KR20120013278A - Organic light device and organic light compound for the same - Google Patents

Abstract

PURPOSE: An organic light emitting diode is provided to have remarkably improved luminous efficiency, luminous brightness, color purity, and luminous life time. CONSTITUTION: An organic light emitting diode comprises a first electrode, a second electrode, and at least one layer of organic membrane between the first electrode and the second electrode. The organic membrane comprises an organic photocompound in chemical formula a. In chemical formula a, A1, A2, A2', A3, A4 and A4' is respectively and independently hydrogen, a substituted or non-substituted C6-50 aryl group, a substituted or non-substituted C2-50 heteroaryl group, a substituted or non-substituted C2-50 cycloalkyl group, a substituted or non-substituted C2-50 heterocycloalkyl group, or saturated or unsaturated hydrocarbon. Ar is hydrogen, or a substituted or non-substituted C6-50 aryl group, a C2-50 heteroaryl group, a C2-50 cycloalkyl group, or C2-50 heterocycloalkyl group, X is 0 or N, O or S, and m is the integer of 1-10.

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, and more particularly, to an organic light emitting device capable of realizing excellent luminous efficiency, emission brightness, color purity, and emission lifetime, and an organic light emitting compound or solar power generation used therefor. It relates to an optical device for use 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, the organic film comprising an organic photo compound of formula a:

<Formula a>

Wherein A1, A2, A2 ', A3, A4 and A4' are each independently or related to hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted A substituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon,

Ar is hydrogen, 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, At least one aryl group or heteroaryl group,

X is 0 or N, O or S,

m is an integer from 1 to 10.

In order to achieve another object of the present invention, an organic optical compound represented by Chemical Formula a is provided.

The organic optical device according to the present invention provides high luminous efficiency, high luminance, high color purity and remarkably 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 solar 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, the organic film comprising an organic photo compound of formula a:

<Formula a>

In the formula for the carbazole carbazole derivatives, A1, A2, A2 ', A3, A4 and A4' are independently or related to each other, hydrogen, a substituted or unsubstituted C6-C50 aryl group, a 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,

Ar is hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group ego,

X is 0 or N, O or S,

m is an integer from 1 to 10.

Furthermore, Ar preferably includes one or more aryl groups or heteroaryl groups.

The inventor of the present invention selects A1, A2, A2 ', A3, A4 and A4' from the substituents of the compound represented by the above formula (A), and develops a variety of carbazole carbazole derivatives to form a hole transport layer (HTL), a hole injection layer To develop an organic optical compound that can be used as various organic films between the first electrode and the second electrode, such as (HIL) or light emitting layer (EML), 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 Chemical 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 Chemical Formula a is suitable for use in an organic film of an organic light emitting device, in particular, a hole transport layer, a hole injection layer, or a light emitting layer, and is used as a dopant material as well as a host material. The compound represented by Chemical Formula a provides a color of blue to green and is suitable for use in a white light emitting device.

A1, A2, A3 and A4 are independent of each other,

A2 and A2 'and A4 and A4' are related to constitute a functional group,

One or both of these functional groups may be substituted or unsubstituted C2-C50 cycloalkyl group, substituted or unsubstituted C2-C50 heterocycloalkyl group, substituted or unsubstituted C6-C50 aryl group, or substituted or unsubstituted C2- C50 heteroaryl group,

Moreover, it is preferable that at least one of said A1, A2, A2 ', A3, A4, and A4' 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, and Si.

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 and Si.

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, A1, A2, A2 ', A3, A4 and A4' are independently or related to each other, hydrogen, phenyl group, tolyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group, anthra Senyl group, benzoanthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, Perylyl group, chloroperylenyl group, pentaphenyl group, pentaxenyl group, tetraphenylenyl group, hexaphenyl group, hexasenyl group, rubisenyl group, coronyl group, trinaphthyleneyl group, heptaphenyl group, heptasenyl group, fluorene Nilyl group, pyrantrenyl group, ovarenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, thiophenyl group, indolyl group, furinyl group, benzimidazolyl group, quinolinyl group, benzothiophenyl group, parathiazinyl Groups, pyrrolyl groups, pyrazolyl groups, imidazolyl groups, imidazolinyl groups, Sazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyridinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthrenyl group, thianthrenyl group, cyclopentyl group, cyclo Hexyl group, oxiranyl group, pyrrolidinyl group, pyrazolidinyl group, imidazolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, di (C6-C50 aryl) amino group, silane group and these It may be selected from the group consisting of derivatives.

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, A1, A2, A2 ', A3, A4 and A4' are independently or related to each other, hydrogen, phenyl group, biphenyl group, tolyl group, naphthyl group, naphthalenylphenyl group, dimethylbenzyl group, pyrenyl group, Phenanthrenyl group, benzo [de] anthracenyl group, benzo [a] anthracenyl group, benzo [b] anthracenyl group, benzo [c] anthracenyl group, 11, 11-dimethylbenzo [de] anthracenyl group, 11 , 11-diethylbenzo [de] anthracenyl group, 11,11-dimethylbenzo [a] anthracenyl group, 11,11-dimethylbenzo [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-ethylcarbazolyl 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) (biphenyl) amino group, (pe ) (Naphthyl) may be selected from amino group, a di (non petil) amino group, di-fluorenyl group, a di -p- tolyl group, a popular silane, and derivatives thereof.

In more detail, according to one embodiment of the present invention, the organic photochemical compound used in the organic photoelectric device of the present invention may have a structure of Formula 1 to 161 (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 161 of Synthesis Examples below. 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. The organic EL device may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron blocking layer, an electron transporting layer, and an electron injecting layer 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,

The organic light emitting device may have a structure including a first electrode / a hole injection layer / a hole transport layer / a light emitting layer / an electron transport layer / an electron injection layer / a second electrode,

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

In this case, at least one of the hole transport layer, the hole injection layer and the light emitting 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. In addition, the compound according to the present invention can also be used as a fluorescent dopant in the light emitting layer.

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 properties 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.

When the hole injection layer is formed by the spin coating method, 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 preferably from about 2000 rpm to 5000 rpm , And the heat treatment temperature for removing the solvent after coating is suitably selected within a temperature range of about 80 캜 to 200 캜.

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 thickness of the hole injection layer may be about 100 Å to 10000 Å, preferably 100 Å to 1000 Å. 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. In the case of forming the hole transporting layer by the vacuum deposition method and the sputtering method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The hole transport layer material may include a compound of Formula a as described above. Or carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole and the like, N, N'-bis (3-methylphenyl) -N, N'- diphenyl- [ Amine having an aromatic condensed ring such as N, N'-tetramethyldisiloxane, -4,4'-diamine (TPD) and N, N'-di (naphthalen- The hole transporting layer may have a thickness of about 50 Å to 1000 Å, preferably 100 Å to 600 Å. When the thickness of the hole transporting layer is less than 50 Å, the hole transporting property may be degraded. When the thickness of the hole transporting layer is more than 1000 Å, 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), coumarine derivatives and the like 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.

When the thickness of the light emitting layer is less than 100 Å, the light emitting characteristics may be degraded. If the thickness of the light emitting layer is more than 1000 Å, 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 the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of 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, an electron transport layer (ETL) is formed by various methods such as a vacuum evaporation method, a spin coating method, and a casting method.

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. When the thickness of the electron transporting layer is less than 100 angstroms, the electron transporting characteristics may be deteriorated. When the thickness of the electron transporting layer exceeds 1000 angstroms, the driving voltage may increase.

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited.

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 substantially the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injection layer may be about 1 A to 100 A, preferably 5 A to 50 A. 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 can be formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like.

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 161. 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 the compound [1], and the intermediate compound of the above compound is represented by [1-1] or the like. In the present specification, the chemical number is represented by the chemical number. For example, the compound represented by the formula (1) is represented by compound 1.

Synthesis Example 1 Synthesis of Compound [1]

5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 4.65 g (19.44 mmol) of 9-ethyl-9H-carbazol-3-yl boronic acid, tetrakis (triphenylphosphine) in a round bottom flask 408 mg (0.353 mmol) of palladium, 5 mL of 2 mol-sodium carbonate solution and 50 mL of toluene were 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 separated and purified through column chromatography using dichloromethane and hexane as a developing solvent, to obtain 5.5 g (89%) of the intermediate compound [1-1] in white.

5.5 g (15.7 mmol) of intermediate compound [1-1] , 2.63 g (15.7 mmol) of carbazole, and 50 mL of toluene were added to a 100 mL round bottom flask, and 70 mg (0.314 mmol) of palladium acetate (II) and sodium tert-butoxide in a nitrogen atmosphere. 2.26 g (23.55 mmol) of the seed and 0.30 mL (0.628 mmol) of tertbutylphosphine (50% toluene solution) were added thereto, and the mixture was stirred under reflux for 10 hours. The reaction solution was cooled to room temperature and 50 mL of methanol was added dropwise. The resulting solid was filtered to yield 3.5 g (51%) of the title compound [1] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.35 (t, 3H), 4.45 (q, 2H), 7.20 ~ 7.50 (m, 7H), 7.61 ~ 7.95 (m, 8H), 8.15 (m, 2H) , 8.27-8.40 (m, 2H)

MS / FAB: 436 (M ⁺ )

Synthesis Example 2 Synthesis of Compound [2]

Synthesis Example 1 In the same manner, the title compound as a yellow solid using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-octyl-9H-carbazol-3-yl boronic acid, and carbazole [2] 4.5 g (49%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.85 (t, 3H), 1.30 (m, 10H), 1.75 (m, 2H), 4.15 (m, 2H), 7.20 ~ 7.40 (m, 5H), 7.51 (m, 2H), 7.60-7.91 (m, 8H), 8.13 (m, 2H), 8.25-8.30 (m, 2H)

MS / FAB: 520 (M ⁺ )

Synthesis Example 3 Synthesis of Compound [3]

Synthesis Example 1 In the same manner, the title compound as a white solid using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole [3] 3.7 g (43%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.21-7.35 (m, 4H), 7.51-7,81 (m, 14H), 7.95-8.15 (m, 5H), 8.45 (m, 1H)

MS / FAB: 484 (M ⁺ )

Synthesis Example 4 Synthesis of Compound [4]

Synthesis Example 1 In the same manner, using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9- (biphenyl-4-yl) -9H-carbazol-3-yl boronic acid, carbazole 3.9 g (39%) of compound [4] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.55 (m, 11H), 7.61-7.80 (m, 11H), 7.95-8.20 (m, 5H), 8.50 (m, 1H)

MS / FAB: 560 (M ⁺ )

Synthesis Example 5 Synthesis of Compound [5]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9- (9,9-dimethyl-9H-floren-2-yl) -9H-carbazol-3-ylboronic acid , Carbazole was used to obtain 4.6 g (43%) of the target compound [5] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.65 (s, 6H), 7.25-7.45 (m, 7H), 7.55 (m, 4H), 7.60-7.70 (m, 4H), 7.80-7.95 (m, 7H), 8.13 (m, 3H), 8.45 (m, 1H)

MS / FAB: 600 (M ⁺ )

Synthesis Example 6 Synthesis of Compound [6]

Synthesis Example 1 In the same manner, the target compound is prepared by using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9- (naphthalen-2-yl) -9H-carbazol-3-yl boronic acid, and carbazole. [6] 4.9 g (52%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.23-7.61 (m, 18H), 7.75-7.80 (m, 4H), 7.85-8.00 (m, 3H), 8.15 (m, 2H), 8.45 (m, 2H)

MS / FAB: 534 (M ⁺ )

Synthesis Example 7 Synthesis of Compound

Synthesis Example 1 Using the same method, the desired compound was prepared using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 6,9-diphenyl-9H-carbazol-3-yl boronic acid and carbazole [7] 3.8 g (38%) were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.23-7.61 (m, 18H), 7.75-7.80 (m, 4H), 7.85-8.00 (m, 3H), 8.15 (m, 2H), 8.45 (m, 1H)

MS / FAB: 560 (M ⁺ )

Synthesis Example 8 Synthesis of Compound [8]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9- (biphenyl-4-yl) -6-phenyl-9H-carbazole-3-ylboronic acid, and carbazole 5.8 g (51%) of the title compound [8] were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.20 to 7.50 (m, 14H), 7.61 to 7.70 (m, 6H), 7.80 (m, 6H), 7.85 to 8.10 (m, 5H), 8.46 (m, 1H)

MS / FAB: 636 (M ⁺ )

Synthesis Example 9 Synthesis of Compound [9]

Synthesis Example 1 In the same manner, the target compound was prepared using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-phenyl-9H-carbazol-3-yl boronic acid, and 3-phenyl-9H-carbazole. [9] 4.8 g (48%) were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.21-7.70 (m, 18H), 7.71-7.79 (m, 4H), 7.95-8.15 (m, 5H), 8.49 (m, 1H)

MS / FAB: 560 (M ⁺ )

Synthesis Example 10 Synthesis of Compound [10]

*

Synthesis Example 1 In the same manner, 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9- (biphenyl-4-yl) -9H-carbazol-3-yl boronic acid, 3-phenyl-9H- Carbazole was used to obtain 5.0 g (44%) of the target compound [10] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25 to 7.55 (m, 14H), 7.60 to 7.81 (m, 12H), 7.90 to 8.13 (m, 5H), 8.50 (m, 1H)

MS / FAB: 636 (M ⁺ )

Synthesis Example 11 Synthesis of Compound [11]

Synthesis Example 1 In the same manner, 1-bromo-4-iodobenzene 5.0g (17.67mmol), 6,9-diphenyl-9H-carbazol-3-yl boronic acid, 3-phenyl-9H-carbazole This gave 5.3 g (47%) of the title compound [11] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.21-7.56 (m, 17H), 7.70 (m, 4H), 7.75-7.80 (m, 5H), 7.95-8.15 (m, 5H), 8.51 (m, 1H)

MS / FAB: 636 (M ⁺ )

Synthesis Example 12 Synthesis of Compound [12]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9- (biphenyl-4-yl) -6-phenyl-9H-carbazol-3-yl boronic acid, 3- Phenyl-9H-carbazole was used to obtain 5.5 g (43%) of the title compound [12] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.55 (m, 17H), 7.65 to 7.70 (m, 6H), 7.75 to 7.85 (m, 7H), 7.85 to 8.00 (m, 4H), 8.15 ( m, 1H), 8.48 (m, 1H)

* MS / FAB: 712 (M ⁺ )

Synthesis Example 13 Synthesis of Compound [13]

Synthesis Example 1 In the same manner, using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-diphenal-9H-carbazole This gave 5.1 g (45%) of the title compound [13] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.75 (m, 21H), 7.75-7.80 (m, 5H), 8.01-8.15 (m, 5H)

MS / FAB: 636 (M ⁺ )

Synthesis Example 14 Synthesis of Compound [14]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-di (naphthalen-1-yl)- 9H-carbazole was used to obtain 5.5 g (42%) of the target compound [14] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.28-7.85 (m, 23H), 8.00-8.20 (m, 9H), 8.40-8.45 (m, 4H)

MS / FAB: 736 (M ⁺ )

Synthesis Example 15 Synthesis of Compound [15]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-di (naphthalen-2-yl)- 9H-carbazole was used to obtain 5.8 g (44%) of the target compound [15] .

* ¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.80 (m, 24H), 7.90-8.00 (m, 9H), 8.10-8.20 (m, 3H)

MS / FAB: 736 (M ⁺ )

Synthesis Example 16 Synthesis of Compound [16]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-di (biphenyl-4-yl) -9H-carbazole was used to obtain 6.8 g (49%) of the target compound [16] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.20 to 7.30 (m, 9H), 7.41 to 7.61 (m, 20H), 7.75 to 7.85 (m, 6H), 8.00 to 8.20 (m, 5H)

MS / FAB: 788 (M ⁺ )

Synthesis Example 17 Synthesis of Compound [17]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-bis (9,9-dimethyl-9H 7.2 g (47%) of the title compound [17] was obtained using -floren-2-yl) -9H-carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.65 (s, 12H), 7.25 ~ 7.65 (m, 19H), 7.72 ~ 7.80 (m, 7H), 7.85 ~ 8.05 (m, 7H), 8.15 (m, 3H)

MS / FAB: 869 (M ⁺ )

Synthesis Example 18 Synthesis of Compound [18]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9- (biphenyl-4-yl) -9H-carbazol-3-yl boronic acid, 3,6-diphenyl -9H-carbazole was used to obtain 6.1 g (48%) of the target compound [18] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.26 to 7.54 (m, 17H), 7.65 to 7.90 (m, 14H), 8.01 to 8.15 (m, 5H)

MS / FAB: 712 (M ⁺ )

Synthesis Example 19 Synthesis of Compound [19]

*

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9- (9,9-dimethyl-9H-floren-2-yl) -9H-carbazol-3-yl boron 7.5 g (43%) of the title compound [19] was obtained using acid, 3,6-bis (9,9-dimethyl-9H-floren-2-yll) -9H-carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.67 (s, 18H), 7.21 ~ 7.31 (m, 4H), 7.48 ~ 7.65 (m, 11H), 7.70 ~ 7.79 (m, 7H), 7.85 ~ 8.20 ( m, 12H)

MS / FAB: 985 (M ⁺ )

Synthesis Example 20 Synthesis of Compound [20]

Synthesis Example 1 in the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-bis (trimethylsilyl) -9H-carba The sol was used to obtain 4.5 g (40%) of the title compound [20] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.31 (s, 18H), 7.26 (m, 3H), 7.48-7.75 (m, 10H), 7.75-7.80 (m, 5H), 7.90-7.81 (m, 4H)

MS / FAB: 628 (M ⁺ )

Synthesis Example 21 Synthesis of Compound [21]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-bis (triphenylsilyl) -9H- Carbazole was used to obtain 5.5 g (31%) of the title compound [21] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.27 to 7.81 (m, 48H), 8.01 to 8.19 (m, 4H)

MS / FAB: 1001 (M ⁺ )

Synthesis Example 22 Synthesis of Compound [22]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-bis (4- (trimethylsilyl) phenyl ) -9H-carbazole was used to obtain 5.0 g (36%) of the target compound [22] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 0.30 (s, 18H), 7.25 (m, 1H), 7.39-7.75 (m, 14H), 7.75-7.81 (m, 9H), 8.05-8.19 (m, 5H)

MS / FAB: 781 (M ⁺ )

Synthesis Example 23 Synthesis of Compound [23]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 6- (diphenylamino) -9-phenyl-9H-carbazol-3-yl boronic acid, 9H-carbazole 5.9 g (51%) of the title compound [23] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.95 to 7.15 (m, 8H), 7.21 to 7.60 (m, 17H), 7.80 to 7.95 (m, 5H), 8.20 to 8.40 (m, 3H)

MS / FAB: 651 (M ⁺ )

Synthesis Example 24 Synthesis of Compound [24]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, N, N-diphenyl-9H-carbazole-3 -Amine was used to obtain 4.9 g (43%) of the title compound [24] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.00-7.20 (m, 8H), 7.25-7.81 (m, 20H), 8.05-8.45 (m, 5H)

MS / FAB: 651 (M ⁺ )

Synthesis Example 25 Synthesis of Compound [25]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9- (4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, 9H-carbazole Was obtained to give 5.0 g (43%) of the title compound [25] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.01-7.18 (m, 8H), 7.23-7.73 (m, 12H), 7.61-7.69 (m, 4H), 7.80 (m, 3H), 7.95-8.15 ( m, 5H), 8.45 (m, 1H)

MS / FAB: 651 (M ⁺ )

Synthesis Example 26 Synthesis of Compound [26]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 6- (diphenylamino) -9- (4- (diphenylamino) phenyl-9H-carbazol-3-yl Boronic acid, 9H-carbazole, was used to obtain 5.8 g (40%) of the target compound [26] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.99 to 7.20 (m, 16H), 7.23 to 7.50 (m, 15H), 7.65 to 7.80 (m, 6H), 7.99 to 8.40 (m, 5H)

MS / FAB: 819 (M ⁺ )

Synthesis Example 27 Synthesis of Compound [27]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9- (4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, N, N- Diphenyl-9H-carbazole-3-amine was used to give 6.8 g (47%) of the title compound [27] .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.00 to 7.18 (m, 16H), 7.21 to 7.75 (m, 15H), 7.60 to 7.80 (m, 6H), 8.01 to 8.15 (m, 4H), 8.50 ( m, 1H)

MS / FAB: 819 (M ⁺ )

Synthesis Example 28 Synthesis of Compound [28]

Synthesis Example 1 In the same manner, 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 6- (diphenylamino) -9-phenyl-9H-carbazol-3-ylboronic acid, N, N-diphenyl -9H-carbazole-3-amine was used to give 6.9 g (48%) of the title compound [28] as a yellow solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.19-6.23 (m, 8H), 6.75-6.84 (m, 8H), 7.19-7.26 (m, 6H), 7.32-7.40 (m, 6H), 7.47- 7.53 (m, 5H), 7.68-7.74 (m, 5H), 7.96-8.02 (m, 2H), 8.19-8.20 (d, 1H), 8.55-8.56 (d, 1H)

MS / FAB: 818 (M ⁺ )

Synthesis Example 29 Synthesis of Compound [29]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 6- (diphenylamino) -9- (4- (diphenylamino) phenyl) -9H-carbazole-3- Ilboronic acid, N, N-diphenyl-9H-carbazol-3-amine, was used to obtain 7.6 g (44%) of the title compound [29] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.62 ~ 6.70 (m, 14H), 6.76 ~ 6.83 (m, 10H), 7.19 ~ 7.24 (m, 12H), 7.29 ~ 7.38 (m, 6H), 7.69 ~ 7.76 (m, 5H), 7.95-7.99 (m, 2H), 8.20-8.21 (d, 1H), 8.54-8.55 (d, 1H)

MS / FAB: 985 (M ⁺ )

Synthesis Example 30 Synthesis of Compound [30]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 6- (diphenylamino) -9-phenyl-9H-carbazol-3-ylboronic acid, N3, N3, N6, 6.9 g (40%) of the target compound [30] as a white solid was obtained using N 6 -tetraphenyl-9H-carbazole-3,6-diamine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.63 ~ 6.69 (m, 13H), 6.75 ~ 6.82 (m, 10H), 7.19 ~ 7.25 (m, 12H), 7.38 ~ 7.47 (m, 5H), 7.56 ~ 7.67 (m, 6H), 7.78-7.82 (m, 3H), 8.01-8.03 (d, 1H), 8.18-8.20 (d, 1H)

MS / FAB: 985 (M ⁺ )

Synthesis Example 31 Synthesis of Compound [31]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 6- (diphenylamino) -9- (4- (diphenylamino) phenyl) -9H-carbazole-3- 9.1 g (45%) of the title compound [31] as a white solid was obtained using ilboronic acid, N 3, N 3, N 6, N 6 -tetraphenyl-9H-carbazole-3,6-diamine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.61-6.70 (m, 19H), 6.75-6.63 (m, 12H), 7.18-7.29 (m, 16H), 7.35-7.39 (m, 4H), 7.65- 7.71 (m, 4H), 7.78-7.82 (m, 3H), 8.01-8.03 (d, 1H), 8.18-8.19 (d, 1H)

MS / FAB: 1152 (M ⁺ )

Synthesis Example 32 Synthesis of Compound [32]

Synthesis Example 1 In the same manner, a white solid using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-phenyl-9H-3,9'-bicarbazole-3'-ylboronic acid, carbazole 5.5 g (48%) of the title compound [32] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25 to 7.35 (m, 7H), 7.52 to 7.69 (m, 13H), 7.79 to 7.84 (m, 3H), 7.93 to 7.99 (m, 3H), 8.16 to 8.22 (m, 3H), 8.53 ~ 8.56 (m, 2H)

MS / FAB: 649 (M ⁺ )

Synthesis Example 33 Synthesis of Compound [33]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-phenyl-9H-3,9'-bicarbazole-3'-ylboronic acid, 9H-3,9'- Bicarbazole was used to obtain 7.3 g (51%) of the title compound [33] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.36 (m, 10H), 7.49 to 7.62 (m, 15H), 7.78 to 7.82 (m, 3H), 7.93 to 8.01 (m, 4H), 8.12 to 8.19 (m, 3H), 8.55 to 8.58 (m, 3H)

MS / FAB: 814 (M ⁺ )

Synthesis Example 34 Synthesis of Compound [34]

Synthesis Example 1 In the same manner, a white solid using 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-phenyl-9H-3,9'-bicarbazole-3'-ylboronic acid, carbazole 6.2 g (54%) of the desired compound [34] were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25 to 7.33 (m, 5H), 7.53 to 7.69 (m, 15H), 7.77 to 7.82 (m, 3H), 7.95 to 8.01 (m, 3H), 8.11 to 8.19 (m, 4H), 8.56-8.57 (d, 1H)

MS / FAB: 649 (M ⁺ )

Synthesis Example 35 Synthesis of Compound [35]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 6 '-(9H-carbazol-9-yl) -9-phenyl-9H-3,9'-bicarbazole 7.2 g (50%) of the title compound [35] as a white solid was obtained using -3'-ylboronic acid and carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.23 to 7.74 (m, 8H), 7.52 to 7.71 (m, 17H), 7.80 to 7.84 (m, 3H), 7.95 to 8.02 (m, 4H), 8.12 to 8.17 (m, 4H), 8.55-8.57 (m, 2H)

MS / FAB: 814 (M ⁺ )

*

Synthesis Example 36 Synthesis of Compound [36]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9-phenyl-9H-3,9'-bicarbazole-3'-ylboronic acid, 9H-3,9'- using non-carbazole, to give the desired compound [36] 6.7g (47%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25 to 7.35 (m, 8H), 7.49 to 7.69 (m, 17H), 7.79 to 7.84 (m, 3H), 7.95 to 8.02 (m, 4H), 8.11 to 8.19 (m, 4H), 8.53-8.55 (m, 2H)

MS / FAB: 814 (M ⁺ )

Synthesis Example 37 Synthesis of Compound [37]

*

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 5,11-diphenyl-5,11-dihydroindolo [3,2-b] carbazole-2-ylbo Lonic acid, carbazole was used to obtain 4.4 g (39%) of the title compound [37] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.31 (m, 5H), 7.44 to 7.68 (m, 17H), 7.76 to 7.80 (m, 3H), 7.96 to 8.01 (m, 2H), 8.11 to 8.16 (m, 3H), 8.55 to 8.56 (d, 1H)

MS / FAB: 649 (M ⁺ )

Synthesis Example 38 Synthesis of Compound [38]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid, 5-phenyl-5,11-dihydroindolo [3 , 2-b] carbazole was used to obtain 4.6 g (40%) of the title compound [38] as a white solid.

* ¹ H NMR (300 MHz, CDCl ₃ ): δ 7.26 to 7.74 (m, 5H), 7.42 to 7.57 (m, 17H), 7.77 to 7.81 (m, 3H), 7.95 to 7.99 (m, 2H), 8.13 ~ 8.18 (m, 3H), 8.54-8.55 (d, 1H)

MS / FAB: 649 (M ⁺ )

Synthesis Example 39 Synthesis of Compound [39]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9- (4- (9H-carbazol-9-yl) phenyl) -9H-carbazol-3-ylboronic acid, Carbazole was used to obtain 4.8 g (42%) of the title compound (39 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.74 (m, 7H), 7.49 to 7.73 (m, 3H), 7.62 to 7.70 (m, 9H), 7.77 to 7.82 (m, 3H), 7.95 to 8.02 (m, 3H), 8.11-8.20 (m, 4H), 8.55-8.57 (m, 2H)

MS / FAB: 649 (M ⁺ )

Synthesis Example 40 Synthesis of Compound [40]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 5- (4- (diphenylamino) phenyl) -11-phenyl-5,11-dihydroindolo [3, 2-b] carbazol-2-ylboronic acid, carbazole, gave 6.6 g (46%) of the title compound [40] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.62-6.68 (m, 6H), 6.81-6.84 (m, 2H), 7.25-7.38 (m, 11H), 7.44-7.68 (m, 12H), 7.78- 7.84 (m, 3H), 7.95-8.00 (m, 2H), 8.11-8.16 (m, 3H), 8.54-8.55 (d, 1H)

MS / FAB: 816 (M ⁺ )

Synthesis Example 41 Synthesis of Compound [41]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 9- (4- (9H-carbazol-9-yl) phenyl) -9H-carbazol-3-ylboronic acid, 9H-3,9'-bicarbazole was used to obtain 6.2 g (43%) of the title compound [41] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.63-6.67 (m, 4H), 6.77-6.63 (m, 4H), 7.20-7.35 (m, 11H), 7.49-7.52 (m, 2H), 7.61- 7.70 (m, 8H), 7.77-7.82 (m, 3H), 7.95-8.02 (m, 3H), 8.13-8.20 (m, 3H), 8.55-8.57 (m, 2H)

MS / FAB: 816 (M ⁺ )

Synthesis Example 42 Synthesis of Compound [42]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-3,9'-bicarbazole-6-ylboronic acid, 9H-3,9'-ratio Carbazole was used to obtain 5.9 g (41%) of the title compound [42] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.22 to 7.35 (m, 10H), 7.47 to 7.69 (m, 15H), 7.76 to 7.80 (m, 3H), 7.95 to 8.02 (m, 4H), 8.14 to 8.21 (m, 3H), 8.54-8.57 (m, 3H)

MS / FAB: 814 (M ⁺ )

Synthesis Example 43 Synthesis of Compound [43]

Synthesis Example 1 In the same manner, 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9- (9-phenyl-9H-carbazole-3-yl) -9H-3,9'-bicarbazole- using 6-Daily acid, 9H-carbazol-3,9'- ratio to give the desired compound as a white solid [43] 6.5g (38%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.36 (m, 11H), 7.48 to 7.72 (m, 19H), 7.78 to 7.81 (m, 3H), 7.93 to 8.01 (m, 5H), 8.13 to 8.20 (m, 4H), 8.53-8.57 (m, 3H)

MS / FAB: 979 (M ⁺ )

Synthesis Example 44 Synthesis of Compound [44]

Synthesis Example 1 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 6- (diphenylamino) -9-phenyl-9H-carbazol-3-ylboronic acid, N, N, 6.0 g (35%) of the title compound [44] as a white solid was obtained using 11-triphenyl-5,11-dihydroindolo [3,2-b] carbozol-2-amine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.62 ~ 6.69 (m, 9H), 6.76 ~ 6.83 (m, 6H), 7.21 ~ 7.32 (m, 9H), 7.49 ~ 7.69 (m, 19H), 7.78 ~ 7.82 (m, 3H), 8.07-8.15 (m, 3H)

MS / FAB: 983 (M ⁺ )

Synthesis Example 45 Synthesis of Compound [45]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 5- (4- (diphenylamino) phenyl) -11-phenyl-5,11-dihydroindolo [3, 2-b] carbazole-2-ylboronic acid, N, N, 11-triphenyl-5,11-dihydroindolo [3,2-b] carbozol-2-amine, to give a white solid [45] 6.5 g (32%) were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.61 to 6.69 (m, 11H), 6.80 to 6.66 (m, 4H), 7.19 to 7.42 (m, 14H), 7.51 to 7.67 (m, 20H), 7.78 to 7.84 (m, 3H), 8.07-8.16 (m, 4H)

MS / FAB: 1148 (M ⁺ )

Synthesis Example 46 Synthesis of Compound [46]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 5,11-diphenyl-5,11-dihydroindolo [3,2-b] carbazole-2-ylbo Lonic acid, 5-phenyl-5,11-dihydroindolo [3,2-b] carbazole, was used to obtain 6.0 g (42%) of the title compound [46] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.38 (m, 5H), 7.43 to 7.70 (m, 24H), 7.76 to 7.82 (m, 3H), 7.96 to 8.02 (m, 2H), 8.11 to 8.17 (m, 3H), 8.55 to 8.56 (d, 1H)

MS / FAB: 814 (M ⁺ )

Synthesis Example 47 Synthesis of Compound [47]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 5- (4- (diphenylamino) phenyl) -11-phenyl-5,11-dihydroindolo [3, 2-b] carbazole-2-6.2g Daily acid, 5-phenyl -5,11- dihydro-indol [3,2-b] the desired compound (47) as a white solid using the carbazole (36%) Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.62 ~ 6.70 (m, 6H), 6.80 ~ 6.83 (m, 2H), 7.21 ~ 7.42 (m, 12H), 7.44 ~ 7.71 (m, 18H), 7.75 ~ 7.81 (m, 3H), 7.96-8.00 (m, 2H), 8.15-8.19 (m, 3H), 8.55-8.56 (d, 1H)

MS / FAB: 981 (M ⁺ )

Synthesis Example 48 Synthesis of Compound [48]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 5,11-diphenyl-5,11-dihydroindolo [3,2-b] carbazole-2-ylbo 5.9 g (34%) of the target compound [48] as a white solid was obtained using lonic acid, N, N, 11-triphenyl-5,11-dihydroindolo [3,2-b] carbozol-2-amine. Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.61-6.67 (m, 5H), 6.79-6.63 (m, 2H), 7.21-7.30 (m, 6H), 7.46-7.68 (m, 27H), 7.77- 7.82 (m, 3H), 8.05-8.14 (m, 4H)

MS / FAB: 981 (M ⁺ )

Synthesis Example 49 Synthesis of Compound [49]

Synthesis Example 1 In the same manner, 5.0 g (17.67 mmol) of 1-bromo-4-iodobenzene, 5- (4- (diphenylamino) phenyl) -11-phenyl-5,11-dihydroindolo [3, 2-b] carbazole-2-ylboronic acid, N, N, 11-triphenyl-5,11-dihydroindolo [3,2-b] carbozol-2-amine, to give a white solid [49] 5.6 g (28%) were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.60-6.68 (m, 5H), 6.81-6.85 (m, 2H), 7.20-7.29 (m, 7H), 7.47-7.72 (m, 31H), 7.75- 7.81 (m, 3H), 7.95-8.01 (m, 2H), 8.11-8.20 (m, 4H)

MS / FAB: 1146 (M ⁺ )

Synthesis Example 50 Synthesis of Compound [50]

Synthesis Example 1 In the same manner, the title compound as a white solid using 4-bromo-4'-iodobiphenyl5.0g (17.67mmol), 9-phenyl-9H-carbazole-3-boronic acid, carbosol [50] 4.3 g (56%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.36 (m, 8H), 7.47 to 7.70 (m, 11H), 7.79 to 7.84 (m, 3H), 7.95 to 7.99 (m, 2H), 8.13 to 8.19 (m, 3H), 8.56-8.57 (d, 1H)

MS / FAB: 560 (M ⁺ )

Synthesis Example 51 Synthesis of Compound [51]

Synthesis Example 1 In the same manner, a white solid using 4-bromo-4'-iodobiphenyl5.0 g (17.67 mmol), 4- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid, carbosol 4.5 g (51%) of the title compound [51] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.36 (m, 12H), 7.49 to 7.70 (m, 11H), 7.77 to 7.81 (m, 3H), 7.96 to 8.00 (m, 2H), 8.15 to 8.21 (m, 3H), 8.54-8.55 (d, 1H)

MS / FAB: 636 (M ⁺ )

Synthesis Example 52 Synthesis of Compound [52]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodotriphenyl5.0 g (17.67 mmol), 4- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid, white with carbozol 3.4 g (42%) of the title compound (52 ) were obtained as a solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.26-7.36 (m, 16H), 7.48-7.68 (m, 11H), 7.76-7.81 (m, 3H), 7.97-8.01 (m, 2H), 8.13- 8.19 (m, 3H), 8.55 to 8.56 (d, 1H)

MS / FAB: 712 (M ⁺ )

Synthesis Example 53 Synthesis of Compound [53]

Synthesis Example 1 In the same manner as 4-bromo-4'-iodotriphenyl5.0g (17.67mmol), 4 '-(9-phenyl-9H-carbazol-3-yl) biphenyl-4-ylboronic acid, carbo The sol was used to obtain 2.8 g (31%) of the title compound (53 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25 to 7.38 (m, 20H), 7.49 to 7.69 (m, 11H), 7.77 to 7.82 (m, 3H), 7.98 to 8.03 (m, 2H), 8.14 to 8.20 (m, 3H), 8.54-8.55 (d, 1H)

MS / FAB: 788 (M ⁺ )

Synthesis Example 54 Synthesis of Compound [54]

Synthesis Example 1 In the same manner, the title compound as a white solid, using 5.0 g (15.02 mmol) of 2-bromo-6-iodonaphthalene, 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole [54] 3.5 g (44%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25 to 7.59 (m, 15H), 7.73 to 7.83 (m, 3H), 7.92 to 8.01 (m, 4H), 8.12 to 8.18 (m, 4H)

MS / FAB: 534 (M ⁺ )

Synthesis Example 55 Synthesis of Compound [55]

Synthesis Example 1 In the same manner, the title compound as a white solid using 5.0 g (15.02 mmol) of 1-bromo-4-iodonaphthalene, 9-phenyl-9H-carbazol-3-yl boronic acid, and carbazole [55] 3.9 g (48%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.58 (m, 16H), 7.83 to 8.10 (m, 9H), 8.55 to 8.56 (d, 1H)

MS / FAB: 535 (M ⁺ )

Synthesis Example 56 Synthesis of Compound [56]

Synthesis Example 1 In the same manner, the title compound as a white solid using 5.0 g (15.02 mmol) of 1-bromo-4-iodonaphthalene, 9-phenyl-9H-carbazol-3-yl boronic acid, and carbazole [56] 3.8 g (47%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.32 (m, 5H), 7.50-7.62 (m, 11H), 7.78 (s, 1H), 8.00-8.19 (m, 7H), 8.42 (d, 1H), 8.54 (d, 1H)

MS / FAB: 534 (M ⁺ )

Synthesis Example 57 Synthesis of Compound [57]

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-fluorene 5.0 g (12.53 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, and carbazole are used. This gave 3.5 g (46%) of the title compound [57] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25 to 7.74 (m, 16H), 7.78 to 7.79 (m, 2H), 7.87 to 8.00 (m, 4H), 8.12 to 8.18 ( m, 4H)

MS / FAB: 600 (M ⁺ )

Synthesis Example 58 Synthesis of Compound [58]

Synthesis Example 1 In the same manner, 2-bromo-8-iodine-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 6.0 g (11.65 mmol), 9 -phenyl -9H- carbazol-3-yl, using the boronic acid, carbazole, to give the desired compound as a white solid [58] 3.8g (45%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 12H), 7.24 to 7.28 (m, 4H), 7.50 to 7.74 (m, 13H), 7.77 to 7.78 (m, 3H), 7.93 to 7.99 ( m, 3H), 8.08-8.18 (m, 5H)

MS / FAB: 716 (M ⁺ )

Synthesis Example 59 Synthesis of Compound [59]

Synthesis Example 1 In the same manner, using 2-bromo-7-iodine-9,10-dihydrophenanthrene 5.0 g (12.99 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole 3.4 g (45%) of the title compound [59] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 2.98 (s, 4H), 7.25 to 7.33 (m, 5H), 7.50 to 7.80 (m, 14H), 7.91 to 8.00 (m, 3H), 8.12 to 8.18 ( m, 4H)

MS / FAB: 586 (M ⁺ )

Synthesis Example 60 Synthesis of Compound [60]

Synthesis Example 1 In the same manner 2-bromo-7-iodine-4,5,9,10-tetrahydropyrene 5.0 g (12.16 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole To obtain 3.5g (47%) of the title compound [60] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 2.99 (s, 8H), 7.25 ~ 7.33 (m, 4H), 7.50 ~ 7.63 (m, 11H), 7.74 ~ 7.77 (m, 3H), 7.94 ~ 8.00 ( m, 2H), 8.12-8.18 (m, 4H)

MS / FAB: 612 (M ⁺ )

Synthesis Example 61 Synthesis of Compound [61]

Synthesis Example 1 In the same manner, the purpose of a white solid using 5.0 g (12.22 mmol) of 1-bromo-4- (4-iodinephenyl) naphthalene, 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole 3.4 g (46%) of Compound [61] were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.59 (m, 20H), 7.78 (s, 1H), 7.94 to 8.00 (m, 3H), 7.12 to 7.18 (m, 5H), 8.54 (d, 1H)

MS / FAB: 610 (M ⁺ )

Synthesis Example 62 Synthesis of Compound [62]

Synthesis Example 1 Purpose of white solid using 5.0 g (12.22 mmol) of 2-bromo-6- (4-iodinephenyl) naphthalene, 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole in the same manner 3.4 g (45%) of Compound [62] were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.36 (m, 9H), 7.50 to 7.68 (m, 10H), 7.73 to 7.77 (m, 2H), 7.83 (s, 1H), 7.92 to 8.00 ( m, 4H), 8.12-8.18 (m, 4H)

MS / FAB: 610 (M ⁺ )

Synthesis Example 63 Synthesis of Compound [63]

Synthesis Example 1 Bromo-7- (4-iodinephenyl) -9,9-dimethyl-9H-fluorene 5.0 g (10.52 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid , Carbazole was used to obtain 3.3 g (46%) of the title compound (63 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25 to 7.63 (m, 20H), 7.78 to 7.79 (m, 2H), 7.87 to 8.01 (m, 4H), 8.12 to 8.18 ( m, 4H)

MS / FAB: 676 (M ⁺ )

Synthesis Example 64 Synthesis of Compound [64]

Synthesis Example 1 In the same manner, 7-bromo-7'-iodine-9,9,9 ', 9'-tetramethyl-9H, 9'H-2,2'-bifluorene 6.0 g (10.15 mmol), 9 3.6 g (45%) of the title compound (64 ) as a white solid was obtained using -phenyl-9H-carbazol-3-yl boronic acid, carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 12H), 7.25 ~ 7.64 (m, 18H), 7.78 ~ 7.79 (m, 4H), 7.87 ~ 8.00 (m, 6H), 8.12 ~ 8.14 ( m, 4H)

MS / FAB: 792 (M ⁺ )

Synthesis Example 65 Synthesis of Compound [65]

Synthesis Example 1 in the same manner as 2-bromo-8- (4-iodinephenyl) -6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 6.0 g ( 10.15mmol), 9- phenyl -9H- carbazol-3-yl, using the boronic acid, carbazole, to give the desired compound as a white solid [65] 3.7g (46%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 12H), 7.25 ~ 7.33 (m, 8H), 7.45 ~ 7.64 (m, 13H), 7.78 ~ 7.79 (m, 3H), 7.93 ~ 8.00 ( m, 3H), 8.09-8.17 (m, 5H)

MS / FAB: 792 (M ⁺ )

Synthesis Example 66 Synthesis of Compound [66]

Synthesis Example 1 In the same manner, 2,6-dibromo-9,9,10,10-tetramethyl-9,10-dihydroandracene 5.0g (12.69mmol), 9-phenyl-9H-carbazole-3- using one acid, carbazole, to give the desired compound as a white solid [66] 3.4g (42%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.74 (s, ¹² H), 7.23 to 7.60 (m, ¹⁹ H), 7.78 (s, 1 H), 7.95 to 7.99 (m, 2H), 8.12 to 8.16 (m, 4H)

MS / FAB: 642 (M ⁺ )

Synthesis Example 67 Synthesis of Compound [67]

Synthesis Example 1 In the same manner as 2-dibromo-6- (4-iodinephenyl) -9,9,10,10-tetramethyl-9,10-dihydroandracene 5.0 g (9.67 mmol), 9-phenyl- 3.0 g (43%) of the title compound [67] as a white solid was obtained using 9H-carbazol-3-yl boronic acid and carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.74 (s, 12H), 7.24 to 7.63 (m, 23H), 7.77 (s, 1H), m 7.96 to 7.99 (m, 2H), 8.12 to 8.17 (m , 4H)

MS / FAB: 718 (M ⁺ )

Synthesis Example 68 Synthesis of Compound [68]

Synthesis Example 1 In the same manner, using 5.0 g (10.89 mmol) of 6-bromo-6'-iodine-2,2'-binapthyl, 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole 3.2 g (44%) of the title compound (68 ) as a white solid was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ7.25-7.36 (m, 5H), 7.50-7.59 (m, 12H), 7.73-7.78 (m, 5H), 7.92-8.00 (m, 6H), 8.12 ~ 8.18 (m, 4H)

MS / FAB: 660 (M ⁺ )

Synthesis Example 69 Synthesis of Compound [69]

Synthesis Example 1 In the same way, 3-bromo-9-iodine-7,7-dimethyl-7H-benzo [de] anthracene 5.0 g (11.13 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, carba using the sol, to give the desired compound as a white solid [69] 3.3g (45%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.86 (s, 6H), 7.01 ~ 7.06 (m, 2H), 7.25 ~ 7.64 (m, 16H), 7.78 ~ 7.79 (m, 2H), 7.92 ~ 8.00 ( m, 4H), 8.12-8.17 (m, 4H)

MS / FAB: 650 (M ⁺ )

Synthesis Example 70 Synthesis of Compound [70]

Synthesis Example 1 5.0 g (11.13 mmol) of 8-bromo-2-iodine-11,11-dimethyl-11H-benzo [b] fluorene, 9-phenyl-9H-carbazol-3-yl boronic acid, Carbazole was used to obtain 3.2 g (44%) of the title compound [70] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.77 (s, 6H), 7.25 to 7.32 (m, 5H), 7.45 to 7.74 (m, 12H), 7.78 to 7.82 (m, 3H), 7.94 to 8.02 ( m, 3H), 8.12-8.15 (m, 4H), 8.27 (s, 1H)

MS / FAB: 650 (M ⁺ )

Synthesis Example 71 Synthesis of Compound [71]

Synthesis Example 1 5.0 g (11.13 mmol) of 3-bromo-9-iodine-11,11-dimethyl-11H-benzo [a] fluorene, 9-phenyl-9H-carbazol-3-yl boronic acid, Carbazole was used to obtain 3.4 g (47%) of the title compound (71 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.86 (s, 6H), 7.25 to 7.32 (m, 5H), 7.46 to 7.63 (m, 12H), 7.78 to 7.83 (m, 3H), 7.96 to 8.00 ( m, 2H), 8.12-8.17 (m, 6H)

MS / FAB: 650 (M ⁺ )

Synthesis Example 72 Synthesis of Compound [72]

Synthesis Example 1 Bromo-7-iodine-5,5-diphenyl-5H-dibenzo [b, d] silore 6.0 g (11.13 mmol), 9-phenyl-9H-carbazole-3- One boronic acid, carbazole, was used to obtain 3.8 g (46%) of the title compound (72 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.23 to 7.58 (m, 25H), 7.78 to 7.79 (m, 3H), 7.89 to 8.01 (m, 4H), 8.12 to 8.17 (m, 4H)

MS / FAB: 740 (M ⁺ )

Synthesis Example 73 Synthesis of Compound [73]

Synthesis Example (1 ) 6.0 g (7.54 mmol) of starting material [73-1], 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole as a white solid target compound [73] 3.4 g ( 45%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.23 to 7.57 (m, 35H), 7.78 to 7.79 (m, 3H), 7.89 to 8.01 (m, 6H), 8.12 to 8.17 (m, 4H)

MS / FAB: 996 (M ⁺ )

Synthesis Example 74 Synthesis of Compound [74]

Synthesis Example 1 Bromo-9-iodine-5,11-diphenyl-5,11-dihydroindolo [3,2-b] carbazole 6.0 g (9.78 mmol), 9-phenyl-9H -carbazol-3-yl, using the boronic acid, carbazole, to give the desired compound as a white solid [74] 3.4g (43%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.24 to 7.82 (m, 25H), 7.78 (s, 1H), 7.94 to 8.00 (m, 2H), 8.10 to 8.17 (m, 5H), 8.44 to 8.49 ( m, 2H)

MS / FAB: 814 (M ⁺ )

Synthesis Example 75 Synthesis of Compound [75]

Synthesis Example 1 In the same way, using 2-bromo-7-iodine-9-phenyl-9H-carbazole 5.0 g (11.16 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole 3.2 g (44%) of the title compound (75 ) were obtained as a solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.22-7.58 (m, 21H), 7.78 (s, 1H), 7.94-8.00 (m, 2H), 8.10-8.17 (m, 6H), 8.47 (d, 1H)

MS / FAB: 649 (M ⁺ )

Synthesis Example 76 Synthesis of Compound [76]

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-fluorene 5.0 g (12.53 mmol), a compound [76-1] , and a target compound as a white solid using carbazole [76 ] to give the 4.1g (43%).

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 6H), 7.24 ~ 7.59 (m, 22H), 7.79 (s, 1H), 7.87 ~ 7.96 (m, 5H), 8.10 ~ 8.13 (m, 4H), 8.48 (d, 1H)

MS / FAB: 765 (M ⁺ )

Synthesis Example 77 Synthesis of Compound [77]

Synthesis Example 1 in the same manner as 2-bromo-7-iodine triphenylene 5.0g (11.55mmol), 9- phenyl -9H- carbazol-3-yl boronic target compound as a white solid using the acid, carbazole [77 ] to give the 3.2g (44%).

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.29 (m, 4H), 7.45-7.82 (m, 9H), 7.86-8.12 (m, 14H), 8.91-8.83 (m, 2H)

MS / FAB: 634 (M ⁺ )

Synthesis Example 78 Synthesis of Compound [78]

Synthesis Example 1 In the same manner, the title compound as a white solid using 2-bromo-11-iodinetriphenylene 5.0g (11.55 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole [78 ] to give the 3.2g (43%).

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.26 to 7.32 (m, 4H), 7.46 to 7.63 (m, 9H), 7.87 to 8.13 (m, 14H), 8.91 to 8.83 (m, 2H)

MS / FAB: 634 (M ⁺ )

Synthesis Example 79 Synthesis of Compound [79]

Synthesis Example 1 In the same manner as 2-bromo-7-iodine-5,5,10,10,15,15-hexamethyl-10,15-dihydro-5H-diindeno [1,2-a: 1 ' , the 2'-c] fluorene 6.0g (9.50mmol), 9- phenyl -9H- carbazol-3-yl, using the boronic acid, carbazole target compound as a white solid [79] 3.3g (42%) Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 18 H), 7.29 to 7.82 (m, ¹⁹ H), 7.77 (s, 1 H), 7.84 to 7.85 (m, 2H), 7.96 to 8.00 (m, 2H), 8.10-8.17 (m, 6H)

MS / FAB: 832 (M ⁺ )

Synthesis Example 80 Synthesis of Compound [80]

Synthesis Example 1 In the same way as 2-bromo-6-iodine-4,4,8,8,12,12-hexamethyl-4,8,12, tetrahydrodibenzo [cd, mn] pyrene 6.0 g ( 10.54 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, carbazole were used to obtain 3.5 g (43%) of the title compound (80 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 18H), 7.10 to 7.18 (m, 6H), 7.24 to 7.33 (m, 8H), 7.50 to 7.63 (m, 8H), 7.77 (s, 1H), 7.89 ~ 7.94 (m, 3H), 8.10 ~ 8.14 (m, 2H)

MS / FAB: 770 (M ⁺ )

Synthesis Example 81 Synthesis of Compound [81]

Synthesis Example 1 In the same manner, using 5.0 g (13.93 mmol) of 4-bromo-4'-iodobiphenyl, 9- (biphenyl-4-yl) -9H-carbazol-3-yl boronic acid, carbazole 3.7 g (42%) of the title compound (81 ) as a white solid were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.42 (m, 15H), 7.53-7.58 (m, 5H), 7.67-7.69 (m, 4H), 7.84-7.90 (m, 2H), 8.02- 8.08 (m, 3H), 8.25 (d, 1H)

MS / FAB: 635 (M ⁺ )

Synthesis Example 82 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9- (biphenyl-4-yl) -9H-carbazol-3-yl boronic acid, 3-phenyl-9H Carbazole was used to obtain 4.3 g (43%) of the title compound (82 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.42 (m, 18H), 7.53-7.58 (m, 6H), 7.67-7.69 (m, 6H), 7.77-7.90 (m, 3H), 8.02- 8.08 (m, 2 H), 8.25 (d, 1 H)

MS / FAB: 713 (M ⁺ )

Synthesis Example 83 Synthesis of Compound [83]

Synthesis Example 1 In the same manner, 5.0 g (13.93 mmol) of 4-bromo-4'-iodobiphenyl, 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-diphenyl-9H-carbazole To give 4.5 g (45%) of the title compound [83] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.19 (m, 5H), 7.31-7.59 (m, 20H), 7.67-7.69 (m, 5H), 7.77 (d, 1H), 7.90 (d, 2H), 8.02-8.08 (m, 3H)

MS / FAB: 713 (M ⁺ )

Synthesis Example 84 Synthesis of Compound

Synthesis Example 1 In the same manner as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 3,6-di (biphenyl-4-yl ) using -9H- carbazole, to give the desired compound [84] 4.9g (41%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.19 (m, 13H), 7.31-7.59 (m, 20H), 7.67-7.69 (m, 5H), 7.77 (d, 1H), 7.90 (d, 2H), 8.02-8.08 (m, 3H)

MS / FAB: 865 (M ⁺ )

Synthesis Example 85 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9- (biphenyl-4-yl) -9H-carbazol-3-yl boronic acid, 3,6-di Phenyl-9H-carbazole was used to obtain 4.7 g (43%) of the title compound [85] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.19 (m, 5H), 7.31-7.42 (m, 16H), 7.53-7.59 (m, 6H), 7.67-7.69 (m, 7H), 7.77 ( d, 1H), 7.90 (d, 2H), 8.02-8.08 (m, 3H)

MS / FAB: 789 (M ⁺ )

Synthesis Example 86 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9- (biphenyl-4-yl) -6-phenyl-9H-carbazol-3-yl boronic acid, 3 , 6-diphenyl-9H-carbazole was used to obtain 4.7 g (39%) of the title compound [86] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 (m, 4H), 7.31-7.42 (m, 20H), 7.58-7.59 (m, 6H), 7.67-7.69 (m, 8H), 7.77 (d, 2H), 7.90 (d, 2H), 8.08 (d, 2H)

MS / FAB: 865 (M ⁺ )

Synthesis Example 87 Synthesis of Compound [87]

Synthesis Example 1 In the same manner as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, N, N-diphenyl-9H-carbazole- using 3-amine, to give the desired compound as a white solid [87] 4.1g (40%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.91 (m, 4H), 7.05 to 7.17 (m, 4H), 7.20 to 7.58 (m, 21H), 7.67 to 7.69 (m, 3H), 7.84 to 7.90 ( m, 2H), 8.02 to 8.08 (m, 2H), 8.25 (d, 1H)

MS / FAB: 728 (M ⁺ )

Synthesis Example 88 Synthesis of Compound [88]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9- (4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, carbazole To give 4.3 g (42%) of the title compound (88 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.93 (m, 6H), 7.11 (t, 2H), 7.20 ~ 7.27 (m, 14H), 7.40 (t, 2H), 7.53 ~ 7.68 (m, 4H) , 7.67-7.69 (m, 3H), 7.84-7.90 (m, 2H), 8.02-8.08 (m, 3H), 8.25 (d, 1H)

MS / FAB: 728 (M ⁺ )

Synthesis Example 89 Synthesis of Compound [89]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 6- (diphenylamino) -9-phenyl-9H-carbazol-3-yl boronic acid and carbazole are used. This gave 4.2 g (41%) of the title compound [89] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.93 (m, 4H), 7.05 to 7.71 (m, 4H), 7.20 to 7.58 (m, 21H), 7.67 to 7.69 (m, 3H), 7.84 to 7.90 ( m, 2H), 8.02 to 8.08 (m, 2H), 8.25 (d, 1H)

* MS / FAB: 728 (M ⁺ )

Synthesis Example 90 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 6- (diphenylamino) -9-phenyl-9H-carbazol-3-yl boronic acid, N, N- Diphenyl-9H-carbazole-3-amine was used to obtain 4.7 g (38%) of the title compound [90] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.93 (m, 8H), 7.05 ~ 7.11 (m, 8H), 7.20 ~ 7.48 (m, 21H), 7.58 (d, 2H), 7.67 ~ 7.69 (m, 3H), 7.84 ~ 7.90 (m, 2H), 8.08 (d, 1H), 8.25 (d, 1H)

MS / FAB: 895 (M ⁺ )

Synthesis Example 91 Synthesis of Compound [91]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9- (4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, N, N 4.4 g (35%) of the title compound [91] as a white solid was obtained using diphenyl-9H-carbazole-3-amine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.93 (m, 10H), 7.05 ~ 7.11 (m, 6H), 7.20 ~ 7.28 (m, 18H), 7.40 (t, 1H), 7.53 ~ 7.58 (m, 3H), 7.67-7.69 (m, 3H), 7.84-7.90 (m, 2H), 8.02-8.08 (m, 2H), 8.25 (d, 1H)

MS / FAB: 895 (M ⁺ )

Synthesis Example 92 Synthesis of Compound

*

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, N3, N3, N6, N6-tetraphenyl-9H -Carbazole-3,6-diamine was used to obtain 4.7 g (38%) of the title compound (92 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.86 (d, 1H), 6.93 (m, 8H), 7.05-7.11 (m, 6H), 7.20-7.75 (m, 25H), 7.67-7.69 (m, 3H), 7.90 (d, 1H), 8.02-8.08 (m, 2H)

MS / FAB: 895 (M ⁺ )

Synthesis Example 93 Synthesis of Compound [93]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 6- (diphenylamino) -9-phenyl-9H-carbazol-3-yl boronic acid, N3, N3, N6, N6- using tetraphenyl -9H- carbazol-3,6-diamine to give the desired compound [93] 4.6g (31%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.86 (d, 1H), 6.93 (m, 12H), 7.05 ~ 7.11 (m, 10H), 7.20 ~ 7.59 (m, 27H), 7.67 ~ 7.69 (m, 3H), 7.90 (d, 1H), 8.08 (d, 1H)

MS / FAB: 1062 (M ⁺ )

Synthesis Example 94 Synthesis of Compound [94]

Synthesis Example 1 In the same way as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 6- (diphenylamino) -9- (4- (diphenylamino) phenyl) -9H-carbazole-3 - to give the one-boronic acid, N, N- diphenyl -9H- carbazol -3- 4.9g amine target compound as a white solid [94] (33%).

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.93 (m, 14H), 7.05 ~ 7.11 (m, 10H), 7.20 ~ 7.28 (m, 22H), 7.58 (d, 2H), 7.67 ~ 7.69 (m, 3H), 7.84 ~ 7.90 (m, 2H), 8.08 (d, 1H), 8.25 (d, 1H)

MS / FAB: 1062 (M ⁺ )

Synthesis Example 95 Synthesis of Compound

*

Synthesis Example 1 In the same way as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 6- (diphenylamino) -9- (4- (diphenylamino) phenyl) -9H-carbazole-3 -yl boronic acid, N3, N3, N6, N6- using tetraphenyl -9H- carbazol-3,6-diamine to give the desired compound [95] 5.0g (29%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.86 (d, 1H), 6.93 (m, 18H), 7.05 ~ 7.11 (m, 12H), 7.20 ~ 7.25 (m, 20H), 7.27 ~ 7.28 (m, 4H), 7.58-7.59 (m, 4H), 7.67-7.69 (m, 3H), 7.90 (d, 1H), 8.08 (d, 1H)

MS / FAB: 1230 (M ⁺ )

Synthesis Example 96 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9- (4- (triphenylsilyl) phenyl) -9H-carbazol-3-yl boronic acid, 3,6 - diphenyl using -9H- carbazole, to give the desired compound [96] 4.7g (35%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.69 (m, 44H), 7.77 (d, 1H), 7.90 (d, 2H), 8.02-8.08 (m, 3H)

MS / FAB: 971 (M ⁺ )

Synthesis Example 97 Synthesis of Compound [97]

Synthesis Example 1 In the same manner as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 5,11-diphenyl-5,11-dihydroindol [3,2-b] carbazol-2-yl the desired compound of boric acid, 5-phenyl-using -5,11- dihydro-indole [3,2-b] carbazole-white solid [97] to give the 3.6g (29%).

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.58 (m, 33H), 7.67 to 7.69 (m, 3H), 7.84 to 7.90 (m, 2H), 8.02 to 8.08 (m, 3H), 8.25 ( d, 1H)

MS / FAB: 891 (M ⁺ )

Synthesis Example 98 Synthesis of Compound [98]

Synthesis Example 1 In the same manner as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 5-phenyl-5,11-dihydroindole [ 3,2-b] carbazole was used to obtain 3.1 g (31%) of the title compound (98 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.58 (m, 26H), 7.67 to 7.69 (m, 3H), 7.84 to 7.90 (m, 2H), 8.02 to 8.08 (m, 3H), 8.25 ( d, 1H)

MS / FAB: 726 (M ⁺ )

Synthesis Example 99 Synthesis of Compound [99]

Synthesis Example 1 In the same manner, using 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9-phenyl-9H-3,9'-bicarbazole-3'-yl boronic acid, carbazole 3.4 g (34%) of the title compound (99 ) were obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.33 (m, 11H), 7.35 to 7.58 (m, 13H), 7.67 to 7.69 (m, 3H), 7.84 to 7.90 (m, 3H), 8.02 to 8.08 (m, 3H), 8.25 (m, 2H)

MS / FAB: 726 (M ⁺ )

Synthesis Example 100 Synthesis of Compound [100]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 3 ', 6', 9-triphenyl-9H-3,9'-bicarbazol-6-yl boronic acid 4.7 g (28%) of the desired compound [100] as a white solid was obtained using 3 ', 6'-diphenyl-9H-3,9'-bicarbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.59 (m, 41H), 7.67 to 7.69 (m, 7H), 7.77 to 7.90 (m, 6H), 8.08 (m, 3H), 8.25 (d, 1H)

MS / FAB: 1196 (M ⁺ )

Synthesis Example 101 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 9-phenyl-9H-3,9'-bicarbazol-3'-yl boronic acid, 3,6-di Phenyl-9H-carbazole was used to obtain 4.2 g (34%) of the title compound (101 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.19 (m, 6H), 7.31 to 7.59 (m, 24H), 7.67 to 7.69 (m, 5H), 7.77 to 7.90 (m, 4H), 8.02 to 8.08 (m, 4 H)

MS / FAB: 878 (M ⁺ )

Synthesis Example 102 Synthesis of Compound [102]

Synthesis Example 1 5.0 g (13.93 mmol) of 4-bromo-4'-iodobiphenyl, 4- (9- (biphenyl-4-yl) -9H-carbazol-3-yl) phenyl boronic acid, Carbazole was used to obtain 3.9 g (39%) of the title compound (102 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.42 (m, 19H), 7.53-7.58 (m, 6H), 7.67-7.69 (m, 5H), 7.84-7.90 (m, 2H), 8.02- 8.08 (m, 3H), 8.25 (d, 1H)

MS / FAB: 713 (M ⁺ )

Synthesis Example 103 Synthesis of Compound [103]

Synthesis Example 1 In the same manner as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 4- (9- (9,9-dimethyl-9H-floren-2-yl) -9H-carbazole- 4.4 g (42%) of the title compound (103 ) as a white solid was obtained using 3-yl) phenyl boronic acid, carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.67 (s, 6H), 7.15 ~ 7.30 (m, 15H), 7.40 ~ 7.51 (m, 4H), 7.53 ~ 7.58 (m, 4H), 7.67 ~ 7.69 ( m, 3H), 7.84-7.90 (m, 4H), 8.02-8.08 (m, 3H), 8.25 (d, 1H)

MS / FAB: 753 (M ⁺ )

Synthesis Example 104 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 4- (9- (biphenyl-4-yl) -6-phenyl-9H-carbazol-3-yl) using phenylboronic acid, carbazole, to give the desired compound as a white solid [104] 4.9g (45%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.42 (m, 22H), 7.53-7.59 (m, 6H), 7.67-7.69 (m, 6H), 7.77-7.90 (m, 3H), 8.02- 8.08 (m, 2 H), 8.25 (d, 1 H)

MS / FAB: 789 (M ⁺ )

Synthesis Example 105 Synthesis of Compound [105]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 4- (9-phenyl-9H-carbazol-3-yl) phenyl boronic acid, 3-phenyl-9H-carba The sol was used to obtain 4.1 g (41%) of the title compound (105 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.58 (m, 26H), 7.67 to 7.69 (m, 4H), 7.77 to 7.90 (m, 3H), 8.02 to 8.08 (m, 2H), 8.25 ( d, 1H)

MS / FAB: 713 (M ⁺ )

Synthesis Example 106 Synthesis of Compound [106]

Synthesis Example 1 In the same manner as 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 4- (9-phenyl-9H-carbazol-3-yl) phenyl boronic acid, 3,6-diphenyl- 9H-carbazole was used to obtain 4.6 g (42%) of the title compound (106 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.19 (m, 9H), 7.31-7.59 (m, 20H), 7.67-7.69 (m, 5H), 7.77 (d, 1H), 7.90 (d, 2H), 8.02-8.08 (m, 3H)

MS / FAB: 789 (M ⁺ )

Synthesis Example 107 Synthesis of Compound [107]

Synthesis Example 1 5.0 g (13.93 mmol) of 4-bromo-4'-iodobiphenyl, 4- (9- (biphenyl-4-yl) -9H-carbazol-3-yl) phenyl boronic acid, 3,6-diphenyl-9H-carbazole was used to obtain 5.2 g (43%) of the title compound [107] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15-7.19 (m, 9H), 7.31-7.42 (m, 16H), 7.53-7.59 (m, 6H), 7.67-7.69 (m, 7H), 7.77 ( d, 1H), 7.90 (d, 2H), 8.02-8.08 (m, 3H)

MS / FAB: 865 (M ⁺ )

Synthesis Example 108 Synthesis of Compound [108]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 4- (9-phenyl-9H-carbazol-3-yl) phenyl boronic acid, 3,6-di (r) 4-yl) -9H- carbazole using to give the desired compound [108] 5.0g (38%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 to 7.19 (m, 17H), 7.31 to 7.59 (m, 20H), 7.67 to 7.69 (m, 5H), 7.77 (d, 1H), 7.90 (d, 2H), 8.02-8.08 (m, 3H)

MS / FAB: 941 (M ⁺ )

Synthesis Example 109 Synthesis of Compound [109]

Synthesis Example 1 In the same manner, 4-bromo-4'-iodobiphenyl 5.0 g (13.93 mmol), 4- (6,9-diphenyl-9H-carbazol-3-yl) phenyl boronic acid, 3,6- Diphenyl-9H-carbazole was used to obtain 5.5 g (46%) of the title compound [109] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.15 (m, 8H), 7.31-7.48 (m, 20H), 7.58-7.59 (m, 4H), 7.67-7.69 (m, 6H), 7.77 (d, 2H), 7.90 (d, 2H), 8.08 (d, 2H)

MS / FAB: 865 (M ⁺ )

Synthesis Example 110 Synthesis of Compound [110]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 4- (9H-carbazol-9-yl) phenylboronic acid, 9- (4- (diphenylamino) phenyl) 3.6 g (42%) of the target compound [110] as a white solid was obtained using -9H-carbazol-3-yl boronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.08 ~ 7.14 (m, 8H), 7.20 ~ 7.29 (m, 18H), 7.50 (t, 2H), 7.63 ~

7.68 (m, 4H), 7.77-7.79 (m, 3H), 7.94-8.00 (m, 2H), 8.12-8.18 (m, 3H), 8.45 (d, 1H)

MS / FAB: 803 (M ⁺ )

Synthesis Example 111 Synthesis of Compound [111]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 4- (9H-carbazol-9-yl) phenylboronic acid, 9- (4- (9H-carbazole-9 -Yl) phenyl) -9H-carbazol-3-yl boronic acid was used to obtain 3.5 g (41%) of the target compound [111] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.73 (m, 15H), 7.50-7.52 (m, 3H), 7.62-7.68 (m, 9H), 7.77-7.79 (m, 3H), 7.94- 8.00 (m, 2H), 8.12-8.18 (m, 2H), 8.45 (d, 1H)

MS / FAB: 801 (M ⁺ )

Synthesis Example 112 Synthesis of Compound [112]

Synthesis Example 1 In the same manner, 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 4- (9H-carbazol-9-yl) phenylboronic acid, 6- (diphenylamino) -9-phenyl- 9H-carbazol-3-yl boronic acid was used to obtain 3.6 g (42%) of the target compound [112] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.08 ~ 7.15 (m, 8H), 7.20 ~ 7.68 (m, 25H), 7.77 ~ 7.79 (m, 3H), 7.94 ~ 8.00 (m, 2H), 8.12 ~ 8.18 (m, 2H), 8.45 (d, 1H)

MS / FAB: 803 (M ⁺ )

Synthesis Example 113 Synthesis of Compound [113]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 4- (3- (diphenylamino) -9H- Carbazol-9-yl) boronic acid was used to obtain 3.4 g (40%) of the title compound (113 ) as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.08 ~ 7.14 (m, 8H), 7.20 ~ 7.68 (m, 25H), 7.77 ~ 7.79 (m, 3H), 7.94 ~ 8.00 (m, 2H), 8.12 ~ 8.18 (m, 2H), 8.45 (d, 1H)

MS / FAB: 803 (M ⁺ )

Synthesis Example 114 Synthesis of Compound

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 4- (3,6-bis (diphenylamino) 3.8 g (38%) of the title compound [114] as a white solid was obtained using -9H-carbazol-9-yl) phenylboronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.95 (d, 1H), 7.03 to 7.14 (m, 14H), 7.20 to 7.29 (m, 17H), 7.38 to 7.68 (m, 12H), 7.77 to 7.79 ( m, 3H), 8.00 (d, 1H), 8.12-8.18 (m, 2H)

MS / FAB: 971 (M ⁺ )

Synthesis Example 115 Synthesis of Compound [115]

Synthesis Example 1 In the same manner, 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 4- (9H-carbazol-9-yl) phenylboronic acid, 6- (diphenylamino) -9- (4 - a (di) phenyl) -9H- carbazol-3-yl target compound as a white solid using the boronic acid [115] 3.9g (40%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.03 ~ 7.14 (m, 16H), 7.20 ~ 7.38 (m, 22H), 7.50 (t, 1H), 7.63 ~ 7.68 (m, 3H), 7.77 ~ 7.79 ( m, 3H), 7.94-8.00 (m, 2H), 8.10-8.12 (m, 2H), 8.45 (d, 1H)

MS / FAB: 971 (M ⁺ )

Synthesis Example 116 Synthesis of Compound

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 4- (3,6-diphenyl-9H-carbazol-9-yl) phenylboronic acid, 6- (diphenyl amino) -9- (4- (diphenylamino) phenyl) -9H- carbazol-3-yl target compound as a white solid using the boronic acid [116] 4.2g (35%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.03 ~ 7.14 (m, 16H), 7.20 ~ 7.25 (m, 16H), 7.37 ~ 7.52 (m, 13H), 7.68 ~ 7.69 (m, 3H), 7.77 ~ 7.79 (m, 5H), 7.87 (d, 1H), 8.00-8.02 (m, 2H), 8.18-8.19 (m, 2H)

MS / FAB: 1123 (M ⁺ )

Synthesis Example 117 Synthesis of Compound

Synthesis Example 1 In the same manner, 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 4- (3- (diphenylamino) -9H-carbazol-9-yl) phenylboronic acid, 9- (4 - a (di) phenyl) -9H- carbazol-3-yl target compound as a white solid using the boronic acid [117] 3.7g (36%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.04 ~ 7.14 (m, 16H), 7.20 ~ 7.38 (m, 22H), 7.61 ~ 7.68 (m, 4H), 7.77 ~ 7.79 (m, 3H), 7.94 ~ 8.00 (m, 2H), 8.12-8.18 (m, 2H), 8.45 (d, 1H)

MS / FAB: 971 (M ⁺ )

Synthesis Example 118 Synthesis of Compound [118]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 9- (4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, 4- (3 , to give the 6-bis (diphenylamino) -9H- carbazol-9-yl) target compound as a white solid using the boronic acid [118] 4.1g (34%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.95 (d, 1H), 7.03 to 7.14 (m, 22H), 7.20 to 7.38 (m, 24H), 7.61 to 7.68 (m, 6H), 7.77 to 7.79 ( m, 3H), 8.00 (d, 1H), 8.12-8.18 (m, 2H)

MS / FAB: 1138 (M ⁺ )

Synthesis Example 119 Synthesis of Compound [119]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol 6- (diphenylamino) -9-phenyl-9H-carbazol-3-yl boronic acid, 4- (3,6- a bis (diphenylamino) -9H- carbazol-9-yl) phenylboronic target compound as a white solid using the acid [119] 3.9g (32%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.95 (d, 1H), 7.03 to 7.14 (m, 22H), 7.20 to 7.25 (m, 20H), 7.38 to 7.69 (m, 11H), 7.77 to 7.79 ( m, 3H), 8.00 (d, 1H), 8.18 (d, 1H)

MS / FAB: 1138 (M ⁺ )

Synthesis Example 120 Synthesis of Compound [120]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 6- (diphenylamino) -9- (4- (diphenylamino) phenyl) -9H-carbazole-3- One boronic acid, 4- (3,6-bis (diphenylamino) -9H-carbazol-9-yl) phenylboronic acid, gave 4.3 g (31%) of the title compound [120] as a white solid. .

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.95 (d, 1H), 7.01 to 7.15 (m, 30H), 7.20 to 7.25 (m, 24H), 7.37 to 7.38 (m, 4H), 7.63 to 7.58 ( m, 4H), 7.77-7.79 (m, 3H), 8.00 (d, 1H), 8.18 (d, 1H)

MS / FAB: 1305 (M ⁺ )

Synthesis Example 121 Synthesis of Compound [121]

Synthesis Example 1 In the same manner 1-bromo-4-iodobenzene 5.0 g (17.67 mmol), 4- (11-phenylindolo [3,2-b] carbazol-5 (11H) -yl) phenylboronic acid 3.7 g (36%) of the target compound [121] as a white solid was obtained using 5,11-diphenyl-5,11-dihydroindolo [3,2-b] carbazol-2-yl boronic acid. It was.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.68 (m, 36H), 7.77-7.79 (m, 3H), 7.94-8.00 (m, 3H), 8.12-8.18 (m, 2H), 8.45- 8.46 (m, 2 H)

MS / FAB: 967 (M ⁺ )

Synthesis Example 122 Synthesis of Compound [122]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 - to give a (biphenyl-4-yl) -9H- carbazol-3-yl boronic target compound as a white solid using the acid, 9H- carbazole [122] 2.0g (34%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.25 ~ 7.52 (m, 13H), 7.63 ~ 7.70 (m, 6H), 7.77 ~ 7.87 (m, 6H), 7.94 ~ 8.00 ( m, 2H), 8.12-8.18 (m, 4H), 8.45 (d, 1H)

MS / FAB: 793 (M ⁺ )

Synthesis Example 123 Synthesis of Compound [123]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 2.3 g (36%) of the title compound [123] as a white solid was obtained using -phenyl-9H-carbazol-3-yl boronic acid, 3,6-diphenyl-9H-carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.29 to 7.70 (m, 23H), 7.77 to 7.80 (m, 4H), 7.83 to 7.87 (m, 3H), 8.00 to 8.02 ( m, 2H), 8.12-8.18 (m, 4H)

MS / FAB: 869 (M ⁺ )

Synthesis Example 124 Synthesis of Compound [124]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 Target compound of a white solid using-(biphenyl-4-yl) -9H-carbazol-3-yl boronic acid, 3,6-di (phenyl-4-yl) -9H-carbazole [124] 2.7 g (34%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.25 to 7.29 (m, 9H), 7.40 to 7.52 (m, 18H), 7.63 to 7.70 (m, 6H), 7.77 to 7.87 ( m, 9H), 8.00-8.02 (m, 2H), 8.12-8.18 (m, 4H)

MS / FAB: 570 (M ⁺ )

Synthesis Example 125 Synthesis of Compound

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 - a (4- (diphenylamino) phenyl) -9H- carbazol-3-yl boronic acid, 9H- carbazol-white target compound [125] of the solid using 2.3g (35%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.03-7.10 (m, 8H), 7.20-7.73 (m, 11H), 7.50-7.75 (m, 3H), 7.63-77.7 ( m, 4H), 7.77-7.80 (m, 2H), 7.83-7.87 (m, 2H), 7.94-8.00 (m, 2H), 8.12-8.18 (m, 4H), 8.45 (d, 1H)

MS / FAB: 884 (M ⁺ )

Synthesis Example 126 Synthesis of Compound

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 2.6 g (34% ) of the title compound as a white solid using-(4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, 3,6-diphenyl-9H-carbazole. ) Was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.03-7.10 (m, 8H), 7.20-7.29 (m, 5H), 7.37-77.7 (m, 4H), 7.77-7.80 ( m, 4H), 7.83-7.87 (m, 3H), 8.00-8.02 (m, 2H), 8.12-8.18 (m, 4H)

MS / FAB: 1036 (M ⁺ )

Synthesis Example 127 Synthesis of Compound [127]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 Target compound of a white solid using-(4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, N, N-diphenyl-9H-carbazol-3-amine [127] 2.5 g (32%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.03 ~ 7.14 (m, 16H), 7.20 ~ 7.38 (m, 15H), 7.50 ~ 7.52 (m, 2H), 7.63 ~ 7.70 ( m, 3H), 7.77-7.80 (m, 2H), 7.83-7.87 (m, 2H), 7.94-8.00 (m, 2H), 8.12-8.18 (m, 3H), 8.45 (d, 1H)

* MS / FAB: 1051 (M ⁺ )

Synthesis Example 128 Synthesis of Compound [128]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 Target compound of a white solid using -phenyl-9H-carbazol- ^3- ylboronic acid, N ³ , N ³ , N ⁶ , N ⁶ -tetraphenyl-9H-carbazole-3,6-dimine [128 ] to give the 2.5g (33%).

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 6.95 (d, 1H), 7.03 ~ 7.14 (m, 14H), 7.20 ~ 7.29 (m, 9H), 7.38 ~ 7.70 (m, 14H), 7.77-7.80 (m, 2H), 7.83-7.87 (m, 2H), 8.00 (d, 1H), 8.12-8.18 (m, 3H)

MS / FAB: 1051 (M ⁺ )

Synthesis Example 129 Synthesis of Compound [129]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 6 2.4 g (31 ) of the target compound as a white solid using-(diphenylamino) -9- (4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, 9H-carbazole. %) Was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.03 ~ 7.14 (m, 16H), 7.20 ~ 7.40 (m, 15H), 7.50 ~ 7.52 (m, 2H), 7.63 ~ 7.70 ( m, 3H), 7.77-7.80 (m, 2H), 7.83-7.87 (m, 2H), 7.94-8.00 (m, 2H), 8.12-8.18 (m, 3H), 8.45 (d, 1H)

MS / FAB: 1051 (M ⁺ )

Synthesis Example 130 Synthesis of Compound [130]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 6 -(Diphenylamino) -9- (4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, N ³ , N ³ , N ⁶ , N ⁶ -tetraphenyl-9H-carbazole 3.1 g (30%) of the desired compound [130] as a white solid was obtained using -3,6-dimine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 6.95 (d, 1H), 7.03 ~ 7.14 (m, 30H), 7.20 ~ 7.25 (m, 16H), 7.37 ~ 7.40 (m, 5H), 7.50 (s, 1H), 7.63 (s, 1H), 7.68-7.70 (m, 3H), 7.77-7.80 (m, 2H), 7.83-7.87 (m, 2H), 8.18 (d, 1H) , 8.15-8.18 (m, 2H)

MS / FAB: 1385 (M ⁺ )

Synthesis Example 131 Synthesis of Compound [131]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 -(4- (diphenylamino) phenyl) -9H-carbazol-3-yl boronic acid, N ³ , N ³ , N ⁶ , N ⁶ -tetraphenyl-9H-carbazole-3,6-dimine 2.7 g (30%) of the title compound [131] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 6.95 (d, 1H), 7.03 ~ 7.14 (m, 22H), 7.20 ~ 7.40 (m, 17H), 7.50 ~ 7.52 (m, 2H), 7.63-7.70 (m, 5H), 7.77-7.80 (m, 2H), 7.83-7.87 (m, 2H), 8.00 (d, 1H), 8.12-8.18 (m, 3H)

MS / FAB: 1218 (M ⁺ )

Synthesis Example 132 Synthesis of Compound

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] florene 5 g (9.70 mmol), 5 , 11-diphenyl-5,11-dihydroindolo [3,2-b] carbazol-2-yl boronic acid, 5-phenyl-5,11-dihydroindolo [3,2-b] carba The sol was used to obtain 2.2 g (29%) of the title compound [132] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.25 to 7.70 (m, 30H), 7.77 to 7.80 (m, 2H), 7.94 to 8.00 (m, 3H), 8.12 to 8.18 ( m, 3H), 8.45-8.46 (m, 2H)

MS / FAB: 1047 (M ⁺ )

Synthesis Example 133 Synthesis of Compound [133]

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 - the phenyl -9H-3,9'- bi-carbazol-3'-yl-boronic acid, using 3,6-diphenyl--9H- carbazol-white solid the title compound [133] 2.3g (30%) Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.29 to 7.70 (m, 28H), 7.77 to 7.80 (m, 4H), 7.83 to 8.00 (m, 6H), 8.12 to 8.18 ( m, 4H), 8.45 (d, 1H)

MS / FAB: 1034 (M ⁺ )

Synthesis Example 134 Synthesis of Compound

Synthesis Example 1 In the same manner, 2-bromo-8-iodo-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b] fluorene 5 g (9.70 mmol), 9 Of a white solid using -phenyl-9H-3,9'-bicarbazol-3'-yl boronic acid, 6- (9H-carbazol-9-yl) -9H-3,9'-bicarbazole the target compound [134] 2.5g (28%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.72 (s, 12H), 7.25 ~ 7.40 (m, 12H), 7.50 ~ 7.70 (m, 19H), 7.77 ~ 7.80 (m, 2H), 7.83 ~ 8.00 ( m, 7H), 8.12-8.18 (m, 6H), 8.45-8.47 (m, 3H)

MS / FAB: 1212 (M ⁺ )

Synthesis Example 135 Synthesis of Compound [135]

Synthesis Example 1 In the same manner as 2-bromo-7-iodo-9,9-dimethyl-9H-florene 5 g (12.52 mmol), 4- (9- (biphenyl-4-yl) -9H-carbazole- 3-1) using a phenylboronic acid, 3,6-diphenyl--9H- carbazole, to give the desired compound [135] 3.3g (38%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.70 (s, 6H), 7.25 to 7.29 (m, 5H), 7.40 to 7.52 (m, 18H), 7.63 to 7.69 (m, 5H), 7.77 to 7.80 ( m, 6H), 7.87-7.83 (m, 3H), 8.00-8.02 (m, 2H), 8.12-8.18 (m, 3H)

MS / FAB: 905 (M ⁺ )

Synthesis Example 136 Synthesis of Compound [136]

Synthesis Example 1 In the same manner, 2-bromo-7-iodo-9,9-dimethyl-9H-florene 5g (12.52 mmol), 4- (9- (4- (diphenylamino) phenyl) -9H-carba a-3-yl) phenylboronic acid target compound as a white solid using 9H- carbazole [136] 2.7g (34%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.70 (s, 6H), 7.03-7.10 (m, 8H), 7.20-7.73 (m, 15H), 7.50-7.75 (m, 3H), 7.63-7.75 ( m, 3H), 7.77-7.80 (m, 2H), 7.87-8.00 (m, 4H), 8.12-8.18 (m, 3H), 8.45 (d, 1H)

MS / FAB: 844 (M ⁺ )

Synthesis Example 137 Synthesis of Compound

Synthesis Example 1 In the same manner, 2-bromo-7-iodo-9,9-dimethyl-9H-florene 5g (12.52 mmol), 4- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid ^{, N 3, N 3, N} 6, N 6 - tetraphenyl the -9H- carbazole-3,6 using the imine to give the desired compound [137] 3.1g (32%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.70 (s, 6H), 6.95 (d, 1H), 7.03-7.10 (m, 14H), 7.20-7.29 (m, 13H), 7.38-7.7.6 (m, 13H), 7.77-7.80 (m, 2H), 7.87-7.73 (m, 2H), 8.00 (d, 1H), 8.12-8.18 (m, 2H)

MS / FAB: 1011 (M ⁺ )

Synthesis Example 138 Synthesis of Compound [138]

Synthesis Example 1 In the same manner, 2-bromo-7-iodo-9,9-dimethyl-9H-florene 5g (12.52 mmol), 9- (biphenyl-4-yl) -9H-carbazol-3-yl to afford the boronic acid, 4- (3,6-diphenyl--9H- carbazol-9-yl) phenylboronic target compound as a white solid using the acid [138] 2.8g (33%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.70 (s, 6H), 7.30 ~ 7.52 (m, 17H), 7.63 ~ 7.69 (m, 8H), 7.77 ~ 7.79 (m, 9H), 7.87 ~ 7.93 ( m, 3H), 8.00-8.02 (m, 2H), 8.12-8.18 (m, 3H)

MS / FAB: 905 (M ⁺ )

Synthesis Example 139 Synthesis of Compound

Synthesis Example 1 In the same manner, 5 g (12.52 mmol) of 2-bromo-7-iodo-9,9-dimethyl-9H-florene, 4- (9H-carbazol-9-yl) phenylboronic acid, 9- ( the 4- (diphenylamino) phenyl) -9H- carbazol-3-yl target compound as a white solid using the boronic acid [139] 3.0g (37%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.70 (s, 6H), 7.03-7.10 (m, 8H), 7.20-7.73 (m, 10H), 7.50-7.7.5 (m, 2H), 7.63-77.6 ( m, 6H), 7.77-7.79 (m, 5H), 7.93-8.00 (m, 4H), 8.12-8.18 (m, 3H), 8.45 (d, 1H)

MS / FAB: 844 (M ⁺ )

Synthesis Example 140 Synthesis of Compound [140]

Synthesis Example 1 In the same manner, 2-bromo-7-iodo-9,9-dimethyl-9H-florene 5g (12.52 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid, 4- (3 3.3 g (34%) of the title compound [140] was obtained using, 6-bis (diphenylamino) -9H-carbazol-9-yl) phenylboronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.70 (s, 6H), 6.95 (d, 1H), 7.03 ~ 7.14 (m, 14H), 7.20 ~ 7.29 (m, 9H), 7.38 ~ 7.68 (m, 14H), 7.77-7.79 (m, 5H), 7.93-8.00 (m, 3H), 8.12-8.18 (m, 2H)

MS / FAB: 1011 (M ⁺ )

Synthesis Example 141 Synthesis of Compound

*

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 9- (biphenyl-4-yl) -carbazol-3-yl boronic acid , by using the carbazole to give the target compound as a white solid [141] 5.1g (60.1%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.3 to 7.52 (m, 13H), 7.5 to 7.79 (m, 9H), 7.9 to 8.18 (m, 7H), 8.55 (d, 1H)

MS / FAB: 676 (M ⁺ )

Synthesis Example 142 Synthesis of Compound

Synthesis Example 1 In the same manner as 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 9 (biphenyl-4-yl) -carbazol-3-yl boronic acid, 3,6-diphenyl-9H-carbazole was used to obtain 6.1 g (58.7%) of the title compound [142] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25 to 7.52 (m, 19H), 7.58 to 7.69 (m, 5H), 7.7 to 7.79 (m, 6H), 7.87 to 8.01 ( m, 5H), 8.12-8.18 (m, 3H)

MS / FAB: 828 (M ⁺ )

Synthesis Example 143 Synthesis of Compound [143]

Synthesis Example 1 In the same manner as 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 9- (4- (diphenylamino) phenyl) -9H-carbazole-3 - using one acid, 3,6-diphenyl--9H- carbazole, to give the desired compound [143] 6.4g (55.5%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 6.63 ~ 6.81 (m, 8H), 7.20 ~ 7.52 (m, 20H), 7.63 ~ 7.69 (m, 3H), 7.77 ~ 7.80 ( m, 4H), 7.87-8.21 (m, 8H)

MS / FAB: 919 (M ⁺ )

Synthesis Example 144 Synthesis of Compound

Synthesis Example 1 In the same way as 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 6- (diphenylamino) -9-phenyl-9H-carbazole-3- 6.0 g (51.2%) of the title compound [144] as a white solid was obtained using mono-boronic acid, N, N-diphenyl-9H-carbazole-3-amine.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 6.63 ~ 6.81 (m, 16H), 7.21 ~ 7.58 (m, 20H), 7.77 ~ 8.02 (m, 6H), 8.18 ~ 8.55 ( m, 2H)

MS / FAB: 934 (M ⁺ )

Synthesis Example 145 Synthesis of Compound

2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol) and 9- (4- (diphenylamino) phenyl) -9H-carbazole in the same manner as in Synthesis example 1 3-yl boronic acid, N3, N3, N6, N6- using tetraphenyl -9H- carbazol -3,6-diamine to give the desired compound [145] 7.1g (51.4%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 5.93-6.63 (m, 15H), 6.78-7.81 (m, 8H), 7.20-7.41 (m, 17H), 7.5-7.63 ( m, 6H), 7.7-8.18 (m, 7H)

MS / FAB: 1101 (M ⁺ )

Synthesis Example 146 Synthesis of Compound [146]

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 9-phenyl-9H-carbazol-3yl-boronic acid, N3, N3, N6, N6- using tetraphenyl -9H- carbazol -3,6-diamine to give the desired compound [146] 6.8g (58.0%) of a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 5.93 ~ 6.81 (m, 15H), 7.2 ~ 7.29 (m, 9H), 7.38 ~ 7.69 (m, 13H), 7.8 ~ 8.12 ( m, 7H)

MS / FAB: 934 (M ⁺ )

Synthesis Example 147 Synthesis of Compound

Synthesis Example 1 In the same manner as in 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 9- (4- (triphenylsilyl) phenyl) -9H-carbazole 6.4 g (50.5%) of the title compound [147] as a white solid was obtained using 3-yl-boronic acid, 3,6-diphenyl-9H-carbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25 to 7.45 (m, 21H), 7.49 to 7.79 (m, 19H), 7.87 to 8.00 (m, 5H), 8.12 to 8.18 ( m, 3H)

MS / FAB: 1010 (M ⁺ )

Synthesis Example 148 Synthesis of Compound

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 5,11-diphenyl-5,11-dihydroindolo [3,2] 6.9 g (59.1% ) of the target compound as a white solid using carbazol-2-yl-boronic acid, 5-phenyl-5,11-dihydroindolo [3,2-b] carbazole. ) Was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25-7.43 (m, 14H), 7.48-7.6 (m, 16H), 7.84-8.00 (m, 6H), 8.12-8.18 ( m, 3H), 8.55 (d, 1H)

MS / FAB: 930 (M ⁺ )

Synthesis Example 149 Synthesis of Compound [149]

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 9-phenyl-9H-carbazol-3yl-boronic acid, 5-phenyl- 6.1 g (63.6%) of the title compound [149] as a white solid was obtained using [3,2-b] carbazole with 5,11-dihydroindole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25-7.7.6 (m, 23H), 7.78-7.99 (m, 6H), 8.12-8.18 (m, 3H), 8.55 (d, 1H),

MS / FAB: 765 (M ⁺ )

Synthesis Example 150 Synthesis of Compound [150]

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 5,11-diphenyl-5,11-dihydroindolo [3,2 -b] carbazol-2-yl-boronic acid, carbazole was used to obtain 5.9 g (61.5%) of the title compound [150] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25-7.7.6 (m, 21H), 7.78-7.99 (m, 7H), 8.12-8.18 (m, 4H), 8.55 (d, 1H)

MS / FAB: 765 (M ⁺ )

 Synthesis Example 151 Synthesis of Compound [151]

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 3 ', 6', 9-triphenyl-9H-3,9'-ratio 6.5 g (42.0%) of the title compound [151] as a white solid was obtained using carbazol-6-yl-boronic acid, 3 ', 6'-diphenyl-9H-3,9'-bicarbazole.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25 to 7.41 (m, 16H), 7.45 to 7.69 (m, 22H), 7.77 to 8.00 (m, 14H), 8.12 to 8.18 ( m, 3H), 8.55 (d, 1H)

MS / FAB: 1234 (M ⁺ )

Synthesis Example 152 Synthesis of Compound [152]

Synthesis Example 1 In the same manner, 2-bromo-7-iodine-9,9-dimethyl-9H-florene 5.0 g (12.53 mmol), 9-phenyl-9H-3,9'-bicarbazol-3'-yl Boronic acid, 3,6-diphenyl-9H-carbazole, was used to obtain 6.6 g (57.4%) of the title compound [152] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25 ~ 7.64 (m, 27H), 7.78 ~ 7.79 (m, 10H), 8.12 ~ 8.18 (m, 4H)

MS / FAB: 917 (M ⁺ )

Synthesis Example 153 Synthesis of Compound [153]

Synthesis Example 1 In the same manner 1-bromo-4-iodonaphthalene 6.0 g (18.0 mmol), 9-phenyl-9H-carbazol-3-yl-boronic acid, 4- (9H-carbazol-9-yl) phenyl using acid to yield the target compound as a white solid [153] 7.3g (66.3%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25-7.73 (m, 4H), 7.45-7.68 (m, 13H), 7.77-7.79 (m, 3H), 7.94-8.18 (m, 7H), 8.45- 8.55 (m, 3H)

MS / FAB: 610 (M ⁺ )

Synthesis Example 154 Synthesis of Compound [154]

*

Synthesis Example 1 In the same manner, 2-bromo-6-iodinenaphthalene 6.0 g (18.0 mmol), 9-phenyl-9H-carbazol-3-yl-boronic acid, 4- (9H-carbazol-9-yl) phenyl using acid to yield the target compound as a white solid [154] 7.0g (63.6%) .

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.25 to 7.33 (m, 4H), 7.45 to 7.79 (m, 18H), 7.92 to 8.1 (m, 4H), 8.12 to 8.55 (m, 4H)

MS / FAB: 610 (M ⁺ )

Synthesis Example 155 Synthesis of Compound [155]

Synthesis Example 1 In the same way as 2-bromo-7-iodine-9,9-dimethyl-9H-florene 6.0 g (15.0 mmol), 9-phenyl-9H-carbazol-3-yl-boronic acid, 4- ( 7.0 g (63.6%) of the title compound [155] as a white solid was obtained using 9H-carbazol-9-yl) phenylboronic acid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 6H), 7.25 to 7.33 (m, 4H), 7.50 to 7.71 (m, 13H), 7.87 to 8.00 (m, 9H), 8.12 to 8.18 ( m, 4H)

MS / FAB: 676 (M ⁺ )

Synthesis Example 156 Synthesis of Compound

Synthesis Example By the same method as one 2,6-dibromo--9,9,10,10- tetramethyl-9,10-dihydro-anthracene 6.0g (15.2mmol), 9- phenyl -9H- carbazol-3-yl -boronic acid, 4- (9H- carbazol-9-yl) phenylboronic target compound as a white solid using the acid [156] 6.1g (50.4%) was obtained

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 12H), 7.25-7.63 (m, 25H), 7.77-7.87 (m, 4H), 8.0-8.18 (m, 5H)

MS / FAB: 794 (M ⁺ )

Synthesis Example 157 Synthesis of Compound

Synthesis Example By the same method as one 2,6-dibromo--9,9,10,10- tetramethyl-9,10-dihydro-anthracene 6.0g (15.2mmol), 9- (biphenyl-4-yl) - carbazole -3-yl-boronic acid, using 3,6-diphenyl--9H- carbazole, to give the desired compound [157] 7.8g (58.8%) of a white solid

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 12H), 7.19 ~ 7.53 (m, 23H), 7.63 ~ 7.79 (m, 9H), 7.87 ~ 8.18 (m, 6H)

MS / FAB: 870 (M ⁺ )

Synthesis Example 158 Synthesis of Compound

Synthesis Example By the same method as one 2,6-dibromo--9,9,10,10- tetramethyl-9,10-di-hydro-anthracene 6.0g (15.2mmol), 9- phenyl -9H- carbazol-3-yl -boronic acid, 4- (9H- carbazol-9-yl) the preparation of the compound [158] 7.1g (64.9%) as a white solid using the boronic acid was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 1.73 (s, 12H), 7.24 to 7.56 (m, 21H), 7.77 to 7.79 (m, 3H), 7.93 to 8.18 (m, 5H), 8.55 (d, 1H)

MS / FAB: 718 (M ⁺ )

Synthesis Example 159 Synthesis of Compound

Synthesis Example 1 In the same manner, a white solid was prepared using 6.0 g (16.7 mmol) of 4-bromo-4'-iodine biphenyl, 9-phenyl-9H-carbazol-3-yl-boronic acid, 10H-phenothiazine. the target compound [159] 6.4g (64.6%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.69-6.97 (m, 4H), 7.24-7.41 (m, 11H), 7.48-7.69 (m, 9H), 7.77-8.19 (m, 4H),

MS / FAB: 592 (M ⁺ )

Synthesis Example 160 Synthesis of Compound

Synthesis Example 1 In the same manner, the purpose of a white solid using 6.0 g (16.7 mmol) of 4-bromo-4'-iodine biphenyl, 9-phenyl-9H-carbazol-3-yl-boronic acid, 10H-phenoxazine 6.4 g (64.6%) of Compound [160] were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.55 ~ 6.77 (m, 6H), 6.88 ~ 6.93 (m, 4H), 7.24 ~ 7.29 (m, 5H), 7.51 ~ 7.59 (m, 9H), 7.77 ~ 8.19 (m, 4 H),

MS / FAB: 576 (M ⁺ )

Synthesis Example 161 Synthesis of Compound

Synthesis Example 1 In the same manner, 4-bromo-4'-iodine biphenyl 6.0 g (16.7 mmol), 9-phenyl-9H-carbazol-3-yl-boronic acid, 5-phenyl-5,10-dihydrofena Gins were used to obtain 6.5 g (59.7%) of the title compound [161] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 6.53 ~ 6.59 (m, 4H), 6.61 ~ 6.82 (m, 9H), 7.19 ~ 7.31 (m, 7H), 7.41 ~ 7.59 (m, 9H), 7.77 ~ 8.21 (m, 4 H),

MS / FAB: 651 (M ⁺ )

Comparative example  One

Using compound a represented by the formula α as a light emitting layer material, 2-TNATA (4,4 ', 4 "tris (N-naphthalen-2-yl) -N-phenylamino) -triphenylamine) represented by formula b Using as a hole injection layer material and using α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) represented by the formula c as a hole transport layer material, An organic light emitting device was manufactured having: 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 top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound a represented by Chemical Formula α was vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 25 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting 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 referred to as Comparative Sample 1.

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

<Formula α> <Formula b>

<Formula c>

Example  1 to 161

ITO / 2-TNATA (80nm) / α 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 -NPD (30nm) / [EML Compound 1-161] (30nm) / Alq3 (30nm) / LiF (0.5nm) / Al (60nm) was prepared. These are referred to as samples 1 to 161, respectively.

Evaluation example  1: Evaluation of Luminescence Characteristics of Comparative Sample 1 and Samples 1 to 161

For Comparative Sample 1 and Samples 1 to 161, 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 480 to 492 nm.

TABLE 1

As shown in Table 1, Samples 1 to 117 showed improved luminescence properties compared to Comparative Sample 1.

Example  162-243

ITO / 2-TNATA (80 nm) in the same manner as in Comparative Example 1, except that HTL compounds were used as the hole transport layer compounds among the compounds disclosed in Synthesis Example as the hole transport layer compounds in Comparative Example 1, respectively. An organic light emitting device was manufactured having a structure of a compound for HTL (30 nm) / general formula α (30 nm) / LiF (0.5 nm) / Al (60 nm). These are called samples 162 to 243, respectively.

Evaluation example  2: Evaluation of Luminescence Characteristics of Comparative Sample 1 and Samples 162 to 243

For Comparative Sample 1 and Samples 162 to 243, Keithley SMU 235 and PR650 were used to evaluate driving voltage, emission luminance, emission efficiency, and emission peak, and the results are shown in Table 2 below. The samples showed blue emission peak values in the range of 456-478 nm.

TABLE 2

As shown in Table 2, Samples 162 to 243 showed improved luminescence properties compared to Comparative Sample 1.

Example  244-322

Compounds for ITO / HIL were prepared in the same manner as in Comparative Example 1 except that HIL compounds were used as the hole injection layer compounds among the compounds disclosed in Synthesis Example instead of the formula b as the hole injection layer compounds. An organic light emitting device having a structure of 80 nm) / α-NPD (30 nm) / chemical formula α (30 nm) / LiF (0.5 nm) / Al (60 nm) was prepared. These are called samples 244 to 322, respectively.

Evaluation example  3: Evaluation of Luminescence Characteristics of Comparative Sample 1 and Samples 244 to 322

For Comparative Sample 1 and Samples 244 to 322, the driving voltage, emission luminance, emission efficiency, and emission peak were evaluated using Keithley SMU 235 and PR650, respectively, and the results are shown in Table 3 below. The samples showed blue emission peak values in the range of 456-464 nm.

TABLE 3

As can be seen in Table 3, Samples 244 to 322 showed improved characteristics 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 Chemical Formula a:
<Formula a>

Wherein A1, A2, A2 ', A3, A4 and A4' are each independently or related to hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted A substituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon,
Ar is hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group ,
X is 0 or N, O or S,
m is an integer from 1 to 10. The method of claim 1,
A1, A2, A3 and A4 are independent of each other,
A2 and A2 'and A4 and A4' are related to constitute a functional group,
One or both of these functional groups may be substituted or unsubstituted C2-C50 cycloalkyl group, substituted or unsubstituted C2-C50 heterocycloalkyl group, substituted or unsubstituted C6-C50 aryl group, or substituted or unsubstituted C2- An organic optical device, characterized in that the C50 heteroaryl 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,
A1, A2, A2 ', A3, A4 and A4' 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 161:

The method of claim 1,
The organic film is an organic optical device, characterized in that the hole transport layer, hole injection layer or light emitting layer. An organic photo compound represented by the following formula a:
<Formula a>

Wherein A1, A2, A2 ', A3, A4 and A4' are each independently or related to hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted A substituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, or a substituted or unsubstituted saturated or unsaturated hydrocarbon,
Ar is hydrogen, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group ego,
X is 0 or N, O or S,
m is an integer from 1 to 10. The method of claim 7, wherein
A1, A2, A3 and A4 are independent of each other,
A2 and A2 'and A4 and A4' are related to constitute a functional group,
One or both of these functional groups may be substituted or unsubstituted C2-C50 cycloalkyl group, substituted or unsubstituted C2-C50 heterocycloalkyl group, substituted or unsubstituted C6-C50 aryl group, or substituted or unsubstituted C2- It is a C50 heteroaryl group, The organic optical compound characterized by the above-mentioned. The method of claim 7, wherein
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 at least one substituent selected from the group consisting of silane groups. The method of claim 7, wherein
An organic photo compound, characterized in that the compound is represented by the formula 1 to 161: