic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.19 (t, 1H), 7.30-7.57 (m, 18H), 8.02-8.06 (m, 3H)

MS / FAB: 459 (M ⁺ )

Synthesis Example 156 Synthesis of Compound

In the same manner as in Synthesis Example 1 , 5,11-diphenyl-5,11-dihydroindole [3,2-b] carbazole and anhydrous phthalic anhydride were used to obtain the target compound [156] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.19 (t, 1H), 7.29 to 7.53 (m, 16H), 7.81 (m, 4H), 8.02 (d, 1H), 8.21 (d, 2H)

MS / FAB: 509 (M ⁺ )

Synthesis Example 157 Synthesis of Compound

Obtained target compound [157] using 5,11-diphenyl-5,11-dihydroindole [3,2-b] carbazole, butyric anhydride and bromobenzene in the same manner as in Synthesis Examples 1 and 2. It was.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.19 (t, 1H), 7.29-7.53 (m, 26H), 7.81 (m, 4H), 8.02 (d, 1H)

MS / FAB: 661 (M ⁺ )

Synthesis Example 158 Synthesis of Compound

Synthesis Example 18 Intermediate compound synthesized using 5,11-diphenyl-5,11-dihydroindole [3,2-b] carbazole, phthalic anhydride and bromobenzene in the same manner as in Synthesis Example 18 [158-1] And 2-chloroquiline were used to obtain the target compound [158] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.30-7.53 (m, 24H), 7.68 (t, 1H), 7.81-7.88 (m, 5H), 7.96-8.02 (m, 3H)

MS / FAB: 712 (M ⁺ )

Synthesis Example 159 Synthesis of Compound

In the same manner as in Synthesis Example 1 , the target compound [159] was obtained using 1,6-diphenyl-1,6-dihydroindole [6,5-f] indole and phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.72 (d, 1H), 7.30 ~ 7.57 (m, 19H), 8.06 (d, 2H)

MS / FAB: 459 (M ⁺ )

Synthesis Example 160 Synthesis of Compound

1,6-diphenyl-1,6-dihydroindole [6,5-f] indole and naphtho [2,3-c] furan-1,3-dione in the same manner as in Synthesis Example 1 Compound [160] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.72 (d, 1H), 7.29 ~ 7.50 (m, 17H), 7.81 (m, 4H), 8.21 (d, 2H)

MS / FAB: 509 (M ⁺ )

Synthesis Example 161 Synthesis of Compound

1,6-diphenyl-1,6-dihydroindole [6,5-f] indole, naphtho [2,3-c] furan-1,3-dione, bromine in the same manner as in Synthesis Examples 1 and 2 Parent compound was used to obtain the target compound [161] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.72 (d, 1H), 7.29 ~ 7.50 (m, 27H), 7.81 (m, 2H), 8.21 (d, 2H)

MS / FAB: 661 (M ⁺ )

Synthesis Example 162 Synthesis of Compound

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2'-c] ple in the same manner as in Synthesis example 1 The target compound [162] was obtained as a yellow solid using Loren and maleic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 to 7.28 (m, 2H), 7.38 to 7.44 (m, 2H), 7.52 to 7.61 (m, 5H), 7.87 (d, 1H), 7.97-8.01 (m, 2H), 8.09 (d, 1H), 8.28 (s, 1H)

MS / FAB: 476 (M ⁺ )

Synthesis Example 163 Synthesis of Compound [163]

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2'-c in the same manner as in Synthesis Examples 1 and 2 ] Florence, maleic anhydride, and bromobenzene were used to obtain the target compound [163] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 to 7.28 (m, 2H), 7.38 to 7.55 (m, 10H), 7.79 to 7.87 (m, 6H), 7.97-8.09 (m, 4H)

MS / FAB: 628 (M ⁺ )

Synthesis Example 164 Synthesis of Compound

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2'-c] ple in the same manner as in Synthesis example 1 Lauren, using anhydrous Fu deoxidation to give the target compound [164] of a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 to 7.28 (m, 2H), 7.38 to 7.44 (m, 4H), 7.55 to 7.61 (m, 2H), 7.76 (s, 1H), 7.87-7.91 (m, 3H), 8.07-8.09 (m, 2H), 8.28-8.32 (m, 2H)

MS / FAB: 526 (M ⁺ )

Synthesis Example 165 Synthesis of Compound

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2'-c in the same manner as in Synthesis Examples 1 and 2 ] Florene, phthalic anhydride, and bromobenzene were used to obtain the target compound [165] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 ~ 7.28 (m, 2H), 7.38 ~ 7.55 (m, 16H), 7.76 (s, 1H) , 7.87 to 7.91 (m, 3H), 8.07 to 8.09 (m, 2H)

MS / FAB: 678 (M ⁺ )

Synthesis Example 166 Synthesis of Compound [166]

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2'-c in the same manner as in Synthesis Examples 1 and 2 ] Plenylene, naphtho [1,2-c] furan-1,3-dione and bromobenzene were used to obtain the target compound [166] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 ~ 7.55 (m, 17H), 7.76 ~ 7.91 (m, 5H), 8.07 ~ 8.12 (m, 3H), 8.93 (d, 1H)

MS / FAB: 728 (M ⁺ )

Synthesis Example 167 Synthesis of Compound [167]

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2'-c in the same manner as in Synthesis Examples 1 and 2 ; Florencio, using furo [3,4-b] pyrazine-5,7-dione, bromobenzene to afford the target compound [167] in a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24-7.28 (m, 2H), 7.38-7.75 (m, 14H), 7.83-7.87 (m, 2H), 8.05-8.09 (m, 2H), 8.74 (s, 2H)

MS / FAB: 680 (M ⁺ )

Synthesis Example 168 Synthesis of Compound [168]

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2' in the same manner as in Synthesis example 1, 2, 22 -c] The desired compound [168] as a yellow solid was obtained using florene, phthalic anhydride, and diphenylamine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.02 ~ 7.08 (m, 12H), 7.20 ~ 7.28 (m, 10H), 7.38 ~ 7.44 (m, 4H), 7.55-7.61 (m, 2H), 7.61 (s, 1H), 7.87-7.91 (m, 3H), 8.00 (s, 1H), 8.09 (d, 1H)

MS / FAB: 861 (M ⁺ )

Synthesis Example 169 Synthesis of Compound

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2' in the same manner as in Synthesis example 1, 2, 19 -c] to give the Florencio, 5-bromo-deoxy anhydrous Fu, bromobenzene, the desired compound in a yellow solid using the boronic acid [169].

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 ~ 7.28 (m, 2H), 7.38 ~ 7.55 (m, 20H), 7.76 (s, 1H) , 7.87 (d, 1H), 7.97 (d, 1H), 8.07-8.13 (m, 3H)

MS / FAB: 755 (M ⁺ )

Synthesis Example 170 Synthesis of Compound

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2' in the same manner as in Synthesis example 1, 2, 19 -c] to give the Florencio, 5-bromo anhydrous Fu deoxy, 2-bromo-naphthalene, the desired compound of the yellow solid using the boronic acid [170].

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 ~ 7.28 (m, 2H), 7.38 ~ 7.61 (m, 16H), 7.73 ~ 7.76 (m, 3H), 7.87-8.00 (m, 8H), 8.07-8.13 (m, 3H)

MS / FAB: 855 (M ⁺ )

Synthesis Example 171 Synthesis of Compound [171]

2-Bromo-5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: in the same manner as in Synthesis examples 1, 2, 22 : 1 ', to give the 2'-c] Florencio, 5-bromo-deoxy anhydrous Fu, bromobenzene, di target compound as a yellow solid using phenylamine [171].

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.03 ~ 7.08 (m, 16H), 7.20 ~ 7.28 (m, 9H), 7.38 ~ 7.41 (m, 3H), 7.51-7.55 (m, 9H), 7.75-7.72 (m, 2H), 7.84-7.87 (m, 2H), 8.07 (s, 1H)

MS / FAB: 1013 (M ⁺ )

Synthesis Example 172 Synthesis of Compound

2,7-Dibromo-5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2 in the same manner as in Synthesis examples 1, 2, 22 -a: 1 ', to give the 2'-c] Florencio, 5-bromo-deoxy anhydrous Fu, bromobenzene, di target compound as a yellow solid using phenylamine [172].

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.03 ~ 7.09 (m, 24H), 7.20 ~ 7.24 (m, 12H), 7.41 ~ 7.52 (m, 10H), 7.62 (d, 1H), 7.75-7.72 (m, 2H), 7.84 (d, 1H), 8.07 (s, 1H)

MS / FAB: 1180 (M ⁺ )

Synthesis Example 173 Synthesis of Compound [173]

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2' in the same manner as in Synthesis example 1, 2, 18 -c] Florencio, using anhydrous Fu deoxidation, bromobenzene, 4-bromo-pyridine to give the desired compound [173] in a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.24 ~ 7.28 (m, 2H), 7.38 ~ 7.61 (m, 11H), 7.76 (s, 1H) , 7.87 to 7.91 (m, 3H), 7.99 (d, 2H), 8.07 to 8.09 (m, 2H), 8.75 (d, 2H)

MS / FAB: 678 (M ⁺ )

Synthesis Example 174 Synthesis of Compound

5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ', 2' in the same manner as in Synthesis example 1, 2, 18 -c] Florencio, using anhydrous Fu deoxidation, bromobenzene, 6-bromo-2,2'-bipyridine, to give the desired compound [174] in a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.83 (s, 12H), 1.89 (s, 6H), 7.12 ~ 7.14 (m, 2H), 7.24 ~ 7.28 (m, 2H), 7.38 ~ 7.76 (m, 14H), 7.87-7.91 (m, 3H), 8.07-8.09 (m, 2H), 8.53 (d, 1H), 8.90 (d, 1H), 9.30 (d, 1H)

MS / FAB: 756 (M ⁺ )

Synthesis Example 175 Synthesis of Compound [175]

Synthesis Example In the same manner as in 1 , compound [175-1] and maleic anhydride were used to obtain the title compound [175] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01 to 7.03 (m, 6H), 7.28 (t, 1H), 7.41 (t, 1H), 7.67 (s, 1H), 7.90-7.96 (m, 2H),

MS / FAB: 415 (M ⁺ )

Synthesis Example 176 Synthesis of Compound [176]

Synthesis Example 1 In the same manner as the compound [175-1] , the desired compound of the yellow solid [176] was obtained using anhydrous phthalic anhydride.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01-7.03 (m, 6H), 7.38-7.39 (m, 3H) , 7.91 ~ 7.92 (m, 2H), 8.13 (s, 1H), 8.19 (s, 1H)

MS / FAB: 465 (M ⁺ )

Synthesis Example 177 Synthesis of Compound

Synthesis Example 1 In the same manner as the compound [175-1] and naphtho [2,3-c] furan-1,3-dione to obtain the target compound [177] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01-7.03 (m, 6H), 7.38-7.39 (m, 3H) , 7.91 ~ 7.92 (m, 4H), 8.13 (s, 1H), 8.19 (s, 1H)

MS / FAB: 515 (M ⁺ )

Synthesis Example 178 Synthesis of Compound

Due to Synthesis Example 1, 2 vortex same way using the compound [175-1], anhydrous Fu deoxidation, bromo-benzene, to give the desired compound [178] in a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01-7.03 (m, 6H), 7.38-7.52 (m, 13H) , 7.91-7.92 (m, 2H)

MS / FAB: 617 (M ⁺ )

Synthesis Example 179 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , compound [175-1] , naphtho [1,2-c] furan-1,3-dione, and bromobenzene were used to obtain the target compound as a yellow solid [179] . .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01-7.03 (m, 6H), 7.38-7.52 (m, 12H) , 7.82-7.91 (m, 3H), 8.12 (d, 1H), 8.93 (d, 1H)

MS / FAB: 667 (M ⁺ )

Synthesis Example 180 Synthesis of Compound

In the same manner as in Synthesis Examples 1 and 2 , compound [175-1] , puro [3,4-b] pyridine-5,7-dione, and bromobenzene were used to obtain the target compound [180] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01 to 7.03 (m, 6H), 7.41 ~ 7.58 (m, 11H) , 7.67 (s, 1H), 8.38 (d, 1H), 8.83 (d, 1H)

MS / FAB: 618 (M ⁺ )

Synthesis Example 181 Synthesis of Compound [181]

In the same manner as in Synthesis Examples 1 and 2 , compound [175-1] , puro [3,4-b] pyrazine-5,7-dione, and bromobenzene were used to obtain the target compound [181] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01-7.03 (m, 6H), 7.41-7.52 (m, 10H) , 7.67 (s, 1H), 8.74 (s, 2H)

MS / FAB: 619 (M ⁺ )

Synthesis Example 182 Synthesis of Compound [182]

In the same manner as in Synthesis Examples 1, 2, and 18 , Compound [175-1] , Phthalic anhydride, bromobenzene, and 4-bromopyridine were used to obtain the target compound [182] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01 to 7.03 (m, 6H), 7.38 ~ 7.52 (m, 8H) , 7.91-7.99 (m, 4H), 8.75 (d, 2H)

MS / FAB: 618 (M ⁺ )

Synthesis Example 183 Synthesis of Compound [183]

In the same manner as in Synthesis Examples 1, 2, and 18 , Compound [175-1] , Phthalic anhydride, bromobenzene, and 2-bromoquinoline were used to obtain the target compound [183] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01-7.03 (m, 6H), 7.34-7.41 (m, 5H) , 7.51 ~ 7.60 (m, 5H), 7.78 (t, 1H), 7.91 ~ 7.98 (m, 3H), 8.06 ~ 8.10 (m, 2H)

MS / FAB: 668 (M ⁺ )

Synthesis Example 184 Synthesis of Compound

In the same manner as in Synthesis Examples 1, 2, and 19 , Compound [175-1] , 5- bromophthalic anhydride, bromobenzene, and phenylboronic acid were used to obtain the title compound [184] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01-7.03 (m, 6H), 7.38-7.52 (m, 16H) , 7.61 (d, 1H), 7.97 (d, 1H), 8.13 (s, 1H)

MS / FAB: 693 (M ⁺ )

Synthesis Example 185 Synthesis of Compound [185]

In the same manner as in Synthesis Examples 1, 2 and 22 , compound [175-1] , 5- bromophthalic anhydride, bromobenzene, and diphenylamine were used to obtain the target compound [185] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.84 (s, 6H), 1.90 (s, 6H), 1.97 (s, 6H), 7.01 to 7.08 (m, 14H), 7.20 ~ 7.22 (m, 4H) , 7.38-7.52 (m, 11H), 7.75 (d, 1H)

MS / FAB: 785 (M ⁺ )

Comparative Example 1

2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2-yl) -N-phenylamino) -triphenylamine) represented by Chemical Formula b using Compound a represented by Chemical Formula a below Is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) represented by Chemical Formula c is used as the hole transport layer material. An organic light emitting device having a structure was prepared: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound a represented by Chemical Formula a was vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 25 nm. Thereafter, an Alq3 compound was vacuum-deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 600 nm (cathode) were sequentially vacuum deposited on the electron transport layer to prepare an organic light emitting device as shown in FIG. 1B. This is called Comparative Sample 1.

In this embodiment and the following examples, the device was fabricated using an EL deposition machine manufactured by DIOB Corporation.

<Formula a> <Formula b>

<Formula c>

Examples 1 to 117

ITO / DNTPD (80nm) / α-NPD in the same manner as in Comparative Example 1, except that Compounds 1 to 117 disclosed in Synthesis Example were used as EML layer compounds instead of Compound a as Comparative Example 1, respectively. An organic light emitting diode having a structure of (30 nm) / [EML Compound 1-185] (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm) was manufactured. These are referred to as samples 1 to 125, respectively.

Evaluation Example 1 Evaluation of Luminescence Characteristics of Comparative Sample 1 and Samples 1 to 125

For Comparative Sample 1 and Samples 1 to 125, Keithley SMU 235 and PR650 were used to evaluate driving voltage, emission luminance, emission efficiency, and emission peak, respectively, and the results are shown in Table 1 below. The samples showed blue emission peak values in the range of 476-522 nm.

TABLE 1

As shown in Table 1, Samples 1 to 125 exhibited improved luminescence properties compared to Comparative Sample 1.

Although the well-known techniques are omitted in the above description, those skilled in the art can easily infer, infer, and reproduce them.

Claims (10)

A first electrode; A second electrode; And an organic optical device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic optical compound represented by Formula A:
<Formula A>

Wherein A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 are each independently or related to hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 hetero An aryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon,
X1, X2, X3, X4 are each 0 (zero), Si, S, Se, O, C or N,
If one of X1 and X2 is zero, the other is not zero.
If one of X3 and X4 is zero, the other is not zero.
If X1, X2, X3 or X4 is zero, the corresponding C2, C1, A1d or A1c is zero
Rings containing X1 and X2 are either resonance or non-resonant. The method of claim 1,
A1a and A1b, A1a and A1c, A1b and A1d, B1 and C1, B2 and C2, and some of A2a and A2b may be related groups,
The functional group is a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. An organic optical device characterized by the above-mentioned. The method of claim 1,
At least one of A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 is a phenyl group. The method of claim 1,
Substituents of the aryl group, heteroaryl group, cycloalkyl group and heterocycloalkyl group,
C1-C50 alkyl group; C1-C50 alkoxy group; C 6 -C 50 aryl groups which are unsubstituted or substituted with C 1 -C 50 alkyl groups or C 1 -C 50 alkoxy groups; C2-C50 heteroaryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; A C5-C50 cycloalkyl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; C5-C50 heterocycloalkyl group which is unsubstituted or substituted with a C1-C20 alkyl group or a C1-C20 alkoxy group; Or one or more substituents selected from the group consisting of a silane group. The method of claim 1,
A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1, and C2 are independent or related to each other,
Hydrogen, phenyl group, tolyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group, anthracenyl group, benzoanthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group , Methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pisenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentaxenyl group, tetraphenylenyl group, hexaphenyl group, Hexenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, fluorenyl group, pyrantrenyl group, obarenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group , Thiophenyl group, indolyl group, furinyl group, benzimidazolyl group, quinolinyl group, benzothiophenyl group, parathiazinyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, imidazolinyl group, oxazolyl group, thia Zolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , Pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, thianthrenyl, cyclopentyl, cyclohexyl, oxiranyl, pyrrolidinyl, pyrazolidinyl, imidazoli An organic optical device, characterized in that selected from the group consisting of a diyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a di (C6-C50 aryl) amino group, a silane group and derivatives thereof. The method of claim 1,
An organic optical device characterized in that the compound is represented by the formula 1 to 185:

An organic photo compound represented by the following formula (A):
<Formula A>

Wherein A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 are each independently or related to hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 hetero An aryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon,
X1, X2, X3, X4 are each 0 (zero), Si, S, Se, O, C or N,
If one of X1 and X2 is zero, the other is not zero.
If one of X3 and X4 is zero, the other is not zero.
If X1, X2, X3 or X4 is zero, the corresponding C2, C1, A1d or A1c is zero
Rings containing X1 and X2 are either resonance or non-resonant. The method of claim 7, wherein
A1a and A1b, A1a and A1c, A1b and A1d, B1 and C1, B2 and C2, and some of A2a and A2b may be related groups,
The functional group is a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group. An organic optical device characterized by the above-mentioned. The method of claim 7, wherein
At least one of A1a, A1b, A1c, A1d, A2a, A2b, B1, B2, C1 and C2 is a phenyl group. The method of claim 7, wherein
An organic photo compound, characterized in that the compound is represented by the formula 1 to 185: