KR20190074099A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same. A compound according to the present invention is used for an organic layer, preferably a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, or an electron injecting layer of the organic electroluminescent device, thereby being able to improve luminous efficiency, driving voltage, lifespan and the like of the organic electroluminescent device.

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 that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, Tang The organic light emitting device having a laminated structure in which the hole layer and the functional layer of the light emitting layer are divided. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.

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

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. 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. Since the phosphorescent material can theoretically improve the luminous efficiency four times higher than that of the fluorescent material, studies on the phosphorescent host materials as well as the phosphorescent dopant are being conducted.

To date, NPB, BCP and Alq ₃ have been widely known as the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, phosphorescent materials having advantages in terms of efficiency improvement of light emitting materials include blue, green and red dopant materials such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ A metal complex compound containing Ir is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, conventional materials have advantages in terms of light emission characteristics, but their thermal stability is lowered due to a low glass transition temperature, and thus the life of the organic light emitting device is not satisfactory. Therefore, development of materials with higher performance is required.

An object of the present invention is to provide a novel organic compound capable of improving the bonding force between holes and electrons while having a high thermal stability due to a high glass transition temperature.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having 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).

[Chemical Formula 1]

In Formula 1,

One of X ₁ and X ₂ is N and the other is C (R ₁₁ )

R ₁ to R ₁₁ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, the combined contiguous groups to form a fused ring, wherein, R ₁ and R _2, R ₂ and R _3, R ₃ and R ₄ must be one of which is to be bonded to each other to form a condensed ring, R ₅ and R _6, R ₆ and R _7, R ₇ and R ₈ must be either each other To form a condensed ring, R ₉ and R ₁₀ are bonded to each other to form a condensed ring,

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,

Aryl group, a heteroaryl alkyl group and R ₁ to R ₁₁ of the L, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, a nitro group, an alkyl group of C1 ~ C40, C ₂ ~ C _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl silyl When substituted by one or more substituent species selected from the group consisting of or being substituted by plural substituents Beach and ring, they may be the same or different from each other.

In addition, the present invention provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes a compound represented by Formula 1 A light emitting device is provided.

At least one organic layer including at least one compound represented by Formula 1 may be selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, and a light emitting layer, and is preferably a light emitting layer. Wherein the compound represented by Formula 1 is a green or red phosphorescent host material.

The compound represented by the formula (1) according to an example of the present invention is excellent in thermal stability, carrier transport ability, and light emitting ability, and can be used as an organic material layer material of an organic electroluminescent device.

1 is a cross-sectional view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

<New Organic Compound>

The novel organic compound according to the present invention is a condensation type dibenzocarbazole based core which has a basic skeleton and various substituents bonded to the basic skeleton,

Specifically, the condensed dibenzocarbazole series core structures have excellent electrochemical stability and excellent carrier transport ability. In particular, the electron and hole transport mobility is very excellent, and the balance of the carriers in the light emitting layer exhibits very excellent properties.

In addition, the compounds represented by Formula 1 have a structural characteristic in which a dibenzocarbazole-based core and at least one electron withdrawing group (EWG) are bonded, It has high transition temperature and excellent thermal stability. Preferably, the EWG should be at least 10 hetero-polycyclic. The molecular weight of the compound is significantly increased due to the heterodyne ring, and the glass transition temperature is improved, thereby exhibiting high thermal stability.

Actually, as shown in the following Table 1, in the compound represented by the formula (1) of the present invention, the compound having a dibenzocarbazole core and at least 10 heterocyclic rings bonded thereto (R1 in Table 1) has a glass transition temperature (Tg) (Compound A in Table 1), which is a compound in which a core of a dibenzocarbazole-based compound and a heterocycle having 9 or fewer carbon atoms are bonded, has a glass transition temperature (Tg) of 97 占 폚. It can be seen that the glass transition temperature (Tg) of the compound R1 according to the present invention is 28 占 폚 higher than the glass transition temperature (Tg) of the control compound A.

compound Tg

125 ℃

97 ℃

In general, the glass transition temperature (Tg) of the organic compound for an organic electroluminescence device must be 110 ° C or higher for commercialization. This is because the post-treatment temperature after the deposition of the organic compound is at least 110 ° C. Since the glass transition temperature (Tg) of the substance bonded to the dibenzocarbazole based core and the heterocycle having 10 or more carbon atoms is 110 ° C or higher, the structure proposed in the present invention has excellent thermal stability and does not deform at high temperatures. Durability and stability can be improved and the lifetime of the device can be efficiently increased.

In addition, the hole and electrons transferred to the light emitting layer are suitable for a red phosphorescent light emitting layer because of excellent charge balance and excellent exciton generation and narrow bandgap of 3.0 eV or less in the compound represented by Chemical Formula 1 . In addition, since the difference between the triplet energy (T1) of the host material and the triplet energy (T1) of the dopant in the phosphorescent light emitting layer is only 0.2 to 0.3 eV, the energy transfer to the dopant is high, The durability and stability of the device are improved and the lifetime of the device can be efficiently increased. Here, the triplet energy (T1) of a common dopant used in a red phosphorescent host is 2.0 eV, and the compound of the formula (1) according to the present invention has a triplet energy (T1) of about 2.2 to 2.3 eV or less, Suitable for phosphorescent host.

In fact, the compounds represented by formula (1) of the present invention exhibit physical characteristics in which most of them can be driven at a low voltage and their lifetime is improved. For example, in Table 2, a bandgap of 2.about.88 eV is suitable for a red phosphorescent host in the case of a dibenzocarbazole-based core and a substance (R1) in which at least 10 hetero rings are bonded to each other. Is less than about 0.3 eV, the energy transfer to the dopant is easy.

The structural form of the compound according to formula (1) with a dibenzocarbazole core also differentiates it from conventional structures. Compounds having an upward direction of the core such as the compound R1 have a plane nature of the dibenzocarbazole core as compared with the compound having the direction of the core outward as in the case of the compound B. If it has planarity, bandgap is reduced and electron and hole transport mobility of the dopant is easy. Indeed, it can be seen that the compound R1 proposed in the present invention has planarity of the dibenzocarbazole core and a bandgap of 0.08 eV smaller than that of the control compound B.

compound rescue
(Structute) Bandgap Triplet energy (T1)

2.88 eV 2.30 eV

2.96 eV 2.32 eV

Due to the above-mentioned facts, the compound represented by the above formula (1) has excellent luminescent properties and therefore can be used as a material for any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer And can preferably be used as a phosphorescent host material in red phosphorescence and green.

Accordingly, when the compound represented by the general formula (1) of the present invention is used as an organic layer material of an organic electroluminescent device, preferably as a light emitting layer material (red and green phosphorescent host) material, a conventional organic layer material (for example, CBP) The efficiency and lifetime characteristics of the organic electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

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

[Chemical Formula 1]

In Formula 1, any one of X ₁ and X ₂ is N and the other is C (R ₁₁ )

R ₁ to R ₁₁ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, the combined contiguous groups to form a fused ring, wherein, R ₁ and R _2, R ₂ and R _3, R ₃ and R ₄ must be one of which is to be bonded to each other to form a condensed ring, R ₅ and R _6, R ₆ and R _7, R ₇ and R ₈ must be either each other To form a condensed ring, R ₉ and R ₁₀ may combine with each other to form a condensed ring.

Wherein, R ₁ to the alkyl group of R _11, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boronic group, aryl boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, a nitro group, the alkyl group of _{C1 ~ C40, C 2 ~ C} 40 alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ C ₆₀ arylboronic group, C ₆ ~ C ₆₀ aryl phosphine of pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

(*는 결합이 이루어지는 부위)로 표시되는 구조는 하기 S-1 내지 S-9으로 표시되는 구조로 이루어진 군에서 선택된다.Preferably,

(* Is a site where bonding is performed) is selected from the group consisting of the structures represented by the following S-1 to S-9.

In the above S-1 to S-9, R &lt; ₁₁ &gt; is the same as defined in the formula (1).

Also, in the compound represented by Formula 1, L is a divalent group linker known in the art and includes a single bond, a C ₆ to C ₁₈ arylene group, and a heteroaromatic group having 5 to 18 hetero atoms And an arylene group.

Examples of the C ₆ -C ₄₀ arylene group and the heteroarylene group having 5 to 40 nuclear atoms include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group, A thiophenylene group, a thiophenylene group, a pyridinylene group, a pyrrolylene group, a pyrrolylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, Rengi and so on. In the present invention, it is preferable that L is selected from a single bond or a phenylene group.

Alkynyl group of the L of the aryl group, a hetero arylene group each independently selected from deuterium, halogen, a cyano group, a nitro group, an alkyl group of _{C1 ~ C40, C 2 ~ C} 40 alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C of ₆ ~ C ₆₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a _{C 6 ~ C 60, C 6} ~ substituted with C ₆₀ or aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ selected from aryl silyl group the group consisting of C ₆₀ one kind of substituent or is unsubstituted, substituted with a plurality of substituents , They may be the same or different from each other.

The compound represented by the formula (1) of the present invention can be further represented by a compound represented by any one of the following formulas (2) to (5).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above Chemical Formulas 2 to 5,

X ₁ , X ₂ , R ₃ to R ₆ , R ₉ , R ₁₀ and L are the same as defined in formula (1).

More specifically, it is preferable that one of X ₁ and X ₂ is N and the other is C (R ₁₁ ) and is selected from the group consisting of the structures represented by the following S-1 to S-9,

L is selected from a single bond or a phenylene group,

R ₁₂ each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ An aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, and is selected from the group consisting of C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl amine.

The compound represented by formula (1) according to an example of the present invention described above can be further compounded into compound structures composed of R1 to R235 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" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 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.

"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, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and may be a linear, branched or cyclic structure . &Lt; / RTI &gt; Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.

"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 of the carbons, preferably one to three carbons, Or &lt; RTI ID = 0.0 &gt; Se. &Lt; / RTI &gt; Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compounds of formula (1) according to one embodiment of the present invention can be synthesized in various ways with reference to synthesis examples. 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) including the compound represented by the formula (1) according to the present invention described above.

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, wherein 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 be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer. &Lt; / RTI &gt; compounds. Preferably, the organic material layer containing the compound represented by Formula 1 may be at least one selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer, The organic material layer containing the compound of Formula 1 may be at least one selected from the group consisting of a light emitting layer, an electron transporting auxiliary layer and an electron transporting layer.

According to an example, the at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the light emitting layer includes a compound represented by Formula 1. [ At this time, the compound represented by Formula 1 is a host material.

According to another example, the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and the electron transporting layer includes a compound represented by the above formula (1). At this time, the compound represented by Formula 1 is a material for forming an electron transport layer.

According to another example, the one or more organic material layers include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer, . At this time, the compound represented by Formula 1 is a material forming an electron transporting auxiliary layer.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may have a conventional structure known in the art. For example, 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 may be sequentially stacked.

1 is a cross-sectional view of an organic electroluminescent device according to an example of the present invention. The organic electroluminescent device includes an anode 10 and a cathode 20 opposed to each other and an organic layer 30 positioned between the anode 10 and the cathode 20. The organic layer 30 includes a hole transporting layer 31, a light emitting layer 32 and an electron transporting layer 34. If necessary, the organic transporting layer 31 may include a hole transporting auxiliary layer 31 positioned between the hole transporting layer 31 and the light emitting layer 32, (33); And / or an electron transporting auxiliary layer (35) positioned between the electron transporting layer (34) and the light emitting layer (32).

In the organic electroluminescent device, holes move to the light emitting layer 32 in an anode at an ionization potential level. At this time, when the organic electroluminescent device includes the electron transporting auxiliary layer 35, holes migrating to the emitting layer 32 are clogged by the high energy barrier of the electron transporting auxiliary layer and diffused into the electron transporting layer 34, And as a result, the electron transporting auxiliary layer 35 functions to confine holes to the light emitting layer. The function of confining the holes to the light emitting layer 32 prevents diffusion of holes to the electron transporting layer 34 that moves the electrons by reduction and suppresses the lifetime degradation due to the irreversible decomposition reaction by oxidation, Thereby contributing to improvement in the lifetime of the organic light emitting device. When the organic electroluminescent device further includes a hole transporting auxiliary layer 33, electrons moving to the emitting layer 32 are blocked by a high energy barrier of the hole transporting auxiliary layer to diffuse or migrate to the hole transporting layer 31 And as a result, the hole transporting auxiliary layer 33 can restrict electrons to the light emitting layer, thereby contributing to improvement in the lifetime of the organic light emitting device.

2 is a cross-sectional view of an organic electroluminescent device according to another example of the present invention. The organic electroluminescent device includes an anode 10 and a cathode 20 opposed to each other and an organic layer 30 positioned between the anode 10 and the cathode 20. The organic layer 30 includes a hole transporting layer 31, a hole transporting auxiliary layer 33, a light emitting layer 32, an electron transporting auxiliary layer 35 and an electron transporting layer 34, A hole injection layer 37 located between the anode 31 and the anode 10; And / or an electron injection layer (36) positioned between the cathode (20) and the electron transport layer (34).

In the present invention, the hole injection layer 37 not only improves the interfacial characteristics between the ITO used as the anode and the organic material used as the hole transport layer 31, but also applied to the top of the ITO whose surface is not smooth, Which softens the surface of the substrate. The material of the hole injection layer 37 may be any material conventionally used in the art without any particular limitation. Examples of the hole injection layer 37 include, but are not limited to, amine-based compounds.

The electron injection layer 36 is a layer which is stacked on the electron transport layer 34 to facilitate injection of electrons from the cathode, ultimately improving the power efficiency. The material of the electron injection layer 36 may be any material conventionally used in the art without any particular limitation. For example, there are such as LiF, Liq, NaCl, CsF, Li ₂ O, BaO, not limited to this.

Meanwhile, the organic electroluminescent device according to the present invention may further include an emission auxiliary layer (not shown) selectively between the hole transporting auxiliary layer 33 and the emission layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light emitting auxiliary layer may include a hole transporting material of the present invention and may be made of the same material as the hole transporting layer 31.

The light emitting layer of the organic electroluminescent device according to the present invention includes a host material. In this case, the compound of Formula 1 may be included as a host material, or may include a host compound other than the compound of Formula 1 as a host . For example, when the compound represented by Formula 1 is used as a light emitting layer material of an organic electroluminescent device, it can be specifically used as a phosphorescent host, a fluorescent host, or a dopant material of a light emitting layer. In particular, a phosphorescent host (green and / Phosphorescent host material).

The organic electroluminescent device according to the present invention may have a structure in which not only an anode, at least one organic layer and at least one cathode are sequentially stacked, but also an insulating layer or an adhesive layer is further included at the interface between the electrode and the organic layer have.

The organic electroluminescent device of the present invention can be manufactured by using a material known in the art and an organic electroluminescent device, except that at least one or more of the above-described organic material layers (for example, an electron transporting auxiliary layer) Method to form another organic material layer and an electrode.

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

The anode material may be made of a conductor having a high work function to facilitate, for example, hole injection. Specific examples of the usable 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 made of a conductor having a low work function for facilitating electron injection, for example. Specific examples of the negative electrode material that can be used include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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 A2

<Step 1> Synthesis of A1

Under nitrogen gas stream, 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), Pd (PPh 3) of naphthalen-2-ylboronic acid, 2.9g (16.9 mmol), 1.0g (5 mol%) 4, and potassium carbonate, 7.0 g (50.6 mmol) of Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) was added thereto and stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A1 (3.6 g, 12.1 mmol, yield 72%).

GC-Mass (299.33 g / mol, measured: 299 g / mol)

(M, 4H), 7.65 (s, 1H), 7.71-7.92 (m, 5H), 8.41-8.88

<Step 2> Synthesis of A2

3.6 g (12.1 mmol) of A1, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed in a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A2 (2.4 g, 9.0 mmol, yield 74%).

GC-Mass (theory: 267.33 g / mol, measured: 267 g / mol)

1H-NMR:? 7.42-7.81 (m, 6H), 8.21-8.68 (m, 6H), 11.55

[ Preparation Example  2] Synthesis of A4

<Step 1> Synthesis of A3

Under nitrogen gas stream, 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), (3-phenylnaphthalen-2-yl) Pd (PPh 3) of boronic acid, 4.2g (16.9 mmol) , 1.0g (5 mol%) 4 , 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A3 (4.6 g, 12.1 mmol, yield 72%).

GC-Mass (theory: 375.43 g / mol, measured: 375 g / mol)

(M, 4H), 7.65 (s, IH), 7.71-7.99 (m, 8H), 8.31 (s, IH), 8.41-8.87

<Step 2> Synthesis of A4

4.6 g (12.1 mmol) of A3, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A4 (3.2 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 343.43 g / mol, measurement: 343 g / mol)

1H, NMR:? 7.13-7.52 (m, 4H), 7.71-7.99 (m, 8H), 8.30

[ Preparation Example  3] Synthesis of A6

<Step 1> Synthesis of A5

Under nitrogen gas stream, 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), [1,2'-binaphthalen] -3-ylboronic acid, Pd (PPh 3 of 5.0g (16.9 mmol), 1.0g ( 5 mol%) 3) _4, and potassium carbonate 7.0g (50.6 mmol) and 80 ml / 40 ml / 40 ml of the insert Toluene / H ₂ O / Ethanol mixture was stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A5 (5.2 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 425.49 g / mol, measured: 425 g / mol)

1 H-NMR:? 7.15-7.51 (m, 4H), 7.64 (s, 1H), 7.69-7.99 (m, 10H), 8.31

<Step 2> Synthesis of A6

5.2 g (12.1 mmol) of A5, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A6 (3.6 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 393.49 g / mol, measured: 393 g / mol)

1 H-NMR:? 7.15-7.51 (m, 4H), 7.69-7.98 (m, 10H), 8.31

[Preparation Example 4] Synthesis of A8

<Step 1> Synthesis of A7

Under nitrogen gas stream, 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), (7-phenylnaphthalen-2-yl) boronic acid, 4.2g (16.9 mmol), Pd (PPh 3) of 1.0g (5 mol%) ₄ , 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A7 (4.6 g, 12.1 mmol, yield 72%).

GC-Mass (theory: 375.43 g / mol, measured: 375 g / mol)

1 H-NMR:? 7.13-7.55 (m, 4H), 7.65 (s, 1H), 7.71-7.99 (m, 8H), 8.31

<Step 2> Synthesis of A8

4.6 g (12.1 mmol) of A7, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A8 (3.2 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 343.43 g / mol, measurement: 343 g / mol)

1 H-NMR:? 7.15-7.54 (m, 4H), 7.72-7.99 (m, 8H), 8.30

[Preparation Example 5] Synthesis of A10

<Step 1> Synthesis of A9

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 6.0 g (16.9 mmol) of (3- (dibenzo [b, d] thiophen-3-yl) naphthalen- (5 mol%) Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the desired compound A9 (5.9 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 481.57 g / mol, measured: 482 g / mol)

1H-NMR:? 7.53-7.91 (m, 8H), 8.01-8.88 (m, 7H), 8.61-8.88 (m, 4H)

<Step 2> Synthesis of A10

5.9 g (12.1 mmol) of A9, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A10 (4.0 g, 9.0 mmol, yield 74%).

GC-Mass (calculated: 449.57 g / mol, measured: 450 g / mol)

1H-NMR:? 7.53-7.90 (m, 8H), 8.01-8.88 (m, 7H), 8.61-8.88 (m, 3H), 11.56

[Preparation Example 6] Synthesis of A12

<Step 1> Synthesis of A11

A solution of 5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene, 6.8 g of ((3- (benzo [b] naphtho [1,2- d] thiophen-10- yl) naphthalen- (16.9 mmol), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / And stirred for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A11 (6.5 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 531.63 g / mol, measured: 532 g / mol)

1H-NMR:? 7.51-7.93 (m, 9H), 8.01-8.89 (m, 7H), 8.61-8.88 (m,

<Step 2> Synthesis of A12

(12.1 mmol) of triphenylphosphine, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A12 (4.6 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 499.63 g / mol, measurement: 500 g / mol)

1H-NMR:? 7.50-7.93 (m, 9H), 8.01-8.89 (m, 7H), 8.61-8.85 (m, 4H)

[Preparation Example 7] Synthesis of A14

<Step 1> Synthesis of A13

(Dibenzo [b, d] thiophen-3-yl) naphthalen-2-yl) boronic acid, 6.0 g (16.9 mmol), 1.0 (PPh ₃ ) ₄ , potassium carbonate (7.0 g, 50.6 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml)

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A13 (5.9 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 481.57 g / mol, measured: 482 g / mol)

1H-NMR:? 7.53-7.92 (m, 8H), 8.01-8.88 (m, 7H), 8.61-8.87 (m, 4H)

&Lt; Step 2 > Synthesis of A14

5.9 g (12.1 mmol) of A13, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A14 (4.6 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 499.57 g / mol, measurement: 500 g / mol)

(M, 8H), 8.01-8.88 (m, 7H), 8.61-8.86 (m, 4H), 11.55

[Preparation Example 8] Synthesis of A16

<Step 1> Synthesis of A15

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 6.0 g (16.9 mmol) of (7- (dibenzo [b, d] thiophen-3-yl) naphthalen- Pd (PPh ₃ ) ₄ and potassium carbonate (7.0 g, 50.6 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A15 (5.9 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 481.57 g / mol, measured: 482 g / mol)

1H-NMR:? 7.52-7.92 (m, 8H), 8.01-8.88 (m, 7H), 8.61-8.87 (m, 4H)

<Step 2> Synthesis of A16

5.9 g (12.1 mmol) of A15, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A16 (4.6 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 499.57 g / mol, measurement: 500 g / mol)

1H-NMR:? 7.51-7.90 (m, 8H), 8.00-8.87 (m, 7H), 8.61-8.87 (m, 3H), 11.57

[Preparation Example 9] Synthesis of A18

<Step 1> Synthesis of A9

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 5.7 g (16.9 mmol) of ((3- (dibenzo [b, d] furan- 3- yl) naphthalen- (PPh ₃ ) ₄ , potassium carbonate (7.0 g, 50.6 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml)

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A17 (5.7 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 465.51 g / mol, measured: 466 g / mol)

1H-NMR:? 7.39-7.82 (m, 8H), 7.95-8.88 (m, 7H), 8.51-8.67 (m,

<Step 2> Synthesis of A18

5.7 g (12.1 mmol) of A17, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A18 (3.9 g, 9.0 mmol, yield 74%).

GC-Mass (calculated: 433.51 g / mol, measured: 433 g / mol)

1 H-NMR:? 7.39-7.82 (m, 8H), 7.95-8.88 (m, 7H), 8.51-8.66

[Preparation Example 10] Synthesis of A20

<Step 1> Synthesis of A21

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 7.0 g (16.9 mmol) of (3- (9-phenyl-9H-carbazol-2-yl) naphthalen- (5 mol%) Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A19 (6.6 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 540.62 g / mol, measured: 540 g / mol)

8H), 7.67-7.98 (m, 7H), 8.15-8.59 (m, 4H), 8.65-8.89 (m, 5H)

<Step 2> Synthesis of A20

6.6 g (12.1 mmol) of A19, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A20 (4.7 g, 9.2 mmol, yield 76%).

GC-Mass (calculated: 508.62 g / mol, measured: 509 g / mol)

(M, 8H), 7.77-7.98 (m, 7H), 8.15-8.59 (m, 4H), 8.65-8.89 (m, 4H), 11.55

[Preparation Example 11] Synthesis of A22

<Step 1> Synthesis of A21

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 6.1 g (16.9 mmol) of (3- (9,9-dimethyl-9H- fluoren-2-yl) naphthalen- 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were placed and stirred at 110 for 3 hours .

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A21 (6.0 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 491.59 g / mol, measured: 492 g / mol)

(M, 8H), 7.95-8.87 (m, 7H), 8.51-8. 67 (m, 4H)

&Lt; Step 2 > Synthesis of A22

6.0 g (12.1 mmol) of A21, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the desired compound A22 (4.2 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 459.59 g / mol, measured: 460 g / mol)

(S, 6H), 7.40-7.81 (m, 8H), 7.95-8.88 (m, 7H), 8.51-8.61

[Preparation Example 12] Synthesis of A24

<Step 1> Synthesis of A23

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 6.0 g (3- (dibenzo [b, e] [1,4] dioxin-2-yl) naphthalen- (PPh ₃ ) ₄ , potassium carbonate (7.0 g, 50.6 mmol) and Toluene / H ₂ O / Ethanol (80 ml / 40 ml / Lt; / RTI &gt;

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A15 (5.9 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 481.51 g / mol, measured: 482 g / mol)

1H-NMR:? 7.40-7.82 (m, 8H), 7.95-8.88 (m, 7H), 8.51-8.66

<Step 2> Synthesis of A24

5.9 g (12.1 mmol) of A23, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed in a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A24 (4.2 g, 9.2 mmol, yield 76%).

GC-Mass (calculated: 449.51 g / mol, measured: 450 g / mol)

1 H-NMR:? 7.41-7.82 (m, 8H), 7.95-8.88 (m, 7H), 8.51-8.61 (m, 3H)

[Preparation Example 13] Synthesis of A25

<Step 1> Synthesis of A25

Under nitrogen gas stream, 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), naphthalen-2-ylboronic acid, Pd (PPh 3) of 2.9g (16.9 mmol), 1.0g ( 5 mol%) 4 , and potassium carbonate 7.0g (50.6 mmol) and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A25 (3.6 g, 12.1 mmol, yield 72%).

GC-Mass (299.33 g / mol, measured: 299 g / mol)

1 H-NMR:? 7.71-7.92 (m, 6H), 8.01-8.38 (m, 5H), 8.45

<Step 2> Synthesis of A26

3.6 g (12.1 mmol) of A25, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A26 (2.4 g, 9.0 mmol, yield 74%).

GC-Mass (theory: 267.33 g / mol, measured: 267 g / mol)

(M, 6H), 8.01-8.35 (m, 4H), 8.45 (s, 1H), 8.55

[Preparation Example 14] Synthesis of A28

<Step 1> Synthesis of A27

₄ Pd (PPh ₃₎ in a nitrogen stream of 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), (1-phenylnaphthalen-2-yl) boronic acid 4.2g (16.9 mmol), 1.0g (5 mol%) and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A27 (4.6 g, 12.1 mmol, yield 72%).

GC-Mass (theory: 375.43 g / mol, measured: 375 g / mol)

(M, 6H), 8.00-8.39 (m, 9H), 8.45 (s, IH), 8.55

<Step 2> Synthesis of A28

4.6 g (12.1 mmol) of A27, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A28 (3.2 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 343.43 g / mol, measurement: 343 g / mol)

(M, 6H), 8.00-8.39 (m, 8H), 8.45 (s, IH), 8.55 (s, IH), 11.57

[Preparation Example 15] Synthesis of A39

<Step 1> Synthesis of A29

₄ Pd (PPh ₃₎ in a nitrogen stream of 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), (7-phenylnaphthalen-2-yl) boronic acid 5.0g (16.9 mmol), 1.0g (5 mol%) and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A29 (4.6 g, 12.1 mmol, yield 72%).

GC-Mass (theory: 375.43 g / mol, measured: 375 g / mol)

1 H-NMR:? 7.73-7.88 (m, 6H), 8.05-8.39 (m, 9H), 8.45

<Step 2> Synthesis of A30

4.6 g (12.1 mmol) of A29, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A30 (3.2 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 343.43 g / mol, measurement: 343 g / mol)

(S, 1H), 8.55 (s, IH), 11.57 (s, IH)

[Preparation Example 16] Synthesis of A32

<Step 1> Synthesis of A31

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 6.0 g (16.9 mmol) of (3- (dibenzo [b, d] thiophen-3-yl) naphthalen- Pd (PPh ₃ ) ₄ and potassium carbonate (7.0 g, 50.6 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A31 (5.9 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 481.57 g / mol, measured: 482 g / mol)

&Lt; 1 &gt; H-NMR: [delta] 7.72-7.95 (m, 8H), 8.07-8.39 (m, 9H)

<Step 2> Synthesis of A32

5.9 g (12.1 mmol) of A31, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed in a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A32 (4.0 g, 9.0 mmol, yield 74%).

GC-Mass (calculated: 449.57 g / mol, measured: 450 g / mol)

(S, IH), 8.55 (s, IH), 11.56 (s, IH), 8.05-8.35 (m,

[Preparation Example 17] Synthesis of A34

<Step 1> Synthesis of A33

A solution of 5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene, 6.0 g (1- (benzo [b] naphtho [1,2- d] thiophen-10- yl) naphthalen- 16.9 mmol), 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / Lt; / RTI &gt;

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A33 (5.9 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 481.57 g / mol, measured: 482 g / mol)

(M, 8H), 8.07-8.42 (m, 11H), 8.49 (s, IH), 8.58

<Step 2> Synthesis of A34

Under nitrogen flow, 33.5.9 g (12.1 mmol) of triphenylphosphine, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were added and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A34 (4.6 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 499.57 g / mol, measurement: 500 g / mol)

(S, 1H), 8.58 (s, 1H), 11.56 (s, 1H), 8.07-8.42

[Preparation Example 18] Synthesis of A36

<Step 1> Synthesis of A35

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 5.7 g (16.9 mmol) of l- (dibenzo [b, d] furan-3-yl) naphthalen- Pd (PPh ₃ ) ₄ and potassium carbonate (7.0 g, 50.6 mmol) and toluene / H ₂ O / ethanol (80 ml / 40 ml / 40 ml) were stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A35 (5.7 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 465.51 g / mol, measured: 467 g / mol)

(M, 8H), 8.07-8.40 (m, 9H), 8.45 (s, IH), 8.55

<Step 2> Synthesis of A36

5.7 g (12.1 mmol) of A35, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A36 (4.2 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 433.51 g / mol, measured: 434 g / mol)

1 H-NMR:? 7.75-7.95 (m, 8H), 8.06-8.35 (m, 8H), 8.46 (s,

[Preparation Example 19] Synthesis of A38

<Step 1> Synthesis of A37

3-yl) naphthalen-2-yl) boronic acid, 7.0 g (16.9 mmol), 1.0 (10.2 mmol) of 1-bromo- (PPh ₃ ) ₄ , potassium carbonate, 7.0 g (50.6 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were added and stirred at 110 ° C. for 3 hours .

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the organic layer solvent, the residue was purified by column chromatography to obtain the target compound A37 (6.6 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 540.62 g / mol, measured: 541 g / mol)

(S, 1H), 8.55 (s, 1H), 8.64-8.89 (m, 5H), 8.07-8.40 (m,

<Step 2> Synthesis of A38

37.6.6 g (12.1 mmol) of triphenylphosphine, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A38 (4.7 g, 9.2 mmol, yield 76%).

GC-Mass (calculated: 508.62 g / mol, measured: 509 g / mol)

(S, 1H), 8.55 (s, 1H), 8.64-8.88 (m, 5H), 11.56 (s, 1H), 8.07-8.40 1H)

[Preparation Example 20] Synthesis of A40

<Step 1> Synthesis of A39

5.1 g (20.2 mmol) of 1-bromo-2-nitrobenzene and 6.1 g (16.9 mmol) of ((1- (9,9-dimethyl- 9H- fluoren- 2- yl) naphthalen- , 1.0 g (5 mol%) of Pd (PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H ₂ O / ethanol were added and stirred at 110 for 3 hours .

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A39 (6.0 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 491.59 g / mol, measured: 492 g / mol)

(S, 6H), 7.75-7.95 (m, 8H), 8.06-8.35 (m, 9H), 8.46

<Step 2> Synthesis of A40

6.0 g (12.1 mmol) of A39, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A40 (4.2 g, 9.2 mmol, yield 76%).

GC-Mass (theory: 459.59 g / mol, measured: 460 g / mol)

1 H-NMR:? 1.61 (s, 6H), 7.75-7.95 (m, 8H), 8.06-8.35 (m, 8H), 8.46 (s,

[Preparation Example 21] Synthesis of A42

<Step 1> Synthesis of A41

Under nitrogen gas stream, 1-bromo-2-nitrobenzene 5.1g (20.2 mmol), Pd (PPh 3) of naphthalen-2-ylboronic acid, 2.9g (16.9 mmol), 1.0g (5 mol%) 4, and potassium carbonate, 7.0 g (50.6 mmol) of Toluene / H ₂ O / Ethanol (80 ml / 40 ml / 40 ml) was added thereto and stirred at 110 for 3 hours.

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A41 (3.6 g, 12.1 mmol, yield 72%).

GC-Mass (299.33 g / mol, measured: 299 g / mol)

(M, 6H), 8.31-8.58 (m, 5H), 8.75 (s,

<Step 2> Synthesis of A42

3.6 g (12.1 mmol) of A41, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed under a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A42 (2.4 g, 9.0 mmol, yield 74%).

GC-Mass (theory: 267.33 g / mol, measured: 267 g / mol)

(M, 4H), 8.75 (s, 1H), 8.95 (s, 1H), 11.55

[Preparation Example 22] Synthesis of A43

<Step 1> Synthesis of A44

(Dibenzo [b, d] thiophen-2-yl) naphthalen-2-yl) boronic acid, 6.0 g (16.9 mmol), 1.0 (PPh ₃ ) ₄ , potassium carbonate, 7.0 g (50.6 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H ₂ O / Ethanol were added and stirred at 110 ° C. for 3 hours .

After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A43 (5.9 g, 12.1 mmol, yield 72%).

GC-Mass (calculated: 481.57 g / mol, measured: 482 g / mol)

(M, 8H), 8.21-8.58 (m, 9H), 8.75 (s,

<Step 2> Synthesis of A44

5.9 g (12.1 mmol) of A31, 8.0 g (30.4 mmol) of triphenylphosphine and 50 ml of 1,2-dichlorobenzene were placed in a nitrogen stream and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed. The organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the desired compound A44 (4.2 g, 9.0 mmol, yield 76%).

GC-Mass (calculated: 449.57 g / mol, measured: 450 g / mol)

(M, 8H), 8.75 (s, 1H), 8.95 (s, 1H), 11.56

[ Synthetic example  1] Synthesis of R1

3.3 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.2 g (6.1 mmol, yield 68%) of the target compound R1.

GC-Mass (calculated: 521.62 g / mol, measured: 522 g / mol)

[ Synthetic example  2] Synthesis of R5

2.4 g (9.0 mmol) of A2, 2-bromo-3-phenylbenzo [f] quinoxaline, 3.3 g (9.9 mmol), 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol) of sodium tert-butoxide, 2.6 g (27.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.2 g (6.1 mmol, yield 68%) of the desired compound R5.

GC-Mass (calculated: 521.62 g / mol, measured: 522 g / mol)

[ Synthetic example  3] Synthesis of R7

4.5 g (9.9 mmol) of 2-chloro-3- (9-phenyl-9H-carbazol-3-yl) benzo [f] quinoxaline, 0.4 g (5 mol%) of A2 0.1 g (0.4 mmol) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine and 2.6 g (27.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.4 g (6.4 mmol, Yield: 71%) of the desired compound R7.

GC-Mass (686.82 g / mol, measured: 687 g / mol)

[ Synthetic example  4] Synthesis of R8

2.4 g (9.0 mmol) of A2, 3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine and 0.4 g (5 mol%) of Pd _{2 dba) 3, tri- tert -butylphosphine 0.1g} (0.4 mmol) and Sodium tert-butoxide 2.6g (27.0 mmol ) and placed in 100 ml of Toluene was stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.2 g (6.1 mmol, yield 68%) of the target compound R8.

GC-Mass (calculated: 527.65 g / mol, measured: 528 g / mol)

[ Synthetic example  5] Synthesis of R10

In a nitrogen stream A2 2.4g (9.0 mmol), 2 -chlorothiochromeno [4,3,2-de] quinazoline 2.7g (9.9 mmol), Pd 2 (dba) of _{0.4g (5 mol%) 3,} tri- tert - 0.1 g (0.4 mmol) of butylphosphine, 2.6 g (27.0 mmol) of sodium tert-butoxide, and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 2.9 g (5.8 mmol, yield 65%) of the desired compound R10.

GC-Mass (calculated: 501.61 g / mol, measured: 502 g / mol)

[ Synthetic example  6] Synthesis of R11

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.4 g (5.6 mmol, yield 61%) of the desired compound R11.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  7] Synthesis of R15

3.3 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.8 g (6.3 mmol, yield 68%) of the target compound R15.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  8] Synthesis of R21

3.6 g (9.0 mmol) of A6, 3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.1 g (6.3 mmol, yield 68%) of the desired compound R21.

GC-Mass (calculated: 647.78 g / mol, measured: 648 g / mol)

[ Synthetic example  9] Synthesis of R25

3.6 g (9.0 mmol) of A6, 3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.8 g (5.8 mmol, yield 63%) of the target compound R25.

GC-Mass (calculated: 647.78 g / mol, measured: 648 g / mol)

[ Synthetic example  10] Synthesis of R31

3.2 g (9.0 mmol) of A8, 3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.8 g (6.3 mmol, yield 68%) of the target compound R31.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  11] Synthesis of R35

In a nitrogen atmosphere A8 3.2g (9.0 mmol), 2 -bromo-3-phenylbenzo [f] quinoxaline 3.4g (9.9 mmol), 0.4g Pd 2 (dba) of _{(5 mol%) 3, tri-} tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.8 g (6.3 mmol, yield 68%) of the target compound R35.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  12] Synthesis of R41

4.0 g (9.0 mmol) of A10, 3.3 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.3 g (6.1 mmol, yield 68%) of the target compound R41.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  13] Synthesis of R45

(9.0 mmol) of A10, 3.3 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.0 g (5.7 mmol, yield 63%) of the objective compound R45.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  14] Synthesis of R51

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.7 g (6.3 mmol, yield 68%) of the target compound R51.

GC-Mass (calculated: 753.92 g / mol, measured: 754 g / mol)

[ Synthetic example  15] Synthesis of R55

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.7 g (6.3 mmol, yield 68%) of the desired compound R55.

GC-Mass (calculated: 753.92 g / mol, measured: 754 g / mol)

[ Synthetic example  16] Synthesis of R61

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.0 g (5.6 mmol, yield 61%) of the target compound R61.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  17] Synthesis of R65

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.4 g (6.3 mmol, yield 68%) of the desired compound R65.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  18] Synthesis of R71

3.3 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol) of sodium tert-butoxide, 2.6 g (27.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.4 g (6.3 mmol, yield 68%) of the desired compound R71.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  19] Synthesis of R75

In a nitrogen stream A16 4.6g (9.0 mmol), 2 -bromo-3-phenylbenzo [f] quinoxaline 3.3g (9.9 mmol), 0.4g Pd 2 (dba) of _{(5 mol%) 3, tri-} tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.4 g (6.3 mmol, yield 68%) of R75 as a target compound.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  20] Synthesis of R81

3.3 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.2 g (6.1 mmol, yield 68%) of the desired compound R81.

GC-Mass (calculated: 687.80 g / mol, measured: 688 g / mol)

[ Synthetic example  21] Synthesis of R85

3.3 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol) of sodium tert-butoxide, 2.6 g (27.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.2 g (6.1 mmol, yield 68%) of the desired compound R85.

GC-Mass (calculated: 687.80 g / mol, measured: 688 g / mol)

[ Synthetic example  22] Synthesis of R91

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.6 g (6.1 mmol, yield 66%) of the desired compound R91.

GC-Mass (calculated: 762.92 g / mol, measured: 763 g / mol)

[ Synthetic example  23] Synthesis of R95

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.8 g (6.3 mmol, yield 68%) of the desired compound R95.

GC-Mass (calculated: 762.92 g / mol, measured: 763 g / mol)

[ Synthetic example  24] Synthesis of R101

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.5 g (6.3 mmol, yield 68%) of the desired compound R101.

GC-Mass (calculated: 713.88 g / mol, measured: 714 g / mol)

[ Synthetic example  25] Synthesis of R105

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.5 g (6.3 mmol, yield 68%) of the target compound R105.

GC-Mass (calculated: 713.88 g / mol, measured: 714 g / mol)

[ Synthetic example  26] Synthesis of R111

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.4 g (6.3 mmol, yield 68%) of the desired compound R111.

GC-Mass (calculated: 703.80 g / mol, measured: 704 g / mol)

[ Synthetic example  27] Synthesis of R115

In a nitrogen stream A24 4.1g (9.0 mmol), 2 -bromo-3-phenylbenzo [f] quinoxaline 3.3g (9.9 mmol), 0.4g Pd 2 (dba) of _{(5 mol%) 3, tri-} tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.4 g (6.3 mmol, yield 68%) of the target compound R115.

GC-Mass (calculated: 703.80 g / mol, measured: 704 g / mol)

[ Synthetic example  28] Synthesis of R121

3.3 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.2 g (6.1 mmol, yield 68%) of the target compound R121.

GC-Mass (calculated: 521.62 g / mol, measured: 522 g / mol)

[ Synthetic example  29] Synthesis of R125

3.3 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.2 g (6.1 mmol, yield 68%) of the target compound R125.

GC-Mass (calculated: 521.62 g / mol, measured: 522 g / mol)

[ Synthetic example  30] Synthesis of R131

3.2 g (9.0 mmol) of A28, 3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol) of sodium tert-butoxide, 2.6 g (27.0 mmol) of sodium tert-butoxide, and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.8 g (6.3 mmol, yield 68%) of the target compound R131.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  31] Synthesis of R135

3.2 g (9.0 mmol) of A28, 3.3 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.8 g (6.3 mmol, yield 68%) of the target compound R135.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  32] Synthesis of R141

3.2 g (9.0 mmol) of A30, 3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.5 g (5.8 mmol, yield 63%) of the target compound R141.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  33] Synthesis of R145

In a nitrogen stream A30 3.2g (9.0 mmol), 2 -bromo-3-phenylbenzo [f] quinoxaline 3.4g (9.9 mmol), 0.4g Pd 2 (dba) of _{(5 mol%) 3, tri-} tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.8 g (6.3 mmol, yield 68%) of the target compound R145.

GC-Mass (calculated: 597.72 g / mol, measured: 598 g / mol)

[ Synthetic example  34] Synthesis of R151

In a nitrogen stream A32 4.0g (9.0 mmol), 2 -bromo-4-phenylbenzo [h] quinazoline 3.3g (9.9 mmol), 0.4g Pd 2 (dba) of _{(5 mol%) 3, tri-} tert -butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.3 g (6.1 mmol, yield 68%) of the target compound R151.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  35] Synthesis of R161

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.7 g (6.3 mmol, yield 68%) of the target compound R161.

GC-Mass (calculated: 753.92 g / mol, measured: 754 g / mol)

[ Synthetic example  36] Synthesis of R165

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.7 g (6.3 mmol, yield 68%) of the target compound R165.

GC-Mass (calculated: 753.92 g / mol, measured: 754 g / mol)

[ Synthetic example  37] Synthesis of R171

3.3 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.2 g (6.1 mmol, yield 68%) of the desired compound R171.

GC-Mass (calculated: 687.80 g / mol, measured: 688 g / mol)

[ Synthetic example  38] Synthesis of R175

3.3 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.2 g (6.1 mmol, yield 68%) of the desired compound R175.

GC-Mass (calculated: 687.80 g / mol, measured: 688 g / mol)

[ Synthetic example  39] Synthesis of R181

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.8 g (6.3 mmol, yield 68%) of the target compound R181.

GC-Mass (calculated: 762.92 g / mol, measured: 763 g / mol)

[ Synthetic example  40] Synthesis of R185

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.8 g (6.3 mmol, yield 68%) of the target compound R185.

GC-Mass (calculated: 762.92 g / mol, measured: 763 g / mol)

[ Synthetic example  41] Synthesis of R191

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.5 g (6.3 mmol, yield 68%) of the desired compound R191.

GC-Mass (calculated: 713.88 g / mol, measured: 714 g / mol)

[ Synthetic example  42] Synthesis of R195

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.5 g (6.3 mmol, yield 68%) of the target compound R195.

GC-Mass (calculated: 713.88 g / mol, measured: 714 g / mol)

[ Synthetic example  43] Synthesis of R201

3.3 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert -butylphosphine 0.1 g (0.4 mmol) of sodium tert-butoxide, 2.6 g (27.0 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . Purification by column chromatography gave 3.2 g (6.1 mmol, yield 68%) of the target compound R201.

GC-Mass (calculated: 521.62 g / mol, measured: 522 g / mol)

[ Synthetic example  44] Synthesis of R205

3.3 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 3.2 g (6.1 mmol, yield 68%) of the target compound R205.

GC-Mass (calculated: 521.62 g / mol, measured: 522 g / mol)

[ Synthetic example  45] Synthesis of R211

3.4 g (9.9 mmol) of 2-bromo-4-phenylbenzo [h] quinazoline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.2 g (6.0 mmol, yield 65%) of the objective compound R211.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Synthetic example  46] Synthesis of R215

3.4 g (9.9 mmol) of 2-bromo-3-phenylbenzo [f] quinoxaline, 0.4 g (5 mol%) of Pd ₂ (dba) ₃ , tri- tert- butylphosphine 0.1 g (0.4 mmol), sodium tert-butoxide (2.6 g, 27.0 mmol), and 100 ml of toluene were placed and stirred at 110 for 4 hours.

After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The residue was purified by column chromatography to obtain 4.4 g (6.3 mmol, yield 68%) of the target compound R215.

GC-Mass (calculated: 703.86 g / mol, measured: 704 g / mol)

[ Example  Fabrication of Red OLED Devices

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) / R 1, R 5, R 7, R 8, R 10, R 11, R 15, R 21, R 25, R 31, R 35, R 41, R 45, R 51, R 55, R16, R65, R71, R75, R81, R85, R91, R95, R101, R105, R111, R115, R121, R125, R131, R135, R141, R145, R151, R161, R165, R171, (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / 10% (piq) ₂ Ir (acac) Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

[ Comparative Example  One]

A red organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound R1 as a luminescent host material in forming the light emitting layer.

[ Comparative Example  2]

A red organic EL device was fabricated in the same manner as in Example 1 except that A was used instead of the compound R1 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

The driving voltage, the luminescent peak and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 46 and Comparative Examples 1 and 2, .

Sample Host Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 1 R1 4.6 621 17.4 Example 2 R5 3.5 621 16.7 Example 3 R7 4.2 621 18.6 Example 4 R8 4.5 621 17.2 Example 5 R10 3.5 621 16.5 Example 6 R11 4.5 621 16.8 Example 7 R15 4.5 621 16.8 Example 8 R21 4.5 621 16.8 Example 9 R25 4.9 621 19.1 Example 10 R31 4.6 621 17.4 Example 11 R35 4.7 621 16.8 Example 12 R41 4.5 621 16.8 Example 13 R45 4.3 621 20.1 Example 14 R51 4.3 621 17.4 Example 15 R55 4.2 621 18.7 Example 16 R61 4.3 621 17.4 Example 17 R65 4.2 621 18.7 Example 18 R71 4.5 621 17.2 Example 19 R75 4.2 621 18.7 Example 20 R81 4.5 621 17.2 Example 21 R85 3.5 621 16.5 Example 22 R91 4.8 621 19.3 Example 23 R95 4.2 621 18.7 Example 24 R101 4.3 621 17.4 Example 25 R105 4.2 621 18.7 Example 26 R111 4.5 621 17.2 Example 27 R115 4.7 621 16.8 Example 28 R121 4.6 621 17.2 Example 29 R125 4.3 621 17.4 Example 30 R131 4.2 621 18.7 Example 31 R135 4.5 621 17.2 Example 32 R141 3.5 621 16.5 Example 33 R145 4.8 621 19.3 Example 34 R151 4.5 621 16.8 Example 35 R161 4.6 621 17.4 Example 36 R165 4.7 621 16.8 Example 37 R171 4.6 621 17.2 Example 38 R175 4.3 621 17.4 Example 39 R181 4.2 621 18.7 Example 40 R185 4.5 621 17.2 Example 41 R191 4.7 621 16.8 Example 42 R195 4.6 621 17.2 Example 43 R201 4.6 621 17.2 Example 44 R205 4.7 621 16.8 Example 45 R211 4.9 621 19.1 Example 46 R215 4.6 621 17.4 Comparative Example 1 CBP 6.2 622 9.3 Comparative Example 2 A 5.6 621 13.9

As shown in Table 3 above, when the compound according to the present invention was used as a material for the light emitting layer of a red organic electroluminescent device (Examples 1 to 46), the conventional organic electroluminescent device using CBP and A as the material of the light emitting layer (Comparative Examples 1 and 2), it can be seen that it shows superior performance in terms of efficiency and driving voltage.

[ Example  47 ~ 49] Fabrication of green organic EL device]

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a green organic EL 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) / compound of each of R7, R8 and R10 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order to obtain an organic EL device.

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

[ Comparative Example  3] Fabrication of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 47 except that CBP was used instead of the compound R7 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  2]

The driving voltage, current efficiency and emission peak at the current density (10) mA / cm2 were measured for each of the green organic EL devices manufactured in Examples 47 to 49 and Comparative Example 3. The results are shown in Table 4 .

Sample Host Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 47 R7 4.2 515 20.3 Example 48 R8 4.1 515 21.3 Example 49 R10 4.0 515 19.9 Comparative Example 3 CBP 6.0 516 13.0

As shown in Table 4, when the compound according to the present invention was used as a material for the light emitting layer of a green organic electroluminescent device (Examples 47 to 49), a conventional organic electroluminescent light emitting device using CBP and B as the material of the light emitting layer It was found that the device exhibited better performance in terms of efficiency and driving voltage as compared with the device (Comparative Example 3).

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transporting auxiliary layer
34: Electron transport layer 35: Electron transport layer
36: electron injection layer 37: hole injection layer

Claims (8)

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

In Formula 1,
One of X ₁ and X ₂ is N and the other is C (R ₁₁ )
R ₁ to R ₁₁ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ aryl phosphine of C ₆₀ pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, the combined contiguous groups to form a fused ring, wherein, R ₁ and R _2, R ₂ and R _3, R ₃ and R ₄ must be one of which is to be bonded to each other to form a condensed ring, R ₅ and R _6, R ₆ and R _7, R ₇ and R ₈ must be either each other To form a condensed ring, R ₉ and R ₁₀ are bonded to each other to form a condensed ring,
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,
Aryl group, a heteroaryl alkyl group and R ₁ to R ₁₁ of the L, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, a nitro group, an alkyl group of C1 ~ C40, C ₂ ~ C _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl silyl Substituted by one or more substituent species selected from the group consisting of or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same as or different from each other. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of Chemical Formulas 2 to 5:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above Chemical Formulas 2 to 5,
X ₁ , X ₂ , R ₃ to R ₆ , R ₉ , R ₁₀ and L are the same as defined in claim 1,
R ₁₂ each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ An aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, and is selected from the group consisting of C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl amine. The method according to claim 1,

(* Is a site where bonding is carried out) is a compound selected from the group consisting of the structures represented by the following S-1 to S-9:

In the above S-1 to S-9, R &lt; ₁₁ &gt; is the same as defined in claim 1. The method according to claim 1,
Wherein L is a single bond or a phenylene group. The method according to claim 1,
The compound represented by the formula (1) is selected from the group consisting of the compounds represented by the following R1 to R235.

The method according to claim 1,
The compound represented by Formula 1 is represented by the following formula: R 1, R 5, R 7, R 8, R 10, R 11, R 15, R 21, R 25, R 31, R 35, R 41, R 45, R 51, R 55, R 61, R 65, R 71, R85, R91, R95, R101, R105, R111, R115, R121, R125, R131, R135, R141, R145, R151, R161, R165, R171, R175, R181, R185, Lt; / RTI &gt;

A cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 6. 8. The method of claim 7,
Wherein at least one organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, and an electron injecting layer.

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