WO2018212463A1 - Organic light-emitting compound, and organic electroluminescent element using same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent element including the same. According to the present invention, the compound is used for an organic layer of the organic electroluminescent element, preferably, for a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer or an electron injection layer so as to enable light-emitting efficiency, driving voltage, lifespan and the like of the organic electroluminescent element to improve.

Description

Organic light emitting compound and organic electroluminescent device using same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent electron transport ability, and the compound in at least one organic material layer, such as characteristics such as luminous efficiency, driving voltage, lifetime This is an improved organic electroluminescent device.

The study of organic electroluminescent (EL) devices (hereafter simply referred to as "organic EL devices") led to blue electroluminescence using anthracene single crystals in 1950, when Bernanose observed organic thin film emission. (Tang) proposed an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer, and then, in order to make a high efficiency and long life organic EL device, each characteristic organic material layer in the device was introduced. This has led to the development of specialized materials used for this.

In the organic EL device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer. The dopant material may 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 such phosphorescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.

Hole injection layer, hole transport layer to date. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material. Particularly, phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) _2, such as blue, green, and red dopant materials. Is being used. To date, CBP has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is very poor, and thus the materials are not satisfactory in terms of lifespan in organic EL devices.

[Preceding technical literature]

[Patent Documents]

Korean Patent Publication No. 10-161417

An object of the present invention is to provide a novel compound that can be used as a hole transport layer material, an electron transport layer material having excellent hole injection ability, hole transport ability, electron injection ability, electron transport ability and the like.

Another object of the present invention is to provide an organic electroluminescent device including the novel compound having a low driving voltage, high luminous efficiency, and an improved lifetime.

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

In Chemical Formula 1,

A and B are the same as or different from each other, and are independently represented by the following formula (2),

In Chemical Formula 2,

* Means the part where the bond is made;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

R is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group of 3 to 40 atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group selected from the group or combine with adjacent groups to form a condensed ring;

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl of R Group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear aryl, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ An alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₁ to C ₄₀ alkylsilyl group, and C ₁ to C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsil When unsubstituted or substituted with one or more substituents selected from the group consisting of a aryl group, they are the same as or different from each other.

In addition, another example of the present invention is an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 above. It provides an organic electroluminescent device comprising the compound represented.

The at least one organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, and is preferably used as a hole transport layer and / or an electron transport layer material.

Since the compound represented by Formula 1 according to an example of the present invention has excellent hole injection ability, hole transport ability, electron injection ability, electron transport ability, etc., the organic material layer material of the organic electroluminescent device, preferably the electron transport layer material, or It can be used as a hole transport layer material.

In addition, the organic electroluminescent device including the compound according to an example of the present invention in the hole transport layer or the electron transport layer can be greatly improved in terms of driving voltage, efficiency, lifetime, and the like. Can be applied effectively.

Hereinafter, the present invention will be described in detail.

1. Organic Compound

The organic compound of the present invention is a compound having, as a basic skeleton, a structure in which two or more substituents are linked directly or through a linker group to an oxathylene-based mother core, and has a structure represented by Chemical Formula 1.

More specifically, the compound represented by Formula 1 of the present invention has a structure in which two or more electron withdrawing groups (EWG) are connected directly or through a linker group to one phenyl group portion of oxanthylene, or one phenyl group of oxanthylene Two or more arylamines, etc., in the portion have a structure connected directly or through a linker group.

Such compounds include oxanthylene-based nuclei having high electron donating group (EDG) properties and substituents having high electron-absorbing electron withdrawing properties (eg, N-containing heterocycles, aromatic rings, and arylamines). Etc.) are formed by combining. In this case, since the compound is a bipolar compound, the recombination of holes and electrons is high, and thus the hole injection / transporting ability, luminous efficiency, driving voltage, lifetime characteristics, durability, and the like can be improved. Moreover, the electron transport ability etc. can also be improved according to the kind of substituents introduce | transduced. Therefore, the compound of Formula 1 may be used as an organic material layer material, preferably a hole transport layer material and an electron transport layer material of the organic EL device.

In addition, the compound represented by the formula (1) by introducing a variety of aromatic ring substituents significantly increase the molecular weight of the compound, the glass transition temperature can be improved, thereby higher thermal than conventional CBP (4,4-dicarbazolylphenyl) It may have stability. Furthermore, the organic electroluminescent device including the compound according to the present invention may be effectively improved in durability and lifespan even in suppressing crystallization of the organic material layer.

Therefore, the compound represented by Formula 1 of the present invention can be used as an organic material layer material of the organic electroluminescent device, preferably a hole transport layer / electron transport layer material.

In addition, the organic electroluminescent device including the compound of Formula 1 may significantly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.

An organic compound according to one embodiment of the present invention is represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

A and B are the same as or different from each other, and are independently represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

* Means the part where the bond is made;

L is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

R is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group of 3 to 40 atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group selected from the group or combine with adjacent groups to form a condensed ring;

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl of R Group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear aryl, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ An alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₁ to C ₄₀ alkylsilyl group, and C ₁ to C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsil When unsubstituted or substituted with one or more substituents selected from the group consisting of a aryl group, they are the same as or different from each other.

According to one embodiment of the present invention, R in Chemical Formula 2 may be a substituent represented by the following Chemical Formula 3.

In Chemical Formula 3,

Z ₁ to Z ₅ are independently C (R ₁ ) or N, at least one of which is N;

R ₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha It is selected from the group consisting of a nil group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group.

According to a preferred embodiment of the present invention, R in Formula 2 may be selected from the group consisting of S ₁ to S ₄₉ , but is not limited thereto.

According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 5.

In Chemical Formula 5,

L ₁ and L ₂ are the same as or different from each other, and are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms, and a heteroarylene group having 5 to 18 nuclear atoms;

R ₂ and R ₃ are hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₆ to C ₆₀ aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C _{60 group} Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ An arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group;

Z ₆ to Z ₁₁ are independently C (R ₄ ) or N, at least one being N;

p and q are independently 1 or 2;

R ₄ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha It is selected from the group consisting of a nil group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group.

According to an example of the present invention, Chemical Formula 5 may be any one of the following Chemical Formulas 7 to 9.

In Chemical Formulas 7 to 9,

L ₁ , L ₂ , R ₂ , R ₃ , Z ₆ to Z ₁₁ , p and q are each as defined in Chemical Formula 5.

According to an embodiment of the present invention, R in Chemical Formula 2 may be a substituent represented by the following Chemical Formula 4.

In Chemical Formula 4,

Ar ₂ and Ar ₃ independently represent a substituted or unsubstituted aryl group, and Ar ₂ and Ar ₃ may form a nitrogen-containing heterocycle together with the nitrogen to which they are bonded.

According to a preferred embodiment of the present invention, R in Formula 2 may be selected from the group consisting of S ₅₀ to S ₅₆ , but is not limited thereto.

According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 6.

In Chemical Formula 6,

L ₃ and L ₄ are the same as or different from each other, and each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms, and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₄ to Ar ₇ independently represent a substituted or unsubstituted aryl group, and Ar ₄ and Ar ₅ and Ar ₆ and Ar ₇ may form a nitrogen-containing heterocycle together with the nitrogen to which they are bonded.

According to a preferred embodiment of the present invention, Chemical Formula 6 may be any one of the following Chemical Formulas 10 to 12.

In Chemical Formulas 10 to 12,

L ₃ , L ₄ and Ar ₄ to Ar ₇ are the same as defined in Chemical Formula 6.

The compound represented by the formula (1) of the present invention described above may be further embodied by the formulas illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.

As used herein, "alkyl" refers to a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, non-limiting examples of which are methyl, ethyl, propyl, isobutyl, sec -Butyl, pentyl, iso-amyl, hexyl and the like.

"Cycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms. Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.

"Heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and having at least one carbon of the ring, preferably 1 to 3 carbon atoms. Carbon is substituted with a hetero atom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine and the like.

"Aryl" means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In this case, the two or more rings may be attached in a simple or condensed form with each other. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.

"Heteroaryl" is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons It is substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). In this case, the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indole Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-iso Sazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

"Alkoxyoxy" means a monovalent functional group represented by R'O-, wherein R 'is an alkyl having 1 to 40 carbon atoms, which may include a linear, branched or cyclic structure. Can be. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Aryloxy" means a monovalent functional group represented by R "O-, and said R" is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

"Alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms, and "alkylboron group" is alkyl having 1 to 40 carbon atoms. Means an boron group substituted with "aryl boron group" means a boron group substituted with an aryl having 6 to 60 carbon atoms, "arylphosphine group" means a phosphine group substituted with an aryl having 1 to 60 carbon atoms, " Arylamine "means an amine substituted with aryl having 6 to 60 carbon atoms.

"Condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.

The compound represented by Formula 1 according to the present invention may be synthesized according to a general synthetic method. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

2. Organic electroluminescent device

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.

More specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, at least one of the at least one organic material layer is It is characterized by including the compound represented by 1. In this case, the compound may include one kind or two or more kinds.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1). Preferably, the organic material layer including the compound of Formula 1 may be a hole transport layer and / or an electron transport layer.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, and may be, for example, a structure in which one or more organic layers are stacked between electrodes. Non-limiting examples thereof include (1) an anode, a light emitting layer, a cathode; (2) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode; Or (3) structures such as an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode.

In addition, as described above, the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention is an organic material layer and an electrode using materials and methods known in the art, except that at least one or more layers of the organic material layer are formed to include the compound represented by Formula 1 of the present invention. It can be prepared by forming a.

The organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet can be used.

In addition, examples of the anode 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.

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

[ Preparation  1] 2,3- bis Synthesis of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxine

2,3-dibromodibenzo [b, e] [1,4] dioxine (50.0 g, 146.2 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2' -bi (1,3,2-dioxaborolane) (74.3 g, 292.4 mmol) and Pd (dppf) ₂ (3.6 g, 4.4 mmol), KOAc (28.7 g, 292.4 mmol) in 1000 mL Toluene, 200 mL EtOH, H _It was added to 200 ml of ₂ O and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the desired compound 2,3-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e using column chromatography ] [1,4] dioxine (42.7 g, yield 67%) was obtained.

¹ H-NMR: δ 1.20 (s, 24H), 6.82 (q, 2H), 6.94-6.95 (m, 4H)

[LCMS]: 437

[ Preparation  2] 2,2'- (dibenzo [b, e] [1,4] dioxine -1,3- diyl ) bis Synthesis of (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

1,3-dibromodibenzo [b, e] [1,4] dioxine (50.0 g, 146.2 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2' -bi (1,3,2-dioxaborolane) (74.3 g, 292.4 mmol) and Pd (dppf) ₂ (3.6 g, 4.4 mmol), KOAc (28.7 g, 292.4 mmol) in 1000 mL Toluene, 200 mL EtOH, H _It was added to 200 ml of ₂ O and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, the desired compound 2,2 '-(dibenzo [b, e] [1,4] dioxine-1,3-diyl) bis (4,4,5, 5-tetramethyl-1,3,2-dioxaborolane) (44.6 g, yield 70%) was obtained.

¹ H-NMR: δ 1.20 (s, 24H), 6.82 (q, 2H), 6.94-6.95 (m, 3H), 7.01 (s, 1H)

[LCMS]: 437

[ Preparation  3] 1,4- bis Synthesis of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxine

1,4-dibromodibenzo [b, e] [1,4] dioxine (50.0 g, 146.2 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2' -bi (1,3,2-dioxaborolane) (74.3 g, 292.4 mmol) and Pd (dppf) ₂ (3.6 g, 4.4 mmol), KOAc (28.7 g, 292.4 mmol) in 1000 mL Toluene, 200 mL EtOH, H _It was added to 200 ml of ₂ O and heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 1,4-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e ] [1,4] dioxine (41.5 g, yield 70%) was obtained.

¹ H-NMR: δ 1.20 (s, 24H), 6.82 (q, 2H), 6.94 (q, 2H), 7.43 (s, 2H)

[LCMS]: 437

[ Preparation  4] 2,4- diphenyl -6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-2-yl) -1,3 Synthesis of, 5-triazine

Target compound of Preparation Example 1 (20.0 g, 45.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.3 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH, and 100 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) Dibenzo [b, e] [1,4] dioxin-2-yl) -1,3,5-triazine (20.1 g, yield 81%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.12 (s, 1H), 7.29 (s, 1H), 7.50-7.52 (m, 6H), 8.36-8.37 (m, 4H)

[LCMS]: 542

[ Preparation  5] 2-([1,1'-biphenyl] -4- yl ) -4-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-2-yl Synthesis of) -1,3,5-triazine

Target compound of Preparation Example 1 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.8 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H ₂ O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-2-yl) -1,3,5-triazine (22.1 g, yield 78%) Got it.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.12 (s, 1H), 7.25 (d, 2H), 7.29 (s, 1H), 7.41- 7.49 (m, 3H), 7.50-7.52 (m, 3H), 7.75 (d, 2H), 7.96 (d, 2H), 8.36-8.37 (m, 2H)

[LCMS]: 618

[ Preparation  6] 4-([1,1'-biphenyl] -4- yl ) -2-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-2-yl Synthesis of pyrimidine

Target compound of Preparation Example 1 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.7 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H ₂ O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (3- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-2-yl) pyrimidine (21.5 g, yield 76%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.12 (s, 1H), 7.29 (s, 1H), 7.41-7.49 (m, 3H), 7.50-7.52 (m, 3H), 7.75 (d, 2H), 7.85 (d, 2H), 8.23 (s, 1H), 8.30 (d, 2H), 8.36-8.37 (m, 2H)

[LCMS]: 617

[ Preparation  7] 2,4- diphenyl -6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) -1,3 Synthesis of, 5-triazine

Target compound of Preparation Example 2 (20.0 g, 45.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.3 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH, and 100 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) Dibenzo [b, e] [1,4] dioxin-1-yl) -1,3,5-triazine (20.1 g, yield 81%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.05 (s, 1H), 7.35 (s, 1H), 7.50-7.52 (m, 6H), 8.36-8.37 (m, 4H)

[LCMS]: 542

[ Preparation  8] 2-([1,1'-biphenyl] -4- yl ) -4-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl Synthesis of) -1,3,5-triazine

Target compound of Preparation Example 2 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.8 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H ₂ O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) -1,3,5-triazine (22.1 g, yield 78%) Got it.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.05 (s, 1H), 7.25 (d, 2H), 7.35 (s, 1H), 7.41- 7.49 (m, 3H), 7.50-7.52 (m, 3H), 7.75 (d, 2H), 7.96 (d, 2H), 8.36-8.37 (m, 2H)

[LCMS]: 618

[ Preparation  9] 4-([1,1'-biphenyl] -4- yl ) -2-phenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl Synthesis of pyrimidine

Target compound of Preparation Example 2 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.7 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H ₂ O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (3- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) pyrimidine (21.5 g, yield 76%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.05 (s, 1H), 7.35 (s, 1H), 7.41-7.49 (m, 3H), 7.50-7.52 (m, 3H), 7.75 (d, 2H), 7.85 (d, 2H), 8.23 (s, 1H), 8.30 (d, 2H), 8.36-8.37 (m, 2H)

[LCMS]: 617

[ Preparation  10] 2,4- diphenyl -6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) -1,3 Synthesis of, 5-triazine

Target compound of Preparation Example 3 (20.0 g, 45.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.3 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH, and 100 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) Dibenzo [b, e] [1,4] dioxin-1-yl) -1,3,5-triazine (20.1 g, yield 81%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.45 (d, 1H), 7.50-7.52 (m, 6H), 7.62 (d, 1H), 8.36-8.37 (m, 4H)

[LCMS]: 542

[ Preparation  11] 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl Synthesis of Dibenzo [b, e] [1,4] dioxin-1-yl) -1,3,5-triazine

Target compound of Preparation Example 3 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.8 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H ₂ O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2-([1,1'-biphenyl] -4-yl) -4-phenyl-6- (4- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) -1,3,5-triazine (22.1 g, yield 78%) Got it.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.25 (d, 2H), 7.41-7.49 (m, 4H), 7.50-7.52 (m, 3H ), 7.62 (d, 1H), 7.75 (d, 2H), 7.96 (d, 2H), 8.36-8.37 (m, 2H)

[LCMS]: 618

[ Preparation  12] 4-([1,1'-biphenyl] -4- yl ) -2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl Synthesis of pyrimidine

Target compound of Preparation Example 3 (20.0 g, 45.9 mmol), 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15.7 g, 45.9 mmol) and Pd (PPh ₃ ) ₄ (2.6 g, 2.3 mmol) and K ₂ CO ₃ (19.0 g, 137.6 mmol) were added to 500 mL of Toluene, 100 mL of EtOH and 100 mL of H ₂ O, and refluxed for 12 hours. It was. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to 4-([1,1'-biphenyl] -4-yl) -2-phenyl-6- (4- (4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) dibenzo [b, e] [1,4] dioxin-1-yl) pyrimidine (21.5 g, yield 76%) was obtained.

¹ H-NMR: δ 1.20 (s, 12H), 6.82 (q, 2H), 6.94 (q, 2H), 7.41-7.49 (m, 4H), 7.50-7.52 (m, 3H), 7.62 (d, 1H) ), 7.75 (d, 2H), 7.85 (d, 2H), 8.23 (s, 1H), 8.30 (d, 2H), 8.36-8.37 (m, 2H)

[LCMS]: 617

[ Synthesis Example  1] Synthesis of Compound A-3

Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ ( 0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-3 (3.8 g, yield 70%) by column chromatography.

[LCMS]: 799

[ Synthesis Example  2] Synthesis of Compound A-6

Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ ( 0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound A-6 (4.0 g, 72% yield).

[LCMS]: 797

[ Synthesis Example  3] Synthesis of Compound A-9

Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-9 (3.7 g, yield 65%) using column chromatography.

[LCMS]: 827

[ Synthesis Example  4] Synthesis of Compound A-14

Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-14 (3.5 g, yield 60%) using column chromatography.

[LCMS]: 859

[ Synthesis Example  5] Synthesis of Compound A-17

Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1,3,5-triazine (4.9 g , 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-17 (3.8 g, 64% yield) using column chromatography.

[LCMS]: 880

[ Synthesis Example  6] Synthesis of Compound A-23

Preferred compound of Preparation Example 1 (3 g, 6.9 mmol) and 4-chloro-2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound A-23 (3.3 g, yield 60%) using column chromatography.

[LCMS]: 799

[ Synthesis Example  7] Synthesis of Compound B-3

Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ ( 0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound B-3 (3.8 g, yield 70%) by column chromatography.

[LCMS]: 799

[ Synthesis Example  8] Synthesis of Compound B-6

Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ ( 0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to obtain the title compound B-6 (4.0 g, 72% yield).

[LCMS]: 797

[ Synthesis Example  9] Synthesis of Compound B-9

Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-9 (3.7 g, yield 65%).

[LCMS]: 827

[ Synthesis Example  10] Synthesis of Compound B-14

Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-14 (3.5 g, yield 60%).

[LCMS]: 859

[ Synthesis Example  11] Synthesis of Compound B-17

Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1,3,5-triazine (4.9 g , 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-17 (3.8 g, 64% yield).

[LCMS]: 880

[ Synthesis Example  12] Synthesis of Compound B-23

Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 4-chloro-2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-23 (3.3 g, yield 60%).

[LCMS]: 799

[ Synthesis Example  13] Synthesis of Compound C-3

Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ ( 0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-3 (3.8 g, yield 70%).

[LCMS]: 799

[ Synthesis Example  14] Synthesis of Compound C-6

Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ ( 0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-6 (4.0 g, 72% yield).

[LCMS]: 797

[ Synthesis Example  15] Synthesis of Compound C-9

Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-9 (3.7 g, yield 65%).

[LCMS]: 827

[ Synthesis Example  16] Synthesis of Compound C-14

Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (4.9 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-14 (3.5 g, yield 60%).

[LCMS]: 859

[ Synthesis Example  17] Synthesis of Compound C-17

Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1,3,5-triazine (4.9 g , 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain a target compound C-17 (3.8 g, yield 64%) by column chromatography.

[LCMS]: 880

[ Synthesis Example  18] Synthesis of Compound C-23

Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 4-chloro-2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (4.7 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol) and K ₂ CO ₃ (2.8 g, 20.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-23 (3.3 g, yield 60%).

[LCMS]: 799

[ Synthesis Example  19] Synthesis of Compound D-2

Target compound of Preparation Example 4 (3 g, 5.5 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g, 5.5 mmol) and Pd (PPh ₃ ) ₄ ( 0.3 g, 0.3 mmol) and K ₂ CO ₃ (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound D-2 (2.6 g, 65% yield).

[LCMS]: 723

[ Synthesis Example  20] Synthesis of Compound D-8

Target compound of Preparation Example 4 (3 g, 5.5 mmol) and 4- (4-chlorophenyl) -2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (2.3 g, 5.5 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.3 mmol) and K ₂ CO ₃ (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound D-8 (2.7 g, 62% yield) using column chromatography.

[LCMS]: 799

[ Synthesis Example  21] Synthesis of Compound E-9

Target compound of Preparation Example 5 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (1.7 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.2 g, 0.3 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound E-9 (2.7 g, 67% yield) by column chromatography.

[LCMS]: 813

[ Synthesis Example  22] Synthesis of Compound E-10

Target compound of Preparation Example 5 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (1.8 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.2 g, 0.3 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the target compound E-10 (2.5 g, 61% yield).

[LCMS]: 829

[ Synthesis Example  23] Synthesis of Compound F-11

Target compound of Preparation Example 6 (3 g, 4.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-3-yl) -6-phenyl-1,3,5-triazine (1.9 g , 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.2 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound F-11 (2.7 g, 66% yield) using column chromatography.

[LCMS]: 838

[ Synthesis Example  24] Synthesis of Compound F-12

Target compound of Preparation Example 6 (3 g, 4.9 mmol) and (4-cyanophenyl) boronic acid (0.7 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.2 mmol), K ₂ CO ₃ (2.0 g , 14.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound F-12 (1.9 g, 66% yield) by column chromatography.

[LCMS]: 592

[ Synthesis Example  25] Synthesis of Compound G-2

Target compound of Preparation Example 7 (3 g, 5.5 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g, 5.5 mmol) and Pd (PPh ₃ ) ₄ ( 0.3 g, 0.3 mmol) and K ₂ CO ₃ (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound G-2 (2.6 g, yield 65%).

[LCMS]: 723

[ Synthesis Example  26] Synthesis of Compound G-8

Target compound of Preparation Example 7 (3 g, 5.5 mmol) and 4- (4-chlorophenyl) -2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (2.3 g, 5.5 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.3 mmol) and K ₂ CO ₃ (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound G-8 (2.7 g, 62% yield).

[LCMS]: 799

[ Synthesis Example  27] Synthesis of Compound H-9

Target compound of Preparation Example 8 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (1.7 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.2 g, 0.3 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound H-9 (2.7 g, yield 67%).

[LCMS]: 813

[ Synthesis Example  28] Synthesis of Compound H-10

Target compound of Preparation Example 8 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (1.8 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.2 g, 0.3 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound H-10 (2.5 g, 61% yield).

[LCMS]: 829

[ Synthesis Example  29] Synthesis of Compound I-11

Target compound of Preparation Example 9 (3 g, 4.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-3-yl) -6-phenyl-1,3,5-triazine (1.9 g , 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.2 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound I-11 (2.7 g, 66% yield).

[LCMS]: 838

[ Synthesis Example  30] Synthesis of Compound I-12

Target compound of Preparation Example 9 (3 g, 4.9 mmol) and (4-cyanophenyl) boronic acid (0.7 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.2 mmol), K ₂ CO ₃ (2.0 g , 14.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound I-12 (1.9 g, yield 66%).

[LCMS]: 592

[ Synthesis Example  31] Synthesis of Compound J-2

Target compound of Preparation Example 10 (3 g, 5.5 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (1.9 g, 5.5 mmol) and Pd (PPh ₃ ) ₄ ( 0.3 g, 0.3 mmol) and K ₂ CO ₃ (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to give the title compound J-2 (2.6 g, yield 65%).

[LCMS]: 723

[ Synthesis Example  32] Synthesis of Compound J-8

Target compound of Preparation Example 10 (3 g, 5.5 mmol) and 4- (4-chlorophenyl) -2-phenyl-6- (4- (pyridin-3-yl) phenyl) pyrimidine (2.3 g, 5.5 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.3 mmol) and K ₂ CO ₃ (2.3 g, 16.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to give the title compound J-8 (2.7 g, 62% yield).

[LCMS]: 799

[ Synthesis Example  33] Synthesis of Compound K-9

Target compound of Preparation Example 11 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (1.7 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.2 g, 0.3 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound K-9 (2.7 g, 67% yield).

[LCMS]: 813

[ Synthesis Example  34] Synthesis of Compound K-10

Target compound of Preparation Example 11 (3 g, 4.9 mmol) and 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine (1.8 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.2 g, 0.3 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, followed by heating to reflux for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound K-10 (2.5 g, 61% yield).

[LCMS]: 829

[ Synthesis Example  35] Synthesis of Compound L-11

Target compound of Preparation Example 12 (3 g, 4.9 mmol) and 2-chloro-4- (9,9-dimethyl-9H-fluoren-3-yl) -6-phenyl-1,3,5-triazine (1.9 g , 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.2 mmol) and K ₂ CO ₃ (2.0 g, 14.6 mmol) were added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O and heated for 12 hours. It was refluxed. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound L-11 (2.7 g, 66% yield) using column chromatography.

[LCMS]: 838

[ Synthesis Example  36] Synthesis of Compound L-12

Target compound of Preparation Example 12 (3 g, 4.9 mmol) and (4-cyanophenyl) boronic acid (0.7 g, 4.9 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.2 mmol), K ₂ CO ₃ (2.0 g , 14.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound L-12 (1.9 g, yield 66%).

[LCMS]: 592

[ Synthesis Example  37] Synthesis of Compound M-2

Target compound of Preparation Example 1 (3 g, 6.9 mmol), 4-bromo-N, N-diphenylaniline (4.5 g, 13.8 mmol), Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol), K ₂ CO ₃ ( 2.8 g, 20.6 mmol) was added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound M-2 (3.3 g, yield 71%).

[LCMS]: 671

[ Synthesis Example  38] Synthesis of Compound M-6

Target compound of Preparation Example 1 (3 g, 6.9 mmol) and 9- (4-bromophenyl) -9H-carbazole (4.4 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol), K ₂ CO ₃ (2.8 g, 20.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound M-6 (3.1 g, yield 68%).

[LCMS]: 667

[ Synthesis Example  39] Synthesis of Compound N-2

Target compound of Preparation Example 2 (3 g, 6.9 mmol), 4-bromo-N, N-diphenylaniline (4.5 g, 13.8 mmol), Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol), K ₂ CO ₃ ( 2.8 g, 20.6 mmol) was added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound N-2 (3.0 g, yield 65%) using column chromatography.

[LCMS]: 671

[ Synthesis Example  40] Synthesis of Compound N-6

Target compound of Preparation Example 2 (3 g, 6.9 mmol) and 9- (4-bromophenyl) -9H-carbazole (4.4 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol), K ₂ CO ₃ (2.8 g, 20.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound N-6 (2.9 g, yield 63%) by column chromatography.

[LCMS]: 667

[ Synthesis Example  41] Synthesis of Compound O-2

Target compound of Preparation Example 3 (3 g, 6.9 mmol), 4-bromo-N, N-diphenylaniline (4.5 g, 13.8 mmol), Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol), K ₂ CO ₃ ( 2.8 g, 20.6 mmol) was added to 50 mL of Toluene, 10 mL of EtOH, and 10 mL of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound O-2 (2.7 g, yield 60%).

[LCMS]: 671

[ Synthesis Example  42] Synthesis of Compound O-6

Target compound of Preparation Example 3 (3 g, 6.9 mmol) and 9- (4-bromophenyl) -9H-carbazole (4.4 g, 13.8 mmol) and Pd (PPh ₃ ) ₄ (0.4 g, 0.3 mmol), K ₂ CO ₃ (2.8 g, 20.6 mmol) was added to 50 ml of Toluene, 10 ml of EtOH, and 10 ml of H ₂ O, and the mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound O-6 (2.9 g, yield 63%).

[LCMS]: 667

Example 1 Fabrication of Blue Organic Electroluminescent Device

Compound A-3 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows. Glass substrates were washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound A-3 (30 nm) ) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.

Examples 2 to 36 Fabrication of Blue Organic Electroluminescent Devices

Compounds A-6, A-9, A-14, A-17, A-23, B-3, B-6, and B-9 synthesized in Synthesis Examples 2 to 36, respectively, instead of the compound A-3 in Example 1 , B-14, B-17, B-23, C-3, C-6, C-9, C-14, C-17, C-23, D-2, D-8, E-9, E -10, F-11, F-12, G-2, G-8, H-9, H-10, I-11, I-12, J-2, J-8, K-9, K-10 An organic electroluminescent device was manufactured in the same manner as in Example 1 except for using L-11 and L-12.

Comparative Example 1 Fabrication of Blue Organic Electroluminescent Device

A blue organic EL device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound A-3 as the electron transporting layer material.

Comparative Example 2 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that ET-1 instead of Compound A-3 was used as the electron transporting layer material.

Comparative Example 3 Fabrication of Blue Organic Electroluminescent Device

A blue organic EL device was manufactured in the same manner as in Example 1, except that Compound A-3 was not used as the electron transporting material.

The structures of ET-1, NPB, AND, and Alq3 used in Examples 1 to 36 and Comparative Examples 1, 2, and 3 are as follows.

[Evaluation Example 1]

For each of the blue organic electroluminescent devices manufactured in Examples 1 to 36 and Comparative Examples 1, 2, and 3, a driving voltage, a current efficiency, and an emission peak at a current density of 10 mA / cm 2 were measured, and the results were as follows. Table 1 shows.

Sample material Drive voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 A-3 3.4 458 6.8 Example 2 A-6 3.6 456 6.9 Example 3 A-9 3.2 457 6.8 Example 4 A-14 3.2 456 7.0 Example 5 A-17 4.6 457 7.1 Example 6 A-23 3.6 456 6.7 Example 7 B-3 3.9 456 6.9 Example 8 B-6 3.6 457 6.7 Example 9 B-9 3.6 456 7.0 Example 10 B-14 3.2 457 7.1 Example 11 B-17 3.2 456 6.8 Example 12 B-23 3.6 456 6.9 Example 13 C-3 3.9 457 6.9 Example 14 C-6 3.9 452 6.8 Example 15 C-9 3.3 448 6.7 Example 16 C-14 3.6 460 6.8 Example 17 C-17 4.1 456 6.9 Example 18 C-23 3.2 456 6.8 Example 19 D-2 3.2 457 6.4 Example 20 D-8 4.1 465 6.8 Example 21 E-9 3.7 455 6.9 Example 22 E-10 3.9 459 7.1 Example 23 F-11 3.8 457 7.1 Example 24 F-12 3.2 452 6.9 Example 25 G-2 3.2 456 6.5 Example 26 G-8 3.6 456 6.7 Example 27 H-9 3.9 457 6.8 Example 28 H-10 3.9 459 6.9 Example 29 I-11 3.3 456 7.1 Example 30 I-12 3.8 455 6.9 Example 31 J-2 3.4 459 6.8 Example 32 J-8 3.2 457 6.4 Example 33 K-9 3.8 452 6.8 Example 34 K-10 4.1 456 6.9 Example 35 L-11 3.7 456 6.7 Example 36 L-12 3.7 457 6.9 Comparative Example 1 Alq ₃ 4.7 459 6.4 Comparative Example 2 4.5 458 6.6 Comparative Example 3 - 4.8 460 6.2

As shown in Table 1, the blue organic electroluminescent devices (Examples 1 to 36) using the compound represented by Chemical Formula 1 according to the present invention in the electron transporting layer include a blue organic electroluminescent device using a conventional Alq3 as the electron transporting layer ( Compared with the comparative example 1) and the blue organic electroluminescent element (comparative example 2) without an electron carrying layer, it turned out that it shows the outstanding performance in driving voltage, light emission peak, and a current efficiency.

Example 37 Fabrication of Organic Electroluminescent Device

After high purity sublimation purification of Compound M-2 synthesized in Synthesis Example 37 by a commonly known method, a blue organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / Compound M-2 (80 nm) / DSH522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq 3 (30) on the prepared ITO transparent electrode as described above. An organic electroluminescent device was manufactured in the order of nm) / LiF (1 nm) / Al (200 nm).

Examples 38 to 42 Fabrication of Blue Organic Electroluminescent Devices

Except for using the compounds M-6, N-2, N-6, O-2, O-6 synthesized in Synthesis Examples 38 to 42 in place of Compound M-2 in Example 37, In the same manner to prepare a blue organic EL device.

Comparative Example 4 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 37, except that NPB was used instead of the compound M-2 used as the hole transport layer in Example 37.

[Evaluation Example 2]

For the blue organic electroluminescent devices manufactured in Examples 37 to 42 and Comparative Example 4, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

Sample material Drive voltage (V) Current efficiency (cd / A) Example 37 M-2 4.4 22.2 Example 38 M-6 4.2 21.9 Example 39 N-2 4.2 20.8 Example 40 N-6 4.1 21.1 Example 41 O-2 4.3 21.7 Example 42 O-6 4.5 21.7 Comparative Example 4 NPB 5.2 18.1

As shown in Table 2, the blue organic EL device (Examples 37 to 42) using the compound represented by Formula 1 according to the present invention as a hole transporting layer material is an organic electroluminescent device using conventional NPB as the hole transporting layer material. Compared with (Comparative Example 4), it was found to show better performance in terms of current efficiency and driving voltage.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.

Claims (12)

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

In Chemical Formula 1, A and B are the same as or different from each other, and are independently represented by the following formula (2), [Formula 2]

In Chemical Formula 2, * Means the part where the bond is made; L is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms; R is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group of 3 to 40 atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ to C ₄₀ , aryloxy group of C ₆ to C ₆₀ , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphanyl group C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylamine group selected from the group or combine with adjacent groups to form a condensed ring; The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl of R Group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear aryl, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ An alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₁ to C ₄₀ alkylsilyl group, and C ₁ to C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsil When unsubstituted or substituted with one or more substituents selected from the group consisting of a aryl group, they are the same as or different from each other. The method of claim 1, R is a compound represented by the following formula (3): [Formula 3]

In Chemical Formula 3, Z ₁ to Z ₅ are independently C (R ₁ ) or N, at least one of which is N; R ₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha It is selected from the group consisting of a nil group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group. The method of claim 1, R is a compound represented by the following formula (4): [Formula 4]

In Chemical Formula 4, Ar ₂ and Ar ₃ independently represent a substituted or unsubstituted aryl group, and Ar ₂ and Ar ₃ may form a nitrogen-containing heterocycle together with the nitrogen to which they are bonded. The method of claim 1, Formula 1 is a compound represented by the following formula (5): [Formula 5]

In Chemical Formula 5, L ₁ and L ₂ are the same as or different from each other, and are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms, and a heteroarylene group having 5 to 18 nuclear atoms; R ₂ and R ₃ are hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₆ to C ₆₀ aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C _{60 group} Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ An arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group; Z ₆ to Z ₁₁ are independently C (R ₄ ) or N, at least one being N; p and q are independently 1 or 2; R ₄ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phospha It is selected from the group consisting of a nil group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group. The method of claim 1, Formula 1 is a compound represented by the following formula (6): [Formula 6]

In Chemical Formula 6, L ₃ and L ₄ are the same as or different from each other, and each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms, and a heteroarylene group having 5 to 18 nuclear atoms; Ar ₄ to Ar ₇ independently represent a substituted or unsubstituted aryl group, and Ar ₄ and Ar ₅ and Ar ₆ and Ar ₇ may form a nitrogen-containing heterocycle together with the nitrogen to which they are bonded. The method of claim 4, wherein Formula 5 is a compound represented by any one of the following formula 7 to formula 9: [Formula 7]

[Formula 8]

[Formula 9]

In Chemical Formulas 7 to 9, L ₁ , L ₂ , R ₂ , R ₃ , Z ₆ to Z ₁₁ , p and q are each as defined in Chemical Formula 5. The method of claim 5, Formula 6 is a compound represented by any one of the following Formula 10 to Formula 12: [Formula 10]

[Formula 11]

[Formula 12]

In Chemical Formulas 10 to 12, L ₃ , L ₄ and Ar ₄ to Ar ₇ are the same as defined in Chemical Formula 6. The method of claim 1, Wherein R is a substituent selected from the group consisting of S ₁ to S ₄₉ :

The method of claim 1, R is a compound selected from the group consisting of S ₅₀ to S _{56 below} .

An organic electroluminescent device comprising an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, At least one of the one or more organic material layers is an organic electroluminescent device comprising the compound according to any one of claims 1 to 7. The method of claim 10, The organic material layer comprising the compound is at least one selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. The method of claim 10, The organic material layer containing the compound is an organic electroluminescent device which is a hole transport layer.