KR101652167B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime by incorporating a novel compound having excellent heat resistance, hole transporting ability, and electron blocking ability into one or more organic layers.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound and an organic electroluminescent device including the same. More specifically, the present invention relates to an arylamine compound having excellent electron-blocking ability and hole-transporting ability, And lifetime of the organic electroluminescent device.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film emission of Bernanose in the 1950s In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. In order to improve the efficiency and lifetime of the organic EL device, the organic EL device has been developed to introduce a characteristic organic material layer in the device, and development of specialized materials used thereon has been continued.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer and holes are injected into the organic layer, respectively. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. A material used as an organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

The luminescent material may be classified into blue, green, and red luminescent materials depending on the luminescent color. In addition, it can be classified into yellow and orange light emitting materials necessary for realizing a better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of phosphorescent materials can theoretically improve luminescence efficiency up to four times that of fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq ₃ and the like represented by the following chemical formulas are widely known as materials used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, there are metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ , , And is used as a red dopant material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional luminescent materials are good in terms of luminescence characteristics, but have poor thermal stability due to their low glass transition temperature (Tg), which is not satisfactory in terms of lifetime in organic EL devices. Therefore, development of an organic electroluminescent device including a luminescent material having excellent performance is required.

On the other hand, in order to realize practical use and improve the characteristics of the organic electroluminescent device, it is necessary not only to constitute the device with the organic material layer having the multilayer structure, but also to have the material, particularly the hole transporting material, This is because molecules with low thermal stability due to heat generated in the device upon voltage application cause low rearrangement due to low crystal stability. Such localized crystallization causes a heterogeneous part, and an electric field This results in deterioration and destruction of the device. Therefore, in consideration of the above-mentioned points, conventionally used hole transport materials include m-MTDATA [4,4 ', 4 "-tris (N-3- methylphenyl- Triphenylamine], TPD [N, N'-diphenyl-N, N'-di ( 3-methylphenyl) -4,4'-diaminobiphenyl] and NPB [N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine].

However, since m-MTDATA and 2-TNATA have low glass transition temperatures (Tg) of 78 ° C and 108 ° C, respectively, they cause problems in the process of mass-production. TPD and NPB also have a fatal disadvantage that the glass transition temperature (Tg) is as low as 60 캜 and 96 캜, respectively, which shortens the lifetime of the device. Therefore, development of an organic electroluminescent device capable of increasing thermal stability and having an excellent hole transporting capability and capable of increasing the luminous efficiency and power efficiency of the organic electroluminescent device is desired.

Japanese Patent Application Laid-Open No. 2001-160489

An object of the present invention is to provide a compound which is excellent in both electron-blocking ability and hole-transporting ability and can be used as a light-emitting auxiliary layer material, a hole transporting layer material, and a hole injection layer material.

Another object of the present invention is to provide an organic electroluminescent device including the above-mentioned novel compound, which has low driving voltage, high luminous efficiency, and improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by the following formula 1:

In Formula 1,

Ar ₁ is a substituent represented by the following formula (2)

Ar ₂ to Ar ₄ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, C ₆ to C ₆₀ arylamine groups,

Provided that at least one of Ar ₂ and Ar ₃ is a substituent represented by the following formula (3);

In the above Chemical Formulas 1 to 3,

* Is the site where the bond is made;

R ₁ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 60 atoms and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group, or they may be bonded to adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring ;

R ₂ is the same or different and is independently selected from the group consisting of a substituted or unsubstituted C ₁ to C ₄₀ alkyl group and a substituted or unsubstituted C ₆ to C ₆₀ aryl group,

n, m and l are each independently an integer of 1 to 3;

a, b, c, d, e, f and g are each independently an integer of 0 to 4,

When the alkyl group, an aryl group, a heteroaryl group and an arylamine group is substituted, each independently represent deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to the A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₆ heteroaryl group, ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ of. When a plurality of substituents are introduced, the plurality of substituents may be the same or different from each other.

In addition, cathode; And one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by Formula 1 .

Here, the one or more organic layers including the compound represented by Formula 1 may be selected from the group consisting of a hole transport layer, an electron blocking layer, and a light-emitting auxiliary layer.

Since the organic electroluminescent device of the present invention contains the compound of Formula 1 having excellent heat resistance, electron mobility and hole transport ability in at least one organic layer, it is possible to greatly improve the light emitting performance, driving voltage, And can be effectively applied to a full color display panel and the like.

Hereinafter, the present invention will be described.

<Novel compound>

The compound of formula (I) according to the present invention is characterized in that a basic core in which two arylamine groups are bonded on both sides of one to four benzene rings as a core, and at least one phenylcarbazole Moiety and a fluorene moiety, and has an asymmetric structure.

The diarylamine core-based organic light emitting compound of Formula 1 has better stability and lifetime characteristics than conventional hole transporting materials, so that the device has excellent driving life and induces an increase in power efficiency There is an advantage that an OLED device with improved power consumption can be manufactured.

Further, the arylamine group, the phenylcarbazole group and the fluorene group each have an electron donor (EDG) characteristic, so that they are stable and have good hole mobility. Accordingly, the compound represented by Formula 1 of the present invention in which the moiety is bonded in an asymmetric structure is advantageous as a hole transporting material which can thermally stabilize and improve hole mobility to maximize efficiency characteristics.

On the other hand, the light-emitting auxiliary layer limits the injection of the triplet exciton into the hole-related layer, and at the same time, has a delta Est (<0.5 eV) To the singleton level. It is then transferred back to the singlet level of the EML to participate in the exciton generation and consequently transition to the triplet level of the EML to eliminate the efficiency loss that would otherwise occur if the prime layer is not provided, EML). &Lt; / RTI &gt; Further, it preferably exhibits a high LUMO value and may also include an electron blocking function.

In addition, it is used to increase the efficiency of the fluorescent blue element. Its role is to have a hole mobility of higher than a certain level (Hole Mobility of NPB) and a value of T1 higher than that of the blue fluorescent light emitting layer. The main role is to prevent the entry into the BIL, limit its activity to the light emitting layer, and convert the triplet exciton into singlet exciton through TTA (TTF) to increase the efficiency. At this time, preferably, BIL may also have an effect of improving the interface characteristics between the hole-related layer and the emission layer (EML), more preferably exhibiting a high LUMO value, and may also include an electron blocking function.

Further, the compound represented by the formula (1) according to the present invention has a basic structure in which phenyl, biphenyl, terphenyl and arylamine groups are bonded to form an electron rich structure, and has excellent hole mobility and high triplet energy A carbazole moiety, and a fluorene moiety, which is advantageous as a light emitting auxiliary layer material capable of maximizing efficiency characteristics.

According to the present invention, in the compound represented by the general formula (1), Ar ₁ has a phenylcarbazole-based substituent represented by the general formula (2), and at least one of Ar ₂ and Ar ₃ has a fluorene-based substituent represented by the general formula (3). Here, * denotes a site where bonding is performed.

In the present invention, Ar ₂ to Ar ₄ having no substituent in Formula 3 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted nucleus atom of 5 to 60 heteroaryl group, and is selected from the group consisting of arylamine-substituted or unsubstituted C ₆ ~ C _60. More specifically, the C ₆ -C ₆₀ aryl group may be selected from a phenyl group, a biphenyl group, a naphthyl group, a phenanthrene group, a pyrene group, a triphenylene group, a fluorene group, The aryl group may be selected from pyridine, pyrimidine, triazine, quinazoline, carbazole, dibenzofuran, dibenzothiophene and the like. The arylamine group of C ₆ to C ₆₀ may be selected from the above-mentioned aryl group and an amine group substituted by a heteroaryl group, but is not particularly limited thereto.

In this case, each of Ar ₂ to Ar ₄ is independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nucleus atoms.

R ₁ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 60 atoms and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group, or they may be bonded to adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring .

R ₂ are the same or different and each independently selected from the group consisting of a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, and a substituted or unsubstituted C ₆ to C ₆₀ aryl group.

(*는 결합이 이루어지는 부위)인 경우가 바람직하다.Herein, R ₂ represents a methyl group, a phenyl group,

(* Is a site where bonding is performed).

n, m and l are each independently an integer of 1 to 3;

a, b, c, d, e, f and g are each independently an integer of 0 to 4;

In the present invention, the substituents described the term "substituted or unsubstituted", that is an alkyl group, an aryl group, a heteroaryl group, and aryl amine groups are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ when substituted the alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ of the C ₆₀ aryl group, the nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, may be substituted with a C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ at least one member selected from the group consisting of an aryl amine of the C _60. When a plurality of substituents are introduced, the plurality of substituents may be the same or different from each other.

In the present invention, the compound represented by the formula (1) may be further represented by a compound represented by the following formula (4) or (5).

(4) represents an asymmetric structure in which both phenylcarbazole moiety and fluorene moiety are bonded to one side of the diarylamine core (i.e., Ar ₂ has the structure of formula (3)). (5) shows an asymmetric structure in which a phenylcarbazole moiety and a fluorene moiety are bonded to each other at both side of the diarylamine core (i.e., Ar ₃ has a structure of the formula (3)).

In Formula 4 or Formula 5,

Ar ₂ to Ar ₄ , R ₁ to R ₂ , and a to f are each as defined in formula (1).

As a preferred example of the present invention, Ar ₂ to Ar ₄ which do not have a substituent structure of the general formula (3) are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group, And a heteroaryl group having 5 to 60 nuclear atoms,

R ₁ are the same or different and each independently represents hydrogen, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted nucleus atom number 5 to 60 heteroaryl groups, and substituted or unsubstituted C ₆ to C ₆₀ arylamine groups,

이며, (이때 *는 결합이 이루어지는 부위를 의미하며),R ₂ are the same or different and each independently represents a methyl group, a phenyl group,

(Where * denotes a site where bonding occurs),

n, m and l are each independently an integer of 1 to 3;

a, b, c, d, e, f and g are each independently an integer of 0 to 4,

When the alkyl group, an aryl group, a heteroaryl group and an arylamine group is substituted, each independently represent deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to the A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₆ heteroaryl group, ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ of. When a plurality of substituents are introduced, the plurality of substituents may be the same or different from each other.

The compound of the present invention described above can be further compounded into a compound represented by any of the following formulas A-1 to B-96 shown below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

In the present invention, alkyl is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, However, the present invention is not limited thereto.

The alkenyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, allyl, Isopropenyl, 2-butenyl, and the like, but the present invention is not limited thereto.

Alkynyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2- 2-propynyl, and the like, but are not limited thereto.

The aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

The heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, aryloxy is a monovalent substituent represented by RO-, and R represents aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The alkyloxy in the present invention is a monovalent substituent group represented by R'O-, wherein R 'is an alkyl having 1 to 40 carbon atoms and includes a linear, branched or cyclic structure . Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

The arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

The cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon of the ring, preferably 1 to 3 carbons, is N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

The alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.

The condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

&Lt; Organic electroluminescent device &

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 is a hole transport layer, an electron blocking layer, or a light-emitting auxiliary layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as a host material.

The compound represented by formula (1) according to the present invention has a basic structure in which phenyl, biphenyl and terphenyl arylamine groups are bonded to form an electron rich structure, and has a high hole mobility and a high trivalent energy. Moiety, fluorene moiety, and thus has an advantage as a light emitting auxiliary layer material capable of maximizing the efficiency characteristics.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, and preferably includes a hole transporting layer, The auxiliary layer may include a compound represented by the above formula (1). On the other hand, an electron injection layer may be further stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device of the present invention can be produced by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.

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

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of N- (4- (9H-carbazol-9-yl) phenyl) -9,9-dimethyl-9H-fluoren-

9.9-dimethyl-9H-fluoren-2-amine, 6.56 g (7.17 mmol) of 9- (4-bromophenyl) -9H-carbazole, 43.94 g (262.79 mmol) of 50.0 g (238.90 mmol) mixture of _{Pd 2 (dba) 3, 4.84} g NaO (t-bu) , and toluene (1000 ml) of _{P (t-bu) 3,} 57.40 g (597.26 mmol) of (23.89 mmol), and for 5 hours at 110 ℃ Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 80.73 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 450.57 g / mol, measured: 450 g / mol)

(M, 2H), 7.90 (m, 2H), 8.15 (d, 2H), 7.30 , &Lt; / RTI &gt; 1H), 8.55 (d, 1H)

[Preparation Example 2] Synthesis of N- (4-chlorophenyl) - [1,1'-biphenyl] -4-amine

1-chloro-4-iodobenzene, 56.77 g (169.22 mmol) of [l, l'-biphenyl] -4-amine and 9.22 g (10.07 mmol) of Pd ₂ (dba) _3, 6.79 g (33.55 mmol) of P (t-bu) _3, 80.60 g (838.75 mmol) of NaO (t-bu) and toluene (1000 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 58.1 g (yield: 62%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 279.76 g / mol, measured: 279 g / mol)

2H), 7.54 (m, 7H), 7.66 (d, 2H), 7.50 (d,

[Preparation Example 3] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren-

2-bromophenanthrene, 0.98 g (1.07 mmol) of Pd ₂ (dba) _{3 and} 0.72 g (3.57 mmol) of the compound synthesized in Preparation Example 2 (10.0 g, 35.74 mmol) and 9.19 g (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.40 g (yield: 70%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 455.98 g / mol, measured: 455 g / mol)

(D, 2H), 7.50 (d, 2H), 7.69 (d, 2H) , 8.80 (d, IH), 8.50 (d, IH), 8.92 (d,

[Preparation Example 4] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren-9-amine

9.0 g (35.74 mmol) of 9-bromophenanthrene, 0.98 g (1.07 mmol) of Pd ₂ (dba) _{3 and} 0.72 g (3.57 mmol) of the compound synthesized in Preparation Example 2 (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.22 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 455.98 g / mol, measured: 455 g / mol)

(D, 2H), 7.50 (d, 2H), 7.69 (d, 2H) , 8.80 (d, IH), 8.50 (d, IH), 8.92 (d,

[Preparation Example 5] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) triphenylen-2-amine

2-bromotriphenylene, 0.98 g (1.07 mmol) of Pd ₂ (dba) _{3 and} 0.72 g (3.57 mmol) of the compound synthesized in Preparation Example 2 (10.0 g, 35.74 mmol) and 10.98 g (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.66 g (yield: 70%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 506.04 g / mol, measured: 506 g / mol)

(D, 2H), 7.50 (m, 5H), 7.75 (m, 5H), 7.80 (d, 2H) , &Lt; / RTI &gt; 3H), 8.90 (d, 2H)

[Preparation Example 6] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen-

Pd ₂ (dba) _{3 and} 0.72 g (3.57 mmol) of Pd ₂ (dib) _3, 0.98 g (1.07 mmol) of 1-bromonaphthalene and 13.55 g (35.74 mmol) of the compound synthesized in Preparation Example 2, (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.44 g (yield: 72%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 405.92 g / mol, measured: 405 g / mol)

2H), 7.50 (m, 11H), 8.00 (m, 2H), 7.24 (d,

[Preparation Example 7] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen-2-amine

Pd ₂ (dba) _{3 and} 0.72 g (3.57 mmol) of Pd ₂ (dib) _3, 0.98 g (1.07 mmol) of 2-bromonaphthalene and 13.55 g (35.74 mmol) of the compound synthesized in Preparation Example 2, (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.00 g (yield: 69%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 405.92 g / mol, measured: 405 g / mol)

2H), 7.60 (d, 2H), 6.69 (d, 2H), 7.05 (d,

[Preparation Example 8] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [b, d] furan-

The synthesized compound in Preparation Example 2 was conducted in a nitrogen atmosphere 10.0 g (35.74 mmol), 8.83 g (35.74 mmol) 2-bromodibenzo [b, d] furan, 0.98 g Pd 2 (dba) of (1.07 mmol) _3, 0.72 g of (3.57 mmol) of P (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.36 g (yield: 65%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 445.94 g / mol, measured: 445 g / mol)

7H), 7.62 (m, 2H), 7.85 (d, IH), 7.54 (d, IH) , 1H)

[Preparation Example 9] Synthesis of N- (4-chlorophenyl) -N- (4- (dibenzo [b, d] furan-4-yl) phenyl) - [1,1'-biphenyl]

A mixture of 10.0 g (35.74 mmol) of the compound synthesized in Preparation Example 2 and 11.55 g (35.74 mmol) of 4- (4-bromophenyl) dibenzo [b, d] furan and 0.98 g (1.07 mmol) of Pd ₂ ) _3, 0.72 g (3.57 mmol) of P (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.36 g (yield: 77%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 522.03 g / mol, measured: 522 g / mol)

(D, 2H), 6.70 (d, 2H), 7.80 (d, 2H)

[Preparation Example 10] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [b, d] thiophen-2-amine

The synthesized compound in Preparation Example 2 was conducted in a nitrogen atmosphere 10.0 g (35.74 mmol), 13.55 g 2-bromodibenzo of (35.74 mmol) [b, d ] thiophene, 0.98 g Pd 2 (dba) of (1.07 mmol) _3, 0.72 g (3.57 mmol) of P (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.20 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 462.00 g / mol, measured: 462 g / mol)

7H), 7.62 (m, 2H), 7.85 (d, IH), 7.54 (d, IH) , 1H)

[Preparation Example 11] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) -9,9-dimethyl-9H-fluoren-

10.0 g (35.74 mmol) of the compound synthesized in Preparation Example 2, 9.76 g (35.74 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene and 0.98 g (1.07 mmol) of Pd _{2 3,} 0.72 g (3.57 mmol) of P (t-bu) _3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.65 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 472.02 g / mol, measured: 472 g / mol)

(M, 3H), 7.24 (m, 3H), 7.50 (m, 2H), 7.62 (m, 8H), 7.85 , 1H)

[Preparation Example 12] Synthesis of N - ([1,1'-biphenyl] -4-yl) -4'-chloro- [1,1'-biphenyl] -4-amine

4'-dichloro-1,1'-biphenyl, 30.34 g (179.29 mmol) of [1,1'-biphenyl] -4-amine and 4.93 g (5.38 mmol) of 40.0 g (179.29 mmol) Of Pd ₂ (dba) _3, 3.63 g (17.93 mmol) of P (t-bu) _3, 43.07 g (448.23 mmol) of NaO (t-bu) and toluene (1000 ml) Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 40.83 g (yield: 64%) of the target compound was obtained by column chromatography.

GC-Mass (355.86 g / mol, measured: 355 g / mol)

1H), 7.40 (t, 1H), 7.54 (m, 10H), 8.12 (d, 2H)

[Preparation Example 13] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) -9,9-dimethyl-9H-fluoren-

To a solution of 10.0 g (28.10 mmol) of the compound prepared in Preparation Example 12, 7.23 g (28.10 mmol) of 2-bromophenanthrene, 0.77 g (0.84 mmol) of Pd ₂ (dba) _{3 and} 0.57 g (2.81 mmol) of P (t-bu) _3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.55 g (yield: 84%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 532.07 g / mol, measured: 532 g / mol)

(M, 2H), 8.80 (m, 2H), 8.20 (m, 2H), 7.47 , 3H), 8.90 (d, 1 H), 8.95 (d, 1 H)

[Preparation Example 14] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) phenanthren-

A mixture of 10.0 g (28.10 mmol) of the compound prepared in Preparation Example 12, 7.23 g (28.10 mmol) of 9-bromophenanthrene, 0.77 g (0.84 mmol) of Pd ₂ (dba) _{3 and} 0.57 g (2.81 mmol) of P (t-bu) _3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.00 g (yield: 80%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 532.07 g / mol, measured: 532 g / mol)

(D, 2H), 8.80 (m, 2H), 8.20 (m, 2H), 7.80 , 3H), 8.90 (d, 1 H), 8.95 (d, 1 H)

[Preparation Example 15] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) phenanthren-

2-bromotriphenylene, 0.77 g (0.84 mmol) of Pd ₂ (dba) _{3 and} 0.57 g (2.81 mmol) of the compound synthesized in Preparation Example 12, 10.0 g (28.10 mmol) (t-bu) _3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.43 g (yield: 76%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 582.13 g / mol, measured: 582 g / mol)

1H), 7.80 (m, 5H), 8.30 (m, 5H), 8.60 (d,

[Preparation Example 16] Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) naphthalen-

1-bromonaphthalene, 0.77 g (0.84 mmol) of Pd ₂ (dba) _{3 and} 0.57 g (2.81 mmol) of the compound synthesized in Preparation Example 12, 10.0 g (28.10 mmol) (t-bu) _3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.97 g (yield: 81%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 482.01 g / mol, measured: 482 g / mol)

7.45 (m, 2H), 7.55 (m, 13H), 8.03 (m, 4H)

[Preparation Example 17] Biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) dibenzo [b, d] furan- synthesis

The synthesized compound from Preparation Example 12 was conducted in a nitrogen atmosphere 10.0 g (28.10 mmol), 6.94 g (28.10 mmol) 2-bromodibenzo [b, d] furan, 0.77 g Pd 2 (dba) of (0.84 mmol) _3, 0.57 g of (2.81 mmol) of P (t-bu) _3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 9.24 g (yield: 63%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 522.03 g / mol, measured: 522 g / mol)

2H), 8.85 (d, IH), 8.15 (d, 2H), 7.50 (d, IH)

[Preparation Example 18] Biphenyl-4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) dibenzo [b, d] thiophen-2-amine synthesis

The synthesized compound from Preparation Example 12 was conducted in a nitrogen atmosphere 10.0 g (28.10 mmol), 7.39 g (28.10 mmol) 2-bromodibenzo [b, d] thiophene, 0.77 g Pd 2 (dba) of (0.84 mmol) _3, 0.57 g of (2.81 mmol) of P (t-bu) _3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 8.31 g (yield: 55%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 538.10 g / mol, measured: 538 g / mol)

2H), 8.85 (d, IH), 8.15 (d, 2H), 7.30 (d, IH)

[Preparation Example 19] Synthesis of N- (4 '- (9H-carbazol-9-yl) - [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-

(10.21 g, 50.21 mmol) of 9,9-dimethyl-9H-carbazole was added to a solution of 20.0 g (50.21 mmol) of 9- -fluoren-2-amine, 1.38 g (1.51 mmol) Pd 2 (dba) NaO (t-bu) of _{3, 1.02 g (5.02 mmol)} P (t-bu) 3, 12.06 g (125.54 mmol) of, and the toluene (300 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.06 g (yield: 52%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 526.67 g / mol, measured: 526 g / mol)

(M, 2H), 7.50 (m, 8H), 7.30 (d, 1H), 6.90 2H), 7.94 (m, 2H), 8.12 (d, 1H), 8.55

[Preparation Example 20] Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-diphenylbenzene-1,4-diamine

A solution of 20.0 g (76.83 mmol) of N1, N4-diphenylbenzene-1,4-diamine, 20.99 g (76.83 mmol) 2-bromo-9,9-dimethyl-9H- fluorene and 2.11 g (2.30 mmol) mixture of _{Pd 2 (dba) 3, 1.56} g (7.68 mmol) of _{P (t-bu) 3,} 18.46 g NaO (t-bu) , and toluene (400 ml) of (192.06 mmol), and for 5 hours at 110 ℃ Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.64 g (yield: 45%) of the title compound was obtained by column chromatography.

GC-Mass (theory: 452.59 g / mol, measured: 452 g / mol)

(M, 3H), 7.20 (m, 7H), 7.30 (d, 4H), 6.60 , 7.61 (d, 1 H), 7.70 (d, 1 H)

[Preparation Example 21] Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-di-p-tolylbenzene-1,4-

N, di-p-tolylbenzene-1,4-diamine, 18.94 g (69.35 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 1.91 g (69.35 mmol) _{2.08 mmol) Pd 2 (dba)} 3, 1.40 g (P (t-bu) of a 6.94 mmol) of _{3, 16.66 g (173.38. mmol} ) of NaO (t-bu), and toluene (400 ml) mixture and 110 the Lt; 0 &gt; C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15 g of the target compound (yield: 54%) was obtained by column chromatography.

GC-Mass (theory: 480.64 g / mol, measurement: 480 g / mol)

(M, 3H), 6.80 (m, 3H), 7.20 (m, 2H), 6.30 , 7H), 7.30 (d, IH), 7.61 (d, IH), 7.70

[Preparation Example 22] Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-di (naphthalen-

N-di (naphthalen-1-yl) benzene-1,4-diamine and 15.16 g (55.49 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene , the _{1.52 g (1.66 mmol) Pd 2} (dba) 3, 1.12 g P (t-bu) 3, 13.33 g NaO (t-bu) , and toluene (400 ml) of (138.72 mmol) of (5.55 mmol) of And the mixture was stirred at 110 DEG C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 17.78 g (yield: 58%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 552.71 g / mol, measured: 552 g / mol)

(D, 1H), 7.05 (d, 2H), 7.36 (d, 1H), 6.40 , 4H), 7.61 (m, 8H), 7.75 (m, 5H)

[Preparation Example 23] Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-di (naphthalen-

N-di (naphthalen-1-yl) benzene-1,4-diamine and 13.24 g (48.48 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene , the _{1.33 g 3, Pd 2 (dba} ) of (1.45 mmol) 0.98 g P ( t-bu) 3, 11.65 g NaO (t-bu) , and toluene (400 ml) of (121.21 mmol) of (4.85 mmol) And the mixture was stirred at 110 DEG C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.17 g (yield: 62%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 604.78 g / mol, measurement: 604 g / mol)

(D, 1H), 7.87 (d, IH), 7.70 (d, IH) , 1H)

[Preparation Example 24] Synthesis of N4- (9,9-dimethyl-9H-fluoren-2-yl) -N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine

N, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine and 16.24 g (59.45 mmol) of 2-bromo-9,9-dimethyl- _{9H-fluorene, 1.63 g Pd 2} (dba) of _{(1.78 mmol) 3, 1.20 g} (5.94 mmol) of _{P (t-bu) 3,} 14.28 g NaO (t-bu) , and toluene (400 of (148.62 mmol) ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 19.49 g (yield: 62%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 528.68 g / mol, measured: 528 g / mol)

(D, IH), 7.60 (m, 6H), 7.85 (d, IH), 7.80 , 1H)

[Preparation Example 25] Synthesis of N4- (9,9-dimethyl-9H-fluoren-2-yl) -N4, N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine

N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine, 14.99 g (54.87 mmol) of 2-bromo-9, 9-dimethyl-9H-fluorene, 1.51 g (1.65 mmol) Pd 2 (dba) 3, 1.11 g (5.49 mmol) of _{P (t-bu) 3,} 13.18 g (137.18 mmol) NaO (t-bu) of And toluene (400 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.80 g (yield: 55%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 556.74 g / mol, measured: 556 g / mol)

(M, 3H), 6.90 (m, 5H), 7.00 (d, 2H), 7.30 (m, 2H) , 6H), 7.85 (m, 6H), 7.90 (d, IH)

[Preparation Example 26] Synthesis of N4- (9,9-dimethyl-9H-fluoren-2-yl) -N4, N4'-di (naphthalen-1-yl) - [1,1'-biphenyl] -4,4'-

(45.81 mmol) of N4, N4'-di- (1,1'-biphenyl) -4,4'-diamine and 14.99 g (45.81 mmol) of 2-bromo -9,9-dimethyl-9H-fluorene, 1.26 g (1.37 mmol) Pd ₂ (dba) _3, 0.93 g (4.58 mmol) P (t- bu) _{3 and} 11.01 g (114.53 mmol) NaO -bu) and toluene (400 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.69 g (yield: 51%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 628.80 g / mol, measurement: 628 g / mol)

7.30 (t, 1H), 7.40 (m, 3H), 7.85 (m, 2H), 7.90 , 12 H), 8.02 (m, 5 H)

[Preparation Example 27] N4, N4'-di ([1,1'-biphenyl] -4-yl) -N4- (9,9-dimethyl-9H- fluoren- 2- yl) - [1,1'-biphenyl] Synthesis of 4'-diamine

Under a stream of nitrogen, 20.0 g (40.93 mmol) of N4, N4'-di ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -4,4'-diamine, 11.18 g 40.93 mmol) 2-bromo-9,9 -dimethyl-9H-fluorene, 1.12 g (1.23 mmol) of _{Pd 2 (dba) 3, 0.83} g (4.09 mmol) of _{P (t-bu) 3,} 9.83 g of ( 102.33 mmol) of NaO (t-bu) and toluene (400 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.67 g (yield: 67%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 680.88 g / mol, measured: 680 g / mol)

1 H), 7.50 (m, 4H), 7.50 (m, 18H), 7.90 (d,

[Preparation Example 28] Synthesis of N- (4- (9H-carbazol-9-yl) phenyl) -9,9-diphenyl-9H-fluoren-

9.7 g (155.18 mmol) of 9,9-diphenyl-9H-fluoren-2-amine and 4.26 g (4.66 mmol) of 9- (4-bromophenyl) -9H- mixture of _{Pd 2 (dba) 3, NaO} (t-bu) , and toluene (1000 ml) of _{P (t-bu) 3,} 37.28 g (387.96 mmol) of 3.14 g (15.52 mmol), and for 5 hours at 110 ℃ Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 72.24 g (yield: 81%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 574.71 g / mol, measured: 574 g / mol)

(D, 1H), 8.55 (m, 2H), 7.50 (m, 2H), 7.50 , 1H)

[Preparation Example 29] Synthesis of N- (4- (9H-carbazol-9-yl) phenyl) -9,9'-spirobi [fluoren] -2-amine

(50.0 g, 155.18 mmol) of 9- (4-bromophenyl) -9H-carbazole, 51.43 g (155.18 mmol) of 9,9'-spirobi [fluoren] -2-amine, 4.26 g mixture of _{Pd 2 (dba) 3, NaO} (t-bu) , and toluene (1000 ml) of _{P (t-bu) 3,} 37.28 g (387.96 mmol) of 3.14 g (15.52 mmol), and for 5 hours at 110 ℃ Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 66.66 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 572.70 g / mol, measured: 572 g / mol)

(D, IH), 7.50 (m, 4H), 7.50 (m, 4H)

[Preparation Example 30] Synthesis of N1- (9,9-diphenyl-9H-fluoren-2-yl) -N1, N4-diphenylbenzene-1,4-diamine

To a solution of 10.0 g (25.17 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene, 8.34 g (25.17 mmol) of N1, N4- diphenylbenzene- 1,4-diamine and 0.69 g mixture of _{Pd 2 (dba) 3, 0.51} g (2.52 mmol) of _{P (t-bu) 3,} 6.05 g NaO (t-bu) , and toluene (150 ml) of (62.92 mmol), and for 5 hours at 110 ℃ Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.31 g (yield: 71%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 576.73 g / mol, measured: 576 g / mol)

7.80 (m, 2H), 8.00 (m, 2H), 7.90 (m, 2H) , 1H)

[Preparation Example 31] Synthesis of N1- (9,9-diphenyl-9H-fluoren-2-yl) -N1, N4-di-p-tolylbenzene-

N, N-di-p-tolylbenzene-1,4-diamine, 0.69 g (25.17 mmol) of 10.0 g (25.17 mmol) of 2-bromo-9,9- diphenyl-9H- Pd ₂ (dba) a _{0.76 mmol) 3, 0.51 g (} 2.52 mmol) of _{P (t-bu) 3,} 6.05 g (62.92 mixture of NaO (t-bu), and toluene (150 ml) of mmol) and 110 ℃ Lt; / RTI &gt; for 5 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.42 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 604.78 g / mol, measurement: 604 g / mol)

(M, 3H), 7.00 (m, 3H), 8.80 (m, 17H), 7.90 (m, , &Lt; / RTI &gt; 2H), 8.00 (d, 1H)

[Preparation Example 32] Synthesis of N1- (9,9-diphenyl-9H-fluoren-2-yl) -N1, N4-di (naphthalen-1-yl) benzene-1,4-

N, N4-di (naphthalen-1-yl) benzene-1,4-diamine (10.0 g, 25.17 mmol) was added dropwise to a solution of 9.07 g (25.17 mmol) of 2-bromo- , 0.69 g (0.76 mmol) Pd 2 (dba) 3, 0.51 g (2.52 mmol) P (t-bu) 3, 6.05 g NaO (t-bu) , and toluene (150 ml) of (62.92 mmol) of the And the mixture was stirred at 110 DEG C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.07 g (yield: 65%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 676.84 g / mol, measured: 676 g / mol)

(M, 2H), 8.00 (m, 2H), 7.90 (m, 2H), 7.40 , 1H)

[Preparation Example 33] Synthesis of N4- (9,9-diphenyl-9H-fluoren-2-yl) -N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine

10.0 g (25.17 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene and 8.47 g (25.17 mmol) of N4, N4'- diphenyl- [1,1'-biphenyl] -4,4 _{'-diamine, 0.69 g Pd 2 (} dba) of _{(0.76 mmol) 3, 0.51 g} (2.52 mmol) of _{P (t-bu) 3,} 6.05 g NaO (t-bu) , and toluene (150 of (62.92 mmol) ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.68 g (yield: 65%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 652.82 g / mol, measured: 652 g / mol)

(M, 6H), 7.80 (d, IH), 7.70 (d, IH)

[Preparation Example 34] Synthesis of N4- (9,9-diphenyl-9H-fluoren-2-yl) -N4, N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine

(10.1 g, 25.17 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene and 8.92 g (25.17 mmol) of N4, N4'- di- p- tolyl- [1,1'- biphenyl] -4,4'-diamine, 0.69 g NaO ( t-bu) of _{(0.76 mmol) Pd 2 (dba} ) 3, 0.51 g P (t-bu) 3, 6.05 g (62.92 mmol) of (2.52 mmol) of And toluene (150 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.68 g (yield: 74%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 680.88 g / mol, measured: 680 g / mol)

(M, 6H), 7.80 (d, IH), 7.70 (d, IH)

[Preparation Example 35] Synthesis of N1- (9,9'-spirobi [fluoren] -2-yl) -N1, N4-diphenylbenzene-1,4-diamine

N1-diphenylbenzene-1,4-diamine, 0.69 g (0.76 mmol) of 2-bromo-9,9'-spirobi [fluorene] and 8.92 g (25.17 mmol) of 10.0 g (25.17 mmol) mixture of _{Pd 2 (dba) 3, 0.51} g (2.52 mmol) of _{P (t-bu) 3,} 6.05 g NaO (t-bu) , and toluene (150 ml) of (62.93 mmol), and for 5 hours at 110 ℃ Lt; / RTI &gt; After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.27 g (yield: 71%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 574.71 g / mol, measured: 574 g / mol)

7.80 (m, 2H), 8.00 (m, 2H), 7.90 (m, 2H) , 1H)

[Preparation Example 36] Synthesis of N1- (9,9'-spirobi [fluoren] -2-yl) -N1, N4-di-p-tolylbenzene-1,4-

(25.17 mmol) of 2-bromo-9,9'-spirobi [fluorene], 7.26 g (25.17 mmol) of N1, N4-di- p-tolylbenzene- 1,4-diamine, 0.69 g (0.76 mmol) of Pd ₂ (dba) _3, 0.51 g (2.52 mmol) of P (t-bu) _3, 6.05 g (62.93 mmol) of NaO (t-bu) and toluene Lt; 0 &gt; C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 9.86 g (yield: 65%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 602.76 g / mol, measured: 602 g / mol)

(M, 3H), 8.80 (m, 17H), 7.90 (m, 5H), 6.70 , &Lt; / RTI &gt; 2H), 8.00 (d, 1H)

[Preparation Example 37] Synthesis of N1- (9,9'-spirobi [fluoren] -2-yl) -N1, N4-di (naphthalen-1-yl) benzene-1,4-diamine

N, N4-di (naphthalen-1-yl) benzene-1,4-dicarboxylic acid dihydrochloride was obtained under a nitrogen stream with the addition of 10 g (25.30 mmol) of 2-bromo-9,9'-spirobi [fluorene] _{diamine, 0.69 g Pd 2 (dba} ) of _{(0.76 mmol) 3, 0.51 g} P (t-bu) 3, 6.08 g NaO (t-bu) , and toluene (150 ml) of (63.24 mmol) of (2.52 mmol) Were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.41 g (yield: 61%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 674.83 g / mol, measured: 674 g / mol)

(M, 2H), 8.00 (m, 2H), 7.90 (m, 2H), 7.40 , 1H)

[Preparation Example 38] Synthesis of N4- (9,9'-spirobi [fluoren] -2-yl) -N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine

A solution of 10. g (25.30 mmol) of 2-bromo-9,9'-spirobi [fluorene] and 8.51 g (25.30 mmol) of N4, N4'- diphenyl- [1,1'- biphenyl] 4'-diamine, 0.69 g (0.76 mmol) of _{Pd 2 (dba) 3, 0.51} g (2.52 mmol) of _{P (t-bu) 3,} 6.08 g (63.24 mmol) NaO (t-bu) , and toluene of ( 150 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.18 g (yield: 74%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 650.81 g / mol, measured: 650 g / mol)

(M, 2H), 7.50 (m, 6H), 7.80 (d, 1H)

[Preparation Example 39] Synthesis of N4- (9,9'-spirobi [fluoren] -2-yl) -N4, N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine

A mixture of 10 g (25.30 mmol) of 2-bromo-9,9'-spirobi [fluorene], 9.22 g (25.30 mmol) of N4, di- p-tolyl- [1,1'-biphenyl ] -4,4'-diamine, 0.69 g (0.76 mmol) Pd ₂ (dba) _3, 0.51 g (2.52 mmol) P (t-bu) _3, 6.08 g (63.24 mmol) NaO ) And toluene (150 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.19 g (yield: 71%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 678.86 g / mol, measured: 678 g / mol)

(M, 2H), 7.50 (m, 6H), 7.80 (d, IH)

[Synthesis Example 1] Synthesis of A-1

Nd-diphenylaniline, 0.61 g (0.67 mmol) of Pd ₂ (dba) _3, 0.45 g (0.13 mmol) of the compound synthesized in Preparation Example 12, 10.0 g (22.19 mmol) (2.22 mmol) of P (t-bu) _3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.55 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 693.88 g / mol, measured: 693 g / mol)

[Synthesis Example 2] Synthesis of A-2

Pd ₂ (dba) of 4-bromo-N, N-di-p-tolylaniline and 0.61 g (0.67 mmol) of compound 10.0 g (22.19 mmol) synthesized in Preparation Example 12, 7.82 g (22.19 mmol) _3, 0.45 g (2.22 mmol) of P (t-bu) _3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.98 g (yield: 81%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 721.93 g / mol, measured: 721 g / mol)

[Synthesis Example 3] Synthesis of A-3

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.57 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ NaO of 1,1'-biphenyl] -4-amine, 0.61 g Pd 2 (dba) of _{(0.67 mmol) 3, 0.45 g} (2.22 mmol) P (t-bu) 3, 5.33 g (55.49 mmol) of ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.21 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)

[Synthesis Example 4] Synthesis of A-12

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.42 g (22.19 mmol) of N- (4-bromophenyl) -N- (naphthalen-1-yl) naphthalen- Pd ₂ (dba) a _{0.67 mmol) 3, 0.45 g (} 2.22 mmol) of P (t-bu) _3, were mixed NaO (t-bu), and toluene (200 ml) of 5.33 g (55.49 mmol) 110 ℃ Lt; / RTI &gt; for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 13.22 g (yield: 78%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)

[Synthesis Example 5] Synthesis of A-11

(10.0 g, 22.19 mmol) and 8.31 g (22.19 mmol) of N- (4-bromophenyl) -N-phenylnaphthalen-1-amine and 0.61 g (0.67 mmol) of Pd ₂ mixing _{dba) 3, 0.45 g (2.22} mmol) of _{P (t-bu) 3,} 5.33 g (NaO (t-bu) , and toluene (200 ml) of 55.49 mmol) and stirred at 110 ℃ for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 13.70 g (yield: 83%) of the desired compound was obtained by column chromatography.

GC-Mass (743.93 g / mol, measured: 743 g / mol)

[Synthesis Example 6] Synthesis of A-89

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.42 g (22.19 mmol) of N- (4-bromophenyl) -N- (naphthalen-2-yl) naphthalen- Pd ₂ (dba) a _{0.67 mmol) 3, 0.45 g (} 2.22 mmol) of P (t-bu) _3, were mixed NaO (t-bu), and toluene (200 ml) of 5.33 g (55.49 mmol) 110 ℃ Lt; / RTI &gt; for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.10 g (yield: 80%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)

[Synthesis Example 7] Synthesis of A-4

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.48 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) -9 , 9-dimethyl-9H-fluoren -2-amine, 0.61 g (0.67 mmol) of Pd ₂ (dba) _3, NaO of 0.45 g P (t-bu) 3, 5.33 g (55.49 mmol) of (2.22 mmol) (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.73 g (yield: 85%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 886.13 g / mol, measured: 886 g / mol)

[Synthesis Example 8] Synthesis of A-5

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.12 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren- (T-bu) _and 5.33 g (55.49 mmol) of Pd ₂ (dba) _3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.41 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)

[Synthesis Example 9] Synthesis of A-6

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.12 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren- _{9-amine, 0.61 g Pd 2} (dba) of _{(0.67 mmol) 3, 0.45 g} (2.22 mmol) of _{P (t-bu) 3,} NaO (t-bu) , and toluene (200 of 5.33 g (55.49 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.45 g (yield: 80%) of the title compound was obtained by column chromatography.

GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)

[Synthesis Example 10] Synthesis of A-8

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.23 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4- chlorophenyl) triphenylen- (T-bu) _and 5.33 g (55.49 mmol) of Pd ₂ (dba) _3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.93 g (yield: 73%) of the title compound was obtained by column chromatography.

GC-Mass (calculated: 920.15 g / mol, measured: 920 g / mol)

[Synthesis Example 11] Synthesis of A-14

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.09 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen- (T-bu) _and 5.33 g (55.49 mmol) of Pd ₂ (dba) _3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.20 g (yield: 87%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)

[Synthesis Example 12] Synthesis of A-68

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.09 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen- (T-bu) _and 5.33 g (55.49 mmol) of Pd ₂ (dba) _3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 13.65 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)

[Synthesis Example 13] Synthesis of A-18

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.90 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [ b, d] furan-2-amine, 0.61 g (0.67 mmol) Pd ₂ (dba) _3, 0.45 g (2.22 mmol) P (t- bu) _3, 5.33 g (55.49 mmol) Bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.32 g (yield: 67%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 860.50 g / mol, measured: 860 g / mol)

[Synthesis Example 14] Synthesis of A-19

Dibenzo [b, d] furan-4-yl) -benzonitrile (10.0 g, 22.19 mmol) synthesized in Preparation Example 12 and 11.59 g (22.19 mmol) P (t-bu) _3, 5.33 g (55.49 mmol) of Pd ₂ (dba) _3, 0.45 g (2.22 mmol) of Phenyl- ) NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 13.92 g (yield: 73%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 936.15 g / mol, measured: 936 g / mol)

[Synthesis Example 15] Synthesis of A-20

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.25 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [ b, d] thiophen-2-amine, 0.61 g (0.67 mmol) Pd ₂ (dba) _3, 0.45 g (2.22 mmol) P (t- bu) _3, 5.33 g (55.49 mmol) Bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.19 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 876.12 g / mol, measured: 876 g / mol)

[Synthesis Example 16] Synthesis of A-25

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 8.88 g (22.19 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4- Pd ₂ of _{(0.67 mmol) (dba) 3} , 0.45 g (2.22 mmol) of P (t-bu) _3, were mixed NaO (t-bu), and toluene (200 ml) of 5.33 g (55.49 mmol) 110 Lt; 0 &gt; C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.82 g (yield: 81%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)

[Synthesis Example 17] Synthesis of A-43

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.00 g (22.19 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- (T-bu) _and 5.33 g (55.49 mmol) of Pd ₂ (dba) _3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.74 g (yield: 76%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)

[Synthesis Example 18] Synthesis of A-44

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.11 g (22.19 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N- -1-yl) naphthalen-1- amine, 0.61 g (0.67 mmol Pd 2 (dba) _{a) 3, 0.45 g (2.22 mmol} ) of _{P (t-bu) 3,} NaO (t of 5.33 g (55.49 mmol) -bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.45 g (yield: 80%) of the title compound was obtained by column chromatography.

GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)

[Synthesis Example 19] Synthesis of A-26

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.51 g (22.19 mmol) of 4'-bromo-N, N-di-p-tolyl- [1,1'- _{amine, 0.61 g Pd 2 (dba} ) of _{(0.67 mmol) 3, 0.45 g} (2.22 mmol) P (t-bu) 3, NaO (t-bu) , and toluene (200 ml) of 5.33 g (55.49 mmol) of Were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.17 g (yield: 68%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 798.02 g / mol, measured: 798 g / mol)

[Synthesis Example 20] Synthesis of A-27

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 12.26 g (22.19 mmol) of N, N-di ([1,1'- biphenyl] -4-yl) -4'- NaO of 1,1'-biphenyl] -4-amine, 0.61 g Pd 2 (dba) of _{(0.67 mmol) 3, 0.45 g} (2.22 mmol) P (t-bu) 3, 5.33 g (55.49 mmol) of ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 13.92 g (yield: 65%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)

[Synthesis Example 21] Synthesis of A-28

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 13.15 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- Pd ₂ (dba) _3, 0.45 g (2.22 mmol) of P ( _1, 1'-biphenyl] -4,9-dimethyl-9H-fluoren- t-bu) _3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.95 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 962.23 g / mol, measured: 962 g / mol)

[Synthesis Example 22] Synthesis of A-37

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.81 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) phenanthren-2-amine, 0.61 g (Pd 2 (dba of _{0.67 mmol)) 3, 0.45 g} 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.70 g (yield: 72%) of the desired compound was obtained by column chromatography.

GC-Mass (946.18 g / mol, measured: 946 g / mol)

[Synthesis Example 23] Synthesis of A-39

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.81 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) phenanthren-9-amine, 0.61 g (Pd 2 (dba of _{0.67 mmol)) 3, 0.45 g} 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.75 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (946.18 g / mol, measured: 946 g / mol)

[Synthesis Example 24] Synthesis of A-40

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 12.92 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) triphenylen-2-amine, 0.61 g (Pd 2 (dba of _{0.67 mmol)) 3, 0.45 g} 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.58 g (yield: 80%) of the target compound was obtained by column chromatography.

GC-Mass (996.13 g / mol, measured: 996 g / mol)

[Synthesis Example 25] Synthesis of A-46

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.70 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) naphthalen-1-amine, 0.61 g (Pd 2 (dba of _{0.67 mmol)) 3, 0.45 g} 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.92 g (yield: 84%) of the title compound was obtained by column chromatography.

GC-Mass (896.13 g / mol, measured: 896 g / mol)

[Synthesis Example 26] Synthesis of A-50

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.59 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (T-bu) of Pd ₂ (dba) _3, 0.45 g (2.22 mmol) of Pd ₂ (dibenzo [b, d] furan- ) _3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 17.45 g (yield: 80%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 936.15 g / mol, measured: 936 g / mol)

[Synthesis Example 27] Synthesis of A-52

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.94 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) dibenzo [b, d] thiophen-2-amine, 0.61 g (0.67 mmol) of _{Pd 2 (dba) 3, 0.45} g (2.22 mmol) of P (t-bu ) _3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.91 g (yield: 80%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 952.21 g / mol, measured: 952 g / mol)

[Synthesis Example 28] Synthesis of A-70

The synthesized compound from Preparation Example 19 was conducted in a nitrogen atmosphere 10.0 g (18.99 mmol), 6.16 g (18.99 mmol) 4-bromo-N, N-diphenylaniline, 0.52 g Pd 2 (dba) of (0.57 mmol) _3, 0.38 g of (1.90 mmol) of P (t-bu) _3, 4.56 g (47.47 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.96 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)

[Synthesis Example 29] Synthesis of A-71

Pd ₂ (dba) ₃ of 4-bromo-N, N-diphenylaniline, 0.52 g (0.57 mmol) of 7.11 g (18.99 mmol) of the compound synthesized in Preparation Example 19 _, 0.38 g (1.90 mmol) of P (t-bu) _3, 4.56 g (47.47 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.68 g (yield: 70%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)

[Synthesis Example 30] Synthesis of A-29

10.0 g (18.99 mmol) of the compound synthesized in Preparation Example 19 and 7.60 g (18.99 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4- (0.57 mmol) of Pd ₂ (dba) _3, 0.38 g (1.90 mmol) of P (t-bu) _3, 4.56 g (47.47 mmol) of NaO (t-bu) and toluene Lt; 0 &gt; C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.25 g (yield: 65%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)

[Synthesis Example 31] Synthesis of A-33

10.0 g (18.99 mmol) of the compound synthesized in Preparation Example 19 and 8.55 g (18.99 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- _{1-amine, 0.52 g Pd 2} (dba) of _{(0.57 mmol) 3, 0.38 g} (1.90 mmol) of _{P (t-bu) 3,} NaO (t-bu) , and toluene (200 of 4.56 g (47.47 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.06 g (yield: 62%) of the target compound was obtained by column chromatography.

GC-Mass (896.13 g / mol, measured: 896 g / mol)

[Synthesis Example 32] Synthesis of A-32

10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.59 g (22.19 mmol) of 4'-chloro-N, N-diphenyl- [1,1 ': 4', 1 " ] -4-amine, 0.61 g (0.67 mmol) Pd ₂ (dba) _3, 0.45 g (2.22 mmol) P (t-bu) _3, 5.33 g (55.49 mmol) NaO (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.08 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)

[Synthesis Example 33] Synthesis of A-81

N, diphenylaniline, 0.48 g (0.52 mmol) of Pd ₂ (dba) _3, 0.35 g (4.40 mmol) of the compound synthesized in Preparation Example 28, 5.64 g (1.74 mmol) of P (t-bu) _3, 4.18 g (43.50 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.11 g (yield: 71%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 818.01 g / mol, measurement: 818 g / mol)

[Synthesis Example 34] Synthesis of A-82

Pd ₂ (dba) of 4-bromo-N, N-di-p-tolylaniline and 0.48 g (0.52 mmol) of the compound synthesized in Preparation Example 28 (10.0 g, 17.40 mmol), 6.13 g _3, 0.35 g (1.74 mmol) of P (t-bu) _3, 4.18 g (43.50 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.04 g (yield: 75%) of the title compound was obtained by column chromatography.

GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)

[Synthesis Example 35] Synthesis of A-85

10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 8.32 g (17.40 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ NaO of 1,1'-biphenyl] -4-amine, 0.48 g Pd 2 (dba) of _{(0.52 mmol) 3, 0.35 g} P (t-bu) 3, 4.18 g (43.50 mmol) of (1.74 mmol) ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.82 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 970.21 g / mol, measured: 970 g / mol)

[Synthesis Example 36] Synthesis of A-84

(10.0 g, 17.40 mmol), 7.38 g (17.40 mmol) of N- (4-bromophenyl) -N- (naphthalen-1-yl) naphthalen- Pd ₂ (dba) a _{0.52 mmol) 3, 0.35 g (} 1.74 mmol) of _{P (t-bu) 3,} 4.18 g (43.50 mixture of NaO (t-bu), and toluene (200 ml) of mmol) and 110 ℃ Lt; / RTI &gt; for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.78 g (yield: 80%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 918.13 g / mol, measured: 918 g / mol)

[Synthesis Example 37] Synthesis of A-83

(4-bromophenyl) -N-phenylnaphthalen-1-amine and 0.48 g (0.52 mmol) of Pd ₂ (0.45 mmol) were added to a solution of 10.0 g (17.40 mmol) mixing _{dba) 3, 0.35 g (NaO} (t-bu) , and toluene (200 ml) of _{P (t-bu) 3,} 4.18 g (43.50 mmol) of a 1.74 mmol) and stirred at 110 ℃ for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.33 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 868.07 g / mol, measured: 868 g / mol)

[Synthesis Example 38] Synthesis of A-86

10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 6.97 g (17.40 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4-amine and 0.48 g (0.52 mmol) of Pd ₂ (dba) _3, 0.35 g (1.74 mmol) of P (t-bu) _3, 4.18 g (43.50 mmol) of NaO (t-bu) and toluene Lt; 0 &gt; C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.11 g (yield: 65%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 818.01 g / mol, measurement: 818 g / mol)

[Synthesis Example 39] Synthesis of A-87

10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 7.45 g (17.40 mmol) of 4'-bromo-N, N-di-p-tolyl- [1,1'- _{amine, 0.48 g Pd 2 (dba} ) of _{(0.52 mmol) 3, 0.35 g} P (t-bu) 3, 4.18 g NaO (t-bu) , and toluene (200 ml) of (43.50 mmol) of (1.74 mmol) Were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.75 g (yield: 67%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)

[Synthesis Example 40] Synthesis of A-88

10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 7.84 g (17.40 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- _{1-amine, 0.48 g Pd 2} (dba) of _{(0.52 mmol) 3, 0.35 g} (1.74 mmol) of _{P (t-bu) 3,} 4.18 g NaO (t-bu) , and toluene (200 of (43.50 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.50 g (yield: 70%) of the desired compound was obtained by column chromatography.

GC-Mass (944.17 g / mol, measured: 944 g / mol)

[Synthesis Example 41] Synthesis of A-89

N, diphenylaniline, 0.48 g (0.52 mmol) of Pd ₂ (dba) _3, 0.35 g (17.46 mmol) of the compound synthesized in Preparation Example 29, 5.66 g (1.75 mmol) of P (t-bu) _3, 4.20 g (43.65 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 9.12 g (yield: 64%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 816.00 g / mol, measured: 816 g / mol)

[Synthesis Example 42] Synthesis of A-90

Pd ₂ (dba) of 4-bromo-N, N-di-p-tolylaniline and 0.48 g (0.52 mmol) of compound 10.0 g (17.46 mmol) prepared in Preparation Example 29, 6.15 g (17.46 mmol) _3, 0.35 g (1.75 mmol) of P (t-bu) _3, 4.20 g (43.65 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 10.91 g (yield: 74%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 844.05 g / mol, measured: 844 g / mol)

[Synthesis Example 43] Synthesis of A-93

10.0 g (17.46 mmol) of the compound synthesized in Preparation Example 29 and 8.32 g (17.46 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ NaO of 1,1'-biphenyl] -4-amine, 0.48 g Pd 2 (dba) of _{(0.52 mmol) 3, 0.35 g} P (t-bu) of _{(1.75 mmol) 3, 4.20 g} (43.65 mmol) ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.55 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (958.19 g / mol, measured: 958 g / mol)

[Synthesis Example 44] Synthesis of A-92

(10.0 g, 17.46 mmol) and 7.41 g (17.46 mmol) of N- (4-bromophenyl) -N- (naphthalen-1-yl) naphthalen- Pd ₂ (dba) a _{0.52 mmol) 3, 0.35 g (} 1.75 mmol) of P (t-bu) _3, were mixed 4.20 g (NaO (t-bu ) , and toluene (200 ml) of 43.65 mmol) 110 ℃ Lt; / RTI &gt; for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.20 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 916.12 g / mol, measured: 916 g / mol)

[Synthesis Example 45] Synthesis of A-91

(4-bromophenyl) -N-phenylnaphthalen-1-amine and 0.48 g (0.52 mmol) of Pd ₂ (0.45 mmol) were added to a solution of 10.0 g (17.46 mmol) of the compound prepared in Preparation Example 29, 6.54 g mixing _{dba) 3, 0.35 g (1.75} mmol) of _{P (t-bu) 3,} 4.20 g (NaO (t-bu) , and toluene (200 ml) of 43.65 mmol) and stirred at 110 ℃ for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 11.34 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 866.06 g / mol, measured: 866 g / mol)

[Synthesis Example 46] Synthesis of A-94

10.0 g (17.46 mmol) of the compound synthesized in Preparation Example 29 and 6.99 g (17.46 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4-amine and 0.48 g (0.52 mmol) of Pd ₂ (dba) _3, 0.35 g (1.75 mmol) of P (t-bu) _3, 4.20 g (43.65 mmol) of NaO (t-bu) and toluene Lt; 0 &gt; C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.93 g (yield: 83%) of the desired compound was obtained by column chromatography.

GC-Mass (892.09 g / mol, measured: 892 g / mol)

[Synthesis Example 47] Synthesis of A-95

To a solution of 10.0 g (17.46 mmol) of the compound prepared in Preparation 29 and 7.48 g (17.46 mmol) of 4'-bromo-N, N-di-p-tolyl- [1,1'- _{amine, 0.48 g Pd 2 (dba} ) of _{(0.52 mmol) 3, 0.35 g} (1.75 mmol) P (t-bu) 3, 4.20 g NaO (t-bu) , and toluene (200 ml) of (43.65 mmol) of Were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 12.21 g (yield: 76%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 920.15 g / mol, measured: 920 g / mol)

[Synthesis Example 48] Synthesis of A-96

10.0 g (17.46 mmol) of the compound synthesized in Preparation Example 29 and 7.86 g (17.46 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- (T-bu) _{3 and} 4.20 g (43.65 mmol) of Pd ₂ (dba) _3, 0.35 g (1.75 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 13.33 g (yield: 81%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 942.15 g / mol, measured: 942 g / mol)

[Synthesis Example 49] Synthesis of B-1

(4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd ₂ (dba) _3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 20 _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 87%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 693.88 g / mol, measured: 693 g / mol)

[Synthesis Example 50] Synthesis of B-2

9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd ₂ (dba) _3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 21 _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 19.05 g (yield: 85%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 721.93 g / mol, measured: 721 g / mol)

[Synthesis Example 51] Synthesis of B-4

The synthesized compound from Preparation Example 22 was conducted in a nitrogen atmosphere 17.15 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.91 g (yield: 72%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 793.99 g / mol, measured: 793.99 g / mol)

[Synthesis Example 52] Synthesis of B-3

The synthesized compound from Preparation Example 23 was conducted in a nitrogen atmosphere 18.77 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.91 g (yield: 72%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 847.07 g / mol, measured: 847 g / mol)

[Synthesis Example 53] Synthesis of B-11

The synthesized compound from Preparation Example 20 was conducted in a nitrogen atmosphere 14.05 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.74 g (yield: 87%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 693.88 g / mol, measured: 693 g / mol)

[Synthesis Example 54] Synthesis of B-12

9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd ₂ (dba) _3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 21 _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 19.05 g (yield: 85%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 721.93 g / mol, measured: 721 g / mol)

[Synthesis Example 55] Synthesis of B-14

The synthesized compound from Preparation Example 22 was conducted in a nitrogen atmosphere 17.15 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.91 g (yield: 72%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 793.99 g / mol, measured: 793.99 g / mol)

[Synthesis Example 56] Synthesis of B-13

(10.0 g, 31.04 mmol) and 9.42 g (31.04 mmol) of N- (4-bromophenyl) -N- (naphthalen-2-yl) naphthalen- Pd ₂ (dba) a _{0.93 mmol) 3, 0.63 g (} 3.10 mmol) of _{P (t-bu) 3,} 7.46 g (77.59 mmol) of the mixture of NaO (t-bu), and toluene (200 ml) 110 ℃ Lt; / RTI &gt; for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 14.10 g (yield: 80%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)

[Synthesis Example 57] Synthesis of B-29

The synthesized compound from Preparation Example 24 was conducted in a nitrogen atmosphere 16.41 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 17.21 g (yield: 72%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)

[Synthesis Example 58] Synthesis of B-30

The synthesized compound from Preparation Example 25 was conducted in a nitrogen atmosphere 17.27 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 19.81 g (yield: 80%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 798.02 g / mol, measured: 798 g / mol)

[Synthesis Example 59] Synthesis of B-32

The synthesized compound from Preparation Example 26 was conducted in a nitrogen atmosphere 19.52 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 20.25 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)

[Synthesis Example 60] Synthesis of B-31

The synthesized compound from Preparation Example 27 was conducted in a nitrogen atmosphere 21.13 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 19.18 g (yield: 67%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)

[Synthesis Example 61] Synthesis of B-41

The synthesized compound from Preparation Example 24 was conducted in a nitrogen atmosphere 16.41 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 17.21 g (yield: 72%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)

[Synthesis Example 62] Synthesis of B-42

The synthesized compound from Preparation Example 25 was conducted in a nitrogen atmosphere 17.27 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 19.81 g (yield: 80%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 798.02 g / mol, measured: 798 g / mol)

[Synthesis Example 63] Synthesis of B-44

The synthesized compound from Preparation Example 26 was conducted in a nitrogen atmosphere 19.52 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 20.25 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)

[Synthesis Example 64] Synthesis of B-43

(3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd ₂ (dba) _3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 27 _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 19.18 g (yield: 67%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)

[Synthesis Example 65] Synthesis of B-55

11.36 g (25.11 mmol) of the compound synthesized in Preparation Example 20 and 10.0 g (25.11 mmol) of 9- (4'-bromo- [1,1'- biphenyl] -4-yl) -9H- To a mixture of 0.69 g (0.75 mmol) Pd ₂ (dba) _3, 0.51 g (2.51 mmol) P (t-bu) _3, 6.03 g (62.77 mmol) NaO (t- And stirred at 110 &lt; 0 &gt; C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.08 g (yield: 78%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)

[Synthesis Example 66] Synthesis of B-56

13.27 g (25.11 mmol) of the compound synthesized in Preparation Example 24 and 10.0 g (25.11 mmol) of 9- (4'-bromo- [1,1'-biphenyl] -4-yl) -9H- To a mixture of 0.69 g (0.75 mmol) Pd ₂ (dba) _3, 0.51 g (2.51 mmol) P (t-bu) _3, 6.03 g (62.77 mmol) NaO (t- And stirred at 110 &lt; 0 &gt; C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 17.21 g (yield: 81%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)

[Synthesis Example 67] Synthesis of B-71

9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd ₂ (dba) _3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 30 _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.50 g (yield: 65%) of the desired compound was obtained by column chromatography.

GC-Mass (theory: 818.01 g / mol, measurement: 818 g / mol)

[Synthesis Example 68] Synthesis of B-72

The synthesized compound from Preparation Example 31 was conducted in a nitrogen atmosphere 18.77 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.02 g (yield: 61%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)

[Synthesis Example 69] Synthesis of B-74

9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd ₂ (dba) _3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 32 _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 15.96 g (yield: 56%) of the title compound was obtained by column chromatography.

GC-Mass (calculated: 918.13 g / mol, measured: 918 g / mol)

[Synthesis Example 70] Synthesis of B-76

The synthesized compound from Preparation Example 33 was conducted in a nitrogen atmosphere 20.26 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.59 g (yield: 67%) of the desired compound was obtained by column chromatography.

GC-Mass (894.11 g / mol, measured: 894 g / mol)

[Synthesis Example 71] Synthesis of B-77

The synthesized compound from Preparation Example 34 was conducted in a nitrogen atmosphere 21.13 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 20.03 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)

[Synthesis Example 72] Synthesis of B-81

9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd ₂ (dba) _3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 35 _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.99 g (yield: 75%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 816.00 g / mol, measured: 816 g / mol)

[Synthesis Example 73] Synthesis of B-82

The synthesized compound from Preparation Example 36 was conducted in a nitrogen atmosphere 18.71 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 20.17 g (yield: 77%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 844.05 g / mol, measured: 844 g / mol)

[Synthesis Example 74] Synthesis of B-84

The synthesized compound from Preparation Example 37 was conducted in a nitrogen atmosphere 20.94 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 18.20 g (yield: 64%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 916.12 g / mol, measured: 916 g / mol)

[Synthesis Example 75] Synthesis of B-85

(20.0 g, 31.04 mmol), 10.0 g (31.04 mmol) of 9- (4-bromophenyl) -9H-carbazole and 0.85 g (0.93 mmol) of Pd ₂ (dba) _{3 in a} nitrogen stream _, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 16.89 g (yield: 61%) of the target compound was obtained by column chromatography.

GC-Mass (892.09 g / mol, measured: 892 g / mol)

[Synthesis Example 76] Synthesis of B-86

The synthesized compound from Preparation Example 39 was conducted in a nitrogen atmosphere 21.07 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) _3, 0.63 g (3.10 mmol) of P (t-bu) _3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO ₄ . After removing the solvent of the filtered organic layer, 17.14 g (yield: 60%) of the desired compound was obtained by column chromatography.

GC-Mass (calculated: 920.15 g / mol, measured: 920 g / mol)

[Example 1] Production of organic EL device

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes And the substrate was transferred to the back vacuum deposition machine.

(60 nm) / Compound A-1 (80 nm) / DS-H522 + 5% DS-501 (300 nm) / BCP (10 nm) / Alq3 (60 nm) synthesized in Synthesis Example 1 nm) / LiF (1 nm) / Al (200 nm).

The structures of m-MTDATA, TCTA, CBP, Ir (ppy) ₃ and BCP are as follows. DS-H522 and DS-501 used in the device fabrication are products of Doosan Electronics BG.

[Examples 2 to 76] Preparation of organic EL device

An organic EL device was manufactured in the same manner as in Example 1 except that the compound synthesized in each of Synthesis Examples 2 to 76 was used instead of Compound A-1 used as a hole transporting layer material in the formation of the hole transport layer in Example 1 Respectively.

[Comparative Example 1] Fabrication of organic EL device

An organic EL device was prepared in the same manner as in Example 1 except that NPB was used as the hole transport layer material instead of the compound A-1 used as the hole transport layer material in forming the hole transport layer in Example 1. The structure of the NPB used is as follows.

[Evaluation Example 1]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples 1 to 76 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 1 Compound A-1 4.1 22.2 Example 2 Compound A-2 4.3 20.1 Example 3 Compound A-3 4.4 21.3 Example 4 Compound A-12 4 22.6 Example 5 Compound A-11 4.5 19.5 Example 6 Compound A-89 4.7 20.1 Example 7 Compound A-4 4.3 21.6 Example 8 Compound A-5 4.5 20.5 Example 9 Compound A-6 4.7 20.6 Example 10 Compound A-8 4.4 21.6 Example 11 Compound A-14 5 20.1 Example 12 Compound A-68 5.1 18.6 Example 13 Compound A-18 4.3 22 Example 14 Compound A-19 4.6 21.2 Example 15 Compound A-20 4.5 21.2 Example 16 Compound A-25 4.4 22.3 Example 17 Compound A-43 5.1 18.3 Example 18 Compound A-44 5 18.9 Example 19 Compound A-26 4.5 21.7 Example 20 Compound A-27 4.7 21.2 Example 21 Compound A-28 4.8 20.8 Example 22 Compound A-37 4.5 21.4 Example 23 Compound A-39 5.1 18.2 Example 24 Compound A-40 5.1 18.5 Example 25 Compound A-46 4.3 22.3 Example 26 Compound A-50 4.6 21.4 Example 27 Compound A-52 4.8 21.6 Example 28 Compound A-70 4.2 22.5 Example 29 Compound A-71 4.7 20.6 Example 30 Compound A-29 4.6 20.2 Example 31 Compound A-33 4.2 22.1 Example 32 Compound A-32 4.6 21.2 Example 33 Compound A-81 4.8 20 Example 34 Compound A-82 4.2 22.3 Example 35 Compound A-85 4.8 21.8 Example 36 Compound A-84 5 19.2 Example 37 Compound A-83 4.5 20.3 Example 38 Compound A-86 5.1 18.5 Example 39 Compound A-87 4.9 20.3 Example 40 Compound A-88 4.8 20.8 Example 41 Compound A-89 4.2 21.4 Example 42 Compound A-90 4.7 18.2 Example 43 Compound A-93 4.6 18.5 Example 44 Compound A-92 4.2 22.3 Example 45 Compound A-91 4.6 21.4 Example 46 Compound A-94 4.8 21.6 Example 47 Compound A-95 4.2 22.5 Example 48 Compound A-96 4.8 20.6 Example 49 Compound B-1 4.8 20 Example 50 Compound B-2 4.2 22.3 Example 51 Compound B-4 4.8 21.8 Example 52 Compound B-3 5 19.2 Example 53 Compound B-11 4.5 20.3 Example 54 Compound B-12 5.1 18.5 Example 55 Compound B-14 4.9 20.3 Example 56 Compound B-13 4.8 20.8 Example 57 Compound B-29 4.2 21.4 Example 58 Compound B-30 4.7 18.2 Example 59 Compound B-32 4.6 18.5 Example 60 Compound B-31 4.2 22.3 Example 61 Compound B-41 4.6 21.4 Example 62 Compound B-42 4.8 21.6 Example 63 Compound B-44 4.2 22.5 Example 64 Compound B-43 4.8 20.6 Example 65 Compound B-55 5 20.2 Example 66 Compound B-56 4.5 20.8 Example 67 Compound B-71 4.5 20.3 Example 68 Compound B-72 5.1 18.5 Example 69 Compound B-74 4.9 20.3 Example 70 Compound B-76 4.8 20.8 Example 71 Compound B-77 4.2 21.4 Example 72 Compound B-81 4.7 18.2 Example 73 Compound B-82 4.6 18.5 Example 74 Compound B-84 4.2 22.3 Example 75 Compound B-85 4.6 21.4 Example 76 Compound B-86 4.8 21.6 Comparative Example 1 NPB 5.2 18.1

As shown in Table 1, the organic EL devices of Examples 1 to 76 using the compound according to the present invention as a hole transporting layer were superior in current efficiency and driving voltage to organic EL devices of Comparative Example 1 using NPB It was found that it exhibits excellent performance.

[Example 77] Production of green organic electroluminescent device

Compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was produced as follows.

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / Compound A-1 (40 nm) / CBP + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.

The structures of m-MTDATA, TCTA, Ir (ppy) 3, CBP and BCP used are as follows.

[Examples 78 to 152] Preparation of green organic electroluminescent device

An organic EL device was fabricated in the same manner as in Example 77 except that the compound synthesized in each of Synthesis Examples 1 to 76 was used instead of A-1 in Example 77. [

[Comparative Example 2] Production of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 77 except that the compound A-1 was not used in Example 77. As a result,

[Evaluation Example 2]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 77 to 152 and Comparative Example 2, respectively, and the results are shown in Table 2 below .

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 77 Compound A-1 6.7 41.9 Example 78 Compound A-2 6.85 42.1 Example 79 Compound A-3 6.8 44.8 Example 80 Compound A-12 6.8 47.5 Example 81 Compound A-11 6.85 41.5 Example 82 Compound A-89 6.9 41.9 Example 83 Compound A-4 6.95 42.4 Example 84 Compound A-5 6.8 42.3 Example 85 Compound A-6 6.9 45.2 Example 86 Compound A-8 6.8 44.6 Example 87 Compound A-14 6.7 44.1 Example 88 Compound A-68 6.65 43.6 Example 89 Compound A-18 6.7 42.6 Example 90 Compound A-19 6.9 44.1 Example 91 Compound A-20 6.8 42.8 Example 92 Compound A-25 6.7 41.4 Example 93 Compound A-43 6.7 41.8 Example 94 Compound A-44 6.65 45.3 Example 95 Compound A-26 6.7 45.1 Example 96 Compound A-27 6.65 42.6 Example 97 Compound A-28 6.6 41.3 Example 98 Compound A-37 6.6 42.1 Example 99 Compound A-39 6.7 41.9 Example 100 Compound A-40 6.9 42.1 Example 101 Compound A-46 6.8 44.8 Example 102 Compound A-50 6.8 47.5 Example 103 Compound A-52 6.85 41.5 Example 104 Compound A-70 6.85 41.9 Example 105 Compound A-71 6.65 42.4 Example 106 Compound A-29 6.6 42.3 Example 107 Compound A-33 6.7 45.2 Example 108 Compound A-32 6.85 44.6 Example 109 Compound A-81 6.7 44.1 Example 110 Compound A-82 6.8 43.6 Example 111 Compound A-85 6.75 42.6 Example 112 Compound A-84 6.8 44.1 Example 113 Synthesis of Compound A-83 6.8 42.8 Example 114 Compound A-86 6.85 41.4 Example 115 Compound A-87 6.9 41.8 Example 116 Compound A-88 6.7 45.3 Example 117 Compound A-89 6.7 45.1 Example 118 Compound A-90 6.65 42.6 Example 119 Compound A-93 6.7 41.3 Example 120 Compound A-92 6.65 42.1 Example 121 Compound A-91 6.6 41.9 Example 122 Compound A-94 6.6 42.1 Example 123 Compound A-95 6.7 44.8 Example 124 Compound A-96 6.9 47.5 Example 125 Compound B-1 6.8 41.5 Example 126 Compound B-2 6.8 41.9 Example 127 Compound B-4 6.7 42.4 Example 128 Compound B-3 6.85 42.3 Example 129 Compound B-11 6.8 45.2 Example 130 Compound B-12 6.8 44.6 Example 131 Compound B-14 6.85 44.1 Example 132 Compound B-13 6.9 43.6 Example 133 Compound B-29 6.95 42.6 Example 134 Compound B-30 6.8 44.1 Example 135 Compound B-32 6.9 42.8 Example 136 Compound B-31 6.8 41.4 Example 137 Compound B-41 6.7 41.8 Example 138 Compound B-42 6.65 45.3 Example 139 Compound B-44 6.7 45.1 Example 140 Compound B-43 6.9 42.6 Example 141 Compound B-55 6.8 41.3 Example 142 [ Compound B-56 6.7 42.1 Example 143 Compound B-71 6.7 44.6 Example 144 Compound B-72 6.65 42.6 Example 145 Compound B-74 6.7 41.8 Example 146 Compound B-76 6.65 45.3 Example 147 Compound B-77 6.6 45.2 Example 148 Compound B-81 6.6 42.7 Example 149 Compound B-82 6.7 41.5 Example 150 Compound B-84 6.9 42.8 Example 151 Compound B-85 6.8 41.8 Example 152 Compound B-86 6.8 45.3 Comparative Example 2 6.93 38.2

As shown in Table 2, the green organic electroluminescent devices of Examples 77 to 152, in which the compound represented by Formula 1 according to the present invention was used as a light emitting material, It was found that the current efficiency and the driving voltage were superior to those of the electroluminescent device.

[Examples 153 to 228] Preparation of red organic electroluminescent device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / Synthesis Examples 1 to 76 (40 nm) / CBP + 10% (piq) 2 Ir (acac) (300 nm) / BCP (10 nm) on the ITO transparent electrode prepared as described above nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structures of m-MTDATA, TCTA, (piq) 2Ir (acac) and CBP used are as follows.

[Comparative Example 3] Production of red organic electroluminescent device

A red organic electroluminescent device was fabricated in the same manner as in Example 153 except that the compound A-1 was not used in Example 153.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 153 Compound A-1 4.9 11.9 Example 154 Compound A-2 5.1 12.1 Example 155 Compound A-3 5.0 14.8 Example 156 Compound A-12 5.0 17.5 Example 157 Compound A-11 5.1 11.5 Example 158 Compound A-89 5.1 11.9 Example 159 Compound A-4 5.2 12.4 Example 160 Compound A-5 5.0 12.3 Example 161 Compound A-6 5.1 15.2 Example 162 Compound A-8 5.0 14.6 Example 163 Compound A-14 4.9 14.1 Example 164 Compound A-68 4.9 13.6 Example 165 Compound A-18 4.9 12.6 Example 166 Compound A-19 5.1 14.1 Example 167 Compound A-20 5.0 12.8 Example 168 Compound A-25 4.9 11.4 Example 169 Compound A-43 4.9 11.8 Example 170 Compound A-44 4.9 15.3 Example 171 Compound A-26 4.9 15.1 Example 172 Compound A-27 4.9 12.6 Example 173 Compound A-28 4.8 11.3 Example 174 Compound A-37 4.8 12.1 Example 175 Compound A-39 4.9 11.9 Example 176 Compound A-40 5.1 12.1 Example 177 Compound A-46 5.0 14.8 Example 178 Compound A-50 5.0 17.5 Example 179 Compound A-52 5.1 11.5 Example 180 Compound A-70 5.1 11.9 Example 181 Compound A-71 4.9 12.4 Example 182 Compound A-29 4.8 12.3 Example 183 Compound A-33 4.9 15.2 Example 184 Compound A-32 5.1 14.6 Example 185 Compound A-81 4.9 14.1 Example 186 Compound A-82 5.0 13.6 Example 187 Compound A-85 5.0 12.6 Example 188 Compound A-84 5.0 14.1 Example 189 Compound A-83 5.0 12.8 Example 190 Compound A-86 5.1 11.4 Example 191 Compound A-87 5.1 11.8 Example 192 Compound A-88 4.3 15.3 Example 193 Compound A-89 4.9 15.1 Example 194 Compound A-90 4.7 12.6 Example 195 Compound A-93 4.5 11.3 Example 196 Compound A-92 4.9 12.1 Example 197 Compound A-91 4.8 11.9 Example 198 Compound A-94 4.8 12.1 Example 199 Compound A-95 4.9 14.8 Example 200 Compound A-96 5.1 17.5 Example 201 Compound B-1 5.0 11.5 Example 202 Compound B-2 5.0 11.9 Example 203 Compound B-4 4.9 12.4 Example 204 Compound B-3 5.1 12.3 Example 205 Compound B-11 5.0 15.2 Example 206 Compound B-12 5.0 14.6 Example 207 Compound B-14 5.1 14.1 Example 208 Compound B-13 5.1 13.6 Example 209 Compound B-29 5.2 12.6 Example 210 Compound B-30 5.0 14.1 Example 211 Compound B-32 5.1 12.8 Example 212 Compound B-31 5.0 11.4 Example 213 Compound B-41 4.9 11.8 Example 214 Compound B-42 4.9 15.3 Example 215 Compound B-44 4.9 15.1 Example 216 Compound B-43 5.1 12.6 Example 217 Compound B-55 5.0 11.3 Example 218 Compound B-56 4.9 12.1 Example 219 Compound B-71 4.9 14.6 Example 220 Compound B-72 4.9 12.6 Example 221 Compound B-74 4.9 11.8 Example 222 Compound B-76 4.9 15.3 Example 223 Compound B-77 4.8 15.2 Example 224 Compound B-81 4.8 12.7 Example 225 Compound B-82 4.9 11.5 Example 226 Compound B-84 5.1 12.8 Example 227 Compound B-85 5.0 11.8 Example 228 Compound B-86 5.0 15.3 Comparative Example 3 5.2 8.2

As shown in Table 3, the red organic electroluminescent devices of Examples 153 to 228, in which the compound represented by Formula 1 according to the present invention was used as a light emitting material, It was found that the current efficiency and the driving voltage were superior to those of the electroluminescent device.

[Examples 229 to 304] Preparation of blue organic electroluminescent device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

Each of the compounds (15 nm) / ADN + 5% DS-405 (manufactured by Doosan Heavy Industries, Ltd.) of DS-205 (Doosan) (80 nm) / NPB (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.

The structure of the ADN used is as follows.

[Comparative Example 4] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was fabricated in the same manner as in Example 229 except that A-1 was not used in Example 229.

[Evaluation Example 4]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices manufactured in Examples 229 to 304 and Comparative Example 4. The results are shown in Table 4 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 229 Compound A-1 4.3 9.2 Example 230 Compound A-2 4.5 7.1 Example 231 Compound A-3 4.6 8.3 Example 232 Compound A-12 4.2 9.6 Example 233 Compound A-11 4.7 6.5 Example 234 Compound A-89 4.9 7.1 Example 235 Compound A-4 4.5 8.6 Example 236 Compound A-5 4.7 7.5 Example 237 Compound A-6 4.9 7.6 Example 238 Compound A-8 4.6 8.6 Example 239 Compound A-14 5.2 7.1 Example 240 Compound A-68 5.3 5.6 Example 241 Compound A-18 4.5 9 Example 242 Compound A-19 4.8 8.2 Example 243 Compound A-20 4.7 8.2 Example 244 Compound A-25 4.6 9.3 Example 245 Compound A-43 5.3 5.3 Example 246 Compound A-44 5.2 5.9 Example 247 Compound A-26 4.7 8.7 Example 248 Compound A-27 4.9 8.2 Example 249 Compound A-28 5.0 7.8 Example 250 Compound A-37 4.7 8.4 Example 251 Compound A-39 5.3 5.2 Example 252 Compound A-40 5.3 5.5 Example 253 Compound A-46 4.5 9.3 Example 254 Compound A-50 4.8 8.4 Example 255 Compound A-52 5.0 8.6 Example 256 Compound A-70 4.4 9.5 Example 257 Compound A-71 4.9 7.6 Example 258 Compound A-29 4.8 7.2 Example 259 Compound A-33 4.4 9.1 Example 260 Compound A-32 4.8 8.2 Example 261 Compound A-81 5.0 7 Example 262 Compound A-82 4.4 9.3 Example 263 Compound A-85 5.0 8.8 Example 264 Compound A-84 5.2 6.2 Example 265 Compound A-83 4.7 7.3 Example 266 Compound A-86 5.3 5.5 Example 267 Compound A-87 5.1 7.3 Example 268 Compound A-88 5.0 7.8 Example 269 Compound A-89 4.4 8.4 Example 270 Compound A-90 4.9 5.2 Example 271 Compound A-93 4.8 5.5 Example 272 Compound A-92 4.4 9.3 Example 273 Compound A-91 4.8 8.4 Example 274 Compound A-94 5.0 8.6 Example 275 Compound A-95 4.4 9.5 Example 276 Compound A-96 5.0 7.6 Example 277 Compound B-1 5.0 7 Example 278 Compound B-2 4.4 9.3 Example 279 Compound B-4 5.0 8.8 Example 280 Compound B-3 5.2 6.2 Example 281 Compound B-11 4.7 7.3 Example 282 Compound B-12 5.3 5.5 Example 283 Compound B-14 5.1 7.3 Example 284 Compound B-13 5.0 7.8 Example 285 Compound B-29 4.4 8.4 Example 286 Compound B-30 4.9 5.2 Example 287 Compound B-32 4.8 5.5 Example 288 Compound B-31 4.4 9.3 Example 289 Compound B-41 4.8 8.4 Example 290 Compound B-42 5.0 8.6 Example 291 Compound B-44 4.4 9.5 Example 292 Compound B-43 5.0 7.6 Example 293 Compound B-55 5.2 7.2 Example 294 Compound B-56 4.7 7.8 Example 295 Compound B-71 4.7 7.3 Example 296 Compound B-72 5.3 5.5 Example 297 Compound B-74 5.1 7.3 Example 298 Compound B-76 5.0 7.8 Example 299 Compound B-77 4.4 8.4 Example 300 Compound B-81 4.9 5.2 Example 301 Compound B-82 4.8 5.5 Example 302 Compound B-84 4.4 9.3 Example 303 Compound B-85 4.8 8.4 Example 304 Compound B-86 5.0 8.6 Comparative Example 4 5.6 4.8

As shown in Table 4, the blue organic electroluminescent devices of Examples 229 to 304, in which the compound represented by Formula 1 according to the present invention was used as a light emitting material, It was found that the device exhibited better performance in terms of efficiency and driving voltage.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

Claims (6)

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

In Formula 1,
Ar ₁ is a substituent represented by the following formula (2)
(2)

Ar ₂ to Ar ₄ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, C ₆ to C ₆₀ arylamine groups,
Provided that at least one of Ar ₂ and Ar ₃ is a substituent represented by the following formula (3);
(3)

In the above Chemical Formulas 2 to 3,
* Is the site where the bond is made;
R ₁ are the same or different and are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, A heteroaryl group having 5 to 60 ring atoms and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group, or they may be bonded to adjacent substituents to form a condensed aromatic ring or condensed heteroaromatic ring &Lt; / RTI &gt;
R ₂ is the same or different and is independently selected from the group consisting of a substituted or unsubstituted C ₁ to C ₄₀ alkyl group and a substituted or unsubstituted C ₆ to C ₆₀ aryl group,
n, m and l are each independently an integer of 1 to 3;
a, b, c, d, e, f and g are each independently an integer of 0 to 4;
When the alkyl group, an aryl group, a heteroaryl group and an arylamine group is substituted, each independently represent deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to the A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₆ heteroaryl group, ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ of. The method according to claim 1,
The compound represented by the formula (1) is represented by the following formula (4) or (5):
[Chemical Formula 4]

[Chemical Formula 5]

Wherein Ar ₂ to Ar ₄ , R ₁ to R ₂ , and a to g are as defined in claim 1, respectively. The method according to claim 1,
Ar ₂ to Ar ₄ which do not have the general formula (3) are the same or different and are each independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group or a substituted or unsubstituted heteroaromatic having 5 to 60 Lt; / RTI &gt; is an aryl group. The method according to claim 1,
R ₁ is the same or different and is each independently hydrogen, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,
R ₂ are the same or different and each independently represents a methyl group, a phenyl group,

&Lt; / RTI &gt; At least one organic compound layer comprising one or more organic compound layers interposed between the anode and the cathode, wherein at least one of the organic compound layers includes at least one compound according to any one of claims 1 to 4 Wherein the organic electroluminescent device comprises: The organic electroluminescent device according to claim 5, wherein the organic compound layer containing the compound is selected from the group consisting of a hole transport layer, an electron blocking layer, and a light-emitting auxiliary layer.