KR20180024891A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device including the same. The compound according to the present invention is used in an organic material layer of an organic electroluminescent device, preferably a light emitting layer, an electron transporting layer, or an electron transporting support layer, thereby improving the luminous efficiency, driving voltage, life span, and the like of the organic electroluminescent device.

Description

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

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

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

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

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials 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.

To date, NPB, BCP and Alq ₃ have been widely known as the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, 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,

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

Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of the A cycloalkyl group, a heterocycloalkyl group having 5 to 7 nuclear atoms, an aryl group having ₆ to ₃₀ carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, a C ₁ to C ₃₀ alkyloxy group, a C ₆ to C ₃₀ An aryloxy group, a C ₁ to C ₃₀ alkylsilyl group, a C ₅ to C ₃₀ arylsilyl group, a C ₁ to C ₃₀ alkylboron group, a C ₆ to C ₃₀ arylboron group, a C ₆ to C ₃₀ An arylphosphanyl group, a C ₆ to C ₃₀ mono or diarylphosphinyl group, and a C ₆ to C ₃₀ arylamine group;

Arylene group and a heteroarylene group, an alkyl group of said Ar ₁ and Ar ₂ of the above L _1, 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 aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, group C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C of Arylsilyl group having 1 to ₆₀ carbon atoms, and when they are substituted with a plurality of 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.

&Quot; 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. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, 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 one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, Click 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.

&Quot; Arylamine " in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

&Quot; 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.

&Quot; 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.

&Quot; 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.

Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.

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

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel compounds of the present invention can be represented by the following formula

[Chemical Formula 1]

In Formula 1,

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

Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of the A cycloalkyl group, a heterocycloalkyl group having 5 to 7 nuclear atoms, an aryl group having ₆ to ₃₀ carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, a C ₁ to C ₃₀ alkyloxy group, a C ₆ to C ₃₀ An aryloxy group, a C ₁ to C ₃₀ alkylsilyl group, a C ₅ to C ₃₀ arylsilyl group, a C ₁ to C ₃₀ alkylboron group, a C ₆ to C ₃₀ arylboron group, a C ₆ to C ₃₀ An arylphosphanyl group, a C ₆ to C ₃₀ mono or diarylphosphinyl group, and a C ₆ to C ₃₀ arylamine group;

Arylene group and a heteroarylene group, an alkyl group of said Ar ₁ and Ar ₂ of the above L _1, 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 aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, group C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C of Arylsilyl group having 1 to ₆₀ carbon atoms, and when they are 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 has an EWG structure that substitutes phenyl group and benzo [d] oxazole for a fluorene structure having excellent thermal stability and carrier transporting ability, and enhances electron mobility to form an interaction with an iridium dopant It is possible to facilitate the energy transfer through the electrode and improve the current efficiency. Therefore, when the compound of the present invention is used as a material of the electron transport layer, the efficiency of the organic electroluminescent device can be increased by improving the performance thereof, the emission efficiency of the device can be improved by contributing to the increase of the number of the excitons, The durability and stability of the device are improved and the life of the device can be efficiently increased.

According to one preferred embodiment of the present invention, the compound may be a compound represented by the following formula 2 or 3:

(2)

(3)

In the above Formulas 2 and 3,

L ₁ , Ar ₁ and Ar ₂ are each as defined in the above formula (1).

According to a preferred embodiment of the present invention, Ar ₁ may be selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group and a heteroaryl group having 5 to 30 nucleus atoms.

According to a preferred embodiment of the present invention, Ar ₁ may be selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.

According to a preferred embodiment of the present invention, L ₁ is either a single bond, may be to the formula A-1 to the linker represented by any one of Formula A-3:

In the above Formulas A-1 to A-3,

* Means the part where the combination is made.

According to a preferred embodiment of the present invention, L ₁ is a single bond or a linker represented by the above formula (A-1).

According to a preferred embodiment of the present invention, Ar ₂ may be a substituent represented by any of the following formulas 4 to 8:

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 4 to 8,

* Denotes the part where the bond is made;

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

Z ₁ to Z ₅ are each independently N or C (R ₃ );

T ₁ is C (R ₄ ) (R ₅ ) or N (R ₆ );

R ₁ and R ₂ 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 aryl phosphazene 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 adjacent to form a fused ring, wherein R ₁ and When there are a plurality of R < ₂ > s, they are the same as or different from each other;

R ₃ to R ₆ 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 ~ aryl phosphazene group of C _60, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C selected from the ₆₀ group consisting of aryl amines, or to combine groups which are adjacent to form a fused ring, wherein R ₃ are plural, they are the same or different from each other;

Alkyl group of the R ₁ to R _6, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other.

According to a preferred embodiment of the present invention, each of R ₁ to R ₆ independently represents a group selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group and a heteroaryl group having 5 to 30 nuclear atoms Can be selected.

According to a preferred embodiment of the present invention, each of R ₁ to R ₆ may be independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.

According to a preferred embodiment of the present invention, the substituent represented by Formula 4 may be a substituent represented by Formula 9:

[Chemical Formula 9]

In the above formula (9)

* Denotes the part where the bond is made;

R ₇ and R ₈ are each independently hydrogen, deuterium, 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 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 phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;

Alkyl group of the R ₇ and R _8, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, 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 a plurality of substituents, they are the same as or different from each other;

Each of Z ₁ , Z ₃ and Z ₅ is as defined in the above formula (4).

According to a preferred embodiment of the present invention, Ar ₂ may be a substituent represented by any one of the following formulas B-1 to B-7:

In the above Formulas B-1 to B-7,

* Denotes the part where the bond is made;

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

R ₁ and R ₂ 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 aryl phosphazene 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 adjacent to form a fused ring, wherein R ₁ and When there are a plurality of R < ₂ > s, they are the same as or different from each other;

R ₇ and R ₈ are each independently hydrogen, deuterium, 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 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 phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;

Wherein R _1, R _2, an alkyl group of R ₇ and R _8, 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 , alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, a nitro group, an alkyl group of _{C 1 ~ C 40, C 2} ~ C _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ group consisting arylsilyl of C ₆₀ in And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁ , R ₂ , R ₇ and R ₈ are each independently a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, And a heteroaryl group.

According to a preferred embodiment of the present invention, each of R ₁ , R ₂ , R ₇ and R ₈ may be independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.

According to a preferred embodiment of the present invention, Ar ₂ may be a substituent represented by the following formula (10):

[Chemical formula 10]

In Formula 10,

* Denotes the part where the bond is made;

R ₉ and R ₁₀ are each independently hydrogen, deuterium, 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 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 phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;

Alkyl group of the R ₉ and R _10, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, 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 When they are substituted or unsubstituted with one or more substituents, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ are each independently selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group and a heteroaryl group having 5 to 30 nuclear atoms Can be selected.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ may each independently be selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group and a fluorenyl group.

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

The compounds of general formula (I) of the present invention can be synthesized according to the general synthetic method (Chem Rev, 60: 313 ( 1960); J. Chem SOC 4482 (1955); Chem Rev. 95:..... 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 >

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, referring to FIG. 1, an anode 10 and a cathode 20 facing each other, 20). ≪ / RTI > Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. A hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32. An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.

2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).

In the present invention, the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO. The layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.

The electron injecting layer 36 is a layer which is stacked on the electron transporting layer to facilitate injection of electrons from the cathode to ultimately improve the power efficiency. For example, LiF, Liq, NaCl, CsF, Li ₂ O, BaO, or the like can be used.

In addition, although not shown in the drawings, the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.

In addition, although not shown in the drawings, a life improving layer may be further included between the electron transporting auxiliary layer 35 and the light emitting layer 32. Holes moving in the organic light emitting device due to the ionization potential level in the light emitting layer 32 are blocked by the high energy barrier of the lifetime enhancing layer and do not diffuse or move to the electron transporting layer and consequently function to limit the holes to the light emitting layer . The function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .

The compound represented by Formula 1 of the present invention has an EWG structure that substitutes phenyl group and benzo [d] oxazole for a fluorene structure having excellent thermal stability and carrier transporting ability, and enhances electron mobility to form an interaction with an iridium dopant It is possible to facilitate the energy transfer through the electrode and improve the current efficiency. Therefore, when the compound of the present invention is used as a material of the electron transport layer, the efficiency of the organic electroluminescent device can be increased by improving the performance thereof, the emission efficiency of the device can be improved by contributing to the increase of the number of the excitons, The durability and stability of the device are improved and the life of the device can be efficiently increased. Therefore, the organic material layer containing the compound represented by Formula 1 is preferably a light emitting layer, an electron transporting layer, or an electron transporting layer, and more preferably an electron transporting layer or an electron transporting layer.

The compound according to the present invention can also be used as a light emitting layer material. Specifically, the compound represented by the above formula (1) can be used as a phosphorescent host, a fluorescent host or a dopant material in a light emitting layer, Green and / or red phosphorescent host material).

In addition, the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.

The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another organic material layer and an electrode.

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

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

The anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal 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  1] 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- -Yl) benzo [d] oxazole By the same procedure as in

<Step 1> Synthesis of N- (2,5- Dibromophenyl ) Benzamide  synthesis

2,5-dibromoaniline (250.9 g, 1.0 mol) was added to the reactor, and methylene chloride (1,000 ml) was added thereto, followed by stirring. Benzoyl chloride (116 mL, 1.0 mol) and pyridine (161.8 mL, 2.0 mol) were added dropwise to the reactor, followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, N- (2,5-dibromophenyl) benzamide (252.1 g, yield 71%) was obtained by column chromatography.

^{1 H-NMR: δ 7.52 (} d 1H), 7.59 (d, 1H), 7.63 (dd, 2H), 7.70 (t, 1H), 7.98 (s, 1H), 8.03 (d, 2H), 9.15 (b , 1H)

[LCMS]: 355

<Step 2> 5- Bromo -2- Phenylbenzo [d] oxazole  synthesis

Preparation Example 1 To a solution of the compound (251.1 g, 710 mmol), K ₂ CO ₃ (196.3 g, 1420 mmol) and DMSO (7100 ml) synthesized in <Step 1> And the mixture was stirred at 140 캜 for 1.5 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and then filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 5-bromo-2-phenylbenzo [d] oxazole (147.9 g, yield 76%) was obtained by column chromatography.

^{1 H-NMR: δ 7.41 (} t, 1H) 7.43 (s, 1H), 7.51 (m, 3H), 7.60 (d, 1H), 8.05 (d, 2H)

[LCMS]: 274.1

<Step 3> Phenyl (2-phenylbenzo [d] oxazol-5-yl) methanone  synthesis

5-Bromo-2-phenylbenzo [d] oxazole (147.9 g, 539.5 mmol) synthesized in Step 2 was placed in a reactor and 1000 ml of THF was added thereto. The resulting mixture was placed in a dry ice bath under stirring, 78 캜. n-BuLi (356.1 ml, 593.5 mmol) was slowly injected with a syringe and stirred for 30 minutes. Benzaldehyde (47.7 g, 449.5 mmol) is dissolved in 100 ml of THF and then slowly added dropwise. Slowly raise to room temperature. After concentrating the reaction, I ₂ (241.0 g, 949.6 mmol), K ₂ CO ₃ (246.1 g, 1780.5 mmol) and 1000 ml of t-BuOH, and the mixture is heated under reflux for 7 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and then filtered with MgSO ₄ .

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, phenyl (2-phenylbenzo [d] oxazol-5-yl) methanone (94.2 g, yield 70%) was obtained as a target compound by column chromatography.

¹ H-NMR: 8 7.41 (m, 3H), 7.55-7.52 s, 1 H)

[LCMS]: 299.3

&Lt; Step 4 > (2'- Chloro - [1,1'-biphenyl] -2-yl) (phenyl) (2- Phenylbenzo [d] oxazole Yl) methanol &lt; / RTI &gt;

To the reactor, 2-bromo-2'-chloro-1,1'-biphenyl (101.0 g, 377.6 mmol) was added and 500 ml of THF was added. The mixture was stirred and placed in a dry ice bath. do. n-BuLi (250 ml, 415.4 mmol) is slowly injected with a syringe and stirred for 30 minutes. Preparation Example 1 Phenyl (2-phenylbenzo [d] oxazol-5-yl) methanone (94.2 g, 314.7 mmol) synthesized in Step 3 was dissolved in 500 ml of THF and slowly added dropwise. The temperature is slowly raised to room temperature to terminate the reaction. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and then filtered with MgSO ₄ . After removal of the solvent of the filtered organic layer, the desired compound (2'-chloro- [1,1'-biphenyl] -2-yl) (phenyl) (2-phenylbenzo [d] oxazole -5-yl) methanol (98.3 g, yield 64%).

¹ H-NMR: 3.65 δ (s, 1H), 7.34-7.36 (m, 5H), 7.38-7.39 (m, 4H), 7.41-7.44 (m, 3H) 7.51-7.52 (m, 2H), 7.55 ( (d, IH), 7.69 (s, IH), 7.72-7.73 (m, 3H)

[LCMS]: 487.9

<Step 5> Synthesis of 5- (4- Chloro -9-phenyl-9H- Fluorene Yl) -2- Phenylbenzo [d] oxazole  synthesis

(2-phenyl- benzo [d] oxazol-5-yl) methanol (98.3 g) synthesized in Step 4 g, 201.4 mmol) were dissolved in 1000 ml of toluene, and 20 ml of sulfuric acid was added with vigorous stirring. The temperature was raised to 100 캜, stirred for 8 hours, and then cooled to room temperature. Setting. After completion of the reaction, the reaction mixture was extracted with methylene chloride and then filtered through MgSO ₄ . After the solvent of the filtered organic layer was removed, the desired compound, 5- (4-chloro-9-phenyl-9H-fluoren-9-yl) -2-phenylbenzo [d] oxazole , Yield: 72%).

^{1 H-NMR: δ 7.11 (} d, 2H), 7.22-7.23 (m, 2H), 7.26-7.28 (m, 2H), 7.33 (t, 2H), 7.38-7.39 (m, 2H), 7.41-7.43 (d, 2H), 7.51 (t, 2H), 7.55-7.56 (m, 2H), 7.67

[LCMS]: 469.9

<Step 6> Synthesis of 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -9-yl) benzo [d] oxazole

Phenylbenzo [d] oxazole (68.1 g, 145.1 mmol) synthesized in Preparation Example 1 (Step 5) and 4, 4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2' -bis (1,3,2-dioxaborolan) (44.2 g, 174.2 mmol) and Pd dppf) Cl ₂ (3.56 g, 4.4 mmol), KOAc (28.5 g, 290.3 mmol) and Xphos (6.9 g, 14.5 mmol) were placed in 1000 ml of 1,4-dioxane and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removal of the solvent of the filtered organic layer, the desired compound 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxa Yl) -9H-fluoren-9-yl) benzo [d] oxazole (46.3 g, yield 69%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.07-7.11 (m, 4H), 7.14-7.17 (m, 3H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41 2H), 7.87 (d, IH), 8.05 (d, 2H), 7.54 (d,

[LCMS]: 561.4

[ Preparation Example  2] phenyl-5- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- -Yl) benzo [d] oxazole By the same procedure as in

The procedure of Preparation Example 1 was repeated except for using 2-bromo-3'-chloro-1,1'-biphenyl as a reactant in Step 4 to obtain 67.1 g (yield: 12%) of the target compound .

^{1 H-NMR: δ 1.24 (} s, 12H), 7.07-7.11 (m, 4H), 7.17 (t, 1H), 7.23 (d, 1H), 7.26-7.33 (m, 3H), 7.34-7.41 (m 2H), 7.55 (d, 2H), 7.56 (s, IH), 7.63

[LCMS]: 561.4

[ Preparation Example  3] 2-phenyl-5- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -Yl) benzo [d] oxazole By the same procedure as in

The procedure of Preparation Example 1 was repeated except that 2-bromo-4'-chloro-1,1'-biphenyl was used as the reactant in Step 4 to obtain 72.7 g (yield 13%) of the desired compound .

^{1 H-NMR: δ 1.24 (} s, 12H), 7.05-7.11 (m, 3H), 7.15-7.17 (m, 2H), 7.23 (d, 1H), 7.26-7.33 (m, 3H), 7.34 (s 2H), 7.55 (d, 2H), 7.56 (s, 1H), 7.67 (d,

[LCMS]: 561.4

[ Preparation Example  4] 2-phenyl-6- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- -Yl) benzo [d] oxazole By the same procedure as in

The procedure of Preparation Example 1 was repeated except that 2,4-dibromoaniline was used as the reactant in Step 1 to obtain 67.1 g (yield: 12%) of the target compound.

^{1 H-NMR: δ 1.24 (} s, 12H), 7.07-7.11 (m, 4H), 7.14-7.17 (m, 3H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41 2H), 7.87 (d, IH), 8.05 (d, 2H), 7.54 (d,

[LCMS]: 561.4

[ Preparation Example  5] 2-phenyl-6- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- -Yl) benzo [d] oxazole By the same procedure as in

The procedure of Preparation Example 4 was repeated except that 2-bromo-3'-chloro-1,1'-biphenyl was used as the reactant in Step 4 to obtain 67.0 g (yield: 12%) of the title compound .

^{1 H-NMR: δ 1.24 (} s, 12H), 7.07-7.15 (m, 6H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41-7.42 (m, 1H), 7.44 (s, IH), 7.51 (t, 2H), 7.63 (s, IH), 7.87

[LCMS]: 561.4

[ Preparation Example  6] 2-phenyl-6- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- -Yl) benzo [d] oxazole By the same procedure as in

The procedure of Preparation Example 4 was repeated except that 2-bromo-4'-chloro-1,1'-biphenyl was used as the reactant in Step 4 to obtain 78.3 g (yield: 14%) of the desired compound .

^{1 H-NMR: δ 1.24 (} s, 12H), 7.07-7.17 (m, 6H), 7.23-7.26 (m, 2H), 7.33-7.34 (m, 4H), 7.41-7.44 (m, 2H), 7.51 (t, 2H), 7.87 (d, 2H), 8.05 (d, 2H)

[LCMS]: 561.4

[ Synthetic example  1] Synthesis of Compound A-3

Preparation of 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol) and diisopropylethylamine and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml for 12 hours And the mixture was heated to reflux. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . The solvent of the filtered organic layer was removed, and the desired compound A-3 (6.6 g, yield 82%) was obtained by column chromatography.

[LCMS]: 742.8

[ Synthetic example  2] Synthesis of Compound A-5

Preparation of 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (5 g, 8.9 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5 -triazine (3.1 g, 8.9 mmol) and _{Pd (PPh 3) 4 (0.5} g, 0.4 mmol), K 2 CO 3 (3.7 g, 26.7 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After the solvent of the filtered organic layer was removed, the desired compound A-5 (4.7 g, yield 72%) was obtained by column chromatography.

[LCMS]: 742.8

[ Synthetic example  3] Synthesis of Compound A-14

Preparation of 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (5 g, 8.9 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- (4- chlorophenyl) -6-phenylpyridine pyrimidine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . The solvent of the filtered organic layer was removed, and then the target compound A-14 (5.1 g, yield 70%) was obtained by column chromatography.

[LCMS]: 817.9

[ Synthetic example  4] Synthesis of Compound A-26

Preparation of 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- -9- yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2- (4- chlorophenyl) -6- phenyl- [l, 2,4] triazolo [ 2.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O And heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound A-26 (4.6 g, yield 74%) was obtained by column chromatography.

[LCMS]: 704.8

[ Synthetic example  5] Synthesis of Compound A-36

Preparation of 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (9 g, 8.9 mmol) and 9 - ([1,1'-biphenyl] -4-yl) -3-chloro-9H-carbazole mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound A-36 (4.5 g, yield 67%) was obtained by column chromatography.

[LCMS]: 752.9

[ Synthetic example  6] Synthesis of Compound B-2

Preparation of 2-phenyl-5- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (4-chloro-phenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml for 12 hours And the mixture was heated to reflux. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound B-2 (4.7 g, yield 71%) was obtained by column chromatography.

[LCMS]: 742.8

[ Synthetic example  7] Synthesis of Compound B-6

Preparation of 2-phenyl-5- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- 4-yl) -4- (4-chlorophenyl) -6-phenyl-isoxazole- a 1,3,5-triazine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) 80 ml of toluene, 20 ml of EtOH and 20 ml of H ₂ O were added and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound B-6 (5.2 g, yield 72%) was obtained by column chromatography.

[LCMS]: 818.9

[ Synthetic example  8] Synthesis of Compound B-13

Preparation of 2-phenyl-5- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (3.1 g, 8.9 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine f8.9 mmol) and _{Pd (PPh 3) 4 (0.5} g, 0.4 mmol), K 2 CO 3 (3.7 g, 26.7 mmol) in toluene 80ml, put in 20ml EtOH, H ₂ O 20ml was heated to reflux for 12 hours . After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, B-13 (4.7 g, yield 72%) was obtained by column chromatography.

[LCMS]: 741.8

[ Synthetic example  9] Synthesis of Compound B-27

Preparation of 2-phenyl-5- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- -9- yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2- (4- chlorophenyl) -6- phenyl- [l, 2,4] triazolo [ 2.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O And heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, B-27 (4.1 g, yield 65%) was obtained by column chromatography.

[LCMS]: 704.8

[ Synthetic example  10] Synthesis of Compound B-35

Preparation of 2-phenyl-5- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- Yl) benzo [d] oxazole (5 g, 8.9 mmol) and 9- (1,1'-yl) -9H-fluoren- 3-chloro -9H- carbazole (3.2 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) to 80 ml of toluene, 20 ml of EtOH and 20 ml of H ₂ O were added and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, B-35 (4.5 g, yield 67%) was obtained by column chromatography.

[LCMS]: 752.9

[ Synthetic example  11] Synthesis of Compound C-4

Preparation of 2-phenyl-5- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- (5 g, 8.9 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl- , 3,5-triazine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80 ml of EtOH, 20 ml of EtOH and 20 ml of H ₂ O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound C-4 (5.2 g, yield 72%) was obtained by column chromatography.

[LCMS]: 818.9

[ Synthetic example  12] Synthesis of Compound C-7

Preparation of 2-phenyl-5- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- Yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2 - ([1,1'-biphenyl] -4- a 1,3,5-triazine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) 80 ml of toluene, 20 ml of EtOH and 20 ml of H ₂ O were added and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C-7 (4.7 g, yield 65%) was obtained by column chromatography.

[LCMS]: 818.9

[ Synthetic example  13] Synthesis of Compound C-12

Preparation of 2-phenyl-5- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- (5 g, 8.9 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenylpyrimidine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C-12 (4.9 g, yield 68%) was obtained by column chromatography.

[LCMS]: 817.9

[ Synthetic example  14] Synthesis of Compound C-22

Preparation of 2-phenyl-5- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- (5 g, 8.9 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- (4- chlorophenyl) -2-phenylpyridine pyrimidine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C-22 (5.2 g, yield 71%) was obtained by column chromatography.

[LCMS]: 817.9

[ Synthetic example  15] Synthesis of Compound C-28

Preparation of 2-phenyl-5- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- -9- yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2- (4-chlorophenyl) mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound C-28 (3.9 g, yield 71%) was obtained by column chromatography.

[LCMS]: 628.7

[ Synthetic example  16] Synthesis of Compound D-3

Preparation of 2-phenyl-6- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol) and diisopropylethylamine and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml for 12 hours And the mixture was heated to reflux. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, D-3 (6.6 g, yield 82%) was obtained by column chromatography.

[LCMS]: 742.8

[ Synthetic example  17] Synthesis of Compound D-5

Preparation of 2-phenyl-6- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (5 g, 8.9 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5 -triazine (3.1 g, 8.9 mmol) and _{Pd (PPh 3) 4 (0.5} g, 0.4 mmol), K 2 CO 3 (3.7 g, 26.7 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, D-5 (4.7 g, yield 72%) was obtained by column chromatography.

[LCMS]: 742.8

[ Synthetic example  18] Synthesis of Compound D-14

Preparation of 2-phenyl-6- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (5 g, 8.9 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2- (4- chlorophenyl) -6-phenylpyridine pyrimidine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, D-14 (5.1 g, yield 70%) of the target compound was obtained by column chromatography.

[LCMS]: 817.9

[ Synthetic example  19] Synthesis of compound D-26

Preparation of 2-phenyl-5- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- -9- yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2- (4- chlorophenyl) -6- phenyl- [l, 2,4] triazolo [ 2.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O And heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, D-26 (4.6 g, yield 74%) was obtained by column chromatography.

[LCMS]: 704.8

[ Synthetic example  20] Synthesis of Compound D-36

Preparation of 2-phenyl-6- (9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- (9 g, 8.9 mmol) and 9 - ([1,1'-biphenyl] -4-yl) -3-chloro-9H-carbazole mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, D-36 (4.5 g, yield 67%) was obtained by column chromatography.

[LCMS]: 752.9

[ Synthetic example  21] Synthesis of Compound E-2

Preparation of 2-phenyl-6- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- (4-chloro-phenyl) -4,6-diphenyl-1,3,5-triazine (3.1 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml for 12 hours And the mixture was heated to reflux. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the target compound B-2 (4.7 g, yield 71%) was obtained by column chromatography.

[LCMS]: 742.8

[ Synthetic example  22] Synthesis of Compound E-6

Preparation of 2-phenyl-6- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- 4-yl) -4- (4-chlorophenyl) -6-phenyl-isoxazole- a 1,3,5-triazine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) 80 ml of toluene, 20 ml of EtOH and 20 ml of H ₂ O were added and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removal of the solvent of the filtered organic layer, the target compound E-6 (5.2 g, yield 72%) was obtained by column chromatography.

[LCMS]: 818.9

[ Synthetic example  23] Synthesis of Compound E-13

Preparation of 2-phenyl-6- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- (3.1 g, 8.9 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine 8.9 mmol) and _{Pd (PPh 3) 4 (0.5} g, 0.4 mmol), K 2 CO 3 (3.7 g, 26.7 mmol) in toluene 80ml, put in 20ml EtOH, H ₂ O 20ml was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . The solvent of the filtered organic layer was removed, and the desired compound E-13 (4.7 g, yield 72%) was obtained by column chromatography.

[LCMS]: 741.8

[ Synthetic example  24] Synthesis of Compound E-27

Preparation of 2-phenyl-6- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- -9- yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2- (4- chlorophenyl) -6- phenyl- [l, 2,4] triazolo [ 2.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O And heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, E-27 (4.1 g, yield 65%) was obtained by column chromatography.

[LCMS]: 704.8

[ Synthetic example  25] Synthesis of Compound E-35

Preparation of 2-phenyl-6- (9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H- (9 g, 8.9 mmol) and 9 - ([1,1'-biphenyl] -3-yl) -3-chloro-9H-carbazole (3.2 g, 8.9 mmol) mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . The solvent of the filtered organic layer was removed, and the objective compound E-35 (4.5 g, yield 67%) was obtained by column chromatography.

[LCMS]: 752.9

[ Synthetic example  26] Synthesis of Compound F-4

Preparation of 2-phenyl-6- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2- yl) -9H- (5 g, 8.9 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl- , 3,5-triazine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80 ml of EtOH, 20 ml of EtOH and 20 ml of H ₂ O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, F-4 (5.2 g, yield 72%) was obtained by column chromatography.

[LCMS]: 818.9

[ Synthetic example  27] Synthesis of Compound F-7

Preparation of 2-phenyl-6- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2- yl) -9H- Yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2 - ([1,1'-biphenyl] -4- a 1,3,5-triazine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) 80 ml of toluene, 20 ml of EtOH and 20 ml of H ₂ O were added and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C-7 (4.7 g, yield 65%) was obtained by column chromatography.

[LCMS]: 818.9

[ Synthetic example  28] Synthesis of Compound F-12

Preparation of 2-phenyl-6- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2- yl) -9H- (5 g, 8.9 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenylpyrimidine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, F-12 (4.9 g, yield: 68%) was obtained by column chromatography.

[LCMS]: 817.9

[ Synthetic example  29] Synthesis of Compound F-22

Preparation of 2-phenyl-6- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2- yl) -9H- (5 g, 8.9 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6- (4- chlorophenyl) -2-phenylpyridine pyrimidine (3.7 g, 8.9 mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, EtOH 20ml, H ₂ O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removal of the solvent of the filtered organic layer, the title compound F-22 (5.2 g, yield 71%) was obtained by column chromatography.

[LCMS]: 817.9

[ Synthetic example  30] Synthesis of Compound F-28

Preparation of 2-phenyl-6- (9-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2- yl) -9H- -9- yl) benzo [d] oxazole (5 g, 8.9 mmol) and 2- (4-chlorophenyl) mmol) and _{Pd (OAc) 2 (0.1 g} , 0.4 mmol), Cs 2 CO 3 (5.8 g, 17.8 mmol), Xphos (0.4 g, 0.9 mmol) in toluene 80ml, placed in EtOH 20ml, H ₂ O 20ml 12 Lt; / RTI &gt; for one hour. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, F-28 (3.9 g, yield 71%) was obtained by column chromatography.

[LCMS]: 628.7

[ Example  1 ~ 30] blue organic Field  Fabrication of light emitting device

A-5, A-14, A-26, A-36, B-2, B-6, B-13, B-27, B- C-7, C-12, C-22, C-28, D-3, D-5, D-14, D-26, D- The blue organic electroluminescent device was fabricated as described below after high-purity sublimation purification was carried out according to a conventionally known method.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate 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 The substrate was transferred to a vacuum evaporator.

(DS-205, Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound A-3 and A-5 , A-14, A-26, A-36, B-2, B-6, B-13, B-27, B-35, C-4, C-7, C- -28, D-3, D-5, D-14, D-26, D-36, E-2, E-6, E-13, E-27, E- (30 nm) / LiF (1 nm) / Al (200 nm) in the order of F-12, F-22 and F-28 were stacked in this order to fabricate an organic electroluminescent device.

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

A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that Alq3 was used instead of Compound A-3 as the electron transport layer material.

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

Except that Compound A-3 was not used as the electron transport layer material,

The blue organic electroluminescent device was fabricated in the same manner as in Example 1.

However, the structures of NPB, AND and Alq3 used in Examples 1 to 20 and Comparative Examples 1 and 2 are as follows.

[ Evaluation example  One]

Current efficiency and emission peak at current density (10) mA / cm &lt; 2 &gt; were measured for each of the blue organic electroluminescent devices manufactured in Examples 1 to 30 and Comparative Examples 1 and 2, Respectively.

Sample material Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 A-3 3.4 458 7.0 Example 2 A-5 4.6 459 7.1 Example 3 A-14 4.1 458 6.8 Example 4 A-26 4.0 455 6.9 Example 5 A-36 4.6 456 6.7 Example 6 B-2 3.2 457 6.7 Example 7 B-6 3.9 456 6.9 Example 8 B-13 3.8 452 7.1 Example 9 B-27 3.6 448 6.9 Example 10 B-35 3.7 460 7.1 Example 11 C-4 3.2 455 6.8 Example 12 C-7 3.6 456 6.8 Example 13 C-12 3.9 457 6.9 Example 14 C-22 3.9 452 6.8 Example 15 C-28 3.3 448 6.7 Example 16 D-3 3.6 460 6.8 Example 17 D-5 3.5 465 6.9 Example 18 D-14 3.9 457 6.8 Example 19 D-26 3.8 456 6.4 Example 20 D-36 4.1 465 6.8 Example 21 E-2 3.6 457 6.9 Example 22 E-6 3.6 456 6.9 Example 23 E-13 3.2 457 7.1 Example 24 E-27 3.2 456 6.8 Example 25 E-35 4.1 455 6.5 Example 26 F-4 3.6 459 6.5 Example 27 F-7 3.7 461 6.9 Example 28 F-12 3.9 464 7.1 Example 29 F-22 3.6 467 7.1 Example 30 F-28 3.8 467 6.7 Comparative Example 1 Alq ₃ 4.7 458 5.6 Comparative Example 2 - 4.8 460 6.2

As shown in Table 1 above, the compound of the present invention was used in the electron transport layer

Compared to the blue organic electroluminescent device (Comparative Example 1) using conventional Alq3 as the electron transport layer and the blue organic electroluminescent device without the electron transport layer (Comparative Example 2), the blue organic electroluminescent devices (Examples 1 to 30) , The emission peak, and the current efficiency.

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

Claims (14)

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

In Formula 1,
L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Ar ₁ and Ar ₂ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ of the A cycloalkyl group, a heterocycloalkyl group having 5 to 7 nuclear atoms, an aryl group having ₆ to ₃₀ carbon atoms, a heteroaryl group having 5 to 30 nuclear atoms, a C ₁ to C ₃₀ alkyloxy group, a C ₆ to C ₃₀ An aryloxy group, a C ₁ to C ₃₀ alkylsilyl group, a C ₅ to C ₃₀ arylsilyl group, a C ₁ to C ₃₀ alkylboron group, a C ₆ to C ₃₀ arylboron group, a C ₆ to C ₃₀ An arylphosphanyl group, a C ₆ to C ₃₀ mono or diarylphosphinyl group, and a C ₆ to C ₃₀ arylamine group;
Arylene group and a heteroarylene group, an alkyl group of said Ar ₁ and Ar ₂ of the above L _1, 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 aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, group C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C of Arylsilyl group having 1 to ₆₀ carbon atoms, 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 said compound is represented by the following formula 2 or 3:
(2)

(3)

In the above Formulas 2 and 3,
L ₁ , Ar ₁ and Ar ₂ are each as defined in claim 1. The method according to claim 1,
Wherein Ar ₁ is selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. The method according to claim 1,
Wherein L ₁ is or a single bond, to the linker represented by any one of Formula A-1) to (A-3, the compound:

In the above Formulas A-1 to A-3,
* Means the part where the combination is made. The method according to claim 1,
Wherein Ar &lt; ₂ &gt; is a substituent represented by any one of the following formulas (4) to (8)
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas 4 to 8,
* Denotes the part where the bond is made;
m and n are each independently an integer of 0 to 4;
Z ₁ to Z ₅ are each independently N or C (R ₃ );
T ₁ is C (R ₄ ) (R ₅ ) or N (R ₆ );
R ₁ and R ₂ 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 aryl phosphazene 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 adjacent to form a fused ring, wherein R ₁ and When there are a plurality of R &lt; ₂ &gt; s, they are the same as or different from each other;
R ₃ to R ₆ 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 ~ aryl phosphazene group of C _60, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C selected from the ₆₀ group consisting of aryl amines, or to combine groups which are adjacent to form a fused ring, wherein R ₃ are plural, they are the same or different from each other;
Alkyl group of the R ₁ to R _6, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other. 6. The method of claim 5,
Each of R ₁ to R ₆ is independently selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. 6. The method of claim 5,
Wherein the substituent represented by Formula 4 is a substituent represented by Formula 9:
[Chemical Formula 9]

In the above formula (9)
* Denotes the part where the bond is made;
R ₇ and R ₈ are each independently hydrogen, deuterium, 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 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 phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;
Alkyl group of the R ₇ and R _8, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, 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 a plurality of substituents, they are the same as or different from each other;
Each of Z ₁ , Z ₃ and Z ₅ is as defined in claim 5. The method according to claim 1,
Wherein Ar &lt; ₂ &gt; is a substituent represented by any one of the following formulas (B-1) to (B-7)

In the above Formulas B-1 to B-7,
* Denotes the part where the bond is made;
m and n are each independently an integer of 0 to 4;
R ₁ and R ₂ 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 aryl phosphazene 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 adjacent to form a fused ring, wherein R ₁ and When there are a plurality of R &lt; ₂ &gt; s, they are the same as or different from each other;
R ₇ and R ₈ are each independently hydrogen, deuterium, 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 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 phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;
Wherein R _1, R _2, an alkyl group of R ₇ and R _8, 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 , alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, a nitro group, an alkyl group of _{C 1 ~ C 40, C 2} ~ C _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ group consisting arylsilyl of C ₆₀ in And when they are substituted with a plurality of substituents, they are the same as or different from each other. 9. The method of claim 8,
Each of R ₁ , R ₂ , R ₇ and R ₈ is independently selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. The method according to claim 1,
Wherein Ar &lt; ₂ &gt; is a substituent represented by the following formula (10):
[Chemical formula 10]

In Formula 10,
* Denotes the part where the bond is made;
R ₉ and R ₁₀ are each independently hydrogen, deuterium, 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 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 phosphazene group, selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of, or by combining the adjacent tile to form a condensed ring;
Alkyl group of the R ₉ and R _10, 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 C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, 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 When they are substituted or unsubstituted with one or more substituents, and when they are substituted with a plurality of substituents, they are the same as or different from each other. 11. The method of claim 10,
Each of R ₉ and R ₁₀ is independently selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms. 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). 14. The method of claim 13,
Wherein the organic material layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transporting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and a light emitting layer.

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