WO2016122178A2 - Organic light-emitting compound and organic electroluminescent element using same - Google Patents

Abstract

The present invention relates to a novel compound having an excellent light-emitting ability, and to an organic electroluminescent element having characteristics, such as high luminous efficiency, a low driving voltage, and long lifespan, by containing the novel compound in at least one organic material layer.

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 a novel organic compound having excellent hole injection and transporting ability, electron injection and transporting ability, light emitting ability, and the like, to one or more organic material layers. The present invention relates to an organic EL device having improved characteristics such as high luminous efficiency, low driving voltage and lifetime.

A study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') that led to blue electroluminescence using anthracene single crystals based on observation of organic thin film emission from Bernasose in the 1950s. In 1987, Tang proposed an organic EL device having a laminated structure divided into functional layers 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 EL 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, 4,4-dicarbazolybiphenyl (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.

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 and transporting ability, electron injection and transporting ability, and light emitting ability.

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,

Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , and Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ and Y At least one of ₁₁ and Y ₁₂ is condensed with a ring represented by Formula 2 to form a condensed ring;

[Formula 2]

In Chemical Formula 2,

The dotted line is the part where condensation takes place;

In Chemical Formulas 1 and 2,

X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ), and Si (Ar ₄ ) (Ar ₅ ) At least one of X ₁ and X ₂ is N (Ar ₁ );

Y ₁ to Y ₁₂ which are not condensed with the ring represented by Formula 2 to form a condensed ring, are the same or different from each other, and each independently N or C (R ₁ );

When there are a plurality of Y ₁₃ to Y ₁₆ , they are the same as or different from each other, and the Y ₁₃ to Y ₁₆ are each independently N or C (R ₁ );

When there are a plurality of R ₁ , they are the same or different from each other, and each R ₁ is independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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 Or a C ₆ -C ₆₀ mono or diarylphosphinyl group and C ₆ -C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring;

If the Ar ₁ to Ar ₅ multiple individuals, all of which are the same or different, wherein Ar ₁ to Ar ₅ is independently hydrogen, C alkyl group of ₁ ~ C _40, a cycloalkyl group of C ₃ ~ C _40, nuclear atomic 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ selected from mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl group consisting of the C ₆₀ amine, or by combining adjacent groups may form a condensed ring;

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 of R ₁ and Ar ₁ to Ar ₅ The phosphine group, mono or diarylphosphinyl group and arylamine group are each independently deuterium, halogen, cyano, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, or 3 to 40 heterocycloheteroatoms 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 ₁ ~ 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 diaryl phosphine blood group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted, being substituted by the substituents Case, the substituent groups bonded to adjacent, may form a condensed ring, when it is substituted with a plurality of substituents, 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).

According to a preferred embodiment of the present invention, the organic material layer comprising the compound represented by Formula 1 is selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a light emission auxiliary layer and a life improvement layer The light emitting layer including the compound represented by Chemical Formula 1 may be used as a phosphorescent host.

"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 to C60 aromatic hydrocarbon combined with a single ring or two or more rings. 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 60 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 60 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 60 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.

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , and Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ and Y At least one of ₁₁ and Y ₁₂ is condensed with a ring represented by Formula 2 to form a condensed ring;

[Formula 2]

In Chemical Formula 2,

The dotted line is the part where condensation takes place;

In Chemical Formulas 1 and 2,

X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ), and Si (Ar ₄ ) (Ar ₅ ) At least one of X ₁ and X ₂ is N (Ar ₁ );

Y ₁ to Y ₁₂ which are not condensed with the ring represented by Formula 2 to form a condensed ring, are the same or different from each other, and each independently N or C (R ₁ );

When there are a plurality of Y ₁₃ to Y ₁₆ , they are the same as or different from each other, and the Y ₁₃ to Y ₁₆ are each independently N or C (R ₁ );

When there are a plurality of R ₁ , they are the same or different from each other, and each R ₁ is independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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 Or a C ₆ -C ₆₀ mono or diarylphosphinyl group and C ₆ -C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring;

If the Ar ₁ to Ar ₅ multiple individuals, all of which are the same or different, wherein Ar ₁ to Ar ₅ is independently hydrogen, C alkyl group of ₁ ~ C _40, a cycloalkyl group of C ₃ ~ C _40, nuclear atomic 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ selected from mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl group consisting of the C ₆₀ amine, or by combining adjacent groups may form a condensed ring;

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 of R ₁ and Ar ₁ to Ar ₅ The phosphine group, mono or diarylphosphinyl group and arylamine group are each independently deuterium, halogen, cyano, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, or 3 to 40 heterocycloheteroatoms 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 ₁ ~ 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 diaryl phosphine blood group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted, being substituted by the substituents Case, the substituent groups bonded to adjacent, may form a condensed ring, when it is substituted with a plurality of substituents, they may be the same or different from each other.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The novel organic compounds according to the present invention are dibenzoazine (5H-dibenzo [b, f] azepine), dibenzooxepine (dibenzo [b, f] oxepine), dibenzothiepine (dibenzo [b, f] thiepine), 5H-dibenzo [b, f] silepine, or a 5-membered heteroaromatic ring moiety condensed with naphthyl to 5H-dibenzo [a, d] cycloheptene. Or an indene moiety, or an indole moiety, to condense to form a basic skeleton, or benzonaphthoazine (7H-benzo [b] naphtho [1,2-f] azepine), Benzonaphthooxepine (benzo [b] naphtho [1,2-f] oxepine), benzonaphthocypine (benzo [b] naphtho [1,2-f] thiepine), benzonaphthosilane (7H-benzo) a 5-membered heteroaromatic ring moiety in which benzene is condensed to [b] naphtho [1,2-f] silepine) or benzonaphthocycloheptene (7H-benzo [b] naphtho [1,2-f] cycloheptene) Or indene moiety or indole moiety condensed It can achieve price.

More specifically, the novel organic compound according to the present invention is characterized by represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , and Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ and Y At least one of ₁₁ and Y ₁₂ , preferably Y ₁ and Y ₂ , Y ₇ and Y ₈ and At least one of Y ₁₁ and Y ₁₂ is condensed with a ring represented by Formula 2 to form a condensed ring;

[Formula 2]

In Chemical Formula 2,

The dotted line is the part where condensation takes place;

In Chemical Formulas 1 and 2,

X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ), and Si (Ar ₄ ) (Ar ₅ ) At least one of X ₁ and X ₂ is N (Ar ₁ ), preferably X ₁ is selected from the group consisting of O, S and N (Ar ₁ ), and X ₂ is N (Ar ₁ ) ;

Y ₁ to Y ₁₂ which are not condensed with the ring represented by Formula 2 to form a condensed ring, are the same or different from each other, and each independently N or C (R ₁ );

When there are a plurality of Y ₁₃ to Y ₁₆ , they are the same as or different from each other, and the Y ₁₃ to Y ₁₆ are each independently N or C (R ₁ );

When there are a plurality of R ₁ , they are the same or different from each other, and each R ₁ is independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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 Or a C ₆ -C ₆₀ mono or diarylphosphinyl group and C ₆ -C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring;

If the Ar ₁ to Ar ₅ multiple individuals, all of which are the same or different, wherein Ar ₁ to Ar ₅ is independently hydrogen, C alkyl group of ₁ ~ C _40, a cycloalkyl group of C ₃ ~ C _40, nuclear atomic 3 To 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ selected from the group consisting of aryl amine group of C _60, or by combining adjacent groups may form a condensed ring;

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 of R ₁ and Ar ₁ to Ar ₅ The phosphine group, mono or diarylphosphinyl group and arylamine group are each independently deuterium, halogen, cyano, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, or 3 to 40 heterocycloheteroatoms 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 ₁ ~ 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 diaryl phosphine blood group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of an aryl amine of the C ₆₀ or may be unsubstituted, being substituted by the substituents Case, the substituent groups bonded to adjacent, may form a condensed ring, when it is substituted with a plurality of substituents, they may be the same or different from each other.

 Since the compound represented by the 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 The temperature is high, not only excellent in thermal stability, but also excellent in carrier transport ability, light emitting ability, and the like. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage of the device is lowered, efficiency and lifespan 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 triplet energy of 2.3 eV or more. In addition, the compound represented by the formula (1) can be adjusted higher than the dopant by introducing a specific substituent on the basic skeleton condensed with a broad singlet energy level and indole derivative having a high triplet energy level Can be used as 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, especially 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.

The compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas M-1 to M-12.

In Formulas M-1 to M-12, X ₁ , X ₂ and Y ₁ to Y ₁₆ are the same as defined in Formula 1.

However, preferably X ₁ is selected from the group consisting of O, S and N (Ar ₁ ), X ₂ may be N (Ar ₁ ).

Also, preferably, Y ₁ to Y ₁₆ may be the same as or different from each other, and all may be C (R ₁ ) or include 1 to 3 N, wherein a plurality of R ₁ are the same or different.

The compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas N-1 to N-12.

In Chemical Formulas N-1 to N-12, X ₁ , Ar _1, and R ₁ are as defined in Chemical Formula 1.

However, preferably, X ₁ may be selected from the group consisting of O, S, and N (Ar ₁ ).

In addition, according to a preferred embodiment of the present invention, the compound represented by Formula 1 may be characterized in that the compound represented by any one of the following formula (3) to (7).

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7,

When there are a plurality of Ar ₁ , they are the same as or different from each other, and Ar ₁ is each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, or a nuclear atom having 3 to 40 heterocycloalkyl groups. , C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group of nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ 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 dia Can be selected from the group consisting of arylphosphinyl group and C ₆ -C ₆₀ arylamine group, or can be combined with adjacent groups to form a condensed ring;

Y ₁ to Y ₁₂ are the same as or different from each other, and each independently N or C (R ₁ );

When there are a plurality of Y ₁₃ to Y ₁₆ , they are the same as or different from each other, and the Y ₁₃ to Y ₁₆ are each independently N or C (R ₁ );

When there are a plurality of R ₁ , they are the same or different from each other, and each R ₁ is independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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 Or a C ₆ -C ₆₀ mono or diarylphosphinyl group and C ₆ -C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring;

Ar ₁ And the alkyl group of R _1, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, a mono or diaryl phosphine blood group and the arylamine groups are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl 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 ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group And it may be unsubstituted or substituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ arylamine group, when substituted with the substituents, Substituents may be bonded to adjacent groups to form a condensed ring, and when substituted with a plurality of substituents, they may be the same or different from each other.

Preferably, in Formulas 3 to 7, Ar ₁ may be an aryl group of C ₆ to C ₆₀ , and in particular, when Ar ₁ is a plurality, at least one may be an aryl group of C ₆ to C ₆₀ , wherein The aryl group may be unsubstituted or substituted with one or more C ₆ -C ₆₀ aryl groups, and when substituted with a plurality of substituents, they may be the same or different from each other.

In addition, in Formula 4, Y ₈ is C (R ₁ ), and R ₁ may be an aryl group of C ₆ to C ₆₀ , more preferably a phenyl group.

According to a preferred embodiment of the present invention, when at least one of Y ₁ to Y ₁₂ that does not form a condensed ring with the ring represented by the formula (2) is C (R ₁ ), at least one of the R ₁ is a phenyl group Can be.

According to one preferred embodiment of the present invention, at least one of R ₁ and Ar ₁ to Ar ₅ may be a phenyl group or a substituent represented by the following formula (8).

[Formula 8]

In Chemical Formula 8,

* Means a moiety bonded to Formula 1;

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

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N;

If individual R ₁₁ are a plurality, all of which are the same or different, R ₁₁ 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 , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₃ C ₄₀ -cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ arylamine group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ alkylboron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or a neighboring tile that Can combine 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, An aryl phosphine group, a mono or diaryl phosphinyl group and an aryl silyl group, the arylene group and hetero arylene group of L ₁ 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 of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group When substituted by one or more substituents selected from the group consisting of a reel or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 8 may be a substituent represented by any one of the following O-1 to O-15.

In Chemical Formulas O-1 to O-15,

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 each independently deuterium, halogen, cyan No 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 of 3 to 40 heterocycloalkyl group , C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl group of nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group , C ₁ ~ C ₄₀ Alkylsilyl 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 dia A arylphosphinyl group and a C ₆ -C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

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 ₆₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ 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 ₆₀ group At least one member selected from the group consisting of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group When substituted or unsubstituted with a substituent, and substituted with a plurality of substituents, they may be the same or different from each other;

L ₁ and R ₁₁ are each as defined in Chemical Formula 8 above.

According to one preferred embodiment of the present invention, Ar ₁ to Ar ₅ are the same as or different from each other, and each independently may be selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline,

Phenyl, pyridine, pyrimidine, triazine, biphenyl, and quinazoline of Ar ₁ to Ar ₅ may be one or more selected from the group consisting of cyano, phenyl, pyridine, pyrimidine, triazine, biphenyl, and quinazoline Substituted or unsubstituted, when substituted with a plurality of substituents, they may be the same or different from each other.

The compound represented by Formula 1 of the present invention may be represented by the following structure in more detail with the following compounds, but is not limited thereto.

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

2. Organic electroluminescent device

On the other hand, 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 (i) an anode, (ii) a cathode and (iii) one or more organic material layers interposed between the anode and the cathode. At least one of the one or more organic material layers includes a compound represented by Chemical Formula 1. In this case, the compound may be used alone, or two or more kinds thereof may be mixed and used.

According to one embodiment of the present invention, the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 It may include a compound represented. Specifically, the organic material layer including the compound of Formula 1 is preferably selected from the group consisting of a light emitting layer, an electron transport layer and a hole transport layer, more preferably may be a light emitting 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, an electron injection layer may be further stacked on the electron transport layer, and as described above, at least one 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 may be represented by Chemical Formula 1 It may include a compound.

In addition, the organic electroluminescent device may include a life improvement layer or an electron transport auxiliary layer between the light emitting layer and the electron transport layer. In this case, the compound represented by Chemical Formula 1 may also be used as a life improvement layer or an electron transport auxiliary 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 metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole 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, and conventional materials known in the art may be used.

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

Preparation Example 1 Synthesis of BIAz-1

<Step 1> Synthesis of 1- (5H-dibenzo [b, f] azin-5-yl) ethanone

5H-dibenzo [b, f] azepine (100.0 g, 517.5 mmol), acetyl chloride (44.3 ml, 621.0 mmol) and toluene (1000 ml) under nitrogen stream were mixed and stirred at 80 ° C. for 2 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated and recrystallized with ethanol to obtain 1- (5H-dibenzo [b, f] azin-5-yl) ethanone (113.2 g, yield 93%).

¹ H-NMR: δ 1.86 (s, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.26-7.45 (m, 8H)

<Step 2> 1- (1aH - dibenzo [b, f] oxy leno [2,3-d] azepin--6 (10bH) - yl) ethanone discuss synthetic

1- (5H-dibenzo [b, f] azin-5-yl) ethanone (113.2 g, 481.3 mmol), meta -chloroperoxybenzoic acid (99.7 g, 577.5 mmol), silica (226.5 g) under nitrogen stream ), NaOCl (226.5 g), acetonitrile (1100 ml) was mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated and extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to give 1- (1aH-dibenzo [b, f] oxyreno [2,3-d] azin-6 (10bH) -yl) ethanone (87.1 g, yield 72 %) Was obtained.

¹ H-NMR: δ 1.95 (s, 3H), 4.28 (s, 2H), 7.26-7.53 (m, 8H)

Step 3 Synthesis of 5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one

1- (1aH-dibenzo [b, f] oxyreno [2,3-d] azin-6 (10bH) -yl) ethanone (87.1 g, 346.5 mmol), lithium iodine (55.7 g, 415.8 mmol) and chloroform (870 ml) were mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction, the mixture was extracted with ethyl acetate and then water was removed with MgSO ₄ , and recrystallized from ethanol to give 5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one (70.5 g, yield 81). %) Was obtained.

¹ H-NMR: δ 2.10 (s, 3H), 3.85 (d, 1H), 4.33 (d, 1H), 7.30-7.40 (m, 5H), 7.51-7.59 (m, 2H), 8.10 (d, 1H )

Step 4 Synthesis of 5-acetyl-10,11- (1H-benzo [g] indolo) -5H-dibenzo [b, f] azepine

5-acetyl-5H-dibenzo [b, f] azepin-10 (11H) -one (70.5 g, 280.7 mmol) and naphthalen-1-ylhydrazine hydrochloride (60.1 g, 308.7 mmol), acetic acid under nitrogen stream (705 ml) was added and the mixture was stirred at 120 ° C for 12 hours.

After completion of the reaction, the mixture was extracted with dichloromethane, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane: MC = 4: 1 (v / v)) to give 5-acetyl-10,11- (1H-benzo [g] indolo) -5H-dibenzo. [b, f] azepine (68.3 g, yield 65%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.25-7.39 (m, 4H), 7.56-7.87 (m, 7H), 8.16 (d, 1H), 8.51 (d, 1H), 9.06 (d, 1H ), 11.36 (b, 1 H)

Step 5 Synthesis of 5-acetyl-10,11- [1-phenylbenzo [g] indolo] -dibenzo [b, f] azepine

5-acetyl-10,11- (1H-benzo [g] indolo) -5H-dibenzo [b, f] azepine (68.3 g, 350.9 mmol), bromobenzene (66.1 g, 421.1 mmol) under nitrogen stream ), Cu (11.1 g, 175.5 mmol), K ₂ CO ₃ (97.0 g, 701.8 mmol) and nitrobenzene (683 ml) were mixed and stirred at 210 ° C. for 12 h.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated and recrystallized with ethanol to give 5-acetyl-10,11- [1-phenyl benzo [g] indolo] -dibenzo [b, f] azepine (123.3 g, yield). 78%).

¹ H-NMR: δ 2.04 (s, 3H), 7.25-7.26 (m, 2H), 7.39-7.58 (m, 9H), 7.77 (d, 1H), 7.87-7.88 (m, 2H), 8.05-8.06 (m, 2H), 8.16 (d, 1H), 8.51 (d, 1H), 9.06 (d, 1H)

Step 6 Synthesis of BIAz-1

5-acetyl-10,11- [1-phenyl benzo [g] indolo] -dibenzo [b, f] azepine (123.3 g, 273.7 mmol), potassium hydroxide (16.9 g, 301.0 mmol) under a nitrogen stream and Ethylene glycol (1233 ml) was mixed and stirred at 200 ° C. for 6 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, followed by removal of water with MgSO ₄ , and purified by column chromatography (hexane: EA = 6: 1 (v / v)) to obtain BIAz-1 (102.9 g, yield 92%). Got it.

¹ H-NMR: δ 6.69-6.87 (m, 4H), 7.16-7.17 (m, 2H), 7.45-7.67 (m, 9H), 8.05-8.06 (m, 2H), 8.16 (d, 1H), 8.51 (d, 1H), 8.83 (d, 1H)

Preparation Example 2 Synthesis of BIAz-2

Step 1 Synthesis of 5-phenyl-5H-dibenzo [b, f] azepine

5H-dibenzo [b, f] azepine (100 g, 517.5 mmol), iodinebenzene (126.7 g, 621.0 mmol), Cu (16.4 g, 258.7 mmol), K ₂ CO ₃ (143.0 g, 1,035.0) under nitrogen stream mmol) and nitrobenzene (1000 ml) were mixed and stirred at 210 ° C. for 12 h.

After the reaction was terminated, extracted with ethyl acetate, concentrated and recrystallized with ethanol to give 5-phenyl-5H-dibenzo [b, f] azepine (100.4 g, 72% yield).

¹ H-NMR: δ 6.63-6.81 (m, 3H), 6.92 (d, 1H), 6.98 (d, 1H), 7.20 (d, 2H), 7.26-7.45 (m, 8H)

<Step 2> 6-phenyl -6,10b- dihydro - 1aH - dibenzo [b, f] oxy leno [2,3-d] azepine synthesis

5-phenyl-5H-dibenzo [b, f] azepine (100.4 g, 372.6 mmol), meta -chloroperoxybenzoic acid (77.2 g, 447.1 mmol), silica (200.7 g), NaOCl under nitrogen stream (200.7 g), acetonitrile (1000 ml) was mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated and extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to give 6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxyreno [2,3-d] azepine (84.0 g, 79% yield). Got.

¹ H-NMR: δ 4.31 (s, 2H), 6.63-6.81 (m, 3H), 7.24-7.53 (m, 10H)

Step 3 Synthesis of 5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) -one

6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxyreno [2,3-d] azepine (84.0 g, 294.3 mmol), lithium iodine (47.3 g, 353.2 mmol) under nitrogen stream ) And chloroform (840 ml) were mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction, the mixture was extracted with ethyl acetate, followed by water removal with MgSO ₄ , and recrystallization from ethanol to 5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) -one (68.0 g, yield 81 %) Was obtained.

¹ H-NMR: δ 3.42 (d, 1H), 4.21 (d, 1H), 6.62-6.74 (m, 3H), 7.25-7.40 (m, 7H), 7.51-7.59 (m, 2H), 8.10 (d , 1H)

Step 4 Synthesis of BIAz-2

5-phenyl-5H-dibenzo [b, f] azepin-10 (11H) -one (68.0 g, 238.4 mmol) and naphthalen-1-ylhydrazine hydrochloride under nitrogen stream (51.1 g, 262.3 mmol) and acetic acid (700 ml) were added and the mixture was stirred at 120 ° C for 12 hours.

After completion of the reaction, the mixture was extracted with dichloromethane, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane: MC = 3: 1 (v / v)) to obtain BIAz-2 (59.4 g, 61% yield).

¹ H-NMR: δ 6.63-6.69 (m, 4H), 6.81-6.87 (m, 3H), 7.16-7.20 (m, 4H), 7.54-7.56 (m, 3H), 7.65-7.67 (m, 2H) , 8.16 (d, 1H), 8.51 (d, 1H), 8.83 (d, 1H), 11.36 (b, 1H)

Preparation Example 3 Synthesis of 13BAz

<Step 1> 1- (naphthalen-1-yl) -1H-indole

1H-indole (100 g, 854.0 mmol), 1-bromonaphthalene (212.1 g, 1024.8 mmol), Cu (27.2 g, 427.0 mmol), K ₂ CO ₃ (236.1 g, 1.70 mol) and nitrobenzene (under nitrogen stream) 3000 ml) were mixed and stirred at 210 ° C. for 12 h.

After completion of the reaction, the mixture was extracted with ethyl acetate and then water was removed with MgSO ₄ , and purified by column chromatography (hexane: EA = 8: 1 (v / v)) to obtain 1- (naphthalen-1-yl) -1H- Indole (182.8 g, yield 88%) was obtained.

¹ H-NMR: δ 6.52 (d, 1H), 6.87 (dd, 1H), 7.33 (dd, 1H), 7.55-7.60 (m, 5H), 7.93-7.94 (m, 2H), 8.06-8.07 (m , 3H)

Step 2 Synthesis of 13BAz

1- (naphthalen-1-yl) -1H-indole (182.8 g, 751.2 mmol), polyphosphoric acid (914 g) under nitrogen stream was mixed and stirred at 100 ° C. for 12 h.

After the reaction was terminated, extracted with water and filtered to give 13BAz (58.5 g, yield 32%).

¹ H-NMR: δ 6.81 (dd, 1H), 6.99-7.05 (m, 3H), 7.25-7.29 (m, 2H), 7.53-7.54 (m, 2H), 7.73 (d, 1H), 8.02-8.07 (m, 2H), 8.21 (d, 1H), 8.42 (b, 1H)

Preparation Example 4 Synthesis of BIAz-3

<Step 1> Synthesis of 1- (13H-benzo [f] naphtho [1,2-b] azin-13-yl) ethanone

13BAz (100.0 g, 411.0 mmol), acetyl chloride (35.2 ml, 493.2 mmol) and toluene (1000 ml) were mixed under nitrogen stream and stirred at 80 ° C. for 2 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated and recrystallized with ethanol to give 1- (13H-benzo [f] naphtho [1,2-b] azin-13-yl) ethanone (102.0 g, 87% yield). )

¹ H-NMR: δ 2.04 (s, 3H), 6.99-7.00 (m, 2H), 7.19-7.28 (m, 3H), 7.48-7.54 (m, 3H), 7.73 (d, 1H), 7.81 (d , 1H), 8.02-8.07 (m, 2H)

<Step 2> 1- (1aH - benzo [f] naphtho [1,2-b] oxy leno [2,3-d] azepin--6 (12bH) - yl) discuss other composited

1- (13H-benzo [f] naphtho [1,2-b] azin-13-yl) ethanone (102.0 g, 357.6 mmol), meta -chloroperoxybenzoic acid (74.0 g, 429.1 mmol) under nitrogen stream ), Silica (204.1 g), NaOCl (204.1 g), acetonitrile (1000 ml) was mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated and extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer and then recrystallized with ethanol to give 1- (1aH-benzo [f] naphtho [1,2-b] oxyreno [2,3-d] azin-6 (12bH) -yl) ethanone. (76.5 g, yield 71%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 4.19-4.20 (m, 2H), 6.91 (d, 1H), 7.12 (dd, 1H), 7.34-7.36 (m, 2H), 7.49-7.53 (m , 3H), 7.74 (d, 1H), 8.03-8.04 (m, 2H)

Step 3 Synthesis of 13-acetyl-8,13 -dihydro- 7H- benzo [f] naphtho [1,2-b] azepine- 7-one

1- (1aH-benzo [f] naphtho [1,2-b] oxyreno [2,3-d] azin-6 (12bH) -yl) ethanone (76.5 g, 253.9 mmol) under a nitrogen stream, Lithium iodine (40.8 g, 304.7 mmol) and chloroform (750 ml) were mixed and stirred at 60 ° C. for 1 hour.

After the reaction was completed, the resultant was extracted with ethyl acetate, followed by removal of water with MgSO ₄ , recrystallization from ethanol, and 13-acetyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azine. -7-one (57.4 g, yield 75%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 3.81 (s, 2H), 7.07 (dd, 1H), 7.21-7.24 (m, 2H), 7.37 (d, 1H), 7.65-7.69 (m, 3H ), 8.10-8.23 (m, 3H)

<Step 4> of 13-acetyl-7,8- (7-phenyl-1H - indolo ) -benzo [f] naphtho [1,2-b] azepine synthesis

13-acetyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azin-7-one (57.4 g, 190.4 mmol) and biphenyl-2-ylhydrazine under a nitrogen stream Hydrochloride (46.2 g, 209.5 mmol) and acetic acid (600 ml) were added thereto, followed by stirring at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with dichloromethane, MgSO ₄ was added and filtered. After the solvent was removed from the organic layer obtained, the residue was purified by column chromatography (hexane: MC = 4: 1 (v / v)) to obtain 13-acetyl-7,8- (7-phenyl-1H-indolo) -benzo [f]. Naphtho [1,2-b] azepine (52.3 g, 61% yield) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.14-7.25 (m, 4H), 7.39-7.54 (m, 8H), 7.77-7.87 (m, 4H), 8.02-8.07 (m, 2H), 11.36 (b, 1H)

Step 5 Synthesis of 13-acetyl-7,8- (7-phenyl-1- (3,5 -diphenylbenzene ) -indolo ) -benzo [f] naphtho [1,2-b] azepine

13-acetyl-7,8- (7-phenyl-1H-indolo) -benzo [f] naphtho [1,2-b] azepine (52.3 g, 237.1 mmol), 1-bromo- under nitrogen stream 3,5-diphenylbenzene (88.0 g, 284.5 mmol), Cu (7.5 g, 118.6 mmol), K ₂ CO ₃ (65.5 g, 474.2 mmol) and nitrobenzene (500 ml) were mixed and 12 hours at 210 ° C. Was stirred.

After the reaction was completed, the mixture was extracted with ethyl acetate, concentrated and recrystallized with ethanol to prepare 13-acetyl-7,8- (7-phenyl-1- (3,5-diphenylbenzene) -indolo) -benzo [f] naph. Earth [1,2-b] azepine (112.7 g, yield 70%) was obtained.

¹ H-NMR: δ 2.04 (s, 3H), 7.19-7.25 (m, 3H), 7.39-7.54 (m, 17H), 7.63 (d, 1H), 7.77-7.78 (m, 2H), 7.87-7.88 (m, 2H), 8.02-8.13 (m, 5H), 8.39 (d, 1H)

Step 6 Synthesis of BIAz-3

13-acetyl-7,8- (7-phenyl-1- (3,5-diphenylbenzene) -indolo) -benzo [f] naphtho [1,2-b] azepine (112.7 g) under nitrogen stream , 166.0 mmol), potassium hydroxide (10.2 g, 182.6 mmol) and ethylene glycol (1100 ml) were mixed and stirred at 200 ° C. for 6 hours.

After completion of the reaction, the mixture was extracted with ethyl acetate, followed by removing moisture with MgSO ₄ , and purified by column chromatography (hexane: EA = 6: 1 (v / v)) to obtain BIAz-3 (93.0 g, yield 88%). Got it.

¹ H-NMR: δ 6.69 (d, 1H), 6.87 (dd, 1H), 7.16-7.19 (m, 3H), 7.41-7.54 (m, 18H), 7.63 (d, 1H), 7.78 (d, 1H ), 7.88 (s, 1H), 8.02-8.13 (m, 5H), 8.39 (d, 1H)

Preparation Example 5 Synthesis of BIAz-4

Step 1 Synthesis of 13-phenyl-13H-benzo [f] naphtho [1,2-b] azepine

13BAz (100 g, 411.0 mmol), iodinebenzene (100.6 g, 493.2 mmol), Cu (13.1 g, 205.5 mmol), K ₂ CO ₃ (113.6 g, 822.0 mmol) and nitrobenzene (1000 ml) under nitrogen stream Mix and stir at 210 ° C. for 12 h.

After completion of the reaction, the mixture was extracted with ethyl acetate, concentrated and recrystallized with ethanol to obtain 13-phenyl-13H-benzo [f] naphtho [1,2-b] azepine (85.3 g, yield 68%).

¹ H-NMR: δ 6.63-6.65 (m, 3H), 6.80-6.81 (m, 2H), 6.99-7.05 (m, 3H), 7.20-7.29 (m, 4H), 7.53-7.54 (m, 2H) , 7.73 (d, 1 H), 8.02-8.07 (m, 2 H)

<Step 2> Synthesis of 6-phenyl-6,12b -dihydro - 1aH - benzo [f] naphtho [1,2-b] oxyreno [2,3- d] azepine

13-phenyl-13H-benzo [f] naphtho [1,2-b] azepine (85.3 g, 267.2 mmol), meta -chloroperoxybenzoic acid (55.3 g, 320.6 mmol), silica (170.7 g) under nitrogen stream ), NaOCl (170.7 g), acetonitrile (850 ml) was mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated and extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer and then recrystallized from ethanol to give 6-phenyl-6,12b-dihydro-1aH-benzo [f] naphtho [1,2-b] oxyreno [2,3-d] azine (60.9 g, yield 68%).

¹ H-NMR: δ 4.20 (s, 2H), 6.56-6.63 (m, 3H), 6.74-6.81 (m, 2H), 6.91 (d, 1H), 7.11-7.20 (m, 4H), 7.49-7.53 (m, 3H), 8.03-8.04 (m, 2H)

Step 3 Synthesis of 13-phenyl-8,13 -dihydro- 7H- benzo [f] naphtho [1,2-b] azepine- 7-one

6-phenyl-6,12b-dihydro-1aH-benzo [f] naphtho [1,2-b] oxyreno [2,3-d] azepine (60.9 g, 181.7 mmol) under nitrogen stream, lithium iodine (29.2 g, 218.0 mmol) and chloroform (600 ml) were mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction, the mixture was extracted with ethyl acetate, followed by removal of water with MgSO ₄ , recrystallization from ethanol, and 13-phenyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azepine. -7-one (45.7 g, yield 75%) was obtained.

¹ H-NMR: δ 3.81 (s, 2H), 6.51 (d, 1H), 6.63-6.69 (m, 3H), 6.81 (dd, 1H), 6.98-7.01 (m, 2H), 7.20-7.21 (m , 2H), 7.37 (d, 1H), 7.65-7.69 (m, 2H), 8.10-8.23 (m, 3H)

Step 4 Synthesis of BIAz-4

13-phenyl-8,13-dihydro-7H-benzo [f] naphtho [1,2-b] azin-7-one (45.7 g, 136.3 mmol) and naphthalen-1-ylhydrazine hydro under nitrogen stream Chloride (29.2 g, 149.9 mmol) and acetic acid (450 ml) were added thereto, followed by stirring at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (hexane: MC = 3: 1 (v / v)) to obtain BIAz-4 (42.5g, 68% yield).

¹ H-NMR: δ 6.63-6.69 (m, 3H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 3H), 7.53-7.67 (m, 8H), 7.78 (d, 1H), 8.02 -8.16 (m, 3H), 8.51 (d, 1H), 11.36 (b, 1H)

Preparation Example 6 Synthesis of BIAz-5

<Step 1> Synthesis of 1a, 10b-dihydrodibenzo [b, f] oxyreno [2,3-d] oxepin

Dibenzo [b, f] oxepin (100.0g, 514.9mmol), meta -chloroperoxybenzoic acid (106.6g, 617.8mmol), silica (200.0g), NaOCl under nitrogen stream (200.0 g), acetonitrile (1000 ml) was mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated and extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to obtain 1a, 10b-dihydrodibenzo [b, f] oxyreno [2,3-d] oxepin (87.7 g, yield 81%).

¹ H-NMR: δ 4.30 (s, 2H), 7.10 (d, 2H), 7.26-7.34 (m, 6H)

Step 2 Synthesis of Dibenzo [b, f] oxepin-10 (11H) -one

1a, 10b-dihydrodibenzo [b, f] oxyreno [2,3-d] oxepin (87.7g, 417.0mmol), lithium iodine (67.0g, 500.4mmol) and chloroform (900ml) under nitrogen stream Were mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction, the mixture was extracted with ethyl acetate, water was removed with MgSO ₄ , and recrystallized from ethanol to obtain dibenzo [b, f] oxepin-10 (11H) -one (69.3 g, yield 79%).

¹ H-NMR: δ 3.51 (d, 1H), 4.42 (d, 1H), 7.05 (t, 1H), 7.19-7.28 (m, 4H), 7.43-7.44 (m, 2H), 7.60 (t, 1H )

Step 3 Synthesis of BIAz-5

Dibenzo [b, f] oxepin-10 (11H) -one (69.3 g, 329.5 mmol) and naphthalen-1-ylhydrazine hydrochloride under nitrogen stream (70.5g, 362.4mmol) and acetic acid (700ml) were added and stirred at 120 ° C for 12 hours.

After completion of the reaction, the mixture was extracted with dichloromethane, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (hexane: MC = 3: 1 (v / v)) to obtain BIAz-5 (56.0 g, yield 51%).

¹ H-NMR: δ 7.20-7.23 (m, 4H), 7.36-7.37 (m, 2H), 7.55-7.56 (m, 2H), 7.67-7.75 (m, 3H), 8.16 (d, 1H), 8.39 (d, 1H), 8.51 (d, 1H), 11.36 (b, 1H)

Preparation Example 7 Synthesis of BAz-6

<Step 1> Synthesis of 1a, 10b-dihydrodibenzo [b, f] oxyreno [2,3-d] thiene

Dibenzo [b, f] thiene (100.0g, 475.5mmol), meta -chloroperoxybenzoic acid (98.5g, 570.6mmol), silica (200.0g), NaOCl under nitrogen stream (200.0 g), acetonitrile (1000 ml) was mixed and stirred at 80 ° C. for 2 hours.

After the reaction was terminated and extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the organic layer and recrystallized with ethanol to obtain 1a, 10b-dihydrodibenzo [b, f] oxyreno [2,3-d] thiene (80.7 g, yield 75%).

¹ H-NMR: δ 4.40 (s, 2H), 7.12-7.16 (m, 4H), 7.45 (t, 2H), 7.70 (d, 2H)

Step 2 Synthesis of Dibenzo [b, f] thiefin-10 (11H) -one

1a, 10b-dihydrodibenzo [b, f] oxyreno [2,3-d] thiene (80.7 g, 356.7 mmol), lithium iodine (57.3.0 g, 428.0 mmol) and chloroform (800 ml) under nitrogen stream ) Was mixed and stirred at 60 ° C. for 1 hour.

After completion of the reaction was extracted with ethyl acetate, water was removed with MgSO ₄ and recrystallized from ethanol to give dibenzo [b, f] thiepin-10 (11H) -one (59.7g, 74% yield).

¹ H-NMR: δ 3.61 (d, 1H), 4.47 (d, 1H), 7.03-7.07 (m, 2H), 7.30-7.33 (m, 2H), 7.44-7.52 (m, 2H), 7.65 (d , 1H), 7.74 (d, 1H)

Step 3 Synthesis of BIAz-6

Dibenzo [b, f] thiefin-10 (11H) -one (59.7 g, 263.9 mmol) and naphthalen-1-ylhydrazine hydrochloride under nitrogen stream (56.5 g, 290.3 mmol) and acetic acid (600 ml) were added thereto, followed by stirring at 120 ° C. for 12 hours.

After completion of the reaction, the mixture was extracted with dichloromethane, MgSO ₄ was added and filtered. The solvent was removed from the obtained organic layer, and then purified by column chromatography (hexane: MC = 3: 1 (v / v)) to obtain BIAz-6 (50.7 g, 55% yield).

¹ H-NMR: δ 7.21-7.25 (m, 4H), 7.47-7.67 (m, 8H), 8.16 (d, 1H), 8.51 (d, 1H), 11.36 (b, 1H)

Synthesis Example 1 Synthesis of A-1

BIAz-1 (2.7g, 6.7mmol), 2-bromo-4,6-diphenylpyridine (2.5g, 8.0mmol), Pd (OAc) ₂ (0.08g, 0.34mmol), P ( t under nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound A-1 (2.7 g, 64% yield).

Mass (Theoretical value: 637.58, Measured value: 637 g / mol)

Synthesis Example 2 Synthesis of A-2

The same procedure as in Synthesis Example 1 was carried out except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. A-2 (2.9 g, yield 68%) was obtained as a compound.

Mass (Theoretical value: 638.57, Measured value: 638 g / mol)

Synthesis Example 3 Synthesis of A-3

Synthesis Example 1 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The same procedure was followed to obtain the target compound A-3 (2.8 g, yield 65%).

Mass (Theoretical value: 638.57, Measured value: 638 g / mol)

Synthesis Example 4 Synthesis of A-4

Same as Synthesis Example 1, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The process was carried out to obtain the title compound A-4 (3.0 g, yield 63%).

Mass (Theoretical value: 714.6, Measured value: 714 g / mol)

Synthesis Example 5 Synthesis of A-5

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same process as in Synthesis Example 1 was performed to obtain A-5 (3.2 g, yield 67%) as a target compound.

Mass (Theoretical value: 715.6, Measured value: 715 g / mol)

Synthesis Example 6 Synthesis of A-6

2- (3-bromophenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Except for using the same procedure as in Synthesis Example 1 to obtain the target compound A-6 (2.9g, 61% yield).

Mass (Theoretical value: 715.6, Measured value: 715 g / mol)

Synthesis Example 7 Synthesis of A-7

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Except for using the same process as in Synthesis Example 1 to give the title compound A-7 (3.5g, 66% yield).

Mass (Theoretical value: 792.64, Measured value: 792 g / mol)

Synthesis Example 8 Synthesis of A-8

Synthesis Example 1 except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazolin (2.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. To obtain the target compound A-8 (3.2g, 64% yield) by the same procedure.

Mass (Theoretical value: 738.6, Measured value: 738 g / mol)

Synthesis Example 9 Synthesis of A-9

Except for using 2- (3-bromophenyl) triphenylene (3.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine The same process as in Synthesis Example 1 was carried out Phosphorus A-9 (3.0 g, yield 63%) was obtained.

Mass (Theoretical value: 710.60, Measured value: 710 g / mol)

Synthesis Example 10 Synthesis of A-10

Except for using 4'-bromobiphenyl-3-carbonitrile (2.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine was subjected to the same procedure as in Synthesis Example 1 A-10 (2.7 g, yield 70%) was obtained.

Mass (Theoretical value: 585.6, Measured value: 585 g / mol)

Synthesis Example 11 Synthesis of B-1

BIAz-2 (2.7g, 6.7mmol), 2-bromo-4,6-diphenylpyridine (2.5g, 8.0mmol), Pd (OAc) ₂ (0.08g, 0.34mmol), P ( t under nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the title compound B-1 (2.9 g, yield 68%).

Mass (Theoretical value: 637.58, Measured value: 637 g / mol)

Synthesis Example 12 Synthesis of B-2

The same procedure as in Synthesis Example 11 was carried out except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Obtaining the compound B-2 (3.0 g, 71% yield).

Mass (Theoretical value: 638.57, Measured value: 638 g / mol)

Synthesis Example 13 Synthesis of B-3

Synthesis Example 11 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The same procedure was followed to obtain the title compound B-3 (2.7 g, yield 63%).

Mass (Theoretical value: 638.57, Measured value: 638 g / mol)

Synthesis Example 14 Synthesis of B-4

The same procedure as in Synthesis Example 11 except that 4- (4-bromophenyl) -2,6-dipyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. This was carried out to obtain B-4 (3.2 g, yield 66%) as a target compound.

Mass (Theoretical value: 714.6, Measured value: 714 g / mol)

Synthesis Example 15 Synthesis of B-5

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine And the same process as in Synthesis Example 11 was obtained to obtain the target compound B-5 (3.4g, yield 70%).

Mass (Theoretical value: 715.6, Measured value: 715 g / mol)

Synthesis Example 16 Synthesis of B-6

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 11 was performed to obtain B-6 (3.1 g, yield 65%) as a target compound.

Mass (Theoretical value: 715.6, Measured value: 715 g / mol)

Synthesis Example 17 Synthesis of B-7

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Except for using the same process as in Synthesis Example 11 to obtain the title compound B-7 (3.3g, 62% yield).

Mass (Theoretical value: 792.64, Measured value: 792 g / mol)

Synthesis Example 18 Synthesis of B-8

Synthesis Example 11 except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazolin (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine To obtain the target compound B-8 (3.4g, 70% yield) by the same procedure.

Mass (Theoretical value: 738.6, Measured value: 738 g / mol)

Synthesis Example 19 Synthesis of B-9

Except for using 2- (3-bromophenyl) triphenylene (3.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine The same process as in Synthesis Example 11 was carried out Phosphorus B-9 (3.0 g, yield 64%) was obtained.

Mass (Theoretical value: 710.60, Measured value: 710 g / mol)

Synthesis Example 20 Synthesis of B-10

Except for using 4'-bromobiphenyl-3-carbonitrile (2.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine was subjected to the same process as in Synthesis Example 11 B-10 (2.7 g, yield 68%) was obtained.

Mass (Theoretical value: 585.6, Measured value: 585 g / mol)

Synthesis Example 21 Synthesis of C-1

BIAz-3 (2.7g, 6.7mmol), 2-bromo-4,6-diphenylpyridine (2.5g, 8.0mmol), Pd (OAc) ₂ (0.08g, 0.34mmol), P ( t under nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the title compound C-1 (3.8 g, yield 66%).

Mass (Theoretical value: 865.87, Measured value: 865 g / mol)

Synthesis Example 22 Synthesis of C-2

The same procedure as in Synthesis Example 21 was carried out except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound C-2 (3.5 g, yield 61%) was obtained.

Mass (Theoretical value: 866.86, Measured value: 866 g / mol)

Synthesis Example 23 Synthesis of C-3

Synthesis Example 21, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The same procedure was followed to obtain the title compound C-3 (3.8 g, yield 65%).

Mass (Theoretical value: 866.86, Measured value: 866 g / mol)

Synthesis Example 24 Synthesis of C-4

Same as Synthesis Example 11 except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The procedure was followed to obtain the title compound C-4 (4.3g, 68% yield).

Mass (Theoretical value: 942.89, Measured value: 942 g / mol)

Synthesis Example 25 Synthesis of C-5

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same process as in Synthesis Example 21 was performed to obtain C-5 (3.9 g, yield 61%) as a target compound.

Mass (Theoretical value: 943.89, Measured value: 943 g / mol)

Synthesis Example 26 Synthesis of C-6

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 21 was performed to obtain C-6 (4.5 g, yield 71%) as a target compound.

Mass (Theoretical value: 943.89, Measured value: 943 g / mol)

Synthesis Example 27 Synthesis of C-7

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Except for using the same procedure as in Synthesis Example 21 to obtain the title compound C-7 (4.9g, 72% yield).

Mass (Theoretical value: 1020.93, Measured value: 1020 g / mol)

 Synthesis Example 28 Synthesis of C-8

Synthesis Example 21 except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazolin (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine C-8 (4.2 g, yield 65%) was obtained by the same procedure as the target compound.

Mass (Theoretical value: 966.89, Measured value: 966 g / mol)

Synthesis Example 29 Synthesis of C-9

Except for using 2- (3-bromophenyl) triphenylene (3.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine The same process as in Synthesis Example 21 was carried out Phosphorus C-9 (4.2 g, yield 66%) was obtained.

Mass (Theoretical value: 938.89, Measured value: 938 g / mol)

Synthesis Example 30 Synthesis of C-10

Except for using 4'-bromobiphenyl-3-carbonitrile (2.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine was subjected to the same process as in Synthesis Example 21 C-10 (3.3 g, 61% yield) was obtained.

Mass (Theoretical value: 813.8, Measured value: 813 g / mol)

Synthesis Example 31 Synthesis of D-1

BIAz-4 (2.7g, 6.7mmol), 2-bromo-4,6-diphenylpyridine (2.5g, 8.0mol), Pd (OAc) ₂ (0.08g, 0.34mmol), P ( t under nitrogen stream -Bu) ₃ (0.16ml, 0.67mmol), NaO ( t -Bu) (1.29g, 13.4mmol) and toluene (70ml) were mixed and stirred at 110 ° C for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the title compound D-1 (3.0 g, yield 65%).

Mass (Theoretical value: 687.64, Measured value: 687 g / mol)

Synthesis Example 32 Synthesis of D-2

The same procedure as in Synthesis Example 31 was carried out except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The compound D-2 (3.2 g, yield 69%) was obtained.

Mass (Theoretical value: 688.63, Measured value: 688 g / mol)

Synthesis Example 33 Synthesis of D-3

Synthesis Example 31, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The same procedure was followed to obtain the title compound D-3 (3.0 g, yield 66%).

Mass (Theoretical value: 688.63, Measured value: 688 g / mol)

Synthesis Example 34 Synthesis of D-4

Same as Synthesis Example 31, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The procedure was followed to obtain the target compound D-4 (3.4g, 67% yield).

Mass (Theoretical value: 764.66, Measured value: 764 g / mol)

Synthesis Example 35 Synthesis of D-5

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same process as in Synthesis Example 31 was performed to obtain D-5 (3.1 g, yield 61%) as a target compound.

Mass (Theoretical value: 765.66, Measured value: 765 g / mol)

Synthesis Example 36 Synthesis of D-6

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 31 was performed to obtain D-6 (3.1 g, yield 61%) as a target compound.

Mass (Theoretical value: 765.66, Measured value: 765 g / mol)

Synthesis Example 37 Synthesis of D-7

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Except for using the same process as in Synthesis Example 31 to give the title compound D-7 (3.6g, 63% yield).

Mass (Theoretical value: 842.7, Measured value: 842 g / mol)

Synthesis Example 38 Synthesis of D-8

Synthesis Example 31 except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazolin (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine To obtain the target compound D-8 (3.5g, 66% yield).

Mass (Theoretical value: 788.66, Measured value: 788 g / mol)

Synthesis Example 39 Synthesis of D-9

Except for using 2- (3-bromophenyl) triphenylene (3.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine The same process as in Synthesis Example 31 was carried out Phosphorus D-9 (3.5 g, yield 69%) was obtained.

Mass (Theoretical value: 760.66, Measured value: 760 g / mol)

Synthesis Example 40 Synthesis of D-10

Except for using 4'-bromobiphenyl-3-carbonitrile (2.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine was subjected to the same procedure as in Synthesis Example 31 to D-10 (3.1 g, yield 72%) was obtained.

Mass (Theoretical value: 635.6, Measured value: 635 g / mol)

Synthesis Example 41 Synthesis of E-1

BIAz-5 (2.7g, 6.7mmol), 2-bromo-4,6-diphenylpyridine (2.5g, 8.0mmol), Pd (OAc) ₂ (0.08g, 0.34mmol), P ( t under nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain E-1 (2.4 g, 64% yield) of the title compound.

Mass (Theoretical value: 562.47, Measured value: 562 g / mol)

Synthesis Example 42 Synthesis of E-2

The same procedure as in Synthesis Example 41 was carried out except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound E-2 (2.6 g, yield 69%) was obtained.

Mass (Theoretical value: 563.46, Measured value: 563 g / mol)

Synthesis Example 43 Synthesis of E-3

Synthesis Example 41, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The same procedure was followed to obtain the target compound E-3 (2.6 g, yield 70%).

Mass (Theoretical value: 563.46, Measured value: 563 g / mol)

Synthesis Example 44 Synthesis of E-4

Same as Synthesis Example 41, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The process was carried out to obtain the title compound E-4 (3.1 g, yield 73%).

Mass (Theoretical value: 639.49, Measured value: 639 g / mol)

Synthesis Example 45 Synthesis of E-5

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 41 was carried out to obtain E-5 (2.8 g, yield 65%) as a target compound.

Mass (Theoretical value: 640.49, Measured value: 640 g / mol)

Synthesis Example 46 Synthesis of E-6

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 41 was performed to obtain E-6 (2.8 g, yield 65%) as a target compound.

Mass (Theoretical value: 640.49, Measured value: 640 g / mol)

Synthesis Example 47 Synthesis of E-7

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Except for using the same process as in Synthesis Example 41 to obtain the title compound E-7 (3.5g, 72% yield).

Mass (Theoretical value: 717.53, Measured value: 717 g / mol)

Synthesis Example 48 Synthesis of E-8

Synthesis Example 41 except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazolin (2.9 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. To obtain the target compound E-8 (3.4g, 77% yield) by the same procedure.

Mass (Theoretical value: 663.49, Measured value: 663 g / mol)

Synthesis Example 49 Synthesis of E-9

Except for using 2- (3-bromophenyl) triphenylene (3.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine The same process as in Synthesis Example 41 was carried out Phosphorus E-9 (3.1 g, yield 73%) was obtained.

Mass (Theoretical value: 635.49, Measured value: 635 g / mol)

Synthesis Example 50 Synthesis of E-10

Except for using 4'-bromobiphenyl-3-carbonitrile (2.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine was subjected to the same procedure as in Synthesis Example 41 E-10 (2.4 g, yield 73%) was obtained.

Mass (Theoretical value: 510.44, Measured value: 510 g / mol)

Synthesis Example 51 Synthesis of F-1

BIAz-6 (2.7g, 6.7mmol), 2-bromo-4,6-diphenylpyridine (2.5g, 8.0mmol), Pd (OAc) ₂ (0.08g, 0.34mmol), P ( t under nitrogen stream -Bu) ₃ (0.16 ml, 0.67 mmol), NaO ( t -Bu) (1.29 g, 13.4 mmol) and toluene (70 ml) were mixed and stirred at 110 ° C. for 5 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the title compound F-1 (2.4g, 63% yield).

Mass (Theoretical value: 578.54, Measured value: 578 g / mol)

Synthesis Example 52 Synthesis of F-2

The same procedure as in Synthesis Example 51 was carried out except that 4-bromo-2,6-diphenylpyrimidine (2.5 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. Compound F-2 (2.7 g, Yield 69%) was obtained.

Mass (Theoretical value: 579.53, Measured value: 579 g / mol)

Synthesis Example 53 Synthesis of F-3

Synthesis Example 51 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The same procedure was followed to obtain the title compound F-3 (2.9 g, 74% yield).

Mass (Theoretical value: 579.53, Measured value: 579 g / mol)

Synthesis Example 54 Synthesis of F-4

Same as Synthesis Example 51, except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (3.1 g, 8.0 mmol) was used instead of 2-bromo-4,6-diphenylpyridine. The process was carried out to obtain the title compound F-4 (3.3 g, yield 76%).

Mass (Theoretical value: 655.56, Measured value: 655 g / mol)

Synthesis Example 55 Synthesis of F-5

Except for using 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same process as in Synthesis Example 51 was performed to obtain F-5 (3.1 g, yield 70%) as a target compound.

Mass (Theoretical value: 656.56, Measured value: 656 g / mol)

Synthesis Example 56 Synthesis of F-6

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Then, the same procedure as in Synthesis Example 51 was performed to obtain F-6 (3.1 g, yield 71%) as a target compound.

Mass (Theoretical value: 656.56, Measured value: 656 g / mol)

Synthesis Example 57 Synthesis of F-7

2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (3.7 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine Except for using the same process as in Synthesis Example 51 to obtain the title compound F-7 (3.6g, 73% yield).

Mass (Theoretical value: 733.60, Measured value: 733 g / mol)

Synthesis Example 58 Synthesis of F-8

Synthesis Example 51 except for using 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazolin (2.9 g, 8.0 mmol) instead of 2-bromo-4,6-diphenylpyridine The same procedure as in the following to obtain the target compound F-8 (3.2g, 70% yield).

Mass (Theoretical value: 679.56, Measured value: 679 g / mol)

Synthesis Example 59 Synthesis of F-9

Except for using 2- (3-bromophenyl) triphenylene (3.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine The same process as in Synthesis Example 51 was carried out Phosphorus F-9 (3.1 g, yield 72%) was obtained.

Mass (Theoretical value: 651.56, Measured value: 651 g / mol)

Synthesis Example 60 Synthesis of F-10

Except for using 4'-bromobiphenyl-3-carbonitrile (2.1g, 8.0mmol) instead of 2-bromo-4,6-diphenylpyridine was subjected to the same procedure as in Synthesis Example 51 F-10 (2.3 g, yield 65%) was obtained.

Mass (Theoretical value: 526.51, Measured value: 526 g / mol)

Examples 1 to 54 Fabrication of Green Organic EL Devices

After the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, 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 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, 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) / 90% of the host compound + 10% Ir (ppy) ₃ (300nm) / BCP (10 nm) / Alq ₃ (30) An organic EL device was fabricated by laminating in order of nm) / LiF (1 nm) / Al (200 nm).

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

Comparative Example 1 Fabrication of Green Organic EL Device

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

[Evaluation Example 1]

For each of the green organic EL devices produced in Examples 1 to 54 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.

Sample Host Driving voltage EL peak Current efficiency (V) (nm) (cd / A) Example 1 A-1 6.77 517 41.3 Example 2 A-2 6.46 515 41.3 Example 3 A-3 6.81 518 39.7 Example 4 A-4 6.68 518 38.9 Example 5 A-5 6.66 517 41.5 Example 6 A-6 6.48 518 39.2 Example 7 A-7 6.48 517 41.3 Example 8 A-9 6.86 515 39.7 Example 9 A-10 6.48 518 38.9 Example 10 B-1 6.48 518 41.3 Example 11 B-2 6.86 517 41.3 Example 12 B-3 6.77 515 41.3 Example 13 B-4 6.66 518 41.2 Example 14 B-5 6.65 518 38.9 Example 15 B-6 6.65 517 41.3 Example 16 B-7 6.64 515 41.3 Example 17 B-9 6.64 518 41.3 Example 18 B-10 6.64 518 41.2 Example 19 C-1 6.81 517 42.2 Example 20 C-2 6.66 515 42 Example 21 C-3 6.81 518 39.7 Example 22 C-4 6.68 518 38.9 Example 23 C-5 6.66 518 41.3 Example 24 C-6 6.7 517 41.3 Example 25 C-7 6.7 515 43.1 Example 26 C-9 6.51 518 43.5 Example 27 C-10 6.77 518 41.4 Example 28 D-1 6.7 515 43.1 Example 29 D-2 6.51 518 43.5 Example 30 D-3 6.77 518 41.4 Example 31 D-4 6.46 518 42.2 Example 32 D-5 6.81 517 42 Example 33 D-6 6.68 515 41.8 Example 34 D-7 6.66 515 41.3 Example 35 D-9 6.48 518 41.2 Example 36 D-10 6.66 518 41.3 Example 37 E-1 6.86 517 41.2 Example 38 E-2 6.77 515 42 Example 39 E-3 6.66 518 39.7 Example 40 E-4 6.77 518 38.9 Example 41 E-5 6.46 515 41.3 Example 42 E-6 6.81 518 41.3 Example 43 E-7 6.73 518 43.1 Example 44 E-9 6.73 517 43.5 Example 45 E-10 6.73 515 41.4 Example 46 F-1 6.48 515 43.1 Example 47 F-2 6.86 518 43.5 Example 48 F-3 6.73 518 41.4 Example 49 F-4 6.48 517 41.5 Example 50 F-5 6.86 515 39.2 Example 51 F-6 6.77 518 41.3 Example 52 F-7 6.66 517 39.7 Example 53 F-9 6.65 518 38.9 Example 54 F-10 6.65 517 41.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1 above, when the compound according to the present invention was used in the light emitting layer of the green organic EL device (Examples 1 to 54), the efficiency and It was confirmed that the driving voltage is excellent.

[Examples 55 to 60] Fabrication of Red Organic EL Devices

The compound synthesized in 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.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, 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) / 90% host compound of Table 2 + 10% (piq) ₂ Ir (acac) (300nm) / BCP (10 nm) / Alq _An organic electroluminescent device was manufactured by stacking ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

Comparative Example 2 Fabrication of Red Organic EL Device

A red organic electroluminescent device was manufactured in the same manner as in Example 55, except for using CBP instead of Compound A-8 of Synthesis Example 8 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 55 to 60 and Comparative Example 2 are as follows.

[Evaluation Example 2]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 55 to 60 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host Driving voltage Current efficiency (V) (cd / A) Example 55 A-8 4.65 11.8 Example 56 B-8 4.74 11.5 Example 57 C-8 4.87 11.8 Example 58 D-8 4.74 11.5 Example 59 E-8 4.87 11.8 Example 60 F-8 4.56 9.6 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used in the light emitting layer of the red organic electroluminescent device (Examples 55 to 60), the efficiency and the efficiency of the conventional CBP were used in the red organic electroluminescent device (Comparative Example 2). It was confirmed that the driving voltage is excellent.

Example 61 Fabrication of Organic EL Device

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-9 (80nm) / DS-H522 + 5% DS-501 (30nm) / BCP (10nm) / Alq3 (30) synthesized in Synthesis Example 9 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.

[Examples 62 to 66] Fabrication of Organic EL Device

Except for using the compound B-9, C-9, D-9, E-9, F-9 synthesized in place of the compound A-9 used as the hole transport layer material in forming the hole transport layer in Example 61, The organic EL device was fabricated in the same manner as in Example 61.

[ Comparative example  3] Fabrication of Organic EL Device

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-9 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.

[Evaluation Example 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 66 and Comparative Example 3, respectively, and the results are shown in Table 3 below.

Sample Hole transport layer Driving voltage (V) Current efficiency (cd / A) Example 61 A-9 4.4 19.8 Example 62 B-9 4.2 19.2 Example 63 C-9 4.3 18.9 Example 64 D-9 4.4 19.2 Example 65 E-9 4.2 18.9 Example 66 F-9 4.9 20.1 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3, the organic EL device (the organic EL device manufactured in each of Examples 61 to 66) using the compounds (A-9 to F-9) according to the present invention as a hole transporting layer, 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.

Example 67 Fabrication of Blue Organic EL Device

Compound A-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic EL device was manufactured as follows.

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

On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / AND + 5% DS-405 (30 nm) / Compound A-1 (5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to prepare an organic EL device.

The structure of NPB, AND and Alq ₃ used at this time is as follows.

Example 68 to Example 108 Fabrication of Blue Organic EL Device

A blue organic EL device was manufactured in the same manner as in Example 67, except that each compound shown in Table 4 was used instead of the compound A-1 used as the life improving layer material in Example 67.

Comparative Example 4 Fabrication of Blue Organic EL Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 67, except that Alq ₃ , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm without including the life improving layer.

Comparative Example 5 Fabrication of Blue Organic EL Device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that instead of using Compound A-1 used as the life improving layer material in Example 67, BCP was used.

The structure of the BCP used at this time is as follows.

[Evaluation Example 4]

For organic electroluminescent devices manufactured in Examples 67 to 109 and Comparative Examples 4 and 5, respectively, driving voltage, current efficiency, emission wavelength, and lifetime (T97) at a current density of 10 mA / cm 2 were measured. It is shown in Table 4 below.

Sample Life Improvement Layer Driving voltage Current efficiency EL peak life span (V) (cd / A) (nm) (hr, T ₉₇ ) Example 67 A-1 4.8 5.9 463 41 Example 68 A-2 4.2 5.9 465 42 Example 69 A-3 5.0 6.0 469 43 Example 70 A-4 5.1 6.2 461 45 Example 71 A-5 5.2 6.3 462 48 Example 72 A-6 4.5 6.4 458 38 Example 73 A-7 5.3 6.0 458 37 Example 74 B-1 5.1 6.1 459 32 Example 75 B-2 5.2 6.1 460 39 Example 76 B-3 4.3 5.9 461 43 Example 77 B-4 4.2 5.9 463 45 Example 78 B-5 4.3 6.4 465 48 Example 79 B-6 4.2 6.3 469 38 Example 80 B-7 4.8 6.1 461 37 Example 81 C-1 4.9 6.1 462 32 Example 82 C-2 5.2 5.9 451 45 Example 83 C-3 5.3 5.9 457 48 Example 84 C-4 5.3 6.3 459 38 Example 85 C-5 5.2 5.9 459 37 Example 86 C-6 5.0 6.4 459 32 Example 87 C-7 5.0 6.3 451 39 Example 88 D-1 4.9 6.1 459 43 Example 89 D-2 4.9 6.1 460 45 Example 90 D-3 4.9 5.9 461 44 Example 91 D-4 5.0 5.9 463 40 Example 92 D-5 4.9 6.3 465 42 Example 93 D-6 4.9 5.9 469 40 Example 94 D-7 4.9 6.2 461 40 Example 95 E-1 4.8 6.1 462 41 Example 96 E-2 4.2 6.1 451 44 Example 97 E-3 4.2 6.0 458 38 Example 98 E-4 4.1 5.9 458 40 Example 99 E-5 4.1 5.9 461 33 Example 100 E-6 4.1 6.0 462 32 Example 101 E-7 4.1 6.2 465 38 Example 102 F-1 4.0 6.3 469 40 Example 103 F-2 5.1 6.4 461 42 Example 104 F-3 5.1 6.0 462 40 Example 105 F-4 5.3 6.1 465 40 Example 106 F-5 4.8 6.1 469 41 Example 107 F-6 4.9 6.0 458 39 Example 108 F-7 5.0 6.1 458 42 Comparative Example 4 - 4.7 5.6 458 32 Comparative Example 5 BCP 5.3 5.9 458 28

As can be seen in Table 4, in the case of the blue organic EL device of Examples 67 to 108 using Compounds A-1 to F-7 as the life improvement layer material, the blue color of Comparative Example 4 without using the life improvement layer The driving voltage is similar to or slightly better than that of the organic EL element, but the current efficiency and lifetime are greatly improved.

In addition, the blue organic EL devices of Examples 67 to 108 are not only excellent in driving voltage and current efficiency, but also have a long life compared to the blue organic EL devices of Comparative Example 5, which use CBP as the hole blocking layer material instead of the life improvement layer. Has been improved.

Example 109 Preparation of Blue Organic EL Device

Compound A-5 synthesized in Synthesis Example 5 was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.

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

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

Example 110 to Example 114 Fabrication of Blue Organic EL Device

A blue organic EL device was manufactured in the same manner as in Example 109, except that each compound shown in Table 5 was used instead of Compound A-5 used as the electron transporting layer material in Example 109.

Comparative Example 6 Fabrication of Blue Organic EL Device

A blue organic electroluminescent device was manufactured in the same manner as in Example 108, except that Alq ₃ , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm without including the life improving layer.

[Evaluation Example 5]

For organic electroluminescent devices prepared in Examples 109 to 114 and Comparative Example 6, the driving voltage, current efficiency, emission wavelength, and lifetime (T97) at a current density of 10 mA / cm 2 were measured, and the results are shown in the following table. 5 is shown.

Sample Electron transport layer Drive voltage (V) Current efficiency (cd / A) Light emitting peak (nm) Example 109 A-5 4.5 5.8 463 Example 110 B-5 4.2 6.1 462 Example 111 C-5 4.0 6.3 460 Example 112 D-5 4.2 5.8 462 Example 113 E-5 4.0 6.1 460 Example 114 F-5 4.7 6.0 459 Comparative Example 6 _ 4.7 5.6 458

As shown in Table 5, in the case of the blue organic EL device of Examples 109 to 114 using the compounds A-5 to F-5 as the electron transporting layer material, the blue organic EL device of Comparative Example 6 using Alq ₃ as the electron transporting layer The driving voltage and current efficiency are further improved.

As such, when the compound of Formula 1 according to the present invention was used as the life improving layer material or the electron transporting layer material, it was confirmed that the driving voltage and the current efficiency were improved, and further, the life characteristics could be greatly improved.

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

Claims (17)

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

In Chemical Formula 1, Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , and Y ₉ and Y ₁₀ , Y ₁₀ and Y ₁₁ and Y At least one of ₁₁ and Y ₁₂ is condensed with a ring represented by Formula 2 to form a condensed ring; [Formula 2]

In Chemical Formula 2, The dotted line is the part where condensation takes place; In Chemical Formulas 1 and 2, X ₁ and X ₂ are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ), and Si (Ar ₄ ) (Ar ₅ ) At least one of X ₁ and X ₂ is N (Ar ₁ ); Y ₁ to Y ₁₂ which are not condensed with the ring represented by Formula 2 to form a condensed ring, are the same or different from each other, and each independently N or C (R ₁ ); When there are a plurality of Y ₁₃ to Y ₁₆ , they are the same as or different from each other, and the Y ₁₃ to Y ₁₆ are each independently N or C (R ₁ ); When there are a plurality of R ₁ , they are the same or different from each other, and each R ₁ is independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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 Or a C ₆ -C ₆₀ mono or diarylphosphinyl group and C ₆ -C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring; Ar ₁ to Ar ₅ are the same as or different from each other, and each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and C of _Is selected from the group consisting of ₆ to C ₆₀ arylamine groups, or combines with adjacent groups to form a condensed ring; An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group of Ar ₁ to Ar ₅ and R ₁ , an aryl phosphine group, a mono- or diaryl phosphine blood group and the arylamine groups are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heteroatoms Cycloalkyl 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 ₁ ~ C ₄₀ alkyl Silyl 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 diaryl phosphine blood group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ aryl amine, or is unsubstituted, substituted by the substituents Wu, when the substituent is bonded to the adjacent groups may form a condensed ring, which is substituted with plural substituents, they may be the same or different from each other. The method of claim 1, Y ₁ and Y ₂ , Y ₇ and Y ₈ and At least one of Y ₁₁ and Y ₁₂ is condensed with a ring represented by the following Formula 2 to form a condensed ring: [Formula 2]

In Chemical Formula 2, Dotted lines and Y ₁₃ to Y ₁₆ are as defined in claim 1. The method of claim 1, Wherein X ₁ is selected from the group consisting of O, S and N (Ar ₁ ), and X ₂ is N (Ar ₁ ). The method of claim 1, Compound represented by the formula (1) is a compound characterized in that the compound represented by any one of the formulas M-1 to M-12:

In Formulas M-1 to M-12, X ₁ , X _2, and Y ₁ to Y ₁₆ are as defined in claim 1. The method of claim 4, wherein Y ₁ to Y ₁₆ may be all C (R ₁ ), or may include 1 to 3 N, and a plurality of R ₁ are the same or different. The method of claim 1, Compound represented by the formula (1) is a compound characterized in that the compound represented by any one of the formulas (N-1) to (N-12):

In Chemical Formulas N-1 to N-12, X ₁ , Ar _1, and R ₁ are as defined in claim ₁ . The method of claim 1, Compound represented by the formula (1) is a compound, characterized in that the compound represented by any one of the following formula (3): [Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7, When there are a plurality of Ar ₁ , they are the same as or different from each other, and Ar ₁ is each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, or a nuclear atom having 3 to 40 heterocycloalkyl groups. , C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group of nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ 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 dia Can be selected from the group consisting of arylphosphinyl group and C ₆ -C ₆₀ arylamine group, or can be combined with adjacent groups to form a condensed ring; Y ₁ to Y ₁₂ are the same as or different from each other, and each independently N or C (R ₁ ); When there are a plurality of Y ₁₃ to Y ₁₆ , they are the same as or different from each other, and the Y ₁₃ to Y ₁₆ are each independently N or C (R ₁ ); When there are a plurality of R ₁ , they are the same or different from each other, and each R ₁ is independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ -C ₄₀ alkyl group, C ₃ -C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups , C ₁ ~ 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 Or a C ₆ -C ₆₀ mono or diarylphosphinyl group and C ₆ -C ₆₀ arylamine group, or combine with an adjacent group to form a condensed ring; Ar ₁ And the alkyl group of R _1, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, a mono or diaryl phosphine blood group and the arylamine groups are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl 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 ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group And it may be unsubstituted or substituted with one or more substituents selected from the group consisting of C ₆ ~ C ₆₀ arylamine group, when substituted with the substituents, Substituents may be bonded to adjacent groups to form a condensed ring, and when substituted with a plurality of substituents, they may be the same or different from each other. The method of claim 7, wherein When the Ar _1, or wherein Ar ₁ multiple individual at least one C ₆ ~ can aryl date of C _60, and the aryl groups being substituted or unsubstituted groups of one or more C ₆ ~ C ₆₀ aryl group, a plurality of substituents When substituted, they are the same or different from each other. The method of claim 7, wherein In Formula 4, Y ₈ is C (R ₁ ), and R ₁ is C ₆ ~ C ₆₀ An aryl group, characterized in that the aryl group. The method of claim 1, At least one of the R _One And Ar _{One To} Ar ₅ A compound characterized in that the phenyl group or a substituent represented by the following formula (8): [Formula 8]

In Chemical Formula 8, * Means a moiety bonded to Formula 1; L ₁ is selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms; Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N; When there are a plurality of R _{11 s} , they are the same as or different from each other, and each R ₁₁ is 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 ₆ ~ C ₆₀ Aryl group, 5 to 40 heteroaryl group of nuclear atoms, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C a cycloalkyl group of ₃ ~ C _40, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C group _{of 6} to arylboronic of C _60, C ₆ to C ₆₀ aryl phosphine group, C ₆ to C ₆₀ mono or diaryl phosphine blood group and a C ₆ - or selected from the group consisting arylsilyl of C ₆₀ of the adjacent May combine with a 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, An aryl phosphine group, a mono or diaryl phosphinyl group and an aryl silyl group, the arylene group and hetero arylene group of L ₁ 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 of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy groups, C ₆ to C ₆₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group When substituted by one or more substituents selected from the group consisting of a reel or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other. The method of claim 10, Substituent represented by the formula (8) is a compound characterized in that the substituent represented by any one of the following formula O-1 to formula O-15:

In Chemical Formulas O-1 to O-15, 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 each independently deuterium, halogen, cyan No 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 of 3 to 40 heterocycloalkyl group , C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl group of nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group , C ₁ ~ C ₄₀ Alkylsilyl 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 dia A arylphosphinyl group and a C ₆ -C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring; 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 ₆₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ 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 ₆₀ group At least one member selected from the group consisting of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group When substituted or unsubstituted with a substituent, and substituted with a plurality of substituents, they may be the same or different from each other; L ₁ and R ₁₁ are each as defined in claim 10. The method of claim 10, L ₁ is a single bond, a phenylene group, a biphenylene group or a carbazolyl compound, characterized in that. The method of claim 1, Ar ₁ to Ar ₅ are the same as or different from each other, each independently selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline, Phenyl, pyridine, pyrimidine, triazine, biphenyl, and quinazoline of Ar ₁ to Ar ₅ may be substituted or not substituted with one or more selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, biphenyl, and quinazoline. And, when substituted with a plurality of substituents, they are the same or different from each other. The method of claim 1, The compound is selected from the group consisting of the following compounds:

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 at least one organic material layer comprises an organic electroluminescent device comprising a compound represented by the formula (1) according to any one of claims 1 to 14. The method of claim 15, The organic material layer including the compound represented by Formula 1 is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer. The method of claim 16, An organic light emitting device, characterized in that the light emitting layer containing the compound represented by the formula (1) is used as a phosphorescent host.