WO2016105054A2

WO2016105054A2 - Organic light emitting compound and organic electroluminescent element using same

Info

Publication number: WO2016105054A2
Application number: PCT/KR2015/014035
Authority: WO
Inventors: 한송이; 김영배; 김회문
Original assignee: 주식회사 두산
Priority date: 2014-12-24
Filing date: 2015-12-21
Publication date: 2016-06-30
Also published as: KR20160077941A; KR102248650B1; WO2016105054A3

Abstract

The present invention relates to a novel compound having excellent light emitting ability, and to an organic electroluminescent element having improved characteristics, such as luminous efficiency, driving voltage, and lifespan, by containing the novel compound in one or more organic material layers.

Description

Organic light emitting compound and organic electroluminescent device using same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to include a novel azepine compound having excellent hole injection and transport ability, light emitting ability, and the like in one or more organic material layers, The present invention relates to an organic EL device having improved characteristics such as driving voltage and lifetime.

The study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') that led to blue electroluminescence using anthracene monocrystals in 1965 from the observation of Bernanose organic thin film emission from the 1950s In 1987, Tang presented an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make high-efficiency, high-life organic EL devices, the development has been made in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

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

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

Hole injection layer, hole transport layer to date. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material. Particularly, phosphorescent materials having a great advantage in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ as blue, green, and red dopant materials. It is used. To date, CBP has shown excellent properties as a phosphorescent host material.

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

[Preceding technical literature]

[Patent Documents]

Republic of Korea Patent Publication 2011-0066763

The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent hole injection, transporting ability, light emitting ability, and the like.

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

The present invention to achieve the above object provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

R ₁ and R ₂ are bonded to each other to form a condensed ring with the formula (2),

[Formula 2]

In Chemical Formula 2,

The dotted line is the part where condensation takes place

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ );

Y ₁ to Y ₁₂ are each independently selected from N or C (R ₃ );

If individual R ₃ is plural, they are the same or different from each other, and the R ₃ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C Alkynyl group of ₂ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, C ₁ C ₆ -C ₄₀ alkyloxy group, C ₆ -C ₆₀ aryloxy group, C ₃ -C ₄₀ alkylsilyl group, C ₆ -C ₆₀ arylsilyl group, C ₁ -C ₄₀ alkyl boron group, C ₆ - of C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, each selected from C ₆ ~ C ₆₀ mono or diaryl phosphine blood group, and the group consisting of C ₆ - aryl amine of the C ₆₀ of and adjacent R ₃ may be bonded to each other to form a condensed aromatic ring or a condensed heteroaromatic ring;

Ar ₁ to Ar ₅ is C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 40 heterocycloheteronuclear Alkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl Group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or A diaryl phosphinyl group and a C ₆ -C ₆₀ arylamine group;

R ₃ , Ar ₁ to Ar ₅ alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl A phosphine group, a mono or diaryl phosphinyl group and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₆ to C ₆₀ aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C _{60 group} Aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl group, and the amine may be substituted with at least one member selected from the group consisting of, optionally substituted with a plurality of substituents Wu they may be the same or different from each other.

The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer One provides an organic electroluminescent device comprising a compound represented by the formula (1).

"Alkyl" as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms 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" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms 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 a C6-C40 aromatic hydrocarbon in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with 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 may also include a form in which the two or more rings are condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means 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" is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

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

By "cycloalkyl" is meant herein monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. 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.

As used herein, the term “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

Compounds of the present invention are dibenzoazine (5H-dibenzo [b, d] azepine), dibenzooxepine (dibenzo [b, d] oxepine), dibenzothiepine (dibenzo [b, d] thiepine), 5-membered heteroaromatic ring moiety, indene moiety, in which benzene is condensed to dibenzosilene (5H-dibenzo [b, d] silepine) or dibenzocycloheptene (5H-dibenzo [a, d] cycloheptene) moiety, or indole moiety is condensed to form a basic skeleton, characterized in that represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

[Formula 2]

In Chemical Formula 2,

The dotted line is the part where condensation takes place

Y ₁ to Y ₁₂ are each independently selected from N or C (R ₃ );

R _3, if multiple individuals which are the same or different from each other, and the R ₃ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C Alkynyl group of ₂ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, C ₁ C ₆ -C ₄₀ alkyloxy group, C ₆ -C ₆₀ aryloxy group, C ₃ -C ₄₀ alkylsilyl group, C ₆ -C ₆₀ arylsilyl group, C ₁ -C ₄₀ alkyl boron group, C ₆ - of C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, each selected from C ₆ ~ C ₆₀ mono or diaryl phosphine blood group, and the group consisting of C ₆ - aryl amine of the C ₆₀ of and adjacent R ₃ may be bonded to each other to form a condensed aromatic ring or a condensed heteroaromatic ring;

Since the compound represented by Chemical Formula 1 has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], the glass transition temperature is high, and thus the thermal stability is excellent. In addition, the carrier transporting ability, the light emitting ability and the like are excellent. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.

In general, in the phosphorescent layer of an organic electroluminescent device, the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved. The compound of Formula 1 has a high triplet energy, by introducing a specific substituent in the basic skeleton condensed with a broad singlet energy level and a high triplet energy level, the energy level can be controlled higher than the dopant It can be used as a host material.

In addition, since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer. Therefore, when the organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, the exciton is prevented from being diffused by the compound, and thus the first exciton is diffused. Unlike conventional organic electroluminescent devices that do not include a barrier layer, the number of excitons that substantially contribute to light emission in the light emitting layer may be increased, thereby improving the luminous efficiency of the device. In addition, even when an organic material layer (hereinafter, referred to as a "life improvement layer") is formed between the light emitting layer and the electron transport layer by using the compound of Formula 1, the diffusion of excitons by the compound of Formula 1 prevents the organic electric field Durability and stability of the light emitting device can be improved, thereby effectively increasing the half life of the device. As such, the compound represented by Chemical Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material other than the host of the light emitting layer.

In addition, the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport. For example, when the compound is bonded to an electron-withdrawing electron (EWG) having a high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron. As such, the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used. On the other hand, when the compound of Formula 1 is combined with an electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., the hole injection and transport is smooth. In addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.

As described above, the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics. . Accordingly, the compound of formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / injection layer Material, light emitting auxiliary layer material, life improving layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, and life improving layer material.

In addition, the compound of Formula 1 has a variety of substituents, particularly aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby conventional light emission It may have a higher thermal stability than the material (eg CBP). In addition, the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.

According to one embodiment of the present invention, the compound of the present invention may combine R ₁ and R ₂ to form a condensed heteroaromatic ring or a condensed aromatic ring represented by the formula (2). Specifically, R ₁ and R ₂ may be bonded to form condensed indene, condensed indole, condensed benzothiophene, condensed benzofuran, condensed benzosilol and the like including one or more of N, O, S, and Si.

More specifically, the compound of the present invention may be represented by the following formula (3) or (4).

[Formula 3]

[Formula 4]

In Chemical Formula 3 or Chemical Formula 4, X ₁ , X ₂ and Y ₁ to Y ₁₂ are as defined in Chemical Formulas 1 and 2.

According to an embodiment of the present invention, in Formulas 3 and 4 X ₁ and X ₂ are each independently O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄₎ (Ar ₅ ), and at least one of them is preferably N (Ar ₁ ).

According to an embodiment of the present invention, in Formulas 3 and 4, Y ₁ to Y ₁₂ are each independently selected from N or C (R ₃ ), and all of them are C (R ₃ ) or one of them is N. desirable.

The compound of the present invention may be specifically selected from the group consisting of compounds represented by Formulas 1-1 to 1-18 below, but is not limited thereto.

In Chemical Formulas 1-1 to 1-18,

Each of Y ₁ to Y ₁₂ and Ar ₁ to Ar ₅ is the same or different, in particular, a plurality of Ar 1 in Formulas 1-1 and 1-6 are the same as or different from each other, as defined in Formulas 1 and 2.

According to a preferred embodiment of the present invention, in Formulas 1 and 2, except that forming condensation, at least one of R ₃ , Ar ₁ to Ar ₅ is an alkyl group of C ₁ ~ C ₄₀ , an aryl group of C ₆ ~ C ₆₀ , It is selected from the group consisting of 5 to 60 heteroaryl groups and C ₆ ~ C ₆₀ arylamine group, the alkyl group, aryl group, heteroaryl group, arylamine group, each independently, deuterium, halogen, cyano group, It may be substituted with at least one member selected from the group consisting of C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ arylamine group. When substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, at least one of R ₃ to Ar ₁ to Ar ₅ except for forming a condensation in the formula (1) and 2 may be a substituent represented by the formula (5) or a phenyl group.

[Formula 5]

In Chemical Formula 5,

* Means a moiety bonded to Formula 1;

L ₁ is a single bond or is selected from the group consisting of C ₆ to C ₁₈ arylene groups and heteroarylene groups having 5 to 18 nuclear atoms, preferably single bond, phenylene group, biphenylene group, carbazolyl group Can;

Z ₁ to Z ₅ are each independently N or C (R ₁₁ ), provided that at least one of Z ₁ to Z ₅ is N and when there are a plurality of R ₁₁ , they are the same or different from each other;

R ₁₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, C ₆ -C ₄₀ aryl group, 5 to 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphinyl group and C ₆ ~ C ₄₀ arylsilyl group selected from the group consisting of, or in combination with adjacent groups (e.g., L, other adjacent R ₁₁ ) condensed ring Can form;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R ₁₁ , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl groups, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ group aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₄₀ aryl silyl groups at least one member selected from the group consisting of When substituted or unsubstituted with a substituent and there are a plurality of the substituents, they may be the same or different from each other.

Examples of the substituent represented by Formula 5 include a substituent represented by the following A-1 to A-15, but is not limited thereto.

In the above A-1 to A-15,

L ₁ and R ₁₁ are each as defined in Formula 5,

n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₁₂ , and when n is an integer of 1 to 4, R ₁₂ is deuterium, halogen, cyano group, nitro C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₄₀ , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ ~ C _{40 60} C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ mono or diaryl phosphine of C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ P Nyl group and C ₆ ~ C _{40 It} is selected from the group consisting of an arylsilyl group, or it may be combined with adjacent groups (eg, L ₁ , R ₁₁ or other R _12, etc.) to form a condensed ring, wherein R ₁₂ is If more than one They are the same or different from each other,

Alkyl group of the R _12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl groups, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ group aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₄₀ aryl silyl groups at least one member selected from the group consisting of When substituted or unsubstituted with a substituent and there are a plurality of the substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention at least one of R ₃ to Ar ₁ to Ar ₅ except for forming a condensation in the formula (1) and 2 may be a substituent represented by the following formula (6).

[Formula 6]

In Chemical Formula 6,

* Means a moiety bonded to Formula 1;

L ₂ is a single bond or is selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, or a phenylene group, a biphenylene group, or a carbazolyl group. Can;

R ₁₃ and R ₁₄ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ Or R ₁₃ and R ₁₄ may combine to form a condensed ring;

The alkyl group, aryl group, heteroaryl group and arylamine group of R ₁₃ and R ₁₄ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of the, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and one substituent at least one selected from the group consisting of C ₆ ~ with an aryl silyl group of C ₄₀ of the When substituted or unsubstituted, and when there are a plurality of said substituents, they may be the same or different from each other.

The compounds of the present invention may be specifically represented as compounds of the structures exemplified below, but are not limited thereto.

2. Organic electroluminescent device

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

More specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers. Includes a compound represented by the formula (1). In this case, the compound may be used alone, or two or more kinds thereof may be mixed and used.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by Formula 1 have. Specifically, the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer.

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

The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a hole transport layer, electron blocking layer, light emission The auxiliary layer may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.

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

The organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.

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

The substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

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

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

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, it is possible to use conventional materials known in the art.

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

[[ 준비예Preparation 1] One]

IA-IA- 1와1 and IA-3의 합성 Synthesis of IA-3

<Step 1> 2 '-(2- Chloro -1H-indol-3-yl)-[1,1'-biphenyl] -2- Amine synthesis

3-bromo-2-chloro-1H-indole (11.5 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane- under nitrogen stream 2-yl)-[1,1'-biphenyl] -2-amine (14.7 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml) then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain 2 '-(2-chloro-1H-indol-3-yl)-[1,1'-biphenyl] -2-amine (11.9 g, yield 75%). )

¹ H-NMR: δ 6.25 (s, 1H), 6.68 (t, 1H), 6.88 (t, 1H), 7.13 (m, 3H), 7.48 (m, 5H), 7.84 (d, 2H), 11.9 ( s, 1 H)

<Step 2> 9,10- Dihydrodibenzo [4,5: 6,7] Aspino [2,3-b] Indole synthesis

2 '-(2-chloro-1H-indol-3-yl)-[1,1'-biphenyl] -2-amine (12.75 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol ), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent of the filtered organic layer was removed, and then purified by column chromatography, 9,10-dihydrodibenzo [4,5: 6,7] azino [2,3-b] indole (7 g, yield 62). %) Was obtained.

¹ H-NMR: δ 4.0 (s, 1H), 6.68 (d, 1H), 7.12 (m, 3H), 7.48 (m, 5H), 7.86 (d, 2H), 11.9 (s, 1H)

Step 3 Synthesis of IA-1 and IA-3

9,10-dihydrodibenzo [4,5: 6,7] azetino [2,3-b] indole (8.47 g, 30.0 mmol), iodobenzene (6.12 g, 30.0 mmol), Cu under a nitrogen stream Powder (0.45 g, 15.0 mmol), K ₂ CO ₃ (12.4 g, 90.0 mmol), nitrobenzene (200 ml) were mixed and stirred at 250 ° C. for 12 h.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain IA-1 (4.62 g, yield 43%) and IA-3 (4.62 g, yield 43%).

IA-1_ ¹ H-NMR: δ 4.01 (s, 1H), 6.68 (d, 1H), 6.88 (t, 1H), 7.15 (t, 1H), 7.46 (m, 10H), 7.73 (d, 1H) , 7.84 (d, 2H), 8.15 (d, 1H)

IA-3_ ¹ H-NMR: δ 6.62 (d, 3H), 6.85 (t, 2H), 7.17 (m, 5H), 7.52 (t, 5H), 7.86 (d, 2H), 11.9 (s, 1H)

[[ 준비예Preparation 2] 2]

IA-2와 IA-4의 합성Synthesis of IA-2 and IA-4

<Step 1> 2 '-(1H-indol-2-yl)-[1,1'-biphenyl]- Amine synthesis

2-bromo-1H-indole (9.80 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) under nitrogen stream -[1,1'-biphenyl] -2-amine (14.7 g, 50.0 mmol), K ₂ C0 ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml ) Was mixed and Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added thereto, followed by stirring at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain 2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2-amine (10.5 g, yield 74%).

¹ H-NMR: δ 6.28 (s, 1H), 6.84 (m, 5H), 7.17 (t, 1H), 7.52 (m, 4H), 7.68 (d, 1H), 7.86 (d, 2H), 11.2 ( s, 1 H)

<Step 2> 2 '-(3- Iodo -1H-indol-2-yl)-[1,1'-biphenyl} -2- Amine synthesis

2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2-amine (5.68 g, 20.0 mmol) and KOH (2.81 g, 50.0 mmol) were dissolved in 80 ml DMF at room temperature. Stir for 20 minutes. I ₂ (5.07 g, 20.0 mmol) dissolved in DMF was added and stirred for 1 hour.

After completion of the reaction, 100 ml of ice water was added and the solids were extracted. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2 '-(3-iodo-1H-indol-2-yl)-[1,1'-biphenyl] -2-amine (7.63 g, yield 93%).

¹ H-NMR: δ 6.25 (s, 1H), 6.71 (d, 1H), 6.93 (m, 3H), 7.15 (t, 1H), 7.53 (t, 3H), 7.65 (d, 1H), 7.92 ( m, 3H), 11.2 (s, 1H)

<Step 3> 9,14- Dihydrodibenzo [4,5: 6,7] azino [3,2-b] Indole synthesis

2 '-(3-iodo-1H-indol-2-yl)-[1,1'-biphenyl] -2-amine (16.4 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent of the filtered organic layer was removed, and then purified by column chromatography, 9,14-dihydrodibenzo [4,5: 6,7] azino [3,2-b] indole (6.55 g, yield 58). %) Was obtained.

¹ H-NMR: δ 4.1 (s, 1H), 6.53 (t, 1H), 6.72 (d, 1H), 6.88 (t, 1H), 7.02 (t, 1H), 7.18 (d, 1H), 7.48 ( m, 4H), 7.68 (d, 1H), 7.86 (d, 2H), 11.2 (s, 1H)

<Step 4> IA- 3 and Synthesis of IA-4

9,14-dihydrodibenzo [4,5: 6,7] azetino [3,2-b] indole (16.9 g, 60.0 mmol) and iodobenzene (6.12 g, 30.0 mmol), Cu under a nitrogen stream Powder (0.45 g, 15.0 mmol), K ₂ CO ₃ (12.4 g, 90.0 mmol), nitrobenzene (200 ml) were mixed and stirred at 250 ° C. for 12 h.

After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain IA-2 (9.46 g, yield 44%) and IA-4 (9.46 g, yield 44%).

IA-2_ ¹ H-NMR: δ 4.08 (s, 1H), 6.67 (d, 1H), 6.85 (t, 1H), 7.27 (m, 3H), 7.52 (m, 9H), 7.86 (d, 2H) , 7.92 (d, 2 H)

IA-4_ ¹ H-NMR: δ 6.64 (m, 4H), 6.84 (t, 2H), 6.97 (t, 1H), 7.18 (t, 3H), 7.52 (m, 4H), 7.65 (d, 1H) , 7.86 (d, 2H), 11.32 (s, 1H)

[[ 준비예Preparation 3] 3]

IA-5의 합성Synthesis of IA-5

<Step 1> 2 '-(2- Chloro Synthesis of -1H-indol-3-yl)-[1,1'-biphenyl] -2-ol

3-bromo-2-chloro-1H-indole (11.5 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane- under nitrogen stream 2-yl)-[1,1'-biphenyl] -2-amine (14.8 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml) then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added thereto and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain 2 '-(2-chloro-1H-indol-3-yl)-[1,1'-biphenyl] -2-ol (11.5 g, 72% yield). )

¹ H-NMR: δ 5.32 (s, 1H), 7.04 (m, 4H), 7.23 (t, 1H), 7.53 (m, 5H), 7.86 (d, 2H), 11.87 (s, 1H)

Step 2 Synthesis of IA-5

2 '-(2-chloro-lH-indol-3-yl)-[1,1'-biphenyl] -2-ol (12.8 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol) ), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound IA-5 (10.4 g, 92% yield).

¹ H-NMR: δ 7.04 (m, 4H), 7.25 (t, 1H), 7.54 (m, 5H), 7.86 (d, 2H), 11.92 (s, 1H)

[[ 준비예Preparation 4] 4]

IA-6의 합성Synthesis of IA-6

<Step 1> 2 '-(2- Chloro -1H-indol-3-yl)-[1,1'-biphenyl] -2- Thiol synthesis

3-bromo-2-chloro-1H-indole (11.5 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane- under nitrogen stream 2-yl)-[1,1'-biphenyl] -2-thiol (15.6 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml) then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography to obtain 2 '-(2-chloro-1H-indol-3-yl)-[1,1'-biphenyl] -2-thiol (13.1 g, yield 78%). )

¹ H-NMR: δ 3.38 (s, 1H), 7.06 (t, 2H), 7.27 (t, 2H), 7.52 (m, 6H), 7.86 (d, 2H), 11.8 (s, 1H)

Step 2 Synthesis of IA-6

2 '-(2-chloro-1H-indol-3-yl)-[1,1'-biphenyl] -2-thiol (13.4 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol ), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound IA-6 (11.3 g, yield 95%).

¹ H-NMR: δ 7.06 (t, 2H), 7.27 (t, 2H), 7.52 (m, 6H), 7.86 (d, 2H), 11.87 (s, 1H)

[[ 준비예Preparation 5] 5]

IA-7의 합성Synthesis of IA-7

<Step 1> 2 '-( benzofuran -2-yl)-[1,1'-biphenyl] -2- Amine synthesis

2-bromobenzofuran (9.85 g, 50.0 mmol) under nitrogen stream, 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[ 1,1'-biphenyl] -2-amine (14.7 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml) After mixing, Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain 2 '-(benzofuran-2-yl)-[1,1'-biphenyl] -2-amine (10.8 g, yield 76%).

¹ H-NMR: δ 6.25 (s, 1H), 6.67 (d, 1H), 6.85 (t, 1H), 7.15 (m, 2H), 7.42 (m, 5H), 7.67 (d, 1H), 7.88 ( d, 3H)

<Step 2> 2 '-(3- Iodobenzofuran -2-yl)-[1,1'-biphenyl] -2- Amine synthesis

2 '-(benzofuran-2-yl)-[1,1'-biphenyl] -2-amine (5.70 g, 20.0 mmol) and KOH (2.81 g, 50.0 mmol) were dissolved in 80 ml DMF and then cooled to 20 at room temperature. Stir for minutes. I ₂ (5.07 g, 20.0 mmol) dissolved in DMF was added and stirred for 1 hour.

After completion of the reaction, ice water is added and the solid is extracted. After removing the solvent of the filtered organic layer using column chromatography to give the target compound 2 '-(3-iodobenzofuran-2-yl)-[1,1'-biphenyl] -2-amine (7.73 g, Yield 94%).

¹ H-NMR: δ 6.24 (s, 1H), 6.66 (d, 1H), 6.85 (t, 1H), 7.14 (t, 1H), 7.45 (m, 5H), 7.64 (d, 1H), 7.87 ( d, 3H)

Step 3 Synthesis of IA-7

2 '-(3-iodobenzofuran-2-yl)-[1,1'-biphenyl] -2-amine (16.45 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol) , P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the organic layer was filtered and purified by column chromatography to give the title compound IA-7 (7.25 g, 64% yield).

¹ H-NMR: δ 4.03 (s, 1H), 6.67 (d, 1H), 6.85 (d, 1H), 7.14 (d, 1H), 7.45 (m, 5H), 7.64 (d, 1H), 7.87 ( d, 3H)

[[ 준비예Preparation 6] 6]

IA-8의 합성Synthesis of IA-8

<Step 1> 2 '-( Benzo [b] thiophene -2-yl)-[1,1'-biphenyl] -2- Amine synthesis

2-bromobenzo [b] thiophene (10.6 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- under nitrogen stream Yl)-[1,1'-biphenyl] -2-amine (14.7 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml) was mixed, and then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added thereto and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain 2 '-(benzo [b] thiophen-2-yl)-[1,1'-biphenyl] -2-amine (11.6 g, yield 77%). Got.

¹ H-NMR: δ 6.25 (s, 1H), 6.65 (d, 1H), 6.86 (t, 1H), 7.14 (t, 1H), 7.49 (m, 5H), 7.68 (s, 1H), 7.83 ( d, 3H), 7.96 (d, 1H)

<Step 2> 2 '-(3- Iodobenzo [b] thiophene -2-yl)-[1,1'-biphenyl] -2- Amine synthesis

2 '-(benzo [b] thiophen-2-yl)-[1,1'-biphenyl] -2-amine (6.03 g, 20.0 mmol) and KOH (2.81 g, 50.0 mmol) dissolved in 80 ml DMF After stirring at room temperature for 20 minutes. I ₂ (5.07 g, 20.0 mmol) dissolved in DMF was added and stirred for 1 hour.

After completion of the reaction, ice water is added and the solid is extracted. After removing the solvent of the filtered organic layer, using column chromatography, the target compound 2 '-(3-iodobenzo [b] thiophen-2-yl)-[1,1'-biphenyl] -2-amine (8.20 g, yield 96%) was obtained.

¹ H-NMR: δ 6.25 (s, 1H), 6.66 (d, 1H), 6.85 (s, 1H), 7.14 (t, 1H), 7.49 (m, 5H), 7.86 (d, 2H), 8.03 ( d, 2H)

Step 3 Synthesis of IA-8

2 '-(3-iodobenzofuran-2-yl)-[1,1'-biphenyl] -2-amine (17.1 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol) , P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound IA-8 (7.90 g, 66% yield).

¹ H-NMR: δ 3.98 (s, 1H), 6.67 (d, 1H), 6.85 (t, 1H), 7.14 (t, 1H), 7.51 (m, 5H), 7.84 (d, 2H), 8.03 ( d, 2H)

[[ 준비예Preparation 7] 7]

IA-9의 합성Synthesis of IA-9

<Step 1> 2 '-( Benzofuran -2-yl)-[1,1'-biphenyl] -2- Amine synthesis

3-bromo-2-chlorobenzofuran (11.6 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2- under nitrogen stream Il)-[1,1'-biphenyl] -2-amine (14.7 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml) was mixed, and then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added thereto and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer and purified by column chromatography to obtain 2 '-(2-chlorobenzofuran-3-yl)-[1,1'-biphenyl] -2-amine (11.8 g, yield 74%). Got it.

¹ H-NMR: δ 6.25 (s, 1H), 6.65 (d, 1H), 6.86 (t, 1H), 7.14 (t, 1H), 7.42 (m, 5H), 7.64 (d, 1H), 7.87 ( d, 3H)

<Step 2> IA- 9 of synthesis

2 '-(2-chlorobenzofuran-3-yl)-[1,1'-biphenyl] -2-amine (12.8 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound IA-9 (7.59 g, yield 67%).

¹ H-NMR: δ 4.02 (s, 1H), 6.66 (d, 1H), 6.85 (t, 1H), 7.14 (t, 1H), 7.45 (t, 5H), 7.64 (d, 1H), 7.88 ( d, 3H)

[[ 준비예Preparation 8] 8]

IA-8의 합성Synthesis of IA-8

<Step 1> 2 '-(2- Chlorobenzo [b] thiophene -3-yl)-[1,1'-biphenyl] -2- Amine synthesis

3-bromo-2-chlorobenzo [b] thiophene (12.4 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaboro under nitrogen stream Lan-2-yl)-[1,1'-biphenyl] -2-amine (14.7 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml) is mixed and then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography to obtain 2 '-(2-chlorobenzo [b] thiophen-3-yl)-[1,1'-biphenyl] -2-amine (12.1 g, yield). 72%).

¹ H-NMR: δ 6.25 (s, 1H), 6.66 (d, 1H), 6.85 (t, 1H), 7.14 (t, 1H), 7.52 (m, 5H), 7.86 (d, 2H), 7.97 ( d, 1H), 8.43 (d, 1H)

<Step 2> IA- 10 of synthesis

2 '-(2-chlorobenzo [b] thiophen-3-yl)-[1,1'-biphenyl] -2-amine (13.4 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound IA-10 (8.14 g, yield 78%).

¹ H-NMR: δ 3.98 (s, 1H), 6.67 (d, 1H), 6.85 (t, 1H), 7.14 (t, 1H), 7.49 (m, 5H), 7.86 (d, 2H), 7.97 ( d, 1H), 8.43 (d, 1H)

[[ 준비예Preparation 9] 9]

IA-11의 합성Synthesis of IA-11

<Step 1> Synthesis of 2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2-ol

2-bromo-1H-indole (9.80 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) under nitrogen stream -[1,1'-biphenyl] -2-ol (14.8 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml ) And then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain 2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2-ol (10.4 g, 73% yield).

¹ H-NMR: δ 5.34 (s, 1H), 6.75 (s, 1H), 7.03 (m, 4H), 7.22 (t, 1H), 7.55 (m, 5H), 7.86 (d, 2H)

<Step 2> 2 '-(3- Iodo Synthesis of -1H-indol-2-yl)-[1,1'-biphenyl] -2-ol

2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2-ol (5.70 g, 20.0 mmol) and KOH (2.81 g, 50.0 mmol) were dissolved in 80 ml DMF at room temperature. Stir for 20 minutes. I ₂ (5.07 g, 20.0 mmol) dissolved in DMF was added and stirred for 1 hour.

After completion of the reaction, ice water is added and the solid is extracted. After removing the solvent of the filtered organic layer using column chromatography to give the target compound 2 '-(3-iodo-1H-indol-2-yl)-[1,1'-biphenyl] -2-ol (7.57 g, yield 92%).

¹ H-NMR: δ 5.33 (s, 1H), 7.03 (m, 4H), 7.23 (t, 1H), 7.45 (t, 2H), 7.66 (d, 2H), 7.92 (d, 3H), 11.2 ( s, 1 H)

Step 3 Synthesis of IA-11

2 '-(3-iodo-1H-indol-2-yl)-[1,1'-biphenyl] -2-ol (16.4 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the organic layer was filtered and purified by column chromatography to give the title compound IA-11 (7.14 g, 63% yield).

¹ H-NMR: δ 7.03 (m, 4H), 7.23 (t, 1H), 7.45 (t, 2H), 7.65 (d, 2H), 7.88 (d, 3H), 11.2 (s, 1H)

[[ 준비예Preparation 10] 10]

IA-12의 합성Synthesis of IA-12

<Step 1> 2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2- Thiol synthesis

2-bromo-1H-indole (9.80 g, 50.0 mmol), 2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) under nitrogen stream -[1,1'-biphenyl] -2-thiol (19.5 g, 50.0 mmol), K ₂ CO ₃ (13.8 g, 100.0 mmol) and 1,4-dioxane / H ₂ O (120 ml / 40 ml ) And then Pd (PPh ₃ ) ₄ (2.88 g, 5 mol%) was added and stirred at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain 2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2-thiol (11.3 g, yield 75%).

¹ H-NMR: δ 3.38 (s, 1H), 6.75 (d, 1H), 6.93 (t, 2H), 7.27 (t, 2H), 7.53 (m, 6H), 7.86 (d, 2H), 11.31 ( s, 1 H)

<Step 2> 2 '-(3- Iodo -1H-indol-2-yl)-[1,1'-biphenyl] -2- Thiol synthesis

2 '-(1H-indol-2-yl)-[1,1'-biphenyl] -2-thiol (6.02 g, 20.0 mmol) and KOH (2.81 g, 50.0 mmol) were dissolved in 80 ml DMF at room temperature. Stir for 20 minutes. I ₂ (5.07 g, 20.0 mmol) dissolved in DMF was added and stirred for 1 hour.

After completion of the reaction, ice water is added and the solid is extracted. The solvent of the filtered organic layer was removed, and then column chromatography was performed to obtain 2 '-(3-iodo-1H-indol-2-yl)-[1,1'-biphenyl] -2-thiol (8.03). g, yield 94%).

¹ H-NMR: δ 3.38 (s, 1H), 6.95 (t, 2H), 7.27 (t, 2H), 7.46 (m, 3H), 7.65 (d, 2H), 7.92 (d, 3H), 11.2 ( s, 1 H)

Step 3 Synthesis of IA-12

2 '-(3-iodo-1H-indol-2-yl)-[1,1'-biphenyl] -2-thiol (17.1 g, 40.0 mmol) and Pd ₂ (dba) ₃ (0.86 g, 1 mmol), P (t-Bu) ₃ (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 150 ml toluene and stirred at 110 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound IA-12 (7.42 g, yield 62%).

¹ H-NMR: δ 6.95 (t, 2H), 7.27 (t, 2H), 7.46 (m, 3H), 7.65 (d, 2H), 7.89 (d, 3H), 11.4 (s, 1H)

[[ 합성예Synthesis Example 1] One]

A-14의 합성Synthesis of A-14

IA-1 (3.58 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound A-14 (4.95 g, 84% yield).

MS [M + 1] ⁺ 590

[[ 합성예Synthesis Example 2] 2]

A-16의 합성Synthesis of A-16

Synthesis Example 1 except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The same method was followed to obtain the target compound A-16 (4.82 g, yield 82%).

MS [M + 1] ⁺ 589

[[ 합성예Synthesis Example 3] 3]

A-17의 합성Synthesis of A-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound A-17 (5.65 g, Yield 85%) was obtained in the same manner as in Synthesis example 1 except that was used.

MS [M + 1] ⁺ 666

[[ 합성예Synthesis Example 4] 4]

A-19의 합성Synthesis of A-19

Except for using 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Was prepared in the same manner as in Synthesis example 1 to obtain the title compound A-19 (5.31 g, yield 80%).

MS [M + 1] ⁺ 665

[[ 합성예Synthesis Example 5] 5]

A-26의 합성Synthesis of A-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound A-26 (5.65 g, yield 75%) was obtained by the same method as Synthesis Example 1, except that 1, -biphenyl] -4-amine (4.76 g, 10.00 mmol) was used.

MS [M + 1] ⁺ 754

[[ 합성예Synthesis Example 6] 6]

A-41의 합성Synthesis of A-41

Same method as in Synthesis Example 1, except using 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound A-41 (4.38 g, yield 78%).

MS [M + 1] ⁺ 563

[[ 합성예Synthesis Example 7] 7]

A-53의 합성Synthesis of A-53

Same method as in Synthesis Example 1, except using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound A-53 (4.26 g, yield 76%).

MS [M + 1] ⁺ 562

[[ 합성예Synthesis Example 8] 8]

A-59의 합성Synthesis of A-59

Use 2-bromo-4- (4- (naphthalen-1-yl) phenyl) quinazolin (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound A-59 (5.51 g, yield 80%) was obtained in the same manner as in Synthesis example 1 except for the following.

MS [M + 1] ⁺ 689

[[ 합성예Synthesis Example 9] 9]

A-64의 합성Synthesis of A-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound A-64 (6.78 g, yield 78%) was obtained.

MS [M + 1] ⁺ 871

[[ 합성예Synthesis Example 10] 10]

B-14의 합성Synthesis of B-14

IA-2 (3.58 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound B-14 (5.07 g, yield 86%).

MS [M + 1] ⁺ 590

[[ 합성예Synthesis Example 11] 11]

B-16의 합성Synthesis of B-16

Synthesis Example 10, except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The same method was followed to obtain the target compound B-16 (5.07 g, yield 84%).

MS [M + 1] ⁺ 589

[[ 합성예Synthesis Example 12] 12]

B-17의 합성Synthesis of B-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound B-17 (5.79 g, yield 87%) was obtained in the same manner as in Synthesis example 10 except for using a).

MS [M + 1] ⁺ 666

[[ 합성예Synthesis Example 13] 13]

B-19의 합성Synthesis of B-19

Except for using 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Was prepared in the same manner as in Synthesis Example 10 to obtain the title compound B-19 (5.45 g, yield 82%).

MS [M + 1] ⁺ 665

[[ 합성예Synthesis Example 14] 14]

B-26의 합성Synthesis of B-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound B-26 (5.80 g, yield 77%) was obtained by the same method as Synthesis Example 10, except using, 1'-biphenyl] -4-amine (4.76 g, 10.00 mmol).

MS [M + 1] ⁺ 754

[[ 합성예Synthesis Example 15] 15]

B-41의 합성Synthesis of B-41

The same method as in Synthesis Example 10 except for using 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The obtained compound B-41 (4.50 g, yield 80%) was obtained.

MS [M + 1] ⁺ 563

[[ 합성예Synthesis Example 16] 16]

B-53의 합성Synthesis of B-53

Same method as in Synthesis Example 10, except that 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound B-53 (4.38 g, yield 78%).

MS [M + 1] ⁺ 562

[[ 합성예Synthesis Example 17] 17]

B-59의 합성Synthesis of B-59

Use 2-bromo-4- (4- (naphthalen-1-yl) phenyl) quinazolin (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound B-59 (5.64 g, Yield 82%) was obtained in the same manner as in Synthesis Example 10 except for the following procedure.

MS [M + 1] ⁺ 689

[[ 합성예Synthesis Example 18] 18]

B-64의 합성Synthesis of B-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 10 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound B-64 (6.96 g, yield 80%) was obtained.

MS [M + 1] ⁺ 871

[[ 합성예Synthesis Example 19] 19]

C-14의 합성Synthesis of C-14

IA-3 (3.58 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the organic layer was filtered and purified by column chromatography to give the title compound C-14 (4.59g, 78% yield).

MS [M + 1] ⁺ 590

[[ 합성예Synthesis Example 20] 20]

C-16의 합성Synthesis of C-16

Synthesis Example 19, except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The same method was followed to obtain the target compound C-16 (4.41 g, yield 75%).

MS [M + 1] ⁺ 589

[[ 합성예Synthesis Example 21] 21]

C-17의 합성Synthesis of C-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound C-17 (5.32 g, Yield 80%) was obtained in the same manner as in Synthesis example 19 except for using).

MS [M + 1] ⁺ 666

[[ 합성예Synthesis Example 22] 22]

C-19의 합성Synthesis of C-19

Except for using 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Was prepared in the same manner as in Synthesis Example 19 to obtain the title compound C-19 (4.85 g, yield 73%).

MS [M + 1] ⁺ 679

[[ 합성예Synthesis Example 23] 23]

C-26의 합성Synthesis of C-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound C-26 (5.12 g, 68% yield) was obtained by the same method as Synthesis Example 19 except for using, 1'-biphenyl] -4-amine (4.76 g, 10.00 mmol).

MS [M + 1] ⁺ 665

[[ 합성예Synthesis Example 24] 24]

C-41의 합성Synthesis of C-41

The same method as in Synthesis Example 19, except that 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The desired compound C-41 (3.93 g, yield 70%) was obtained.

MS [M + 1] ⁺ 754

[[ 합성예Synthesis Example 25] 25]

C-53의 합성Synthesis of C-53

Same method as in Synthesis Example 19, except using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound C-53 (3.65 g, yield 65%).

MS [M + 1] ⁺ 602

[[ 합성예Synthesis Example 26] 26]

C-59의 합성Synthesis of C-59

Use 2-bromo-4- (4- (naphthalen-1-yl) phenyl) quinazolin (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound C-59 (4.94 g, Yield 72%) was obtained in the same manner as in Synthesis example 19 except for the following.

MS [M + 1] ⁺ 563

[[ 합성예Synthesis Example 27] 27]

C-64의 합성Synthesis of C-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 19 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound C-64 (6.17 g, yield 71%) was obtained.

MS [M + 1] ⁺ 562

[[ 합성예Synthesis Example 28] 28]

D-14의 합성Synthesis of D-14

IA-4 (3.58 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound D-14 (4.83 g, yield 82%).

MS [M + 1] ⁺ 590

[[ 합성예Synthesis Example 29] 29]

D-16의 합성Synthesis of D-16

Synthesis Example 28, except that 4-chloro-2,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same method was followed to obtain the target compound D-16 (4.65 g, yield 79%).

MS [M + 1] ⁺ 589

[[ 합성예Synthesis Example 30] 30]

D-17의 합성Synthesis of D-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using), the same method as in Synthesis Example 28 was carried out to obtain the target compound D-17 (5.59 g, yield 84%).

MS [M + 1] ⁺ 666

[[ 합성예Synthesis Example 31] 31]

D-19의 합성Synthesis of D-19

Except for using 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (3.43 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Was prepared in the same manner as in Synthesis Example 28 to obtain the title compound D-19 (5.65 g, 85% yield).

MS [M + 1] ⁺ 665

[[ 합성예Synthesis Example 32] 32]

D-26의 합성Synthesis of D-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound D-26 (5.72 g, yield 76%) was obtained by the same method as Synthesis Example 28 except for using, 1'-biphenyl] -4-amine (4.76 g, 10.00 mmol).

MS [M + 1] ⁺ 754

[[ 합성예Synthesis Example 33] 33]

D-41의 합성Synthesis of D-41

The same method as in Synthesis 28, except that 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The desired compound D-41 (4.50 g, yield 80%) was obtained.

MS [M + 1] ⁺ 563

[[ 합성예Synthesis Example 34] 34]

D-53의 합성Synthesis of D-53

Same method as in Synthesis Example 28, except using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound D-53 (4.21 g, yield 75%).

MS [M + 1] ⁺ 562

[[ 합성예Synthesis Example 35] 35]

D-59의 합성Synthesis of D-59

Use 2-bromo-4- (4- (naphthalen-1-yl) phenyl) quinazolin (4.11 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound D-59 (5.64 g, Yield 82%) was obtained in the same manner as in Synthesis Example 28 except for the following procedure.

MS [M + 1] ⁺ 689

[[ 합성예Synthesis Example 36] 36]

D-64의 합성Synthesis of D-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 28 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound D-64 (6.26 g, yield 72%) was obtained.

MS [M + 1] ⁺ 871

[[ 합성예Synthesis Example 37] 37]

E-14의 합성Synthesis of E-14

IA-5 (2.83 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound E-14 (3.60 g, 70% yield).

MS [M + 1] ⁺ 515

[[ 합성예Synthesis Example 38] 38]

E-17의 합성Synthesis of E-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound E-17 (4.48 g, 76% yield) was obtained in the same manner as in Synthesis example 37 except for using a).

MS [M + 1] ⁺ 591

[[ 합성예Synthesis Example 39] 39]

E-26의 합성Synthesis of E-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound E-26 (4.95 g, 73% yield) was obtained by the same method as Synthesis Example 37, except that 1, -biphenyl] -4-amine (4.76 g, 10.00 mmol) was used.

MS [M + 1] ⁺ 679

[[ 합성예Synthesis Example 40] 40]

E-41의 합성Synthesis of E-41

Same method as in Synthesis Example 37, except for using 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound E-41 (3.31 g, yield 68%).

MS [M + 1] ⁺ 488

[[ 합성예Synthesis Example 41] 41]

E-53의 합성Synthesis of E-53

The same method as in Synthesis Example 37 except for using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The obtained compound E-53 (3.64 g, yield 75%) was obtained.

MS [M + 1] ⁺ 487

[[ 합성예Synthesis Example 42] 42]

E-64의 합성Synthesis of E-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 37 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound E-64 (5.72 g, Yield 72%) was obtained.

MS [M + 1] ⁺ 795

[[ 합성예Synthesis Example 43] 43]

F-14의 합성Synthesis of F-14

IA-6 (2.99 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound F-14 (3.82 g, yield 72%) by column chromatography.

MS [M + 1] ⁺ 531

[[ 합성예Synthesis Example 44] 44]

F-17의 합성Synthesis of F-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using), the same method as in Synthesis Example 43 was carried out to obtain the target compound F-17 (4.79 g, yield 79%).

MS [M + 1] ⁺ 607

[[ 합성예Synthesis Example 45] 45]

F-26의 합성Synthesis of F-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound F-26 (4.86 g, yield 70%) was obtained in the same manner as in Synthesis Example 43, except that 1, -biphenyl] -4-amine (4.76 g, 10.00 mmol) was used.

MS [M + 1] ⁺ 695

[[ 합성예Synthesis Example 46] 46]

F-41의 합성Synthesis of F-41

The same method as in Synthesis 43, except that 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) is used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. This carried out the title compound F-41 (3.27 g, yield 65%).

MS [M + 1] ⁺ 504

[[ 합성예Synthesis Example 47] 47]

F-53의 합성Synthesis of F-53

Same method as in Synthesis Example 43, except using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound F-53 (3.41 g, yield 68%).

MS [M + 1] ⁺ 503

[[ 합성예Synthesis Example 48] 48]

F-64의 합성Synthesis of F-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 43 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound F-64 (5.92 g, yield 73%) was obtained.

MS [M + 1] ⁺ 812

[[ 합성예Synthesis Example 49] 49]

G-14의 합성Synthesis of G-14

IA-7 (2.83 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound G-14 (3.85 g, yield 75%).

MS [M + 1] ⁺ 515

[[ 합성예Synthesis Example 50] 50]

G-17의 합성Synthesis of G-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound G-17 (4.90 g, Yield 83%) was obtained in the same manner as in Synthesis Example 49 except for using a).

MS [M + 1] ⁺ 591

[[ 합성예Synthesis Example 51] 51]

G-26의 합성Synthesis of G-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound G-26 (5.22 g, yield 77%) was obtained by the same method as Synthesis Example 49 except for using, 1'-biphenyl] -4-amine (4.76 g, 10.00 mmol).

MS [M + 1] ⁺ 679

[[ 합성예Synthesis Example 52] 52]

G-41의 합성Synthesis of G-41

Same procedure as in Synthesis 49 except for using 2-bromo-4-phenylquinazoline (2.85 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The desired compound G-41 (3.51 g, yield 72%) was obtained.

MS [M + 1] ⁺ 488

[[ 합성예Synthesis Example 53] 53]

G-53의 합성Synthesis of G-53

Same method as in Synthesis 49, except that 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound G-53 (3.79 g, yield 78%).

MS [M + 1] ⁺ 487

[[ 합성예Synthesis Example 54] 54]

G-64의 합성Synthesis of G-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 49 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound G-64 (5.64 g, yield 71%) was obtained.

MS [M + 1] ⁺ 795

[[ 합성예Synthesis Example 55] 55]

H-14의 합성Synthesis of H-14

IA-8 (2.99 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound H-14 (3.92 g, 74% yield).

MS [M + 1] ⁺ 531

[[ 합성예Synthesis Example 56] 56]

H-17의 합성Synthesis of H-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound H-17 (4.97 g, 82% yield) was obtained in the same manner as in Synthesis Example 55 except for using).

MS [M + 1] ⁺ 607

[[ 합성예Synthesis Example 57] 57]

H-26의 합성Synthesis of H-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound H-26 (5.07 g, 73% yield) was obtained by the same method as Synthesis Example 55 except for using, l'-biphenyl] -4-amine (4.76 g, 10.00 mmol).

MS [M + 1] ⁺ 695

[[ 합성예Synthesis Example 58] 58]

H-41의 합성Synthesis of H-41

The same method as in Synthesis Example 55 except for using 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The desired compound H-41 (3.42 g, yield 68%) was obtained.

MS [M + 1] ⁺ 504

[[ 합성예Synthesis Example 59] 59]

H-53의 합성Synthesis of H-53

Same method as in Synthesis Example 55 except for using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine This carried out the title compound H-53 (3.76 g, yield 75%).

MS [M + 1] ⁺ 503

[[ 합성예Synthesis Example 60] 60]

H-64의 합성Synthesis of H-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 55 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound H-64 (5.43 g, yield 67%) was obtained.

MS [M + 1] ⁺ 812

[[ 합성예Synthesis Example 61] 61]

I-14의 합성Synthesis of I-14

IA-9 (2.83 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the organic layer was filtered and purified by column chromatography to give the title compound I-14 (3.75 g, 73% yield).

MS [M + 1] ⁺ 515

[[ 합성예Synthesis Example 62] 62]

I-17의 합성Synthesis of I-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound I-17 (4.54 g, Yield 77%) was obtained in the same manner as in Synthesis Example 61 except for using a).

MS [M + 1] ⁺ 591

[[ 합성예Synthesis Example 63] 63]

I-26의 합성Synthesis of I-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound I-26 (5.02 g, yield 74%) was obtained by the same method as Synthesis Example 61 except for using 1'-biphenyl] -4-amine (4.76 g, 10.00 mmol).

MS [M + 1] ⁺ 679

[[ 합성예Synthesis Example 64] 64]

I-41의 합성Synthesis of I-41

Same method as in Synthesis Example 61, except that 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The desired compound I-41 (3.26 g, yield 67%) was obtained.

MS [M + 1] ⁺ 488

[[ 합성예Synthesis Example 65] 65]

I-53의 합성Synthesis of I-53

Same procedure as in Synthesis Example 61, except using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The obtained compound I-53 (3.26 g, yield 67%) was obtained.

MS [M + 1] ⁺ 487

[[ 합성예Synthesis Example 66] 66]

I-64의 합성Synthesis of I-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 61 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound I-64 (5.56 g, yield 70%) was obtained.

MS [M + 1] ⁺ 795

[[ 합성예Synthesis Example 67] 67]

J-14의 합성Synthesis of J-14

IA-10 (2.99 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound J-14 (3.60 g, yield 68%).

MS [M + 1] ⁺ 531

[[ 합성예Synthesis Example 68] 68]

J-17의 합성Synthesis of J-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using), the same method as in Synthesis Example 67 was performed to obtain the target compound J-17 (4.55 g, yield 75%).

MS [M + 1] ⁺ 607

[[ 합성예Synthesis Example 69] 69]

J-26의 합성Synthesis of J-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound J-26 (4.51 g, 65% yield) was obtained in the same manner as in Synthesis Example 67, except that 1, -biphenyl] -4-amine (4.76 g, 10.00 mmol) was used.

MS [M + 1] ⁺ 695

[[ 합성예Synthesis Example 70] 70]

J-41의 합성Synthesis of J-41

The same method as in Synthesis Example 67 except for using 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. This carried out the title compound J-41 (3.17 g, yield 63%).

MS [M + 1] ⁺ 504

[[ 합성예Synthesis Example 71] 71]

J-53의 합성Synthesis of J-53

Same method as in Synthesis Example 67, except using 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The obtained compound J-53 (3.51 g, yield 70%) was obtained.

MS [M + 1] ⁺ 503

[[ 합성예Synthesis Example 72] 72]

J-64의 합성Synthesis of J-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 67 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound J-64 (5.92 g, yield 73%) was obtained.

MS [M + 1] ⁺ 812

[[ 합성예Synthesis Example 73] 73]

K-14의 합성Synthesis of K-14

IA-11 (2.83 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound K-14 (4.05 g, yield 79%).

MS [M + 1] ⁺ 515

[[ 합성예Synthesis Example 74] 74]

K-17의 합성Synthesis of K-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound K-17 (4.84 g, 82% yield) was obtained in the same manner as in Synthesis Example 73 except for using).

MS [M + 1] ⁺ 591

[[ 합성예Synthesis Example 75] 75]

K-26의 합성Synthesis of K-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound K-26 (5.36 g, 79% yield) was obtained in the same manner as in Synthesis Example 73, except that 1, -biphenyl] -4-amine (4.76 g, 10.00 mmol) was used.

MS [M + 1] ⁺ 679

[[ 합성예Synthesis Example 76] 76]

K-41의 합성Synthesis of K-41

The same method as in Synthesis 73, except that 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The desired compound K-41 (3.65 g, yield 75%) was obtained.

MS [M + 1] ⁺ 488

[[ 합성예Synthesis Example 77] 77]

K-53의 합성Synthesis of K-53

Same method as in Synthesis 73, except that 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The desired compound K-53 (4.03 g, yield 83%) was obtained.

MS [M + 1] ⁺ 487

[[ 합성예Synthesis Example 78] 78]

K-64의 합성Synthesis of K-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 73 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound K-64 (6.04 g, yield 76%) was obtained.

MS [M + 1] ⁺ 795

[[ 합성예Synthesis Example 79] 79]

L-14의 합성Synthesis of L-14

IA-12 (2.99 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol ), P (t-Bu) ₃ (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound L-14 (3.97 g, yield 75%) by column chromatography.

MS [M + 1] ⁺ 531

[[ 합성예Synthesis Example 80] 80]

L-17의 합성Synthesis of L-17

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound L-17 (5.15 g, Yield 85%) was obtained in the same manner as in Synthesis Example 79 except for using a).

MS [M + 1] ⁺ 607

[[ 합성예Synthesis Example 81] 81]

L-26의 합성Synthesis of L-26

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine A target compound L-26 (5.69 g, 82% yield) was obtained in the same manner as in Synthesis Example 79, except that 1, -biphenyl] -4-amine (4.76 g, 10.00 mmol) was used.

MS [M + 1] ⁺ 695

[[ 합성예Synthesis Example 82] 82]

L-41의 합성Synthesis of L-41

The same method as in Synthesis Example 79 except for using 2-bromo-4-phenylquinazolin (2.85 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The desired compound L-41 (3.67 g, yield 73%) was obtained.

MS [M + 1] ⁺ 504

[[ 합성예Synthesis Example 83] 83]

L-53의 합성Synthesis of L-53

The same method as in Synthesis 79, except that 8- (4-bromophenyl) quinoline (2.84 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound L-53 (3.97 g, yield 79%) was obtained.

MS [M + 1] ⁺ 503

[[ 합성예Synthesis Example 84] 84]

L-64의 합성Synthesis of L-64

N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 79 was carried out except that 1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.93 g, 10.00 mmol) was used. Compound L-64 (5.67 g, yield 70%) was obtained.

MS [M + 1] ⁺ 812

[[ 실시예Example 1~32] 1-32]

Fabrication of Green Organic EL Devices

Compounds A-14 to L-17 synthesized in Synthesis Examples 1 to 80 were subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / A-14 to L-17 each compound + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) / Alq on the thus prepared ITO transparent electrode _An organic EL device was fabricated by stacking ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

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

[[ 비교예Comparative example 1] One]

녹색 유기 EL 소자의 제작Fabrication of Green Organic EL Devices

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound A-14 as a light emitting host material when forming the emission layer.

[[ 평가예Evaluation example 1] One]

For each of the green organic EL devices produced in Examples 1 to 32 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. It was.

샘플Sample	호스트Host	구동전압(V)Driving voltage (V)	EL 피크(nm)EL peak (nm)	전류효율(cd/A)Current efficiency (cd / A)
실시예 1Example 1	A-14A-14	6.786.78	517517	40.240.2
실시예 2Example 2	A-16A-16	6.836.83	518518	41.541.5
실시예 3Example 3	A-17A-17	6.796.79	517517	40.640.6
실시예 4Example 4	A-19A-19	6.846.84	516516	42.342.3
실시예 5Example 5	B-14B-14	6.826.82	518518	40.440.4
실시예 6Example 6	B-16B-16	6.776.77	518518	41.341.3
실시예 7Example 7	B-17B-17	6.656.65	517517	42.942.9
실시예 8Example 8	B-19B-19	6.856.85	518518	41.841.8
실시예 9Example 9	C-14C-14	6.786.78	517517	40.340.3
실시예 10Example 10	C-16C-16	6.756.75	517517	41.641.6
실시예 11Example 11	C-17C-17	6.856.85	518518	40.740.7
실시예 12Example 12	C-19C-19	6.896.89	518518	40.840.8
실시예 13Example 13	D-14D-14	6.746.74	516516	41.341.3
실시예 14Example 14	D-16D-16	6.826.82	518518	41.941.9
실시예 15Example 15	D-17D-17	6.836.83	517517	45.245.2
실시예 16Example 16	D-19D-19	6.746.74	518518	41.941.9
실시예 17Example 17	E-14E-14	6.796.79	518518	42.342.3
실시예 18Example 18	E-17E-17	6.696.69	517517	41.741.7
실시예 19Example 19	F-14F-14	6.686.68	516516	42.742.7
실시예 20Example 20	F-17F-17	6.846.84	518518	40.840.8
실시예 21Example 21	G-14G-14	6.756.75	517517	41.341.3
실시예 22Example 22	G-17G-17	6.796.79	517517	42.242.2
실시예 23Example 23	H-14H-14	6.676.67	518518	40.640.6
실시예 24Example 24	H-17H-17	6.736.73	517517	41.241.2
실시예 25Example 25	I-14I-14	6.826.82	518518	40.740.7
실시예 26Example 26	I-17I-17	6.856.85	517517	41.341.3
실시예 27Example 27	J-14J-14	6.726.72	518518	41.941.9
실시예 28Example 28	J-17J-17	6.836.83	516516	42.842.8
실시예 29Example 29	K-14K-14	6.726.72	517517	41.041.0
실시예 30Example 30	K-17K-17	6.886.88	516516	42.942.9
실시예 31Example 31	L-14L-14	6.826.82	516516	43.543.5
실시예 32Example 32	L-17L-17	6.786.78	517517	42.542.5
비교예 1Comparative Example 1	CBPCBP	6.936.93	516516	38.238.2

As shown in Table 1, when the compounds (A-14 to L-17) according to the present invention were used as the light emitting layer of the green organic EL device (Examples 1-32), the green organic EL device using the conventional CBP (compared to Compared with Example 1, it can be seen that it shows better performance in terms of efficiency and driving voltage.

[[ 실시예Example 33~60] 33 ~ 60]

적색 유기 EL 소자의 제작Fabrication of Red Organic EL Devices

The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.

M-MTDATA (60 nm) / TCTA (80 nm) / A-41 to L-53 + 10% (piq) ₂ Ir (acac) (30nm) / BCP (10 nm) / An organic electroluminescent device was manufactured by laminating in order of Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

[[ 비교예Comparative example 2] 2]

적색 유기 EL 소자의 제작Fabrication of Red Organic EL Devices

A red organic electroluminescent device was manufactured in the same manner as in Example 33, except that CBP was used instead of the compound of Synthesis Example 6 as a light emitting host material when forming the emission layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP, and BCP used in Examples 33 to 60 and Comparative Example 2 are as follows.

[[ 평가예Evaluation example 2] 2]

For each organic electroluminescent device manufactured in Examples 33 to 60 and Comparative Example 2, the driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

샘플Sample	호스트Host	구동전압(V)Driving voltage (V)	전류효율(cd/A)Current efficiency (cd / A)
실시예 33Example 33	A-41A-41	4.894.89	13.313.3
실시예 34 Example 34	A-53A-53	4.924.92	12.912.9
실시예 35Example 35	A-59A-59	4.874.87	12.712.7
실시예 36Example 36	B-41B-41	4.934.93	13.213.2
실시예 37Example 37	B-53B-53	4.884.88	12.812.8
실시예 38Example 38	B-59B-59	4.874.87	13.413.4
실시예 39Example 39	C-41C-41	4.834.83	12.612.6
실시예 40Example 40	C-53C-53	4.844.84	12.912.9
실시예 41Example 41	C-59C-59	4.924.92	13.613.6
실시예 42Example 42	D-41D-41	4.874.87	13.213.2
실시예 43Example 43	D-53D-53	4.934.93	12.912.9
실시예 44Example 44	D-59D-59	4.924.92	13.613.6
실시예 45Example 45	E-41E-41	4.984.98	12.812.8
실시예 46Example 46	E-53E-53	4.894.89	13.213.2
실시예 47Example 47	F-41F-41	4.834.83	12.012.0
실시예 48Example 48	F-53F-53	4.824.82	13.213.2
실시예 49Example 49	G-41G-41	4.934.93	12.712.7
실시예 50Example 50	G-53G-53	4.874.87	12.912.9
실시예 51Example 51	G-41G-41	4.934.93	13.413.4
실시예 52Example 52	G-53G-53	4.874.87	12.912.9
실시예 53Example 53	I-41I-41	4.894.89	13.813.8
실시예 54Example 54	I-53I-53	4.924.92	12.412.4
실시예 55Example 55	J-41J-41	4.834.83	13.013.0
실시예 56Example 56	J-53J-53	4.884.88	12.212.2
실시예 57Example 57	K-41K-41	4.894.89	13.913.9
실시예 58Example 58	K-53K-53	4.934.93	12.512.5
실시예 59Example 59	L-41L-41	4.924.92	13.613.6
실시예 60Example 60	L-53L-53	4.854.85	12.312.3
비교예 2Comparative Example 2	CBPCBP	5.255.25	8.28.2

As shown in Table 2 above, when the compound according to the present invention was used as a material of the light emitting layer of the red organic electroluminescent device (Examples 33-60), a red organic electroluminescent device using a conventional CBP as a material of the light emitting layer (Comparative Example) Compared with 2), it shows excellent performance in terms of efficiency and driving voltage.

[[ 실시예Example 61] 61]

유기 EL 소자의 제작Fabrication of Organic EL Devices

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and the substrate was cleaned for 5 minutes using UV. The substrate was then transferred to a vacuum depositor.

M-MTDATA (60nm) / Compound A-26 (80nm) / DS-H522 + 5% DS-501 (30nm) / BCP (10nm) / Alq3 (30) synthesized in Example 5 on the prepared ITO transparent electrode An organic EL device was manufactured in the order of nm) / LiF (1 nm) / Al (200 nm).

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

[[ 실시예Example 62 ~ 84] 62 to 84]

유기 EL 소자의 제작Fabrication of Organic EL Devices

An organic EL device was manufactured in the same manner as in Example 61, except that A-64 to L-64 were used instead of the compound A-26 used as the hole transport layer material in forming the hole transport layer in Example 61.

[[ 비교예Comparative example 3] 3]

유기 EL 소자의 제작Fabrication of Organic EL Devices

An organic EL device was manufactured in the same manner as in Example 61, except that NPB was used as the hole transport layer material instead of Compound A-26 used as the hole transport layer material when forming the hole transport layer in Example 61. The structure of the NPB used is as follows.

[[ 평가예Evaluation example 3] 3]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples 61 to 39 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

샘플Sample	정공수송층Hole transport layer	구동 전압(V)Drive voltage (V)	전류효율(cd/A)Current efficiency (cd / A)
실시예 61Example 61	A-26A-26	4.84.8	20.820.8
실시예 62Example 62	A-64A-64	4.94.9	20.320.3
실시예 63Example 63	B-26B-26	4.74.7	20.420.4
실시예 64Example 64	B-64B-64	4.84.8	20.420.4
실시예 65Example 65	C-26C-26	4.84.8	20.420.4
실시예 66Example 66	C-64C-64	4.74.7	20.220.2
실시예 67Example 67	D-26D-26	4.74.7	21.321.3
실시예 68 Example 68	D-64D-64	4.64.6	21.521.5
실시예 69Example 69	E-26E-26	4.84.8	21.221.2
실시예 70Example 70	E-64E-64	4.94.9	22.322.3
실시예 71Example 71	F-26F-26	4.94.9	21.121.1
실시예 72Example 72	F-64F-64	4.84.8	20.420.4
실시예 73Example 73	G-26G-26	4.84.8	20.920.9
실시예 74Example 74	G-64G-64	4.74.7	22.122.1
실시예 75Example 75	H-26H-26	5.05.0	20.820.8
실시예 76Example 76	H-64H-64	5.15.1	21.421.4
실시예 77Example 77	I-26I-26	4.84.8	21.621.6
실시예 78Example 78	I-64I-64	4.94.9	21.721.7
실시예 79Example 79	J-26J-26	4.74.7	22.322.3
실시예 80Example 80	J-64J-64	4.74.7	20.720.7
실시예 81Example 81	K-26K-26	5.15.1	20.920.9
실시예 82Example 82	K-64K-64	5.05.0	20.420.4
실시예 83Example 83	L-26L-26	4.74.7	21.421.4
실시예 84Example 84	L-64L-64	4.74.7	21.221.2
비교예 3Comparative Example 3	NPBNPB	5.25.2	18.118.1

As shown in Table 3, the organic EL device (the organic EL device manufactured in each of Examples 61 to 84) using the compounds (A-26 to L-64) according to the present invention as the hole transport layer was conventionally used NPB. Compared with the organic EL device (organic EL device of Comparative Example 3), it was found that the device exhibited better performance in terms of current efficiency and driving voltage.

Claims

Compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

R 1 and R 2 are bonded to each other to form a condensed ring with the formula (2),

[Formula 2]

In Chemical Formula 2,

The dotted line is the part where condensation takes place

X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 );

Y 1 to Y 12 are each independently selected from N or C (R 3 );

R 3 is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group selected from each of the adjacent R 3 is bonded to each other condensed aromatic Can form a ring or a condensed heteroaromatic ring;

Ar 1 to Ar 5 is C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, 3 to 40 heterocycloheteronuclear Alkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl Group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 mono or A diaryl phosphinyl group and a C 6 -C 60 arylamine group;

R 3 , Ar 1 to Ar 5 alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl A phosphine group, a mono or diaryl phosphinyl group and an arylamine group are each independently a C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 A cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 1 to C 40 alkyloxy group, a C 6 to C 60 group Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 an aryl phosphine group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 aryl group, and the amine may be substituted with at least one member selected from the group consisting of, optionally substituted with a plurality of substituents Wu they may be the same or different from each other.
The method of claim 1,

Compounds, characterized in that the compound represented by the formula (3) and formula (4):

[Formula 3]

[Formula 4]

In Chemical Formulas 3 and 4,

X 1 , X 2 and Y 1 to Y 12 are as defined in claim 1.
The method according to claim 1 or 2,

At least one of X 1 and X 2 is N (Ar 1 ).
The method according to claim 1 or 2,

Y 1 to Y 12 are each independently selected from N or C (R 3 ), all of which are C (R 3 ) or one of them is N.
The method of claim 1,

Compounds, characterized in that the compound is represented by the formula 1-1 to formula 1-18:

In Chemical Formulas 1-1 to 1-18,

Y 1 to Y 12 and Ar 1 to Ar 5 are as defined in claim 1 .
The method of claim 1,

At least one of R 3 and Ar 1 to Ar 5 except forming a condensation is an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and C 6 to C A compound characterized in that it is selected from the group consisting of 60 arylamine groups.
The method of claim 6,

The alkyl group, aryl group, heteroaryl group and arylamine group of R 3 , Ar 1 to Ar 5 are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, It may be substituted with one or more selected from the group consisting of 5 to 60 heteroaryl groups, C 6 ~ C 60 arylamine groups, and when substituted with a plurality of substituents, they may be the same or different from each other Compound made into.
The method of claim 1,

At least one of R 3 , Ar 1 to Ar 5 , except for forming a condensation, is selected from a substituent represented by the following formula (5), or a phenyl group:

[Formula 5]

In Chemical Formula 5,

* Means a moiety bonded to Formula 1;

L 1 is selected from the group consisting of or a single bond, or C 6 ~ C 18 arylene group and a 5 to 18 nuclear atoms of the heteroarylene group,

Z 1 to Z 5 are each independently N or C (R 11 ), provided that at least one of Z 1 to Z 5 is N and when there are a plurality of R 11 , they are the same or different from each other;

R 11 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 40 aryl group, 5 to 40 heteroaryl groups, C 6 to C 40 aryloxy groups, C 1 to C 40 alkyloxy groups, C 3 to C 40 cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, A C 6 -C 40 mono or diarylphosphinyl group and a C 6 -C 40 arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R 11 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 aryl group, 5 to 40 heteroaryl groups, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 An arylamine group, a C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 40 group aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 mono or diaryl phosphine blood group and a C 6 ~ C 40 aryl silyl groups at least one member selected from the group consisting of When substituted or unsubstituted with a substituent and there are a plurality of the substituents, they may be the same or different from each other.
The method of claim 8,

Formula 5 is a compound represented by the following formula A-1 to A-15.

In the above A-1 to A-15,

L 1 and R 11 are each as defined in Formula 5,

n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R 12 , and when n is an integer of 1 to 4, R 12 is deuterium, halogen, cyano group, nitro C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom of 3 to 40 heterocycloalkyl group, C 6 Aryl group of ~ C 40 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 ~ C 40 60 C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ mono or diaryl phosphine of C 40 aryl phosphine group, C 6 ~ C 40 P Or a arylsilyl group of C 6 to C 40 , or may be combined with an adjacent group to form a condensed ring, and when there are a plurality of R 12 , they are the same or different from each other;

Alkyl group of the R 12, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 aryl group, 5 to 40 heteroaryl groups, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 An arylamine group, a C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 40 group aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 mono or diaryl phosphine blood group and a C 6 ~ C 40 aryl silyl groups at least one member selected from the group consisting of When substituted or unsubstituted with a substituent and there are a plurality of the substituents, they may be the same or different from each other.
The method of claim 1,

At least one of R 3 and Ar 1 to Ar 5 except for forming a condensation is a substituent represented by Formula 6 below:

[Formula 6]

In Chemical Formula 6,

* Means a moiety bonded to Formula 1;

L 2 is selected from the group consisting of or a single bond, or C 6 ~ C 18 arylene group and a 5 to 18 nuclear atoms of the heteroarylene group,

R 13 and R 14 are each independently a C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 Or R 13 and R 14 may combine to form a condensed ring;

The alkyl group, aryl group, heteroaryl group and arylamine group of R 13 and R 14 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, alkyloxy group of C 1 ~ C 40 of the, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 mono or diaryl phosphine blood group and one substituent at least one selected from the group consisting of C 6 ~ with an aryl silyl group of C 40 of the When substituted or unsubstituted, and when there are a plurality of said substituents, they may be the same or different from each other.
The method of claim 1,

Compounds characterized in that the compound is selected from the group consisting of:
The method of claim 1,

A compound comprising a nitrogen-containing heterocycle further bonded to the compound.
The method of claim 1,

At least one substituent selected from the group consisting of an arylamine group, a carbazole group, a terphenyl group, and a triphenylene group is further bonded to the compound.
An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more layers of organic material interposed between the anode and the cathode,

At least one of the one or more organic material layer comprises an organic electroluminescent device, characterized in that the compound of claim 1.
The method of claim 14,

The compound is used as a phosphorescent host of the light emitting layer.
The method of claim 14,

The compound is an organic electroluminescent device, characterized in that used as an electron transport layer.
The organic electroluminescent device according to claim 14, wherein the compound is used as a hole transport layer.