KR20170074649A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel compound and an organic electroluminescent device including the same. The compound according to the present invention is used in an organic compound layer of an organic electroluminescent device, preferably a light emitting layer, an electron transporting layer, a hole transporting layer, The luminous efficiency, the driving voltage, the life and the like of the electroluminescent device can be improved.

Description

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

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

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

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

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials to realize better natural colors. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP and Alq ₃ are widely known as electron transporting layer materials and anthracene derivatives as light emitting layer materials. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.

However, conventional organic material layers are advantageous from the viewpoint of light emitting properties, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of the organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

The present invention has been made to solve the above problems and it is an object of the present invention to provide a novel compound capable of improving the efficiency, lifetime and stability of the organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

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

l, m and n are each independently an integer of 0 to 4;

At least one of R ₁ to R ₃ is a substituent represented by the following general formula (2), and the others are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, alkynyl of C ₂ ~ C _40, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, 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 a C ₆ ~ group is selected from the group consisting of an aryl amine of the C ₆₀ or adjacent To form a condensed ring, and when there is a plurality of R ₁ to R ₃ each, they are the same or different;

Ar ₁ to Ar ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an arylamine, or, by combining groups adjacent to form a condensed ring;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group and alkylsilyl group of R ₁ to R ₃ and Ar ₁ to Ar ₅ A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl A boron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group , When they are substituted with a plurality of substituents, they may be the same or different from each other;

(2)

In Formula 2,

* Denotes the part where the bond is made;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a C ₆ to C ₆₀ arylene group and a heteroarylene group having 5 to 60 nuclear atoms;

The arylene group and the heteroarylene group of L ₁ and L ₂ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryl of C ₆₀ An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ selected from the group consisting arylsilyl of C ₆₀ one kind of substituent or being unsubstituted , When they are substituted with a plurality of substituents, they may be the same or different from each other;

Ar ₆ is a substituent selected from the group consisting of the following formulas A-1 to A-11;

In the above Formulas A-1 to A-11,

* Denotes the part where the bond is made;

Z ₁ to Z ₁₀ are each independently N or C (R ₉ );

Any one of Z ₁ to Z ₄ bonded to L ₂ in the above formulas A-2 and A-6 is C (R ₉ ), wherein R ₉ is a member;

T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C (R ₁₀ ) (R ₁₁ ), N (R ₁₂ ), O and S, but not both T ₁ and T ₂ are single bonds;

p is an integer from 0 to 3;

q and r are each independently an integer of 0 to 4;

R ₄ and R ₅ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine blood group and the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ of the R ₄ and R ₅ in each case a plurality of individuals which the same or different from each other ;

R ₆ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ C ₆₀ of the aryl phosphine is selected from the pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group, and the group consisting of an aryl amine of the C ₆ ~ C ₆₀ of, in the case where the R ₉ multiple individuals which are the same or different from each other;

Alkyl groups of the R ₄ to R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .

"Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.

As used herein, the term "alkenyl" is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

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

"Aryl" in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such 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.

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

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

"Alkylsilyl" in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.

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

The compound represented by the formula (1) according to the present invention has excellent thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 according to the present invention is used as a material for an organic electroluminescent device, an organic electroluminescent device having excellent light emitting performance, a low driving voltage, a high efficiency and a long life can be manufactured , And further, a full color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel organic compounds according to the present invention may be used in combination with a tribenzo [b, f] azepine moiety, a tribenzo [b, d, f] oxepine moiety, a tribenzo [ b, d, f] thiepine moiety, a tribenzo [b, d] selenepine moiety or a tribenzo [b, d, f] silepine moiety, A structure in which various aryl groups, heteroaryl groups or arylamine groups such as dibenzofuran, dibenzosilyl, dibenzoselenophene, carbazole, fluorene, triphenylene and / or triazine moiety are bonded, Is characterized by being represented by the following formula (1)

[Chemical Formula 1]

In Formula 1,

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

l, m and n are each independently an integer of 0 to 4;

At least one of R ₁ to R ₃ is a substituent represented by the following general formula (2), and the others are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, alkynyl of C ₂ ~ C _40, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, 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 a C ₆ ~ group is selected from the group consisting of an aryl amine of the C ₆₀ or adjacent To form a condensed ring, and when there is a plurality of R ₁ to R ₃ each, they are the same or different;

Ar ₁ to Ar ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ groups of the aryl amine group selected or adjacent from the group consisting of (e.g., adjacent R _1, or R ₃ and so on) To form a condensed ring;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group and alkylsilyl group of R ₁ to R ₃ and Ar ₁ to Ar ₅ A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl A boron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group , When they are substituted with a plurality of substituents, they may be the same or different from each other;

 (2)

In Formula 2,

* Denotes the part where the bond is made;

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a C ₆ to C ₆₀ arylene group and a heteroarylene group having 5 to 60 nuclear atoms;

The arylene group and the heteroarylene group of L ₁ and L ₂ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryl of C ₆₀ An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ selected from the group consisting arylsilyl of C ₆₀ one kind of substituent or being unsubstituted , When they are substituted with a plurality of substituents, they may be the same or different from each other;

Ar ₆ is a substituent selected from the group consisting of the following formulas A-1 to A-11;

In the above Formulas A-1 to A-11,

* Denotes the part where the bond is made;

Z ₁ to Z ₁₀ are each independently N or C (R ₉ );

Any one of Z ₁ to Z ₄ bonded to L ₂ in the above formulas A-2 and A-6 is C (R ₉ ), wherein R ₉ is a member;

T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C (R ₁₀ ) (R ₁₁ ), N (R ₁₂ ), O and S, but not both T ₁ and T ₂ are single bonds;

p is an integer from 0 to 3;

q and r are each independently an integer of 0 to 4;

R ₄ and R ₅ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine blood group and the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ of the R ₄ and R ₅ in each case a plurality of individuals which the same or different from each other ;

R ₆ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60, wherein R ₉ to R ₁₂ in each case a plurality of individual, they are equal to each other Or different;

Alkyl groups of the R ₄ to R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

The compound represented by Formula 1 of the present invention has a higher molecular weight than conventional organic electroluminescence device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), and has a high glass transition temperature, And has excellent hole injecting ability, hole transporting ability, and light emitting ability. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

Specifically, since a tribenzo [b, f] azepine moiety can have both a moiety having a good hole transporting ability and a moiety having a good electron transporting ability depending on the characteristics of a bonded substituent , The compound of the present invention has hole mobility or electron mobility of more than a certain level and can be used as a hole transport layer of an organic electroluminescent device.

In addition, since the compound of Formula 1 has a structure in which an electron-withdrawing group (EWG) having a high electron absorbing property is bonded, the entire molecule has bipolar characteristics, so that the binding force between holes and electrons can be enhanced. Therefore, the compound of the formula (1) can exhibit excellent luminescent characteristics and can be applied to a blue, green or red phosphorescent light-emitting layer material of an organic electroluminescent device.

As described above, the compound represented by Formula 1 can improve phosphorescence characteristics of the organic electroluminescent device, improve the hole injection / transport ability, luminous efficiency, driving voltage, lifetime characteristics, etc., The electron transporting ability and the like can be improved. Therefore, the compound of the formula (1) according to the present invention can be used for the organic electroluminescent device, preferably an organic layer material, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), a hole and electron transport layer material, Materials, and more preferably phosphorescent light-emitting layer materials.

In addition, the compound of formula (1) has various substituents, especially aryl groups and / or heteroaryl groups, introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, For example, CBP). ≪ / RTI > The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer. Therefore, the organic electroluminescent device comprising the compound of Formula 1 according to the present invention can greatly improve performance and lifetime characteristics. As a result, the organic light emitting device having improved performance and lifetime characteristics can maximize the performance of the full color organic light emitting panel.

That is, when the compound of Formula 1 according to the present invention is used as a hole and electron injection / transport layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material, a conventional organic layer material (for example, CBP) The efficiency and lifetime of the organic electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

According to a preferred embodiment of the present invention, X ₁ may be selected from the group consisting of O, S and N (Ar ₁ ), more preferably O or S.

According to a preferred embodiment of the present invention, when X ₁ is N (Ar ₁ ), Ar ₆ is preferably selected from the group consisting of Formulas A-1 to A-3 and A-5 to A-11 In this case, when Ar ₆ is A-3, T ₁ and T ₂ are not both N (R ₁₂ ).

According to a more preferred embodiment of the present invention, when X ₁ is N (Ar ₁ ), Ar ₆ may be selected from the group consisting of A-5 to A-11, more preferably A-5 To A-9.

According to a preferred embodiment of the present invention, each of R ₉ to R ₁₂ may independently be selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group and a C ₆ to C ₆₀ aryl group, A methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group and a naphthalenyl group.

According to a preferred embodiment of the present invention, in the above formula (A-9), R ₆ and R ₇ are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group and a C ₆ to C ₆₀ aryl group And more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, phenyl, biphenyl, naphthalenyl and fluorenyl groups.

According to a preferred embodiment of the present invention, at least one of Ar ₁ to Ar ₅ is a substituent represented by the following general formula (3) in view of luminous efficiency, but is not limited thereto:

(3)

In Formula 3,

* Denotes the part where the bond is made;

L ₃ is selected from the group consisting of a single bond, an arylene group having ₆ to ₆₀ carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;

Y ₁ to Y ₅ are each independently N or C (R ₁₃ );

R ₁₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C selected from the ₆₀ group consisting of aryl amines, or by combining together with the adjacent group (e. g., L _3, or other R _13, and so on) that condensed ring And when a plurality of R < ₁₃ > s are present, they may be the same or different from each other;

Aryl group and a heteroaryl group of the alkylene group, R ₁₃ in the L _3, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, aryloxy C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkoxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, 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 ~ C ₆₀ aryl silyl group of , And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, each of L ₁ and L ₂ is independently a linker selected from the group consisting of the following formulas (B-1) to (B-12) :

In the above Formulas B-1 to B-12,

* Denotes the part where the bond is made;

R ₁₄ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;

Alkyl group of the R _14, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to 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 ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, when X ₁ is N (Ar ₁ ), L ₁ and L ₂ are each independently selected from the group consisting of the aforementioned formulas B-1 to B-4 and B-7 to B-12 , And more preferably from the group consisting of formulas B-1 to B-4.

The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:

In the present invention, the compound represented by Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960), J. Chem. SOC. 4482 (1955) 2457 (1995)). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic Field  Light emitting element

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

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used singly or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI > Preferably, the organic compound layer containing the compound represented by Formula 1 may be a light emitting layer, a hole transporting layer, an electron transporting layer, or an electron transporting supporting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, which may include a compound represented by the above formula (1) as a host material. Thus, when the compound represented by Formula 1 is incorporated as a light emitting layer material of an organic electroluminescent device, preferably a green phosphorescent host, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency and power efficiency), lifetime, luminance and driving voltage, etc., can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked. At this time, an electron transporting auxiliary layer may be further laminated between the light emitting layer and the electron transporting layer, and an electron injection layer may further be laminated on the electron transporting layer. In the present invention, at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron transporting auxiliary layer, and the electron injecting layer may include the compound represented by the formula (1) Transporting layer or electron transporting-supporting layer may contain a compound represented by the above formula (1).

In addition, the structure of the organic electroluminescent device of the present invention may be a structure in which not only an anode, one or more organic compound layers and a cathode are sequentially laminated but also an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic compound layer.

The organic electroluminescent device of the present invention can be produced by a method described in the related art (1), except that at least one of the organic material layers (for example, a light emitting layer, an electron transporting layer, a hole transporting layer, or an electron transporting supporting layer) May be produced by forming other organic layers and electrodes using materials and methods known in the art.

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

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

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

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

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

[ Preparation Example  One] Core1  Synthesis of

<Step 1> Synthesis of N- (2- Bromophenyl )-2'- Chlorobiphenyl -2- Amine  Synthesis of

Chlorobiphenyl-2-amine (50 g, 245.5 mmol), 1-bromo-2-iodobenzene (83.3 g, 294.6 mmol), Pd (OAc) ₂ (2.75 g, 12.25 mmol) P (t-Bu) ₃ (4.95 g, 24.55 mmol), NaO t- Bu (47.2 g, 491 mmol) and xylene (1,000 ml) were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 6: 1 (v / v)) to give N- (2-bromophenyl) -Chlorobiphenyl-2-amine (47.1 g, yield 54%).

^{1 H-NMR: δ 4.0 (} b, 1H), 6.52 (d, 1H), 6.69-6.70 (m, 2H), 6.87 (dd, 1H), 7.14-7.16 (m, 2H), 7.35-7.39 (m , 2H), 7.54-7.55 (m, 3H), 7.73 (d, IH)

&Lt; Step 2 > 2- Chloro -9H- Tribenzo [b, d, f] azepine  Synthesis of

(47.5 g, 132.5 mmol), t-BuOK (29.7 g, 265.0 mmol) and liquid ammonia (1,000 mL) were mixed in a nitrogen stream under nitrogen atmosphere And stirred at 100 &lt; 0 &gt; C for 3 hours.

After the reaction was completed, it was extracted from water and then filtered to obtain 2-chloro-9H-tribenzo [b, d, f] azepine (12.8 g, yield 35%).

^{1 H-NMR: δ 6.68-6.69 (} m, 2H), 6.87-6.88 (m, 2H), 7.16-7.17 (m, 2H), 7.51-7.54 (m, 3H), 7.79 (d, 1H), 8.07 (s, 1 H), 8.42 (b, 1 H)

<Step 3> Of Core1  synthesis

(12.8 g, 46 mmol), iodobenzene (11.28 g, 55.3 mmol), Cu (1.46 g, 23 mmol), K ₂ CO ₃ (12.7 g, 92 mmol) and nitrobenzene (200 ml) were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, remove the water in the following MgSO ₄ and extracted with ethyl acetate, and purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to give the Core1 (11.7 g, yield 72%).

^{1 H-NMR: δ 7.08-7.24 (} m, 7H), 7.38 (m, 4H), 7.65 (d, 1H), 7.92 (d, 1H), 8.14 (m, 2H)

[ Preparation Example  2] Core2  Synthesis of

The procedure of Step 3 of Preparation Example 1 was repeated except that 3-bromo-1,1'-biphenyl (10 g, 43.2 mmol) was used instead of iodobenzene to obtain the target compound Core2 (8.3 g, yield 54%).

^{1 H-NMR: δ 7.12-7.18 (} m, 4H), 7.25 (s, 1H), 7.39-7.64 (m, 9H), 7.76 (m, 2H), 7.94 (d, 1H), 8.12 (m, 3H )

[ Preparation Example  3] Core3  Synthesis of

The procedure of Step 3 of Preparation Example 1 was repeated except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (13.3 g, 43.2 mmol) was used instead of iodobenzene The target compound Core3 (8.7 g, yield 48%) was obtained.

^{1 H-NMR: δ 7.08 (} m, 2H), 7.32-7.55 (m, 12H), 7.67 (m, 2H), 7.78 (m, 4H), 7.93 (d, 1H), 8.18 (m, 2H)

[ Preparation Example  4] Core4  Synthesis of

<Step 1> Synthesis of N- (2- Bromo -5- Chlorophenyl ) - [1,1'-biphenyl] -2- Amine  synthesis

The procedure of Step 1 of Preparation Example 1 was repeated except that 1-bromo-4-chloro-2-iodobenzene (112 g, 354.5 mmol) was used instead of 1-bromo- (2-bromo-5-chlorophenyl) - [1,1'-biphenyl] -2-amine (55 g, yield 52%).

^{1 H-NMR: δ 6.92 (} d, 1H), 7.11 (m, 3H), 7.33 (s, 1H), 7.37-7.46 (m, 6H), 8.18 (d, 1H), 10.4 (s, 1H)

<Step 2> 7- Chloro -9H- Tribenzo [b, d, f] azepine  synthesis

Instead of N- (2-bromo-5-chlorophenyl) - [1,1'-biphenyl- Chloro-9H-tribenzo [b, d, f] -quinolinone was obtained by carrying out the same procedure as Step 2 of Preparation Example 1, Azepine (16.1 g, yield 38%).

^{1 H-NMR: δ 7.12 (} m, 3H), 7.37 (m, 2H), 7.58-7.67 (m, 4H), 8.04 (m, 2H), 8.13 (d, 1H)

<Step 3> Core4  synthesis

Except that 7-chloro-9H-tribenzo [b, d, f] azepine (16 g, 57.6 mmol) was used instead of 2-chloro-9H-tribenzo [ The procedure of Step 3 of Example 1 was repeated to obtain Core4 (12.6 g, yield 62%) as a target compound.

^{1 H-NMR: δ 6.98-7.24 (} m, 7H), 7.41 (m, 2H), 7.66 (m, 4H), 8.03 (m, 2H), 8.12 (d, 1H)

[ Preparation Example  5] Core5  Synthesis of

<Step 1> Synthesis of N- (2- Bromo -4- Chlorophenyl ) Biphenyl-2- Amine  Synthesis of

The procedure of Step 1 of Preparation Example 1 was repeated except that 2-bromo-4-chloro-1-iodobenzene (112 g, 354.5 mmol) was used instead of 1-bromo- N- (2-bromo-4-chlorophenyl) biphenyl-2-amine (60 g, yield 57%) as a compound.

^{1 H-NMR: δ 7.06-7.20 (} m, 5H), 7.37-7.44 (m, 5H), 7.68 (s, 1H), 8.14 (d, 1H), 10.88 (s, 1H)

<Step 2> 6- Chloro -9H- Tribenzo [b, d, f] azepine  synthesis

Instead of N- (2-bromo-4-chlorophenyl) biphenyl-2-amine (60 g , 167.2 mmol), the target compound, 6-chloro-9H-tribenzo [b, d, f] azepine (16.7 g, yield 36 %).

^{1 H-NMR: δ 7.16-7.39 (} m, 6H), 7.63 (m, 2H), 8.02 (m, 3H), 8.14 (d, 1H)

<Step 3> Core5  synthesis

Except that 6-chloro-9H-tribenzo [b, d, f] azepine (16.7 g, 60.2 mmol) was used instead of 2-chloro-9H-tribenzo [ The procedure of Step 3 of Preparation Example 1 was repeated to obtain Core5 (13.8 g, yield 65%) as a target compound.

^{1 H-NMR: δ 7.02-7.36 (} m, 10H), 7.66 (m, 2H), 7.93 (m, 3H), 8.15 (d, 1H)

[ Preparation Example  6] Core6  Synthesis of

&Lt; Step 1 > N- (5'- Chloro -2'- Hydroxy - [1,1'-biphenyl] -2-yl) Acetamide  synthesis

(50 g, 241.02 mmol), (2-acetamidophenyl) boronic acid (51.75 g, 289.2 mmol), K2CO3 (99.9 g, 723.06 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh3) 4 (8.35 g, 7.23 mmol) was added thereto and stirred at 80 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 6: 1 (v / v)) to obtain N- (5'-chloro-2'-hydroxy- [1,1'- -2-yl) acetamide (46.6 g, yield 74%).

¹ H-NMR :? 2.24 (s, 3H), 7.32 (t, IH), 7.55 (m, 2H), 7.83 s, 1 H)

<Step 2> 2 '- Acetamido -5- Chloro - [1,1'-biphenyl] -2-yl Trifluoromethanesulphonate Synthesis of phonate

(46.6 g, 178.05 mmol) and pyridine (21.1 g, 267.08 mmol) were added to a solution of N- (5'-chloro-2'-hydroxy- [1,1'- After dropping to 0 ° C, triflic anhydride (60.2 g, 213.6 mmol) was added dropwise to 1,000 ml of MC and stirred at 25 ° C for 5 hours. After the reaction was completed, the residue was purified by column chromatography (Hexane: EA = 30: 1 (v / v)) to obtain 2'-acetamido-5-chloro- [1,1'-biphenyl] To obtain fluoromethane sulfonate (63 g, yield 90%).

^{1 H-NMR: δ 2.22 (} s, 3H), 7.30 (t, 1H), 7.42-7.58 (m, 4H), 8.08 (d, 1H), 10.06 (s, 1H)

<Step 3> N - (5'- Chloro -2''- Methoxy - [1,1 ': 2', 1 &quot; - Terphenyl ]-2 days) Acetamate Synthesis of de

Acetamido-5-chloro- [1,1'-biphenyl] -2-yl trifluoromethanesulfonate (63 g, 159.99 mmol) instead of 2-bromo-4- , 2- (2-methoxyphenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (44.9 g, 191.99 mmol ) Was prepared in the same manner as in the step 1 of Preparation Example 6, except that N- (5'-chloro-2'-methoxy- [1,1 ': 2', 1 " ] -2-yl) acetamide (40.5 g, yield 72%).

^{1 H-NMR: δ 2.18 (} s, 3H), 3.79 (s, 3H), 7.15 (m, 2H), 7.35 (t, 1H), 7.44-7.62 (m, 4H), 7.95 (d, 1H), 8.16 (s, 1 H), 8.25 (d, 1 H), 10.08 (s, 1 H)

<Step 4> N - (5'- Chloro -2''- Hydroxy - [1,1 ': 2', 1 &quot; - Terphenyl ]-2 days) Acetone Synthesis of mide

(40.5 g, 115.11 mmol), 47 &lt; RTI ID = 0.0 &gt; % HBr (2.09 g, 25.9 mmol) and 4 g of Aliquat 336 were mixed and stirred at 110 ° C for 6 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain N- (5'- 2-yl) acetamide (31.8 g, yield 92%) was obtained in the form of a white solid.

^{1 H-NMR: δ 2.20 (} s, 3H), 7.02 (m, 2H), 7.28 (m, 2H), 7.49-7.65 (m, 3H), 7.90 (m, 2H), 8.44 (s, 1H), 7.80 (d, 1 H), 9.04 (s, 1 H), 10.10 (s, 1 H)

<Step 5> of core6  synthesis

2-yl) acetamide (31.8 g, 94.13 mmol) and acetic acid (1 mL) were added to a solution of N- (5'- (800 ml) were mixed and stirred at 120 ° C for 6 hours.

After completion of the reaction, acetic acid was removed, and the mixture was extracted with ethyl acetate. The extract was dried over MgSO ₄ and purified by column chromatography (hexane: EA = 2: 1 (v / v) ).

¹ H-NMR :? 7.18 (m, 4H), 7.45 (m, 2H), 7.63 (d,

[ Preparation Example  7] Core7  Synthesis of

Chlorotribenzo [b, d, f] oxepin (10 g, 35.87 mmol), 3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane 2-yl) -9H- carbazole (12.6 g, 43.05 mmol), Cs2CO3 (35 g, 107.61 mmol), X-Phos (1.7 g, 3.58 mmol) and _{THF / H 2 O (200 ml} / 50 ml) Pd (OAc) 2 (0.4 g, 1.79 mmol) was added thereto, followed by stirring at 80 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the filtrate was added with MgSO4. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain Core7 (10.7 g, yield 73%).

^{1 H-NMR: δ 7.20 (} m, 5H), 7.35-7.50 (m, 4H), 7.65 (d, 1H), 7.80 (d, 1H), 8.02 (m, 4H), 8.18 (m, 3H), 12.08 (s, 1 H)

[ Preparation Example  8] Core8  Synthesis of

<Step 1> N - (5'- Chloro -2''-( Methyl thio ) - [1,1 ': 2', 1 &quot; - Terphenyl ]-2 days) Acetone Synthesis of mide

4,4,5,5-tetramethyl-2- (2- ((2-methoxyphenyl) -4,4,5,5-tetramethyl- Methylthio) phenyl) -1,3,2-dioxaborolane (38.1 g, 152.37 mmol) was used in place of N- (5'-chloro -2 '' - (methylthio) - [1,1 ': 2', 1 "-terphenyl] -2-yl) acetamide (33.1 g, yield 71%).

^{1 H-NMR: δ 2.20 (} s, 3H), 2.48 (s, 3H), 7.28 (m, 2H), 7.42-7.68 (m, 5H), 7.94 (d, 1H), 8.18 (s, 1H), 8.26 (d, 1 H), 10.4 (s, 1 H)

<Step 2> N - (5'- Chloro -2''- Mercapto - [1,1 ': 2', 1 &quot; - Terphenyl ]-2 days) Acetamate Synthesis of de

Instead of N- (5'-chloro-2 '' - methoxy- [1,1 ': 2', 1 '' - terphenyl] -2- Was prepared in the same manner as in steps 4 and 5 of Preparation Example 6 except for using 3- (methylthio) - [1,1 ': 2', 1 "-terphenyl] -2-yl) acetamide (33.1 g, 89.97 mmol) The same procedure was followed to obtain 28.6 g (yield 90%) of N- (5'-chloro-2 "-mercapto- [1,1 ': 2', 1" ).

^{1 H-NMR: δ 2.18 (} s, 3H), 4.0 (s, 1H), 7.35 (m, 3H), 7.47-7.65 (m, 5H), 7.90 (d, 1H), 8.16 (s, 1H), 8.25 (d, 1 H), 10.4 (s, 1 H)

<Step 3> core8  synthesis

Instead of N- (5'-chloro-2 '' - hydroxy- [1,1 ': 2', 1 '' - terphenyl] -2- The same procedure as in step 5 of Preparation Example 6 was repeated except for using 2-mercapto- [1,1 ': 2', 1 "-terphenyl] -2-yl) acetamide (28.6 g, 80.82 mmol) To obtain core 8 (15.4 g, yield 65%).

^{1 H-NMR: δ 7.18-7.35 (} m, 4H), 7.63 (m, 5H), 7.91 (d, 1H), 8.18 (s, 1H)

[ Preparation Example  9] Core9  Synthesis of

The same procedure as Preparation Example 7 was repeated except that 2-chlorotribenzo [b, d, f] thiepine (10 g, 33.92 mmol) was used instead of 2-chlorotribenzo [b, d, To give Core 9 (10.4 g, yield 72%).

^{1 H-NMR: δ 7.21-7.36 (} m, 6H), 7.54-7.66 (m, 6H), 7.79 (d, 1H), 7.87 (s, 1H), 8.02 (d, 1H), 8.17 (m, 3H ), 12.04 (s, 1 H)

[ Synthetic example  One] Inv3  synthesis

(3.0 g, 8.47 mmol) and 2- (3- (dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl- -dioxa view it is (3.76 g, 10.17 mmol), Pd (OAc) 2 (0.09 g, 0.42mmol), Cs 2 CO 3 (8.27 g, 25.43 mmol), X-Phos (0.4 g, 0.84 mmol) and Toluene (80 ml) was mixed and then stirred at 110 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography (Hexane: MC = 4: 1 (v / v) ). Mass (theory: 561.68, measurement: 561 g / mol)

[ Synthetic example  2] Inv13  synthesis

Instead of 2- (3- (dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborane. Phenyl-6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2- yl) - [ ) -1,3,5-triazine (5.2 g, 10.17 mmol) was used in the same manner as in Synthesis Example 1 to obtain the target compound Inv13 (3.87 g, yield 65%).

Mass (theory: 702.86, measurement: 702 g / mol)

[ Synthetic example  3] Inv20  synthesis

2N - ([1 (phenylmethoxy) phenyl] -4,4,5,5-tetramethyl-1,3,2- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) - [ Inv20 (3.7 g, yield 61%) was obtained in the same manner as in Synthesis Example 1, except that 1,1'-biphenyl] -4-amine (5.32 g, 10.17 mmol) .

Mass (theory: 714.91, measured: 714 g / mol)

[ Synthetic example  4] Inv21  synthesis

N - ([1, 2-dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,2- , 1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Inv21 (3.95 g, yield 62%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 1-phenyl-9H-fluorene-2-amine (5.7 g, 10.17 mmol) .

Mass (theory: 754.98, measured: 754 g / mol)

[ Synthetic example  5] Inv30's  synthesis

(Dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,2- Instead of 2-dioxaborolane, there was obtained 4,4,5,5-tetramethyl-2- (3- (triphenylen-2-yl) phenyl) -1,3,2-dioxaborolane , 8.37 mmol), the procedure of Synthetic Example 1 was repeated to obtain the desired compound Inv30 (3.9 g, yield 67%).

Mass (theory: 697.88, measurement: 697 g / mol)

[ Synthetic example  6] Inv36  synthesis

Instead of 4,4,5,5-tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxaborolane, 2,4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine (3.6 g, 8.37 mmol) (Inv36) (4.15 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 5 above.

Mass (theory: 702.86, measurement: 702 g / mol)

[ Synthetic example  7] Of Inv46  synthesis

Instead of 4,4,5,5-tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxabororane, N - Phenyl] -2-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan- The procedure of Synthesis Example 5 was repeated, except that 9H-fluorene-2-amine (4.7 g, 8.37 mmol) was used to obtain Inv46 (4.0 g, yield 58%).

Mass (theory: 831.08, measurement: 831 g / mol)

[ Synthetic example  8] Inv61  synthesis

(Dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-l, 3,3- (Dibenzo [b, d] thiophen-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,2-dioxa The procedure of Synthesis Example 1 was repeated except that borane (3.9 g, 10.17 mmol) was used to obtain Inv61 (3.2 g, yield 66%) as a target compound.

Mass (theory: 577.75, measurement: 577 g / mol)

[ Synthetic example  9] Inv70  synthesis

2 - [(4-fluorophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2- (3- (dibenzo [b, Biphenyl] -4-yl) -4-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- , And 3,5-triazine (4.4 g, 10.17 mmol) were used in place of the compound obtained in the above Synthesis Example 8 to obtain the target compound Inv70 (3.6 g, yield 68%).

Mass (theory: 626.76, measurement: 626 g / mol)

[ Synthetic example  10] Inv78  synthesis

4 - [(4-fluorophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2- (3- (dibenzo [b, Biphenyl] -4-yl) -2-phenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- ) Phenyl) pyrimidine (5.2 g, 10.17 mmol) was used in place of the compound obtained in Synthesis Example 8 to obtain the desired compound Inv78 (3.74 g, yield 63%).

Mass (theory: 701.87, measurement: 701 g / mol)

[ Synthetic example  11] Inv90  synthesis

(Dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,5- Tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxaborolane (4.37 g , 10.17 mmol), the procedure of Synthetic Example 1 was repeated to give the desired compound, Inv90 (3.32 g, yield 63%).

Mass (theory: 621.78, found: 621 g / mol)

[ Synthetic example  12] Inv105  synthesis

Instead of 4,4,5,5-tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxabororane, N - Phenyl] -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan- (3.77 g, yield 59%) was obtained in the same manner as in Synthesis Example 11, except that 9H-fluorene-2-amine (5.7 g, 10.17 mmol) was used.

Mass (theory: 754.98, measured: 754 g / mol)

[ Synthetic example  13] Inv107  synthesis

Instead of 4,4,5,5-tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxabororane, N - Phenyl] -4-yl) -9,9-dimethyl-N- (4 '-( 4,4,5,5-tetramethyl-1,3,2-dioxabororen- The same procedure as in Synthesis Example 11 was carried out except that 9-fluoro-2-aminopyridine (6.5 g, 10.17 mmol) was used in place of the target compound, Inv107 (4.2 g, yield 60%).

Mass (theory: 831.08, measurement: 831 g / mol)

[ Synthetic example  14] Inv120  synthesis

(Dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,5- Instead of 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) -1,3,5-triazine (5.6 g, 12.94 mmol) was used in the same manner as in Synthesis Example 1 to obtain the desired compound Inv120 (3.4 g, yield 73%).

Mass (theory: 551.65, measurement: 551 g / mol)

[ Synthetic example  15] Inv121  synthesis

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) Instead of azine, 2,4-diphenyl-6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2- yl) - [ Biphenyl] -3-yl) -1,3,5-triazine (6.6 g, 12.94 mmol) was used in place of the target compound, Inv121 (3.88 g, yield 73 %).

Mass (theory: 627.75, measurement: 627 g / mol)

[ Synthetic example  16] Inv128  synthesis

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) (3.95 g, 12.94 mmol) was obtained by carrying out the same procedure as in Synthesis Example 14, except that the title compound, Inv128 (3.95 g, Yield: 66%).

Mass (theory: 639.8, measurement: 639 g / mol)

[ Synthetic example  17] Inv138  synthesis

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)) - 1,3,5- Instead of 9 - ([1,1'-biphenyl] -3- yl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- (3.33 g, yield 70%) was obtained in the same manner as in Synthesis Example 14, except that 9H-carbazole (5.76 g, 12.94 mmol) was used.

Mass (theory: 561.68, measurement: 561 g / mol)

[ Synthetic example  18] Inv144  synthesis

(3.0 g, 7.3 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.0 g, 8.8 mmol) and Pd (OAc) 2 (0.15 g, 0.73 mmol) and toluene (80 ml) were mixed, and the mixture was stirred at 110 占 폚 for 12 hours at 110 占 폚, Lt; / RTI &gt;

Reacting the extracted with ethyl acetate and then terminated, and then, dried with MgSO ₄ and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to give the desired compound of Inv144 (4.37 g, yield: 72% ).

Mass (theory: 716.84, measurement: 716 g / mol)

[ Synthetic example  19] Inv152  synthesis

Except that 2-chloro-4-phenylquinazoline (2.1 g, 8.79 mmol) was used instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5- The procedure of Example 18 was followed to obtain the desired compound Inv152 (3.3 g, yield 64%).

Mass (theory: 614.72, measurement: 614 g / mol)

[ Synthetic example  20] Inv154  synthesis

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -7H-benzo (3.43 g, yield 61%) was obtained by carrying out the same procedure as in Synthesis Example 14, except that [c] carbazole (7.0 g, 12.94 mmol) was used.

Mass (theory: 663.78, found: 663 g / mol)

[ Synthetic example  21] Inv155  synthesis

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) (4 - ([1,1'-biphenyl] -4-yl) quinazolin-2-yl) -10- (4,4,5,5-tetramethyl- The same procedure as in Synthesis Example 14 was carried out except that 7-benzyl [c] carbazole (8.0 g, 12.94 mmol) was used in place of the target compound, Inv155 , Yield: 59%).

Mass (theory: 739.88, found: 739 g / mol)

[ Synthetic example  22] Inv156  synthesis

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) Yl) -10- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) (3.5 g, yield 59%) was obtained by carrying out the same processes as in Synthesis Example 14, except that 7,7-benzodioxol-7H-benzo [c] carbazole (7.7 g, 12.94 mmol) was used.

Mass (theory: 713.84, measurement: 713 g / mol)

[ Synthetic example  23] Inv162  synthesis

(Dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,2- Except that 4,4,5,5-tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxaborolane (5.26 g , 12.24 mmol), the procedure of Synthetic Example 1 was repeated to give the desired compound Inv162 (3.38 g, yield 71%).

Mass (theory: 562.73, measured: 562 g / mol)

[ Synthetic example  24] Inv170  synthesis

Instead of 4,4,5,5-tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxaborolane, 2,4- 4 '- (4,4,5,5-tetramethyl-1,3,2-dioxabororen-2-yl) - [1,1'- biphenyl] -3- , And 5-triazine (6.26 g, 12.24 mmol) were used in place of the compound obtained in the above Synthesis Example 23 to give the desired compound Inv170 (3.7 g, yield 68%).

Mass (theory: 643.81, measurement: 643 g / mol)

[ Synthetic example  25] Inv177  synthesis

Instead of 4,4,5,5-tetramethyl-2- (3- (triphenylene-2-yl) phenyl) -1,3,2-dioxabororane, N - Phenyl] -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxabororan- (3.65 g, yield 62%) was obtained in the same manner as in Synthesis Example 23, except that 9H-fluorene-2-amine (6.89 g, 12.24 mmol) was used.

Mass (theory: 695.92, measurement: 695 g / mol)

[ Synthetic example  26] Inv191  synthesis

Except that Core 9 (3.0 g, 7.05 mmol) was used instead of Core 7 and 2- (4-chlorophenyl) -4,6-dioxolane was used instead of 2- (3-chlorophenyl) (4.59 g, yield: 73%) was obtained by carrying out the same procedure as in Synthesis Example 18, except that 2,2-dimethyl-2-phenyl-1,3,5-triazine (2.9 g, 8.46 mmol) .

Mass (theory: 732.91, measurement: 732 g / mol)

[ Synthetic example  27] Inv193  synthesis

Instead of 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4, (5.0 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 26, except that 6-diphenyl-1,3,5-triazine (3.54 g, 8.46 mmol) .

Mass (theory: 808.27, measurement: 808 g / mol)

[ Synthetic example  28] Inv199  synthesis

3- (4,6-diphenyl-phenyl) -1,3,2-dioxabororane was used in place of 4,4,5,5-tetramethyl-2- (3- Triazin-2-yl) -9-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- -Carbazole (7.34 g, 12.24 mmol) was used in place of the compound obtained in Example 23 to obtain the target compound Inv199 (4.15 g, yield 67%).

Mass (theory: 732.23, measurement: 732 g / mol)

[ Synthetic example  29] Inv202  synthesis

(4-phenylquinazoline-2) was used in place of 4,4,5,5-tetramethyl-2- (3- (triphenylene- -7H-benzo [c] carbazole (6.7 g, 12.24 mmol) was added dropwise to a solution of 1- (4,4,5,5-tetramethyl- (3.74 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 23 except that

Mass (theory: 679.21, measurement: 679 g / mol)

[ Synthetic example  30] Inv203  synthesis

7- (4 - ([1,1,1] dioxaborolane) was used in place of 4,4,5,5-tetramethyl-2- (3- Yl) -7- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -biphenyl] -4-yl) quinazolin- -Benzo [c] carbazole (7.63 g, 12.24 mmol) in the same manner as in Synthesis Example 23, the title compound, Inv203 (3.95 g, yield 62%) was obtained.

Mass (theory: 755.24, measurement: 755 g / mol)

[ Synthetic example  31] Inv204  synthesis

7- (4-phenylbenzo [h] thiophen-2-yl) phenyl) -1,3,2-dioxaborolane was used in the place of 34,4,5,5-tetramethyl- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) -7H-benzo [c] carbazole , 12.24 mmol), the procedure of Synthetic Example 23 was repeated to obtain the desired compound Inv204 (3.5 g, yield 57%).

Mass (theory: 729.22, measurement: 729 g / mol)

[ Synthetic example  32] Inv216  synthesis

(Dibenzo [b, d] furan-4-yl) phenyl) -4,4,5,5-tetramethyl-1,3,5- Instead of 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) phenyl) -1,3,5-triazine (3.1 g, 7.12 mmol) was used in place of the compound obtained in the above Synthesis Example 1 to obtain the desired compound Inv216 (4.7 g, yield 72%).

Mass (theory: 778.31, measured: 778 g / mol)

[ Example  1 to 16] green organic Field  Fabrication of light emitting device

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

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

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent electrode + host compound + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

[ Comparative Example  1] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound Inv3 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

Current efficiency and emission peak at current density (10) mA / cm &lt; 2 &gt; were measured for each of the green organic electroluminescent devices manufactured in Examples 1 to 16 and Comparative Example 1, Respectively.

Sample Host Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 1 Inv3 6.63 517 38.9 Example 2 Inv13 6.61 518 42.5 Example 3 Inv30 6.48 517 39.2 Example 4 Inv36 6.49 515 41.8 Example 5 Inv61 6.76 518 39.7 Example 6 Inv90 6.45 518 38.9 Example 7 Inv120 6.42 517 41.8 Example 8 Inv121 6.76 515 42.4 Example 9 Inv138 6.72 518 40.1 Example 10 Inv144 6.64 518 42.2 Example 11 Inv162 6.68 517 39.8 Example 12 Inv170 6.74 515 41.7 Example 13 Inv191 6.64 518 42.2 Example 14 Inv193 6.62 518 41.8 Example 15 Inv199 6.81 517 42.4 Example 16 Inv216 6.66 515 41.2 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound according to the present invention was used for the light emitting layer of the green organic electroluminescent device (Examples 1 to 16), compared with the case where the conventional CBP was used for the green organic electroluminescent device (Comparative Example 1) It was confirmed that the efficiency and the driving voltage were excellent.

[ Example  17 to 23] Red organic Field  Fabrication of light emitting device

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

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

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent electrode + 10% (piq) ₂ Ir (acac) (300 nm) / BCP ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  2] Red organic Field  Fabrication of light emitting device

A red organic electroluminescent device was fabricated in the same manner as in Example 17, except that CBP was used instead of the compound Inv152 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 17 to 23 and Comparative Example 2 are as follows.

[ Evaluation example  2]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 17 to 23 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host Driving voltage
(V) Current efficiency
(cd / A) Example 17 Inv152 4.64 11.2 Example 18 Inv154 4.83 11.6 Example 19 Inv155 4.76 10.8 Example 20 Inv156 4.85 11.5 Example 21 Inv202 4.81 11.8 Example 22 Inv203 4.66 10.2 Example 23 Inv204 4.58 10.6 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used for the light emitting layer of the red organic electroluminescent device (Examples 17 to 23), the efficiency and the efficiency of the conventional CBP were higher than those of the red organic electroluminescent device It was confirmed that the driving voltage was excellent.

[ Example  24 to 30] Organic Field  Fabrication of light emitting device

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

 M-MTDATA (60 nm) / compound (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF 1 nm) / Al (200 nm).

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

[ Comparative Example  3] Organic Field  Fabrication of light emitting device

An organic electroluminescent device was prepared in the same manner as in Example 61, except that NPB was used as the hole transport layer material instead of the compound Inv20 used as the hole transport layer material in forming the hole transport layer in Example 24. The structure of the NPB used is as follows.

[ Evaluation example  3]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 24 to 30 and Comparative Example 3, respectively, and the results are shown in Table 3 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 24 Inv20 4.9 19.5 Example 25 Inv21 4.8 20.0 Example 26 Inv46 5.0 19.8 Example 27 Inv105 4.4 19.2 Example 28 Inv107 4.2 18.9 Example 29 Inv128 4.3 19.7 Example 30 Inv177 4.3 19.7 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3, the organic electroluminescent devices (Examples 24 to 30) using the compounds (Inv24 to Inv177) according to the present invention as the hole transporting layer were the same as the organic electroluminescent devices using the NPB (Comparative Example 3) The current efficiency and the driving voltage are superior to each other.

[ Example  31 to 36] Blue organic Field  Fabrication of light emitting device

Inv13 to Inv191 were subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was produced as follows.

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

(5 nm) / Alq3 (25 nm) / (5 nm) / (5 nm) of the following Table 4 on the ITO transparent electrode prepared as described above, DS-205 (80 nm) / NPB LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structures of NPB, ADN and Alq ₃ used in this case are as follows.

[ Comparative Example  4] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 31 except that the electron transporting auxiliary layer was not included and Alq ₃ , which is an electron transporting layer material, was deposited at 30 nm instead of 25 nm.

[ Comparative Example  5] Blue organic Field  Fabrication of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 37 except that the compound Inv13 used as the electron transport layer material in Example 31 was not used but BCP was used.

The structure of the BCP used is as follows.

[ Evaluation example  4]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices prepared in Examples 31 to 36, Comparative Examples 4 and 5, respectively, Respectively.

Sample Electron transporting auxiliary layer Driving voltage
(V) Current efficiency
(cd / A) Emission peak
(nm) Example 31 Inv13 4.3 5.9 463 Example 32 Inv70 4.4 5.9 462 Example 33 Inv78 4.8 6.3 459 Example 34 Inv121 4.2 6.2 458 Example 35 Inv170 5.0 6.1 460 Example 36 Inv191 5.1 6.1 458 Comparative Example 4 - 4.7 5.6 458 Comparative Example 5 BCP 5.3 5.9 458

As can be seen from Table 4, in the case of the blue organic electroluminescent devices of Examples 31 to 36 in which the compounds Inv13 to Inv191 were used as the electron transporting auxiliary layer materials, the blue organic electroluminescent device of Comparative Example 4 in which the electron transporting auxiliary layer was not used The driving voltage is similar or slightly better than that of the light emitting device, but the current efficiency is greatly improved. It was also found that BCP exhibited better performance in both current efficiency and driving voltage as compared with Comparative Example 5 using BCP as an electron transporting auxiliary layer.

[ Example  37 to 42] Blue organic Field  Fabrication of light emitting device

Inv13 to Inv191 were subjected to high purity sublimation purification by a conventionally known method, and blue organic electroluminescent devices were produced as follows.

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

DS-405 (30 nm) / compound (30 nm) / LiF (1 nm) / Al (30 nm) shown in Table 5 were formed on the ITO transparent electrode prepared above, (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Evaluation example  5]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 37 to 42 and Comparative Example 4, respectively, and the results are shown in Table 5 below .

Sample Electron transport layer Driving voltage
(V) Current efficiency
(cd / A) Emission peak
(nm) Example 37 Inv13 4.4 6.0 456 Example 38 Inv70 4.7 5.8 457 Example 39 Inv78 4.5 5.8 463 Example 40 Inv121 4.2 6.1 462 Example 41 Inv170 4.0 6.1 460 Example 42 Inv191 4.1 6.3 464 Comparative Example 4 Alq3 4.7 5.6 458

As shown in Table 5, the blue organic electroluminescent devices of Examples 37 to 42 were further improved in driving voltage and current efficiency as compared with the blue organic electroluminescent devices of Comparative Example 6 using Alq ₃ as the electron transporting layer.

As described above, it was confirmed that when the compound of Formula 1 according to the present invention is used as an electron transport layer material or an electron transporting layer material, the driving voltage is lowered and the current efficiency is improved.

Claims (13)

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

In Formula 1,
X ₁ is selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ );
l, m and n are each independently an integer of 0 to 4;
At least one of R ₁ to R ₃ is a substituent represented by the following general formula (2), and the others are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, alkynyl of C ₂ ~ C _40, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, 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 a C ₆ ~ group is selected from the group consisting of an aryl amine of the C ₆₀ or adjacent To form a condensed ring, and when there is a plurality of R ₁ to R ₃ each, they are the same or different;
Ar ₁ to Ar ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ by groups bonded to adjacent or selected from the group consisting of an aryl amine of the C ₆₀ can form a condensed ring;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group and alkylsilyl group of R ₁ to R ₃ and Ar ₁ to Ar ₅ A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl A boron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group , When they are substituted with a plurality of substituents, they may be the same or different from each other;
(2)

In Formula 2,
* Denotes the part where the bond is made;
L ₁ and L ₂ are each independently selected from the group consisting of a single bond, a C ₆ to C ₆₀ arylene group and a heteroarylene group having 5 to 60 nuclear atoms;
The arylene group and the heteroarylene group of L ₁ and L ₂ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryl of C ₆₀ An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ selected from the group consisting arylsilyl of C ₆₀ one kind of substituent or being unsubstituted , When they are substituted with a plurality of substituents, they may be the same or different from each other;
Ar ₆ is a substituent selected from the group consisting of the following formulas A-1 to A-11;

In the above Formulas A-1 to A-11,
* Denotes the part where the bond is made;
Z ₁ to Z ₁₀ are each independently N or C (R ₉ );
Any one of Z ₁ to Z ₄ bonded to L ₂ in the above formulas A-2 and A-6 is C (R ₉ ), wherein R ₉ is a member;
T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C (R ₁₀ ) (R ₁₁ ), N (R ₁₂ ), O and S, but not both T ₁ and T ₂ are single bonds;
p is an integer from 0 to 3;
q and r are each independently an integer of 0 to 4;
R ₄ and R ₅ are each independently a heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or is selected from diaryl phosphine blood group and the group consisting of C ₆ ~ with an aryl amine of the C ₆₀ of the R ₄ and R ₅ in each case a plurality of individuals which the same or different from each other ;
R ₆ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60, wherein R ₉ to R ₁₂ in each case a plurality of individual, they are equal to each other Or different;
Alkyl groups of the R ₄ to R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _60, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other. The method according to claim 1,
Wherein X ₁ is a compound selected from the group consisting of O, S and N (Ar _1). The method according to claim 1,
Wherein X &lt; _{1 &gt;} is O or S; The method according to claim 1,
When the X ₁ is a N (Ar _1), Ar ₆ is selected from the group consisting of Formula A-1 to A-3 and A-5 to A-11, T ₁ and T ₂ are both N (R ₁₂ &Lt; / RTI &gt; The method according to claim 1,
When X ₁ is N (Ar ₁ ), Ar ₆ is selected from the group consisting of Formulas A-5 to A-11. The method according to claim 1,
Wherein at least one of Ar ₁ to Ar ₅ is a substituent represented by the following general formula:
(3)

In Formula 3,
* Denotes the part where the bond is made;
L ₃ is selected from the group consisting of a single bond, an arylene group having ₆ to ₆₀ carbon atoms and a heteroarylene group having 5 to 60 nuclear atoms;
Y ₁ to Y ₅ are each independently N or C (R ₁₃ );
R ₁₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, the combined group and the adjacent may form a condensed ring, when the R ₁₃ multiple individual They are the same or different from each other;
Aryl group and a heteroaryl group of the alkylene group, R ₁₃ in the L _3, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, aryloxy C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkoxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, 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 ~ C ₆₀ aryl silyl group of , And when they are substituted with a plurality of substituents, they may be the same or different from each other. The method according to claim 1,
Wherein L ₁ and L ₂ are each independently selected from the group consisting of the following formulas B-1 to B-12:

In the above Formulas B-1 to B-12,
* Denotes the part where the bond is made;
R ₁₄ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;
Alkyl group of the R _14, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to 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 ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different. The method according to claim 1,
When X ₁ is N (Ar ₁ ), L ₁ and L ₂ are each independently selected from the group consisting of the following formulas B-1 to B-4 and B-7 to B-12:

In the above Formulas B-1 to B-4 and B-7 to B-12,
* Denotes the part where the bond is made;
R ₁₄ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C _60;
Alkyl group of the R _14, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to 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 ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different. The method according to claim 1,
R ₉ to R ₁₂ are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, and a C ₆ to C ₆₀ aryl group. The method according to claim 1,
R ₆ and R ₇ are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, and a C ₆ to C ₆₀ aryl group. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound represented by the general formula (1). 13. The method of claim 12,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron transporting auxiliary layer, an electron injecting layer, a lifetime improving layer, a light emitting layer and a light emitting auxiliary layer.