KR20180065246A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electro luminescence device comprising the same, wherein the compound according to the present invention is used in in an organic material layer of an organic electroluminescence device, preferably a light emitting layer, so that the luminous efficiency, the driving voltage and the life of the organic electroluminescence 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.

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.

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

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

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

[Chemical Formula 1]

In Formula 1,

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

Ring Q ₁ is C ₆ -C ₃₀ arene or heteroarylene having 5 to 30 nuclear atoms;

R ₁ and R ₂ 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

R ₃ to R ₅ is a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ each independently represent a deuterium, a halogen, a cyano group, 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 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 ₃ to R ₅ in each case a plurality of individual, they are equal to each other, or Different;

Alkyl group of the R ₁ to R _5, 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 or different from each other;

Ar ₁ is a substituent represented by the following formula (2);

(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 direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

R ₆ is 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 arylphosphate 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;

Wherein L ₁ and the arylene group and a heteroarylene group, an alkyl group of the R ₆ of the L _2, 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, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as 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 .

"Halogen" in the present invention means fluorine, chlorine, bromine or iodine.

"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,

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

Ring Q ₁ is C ₆ -C ₃₀ arene or heteroarylene having 5 to 30 nuclear atoms;

R ₁ and R ₂ 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

R ₃ to R ₅ is a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ each independently represent a deuterium, a halogen, a cyano group, 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 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 ₃ to R ₅ in each case a plurality of individual, they are equal to each other, or Different;

Alkyl group of the R ₁ to R _5, 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 or different from each other;

Ar ₁ is a substituent represented by the following formula (2);

(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 direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;

R ₆ is 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 arylphosphate 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;

Wherein L ₁ and the arylene group and a heteroarylene group, an alkyl group of the R ₆ of the L _2, 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, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

In the present invention, the compound represented by the general formula (1) includes a spiroacridine-based moiety, has excellent electrochemical stability, has a high glass transition temperature and carrier transporting ability, The light emitting efficiency is increased. Further, the substituent of an electron-withdrawing group (EWG) is bonded to the moiety so that the electron mobility is particularly excellent, and the glass transition temperature and thermal stability are excellent.

In the present invention, since the compound represented by Formula 1 is excellent in electron transporting ability and light emitting property, the compound of Formula 1 can be used as a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, It can be used as a material.

Preferably used as a material of any one of a light emitting layer of green phosphorescence, an electron transporting layer and an electron transporting layer which is further laminated on the electron transporting layer. In addition, since the electron transporting layer has high triplet energy, it can exhibit excellent efficiency due to the triplet-triplet fusion (TTF) effect.

Further, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. The number of the excitons contributing to light emission in the light emitting layer can be increased to improve the light emitting efficiency of the device and the durability and stability of the device can be improved and the lifetime of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that can be driven at low voltage, thereby improving lifetime.

According to a preferred embodiment of the present invention, each of R ₁ and R ₂ is independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms Selected,

The alkyl, aryl and heteroaryl groups of R ₁ and R ₂ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. 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 and R ₂ are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl and triazinyl groups ≪ / RTI >

Wherein R ₁ and methyl groups in R _2, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group each independently C alkyl group of ₁ ~ C _40, C ₆ ~ An aryl group of C ₆₀ , and a heteroaryl group having 5 to 60 nuclear atoms, 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 and R ₂ are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl and triazinyl groups ≪ / RTI >

A methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group of R ₁ and R ₂ are each independently an ethyl group, A phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group, 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, the ring Q ₁ may be represented by any one of the following formulas (3) to (6), preferably represented by any one of the following formulas (3)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 3 to 6,

The dotted line means a moiety in which the condensation is carried out in the above formula (1);

m and R < ₃ > are the same as defined in the above formula (1).

According to a preferred embodiment of the present invention, L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of the following formulas A-1 to A-4, more preferably a direct bond Lt; RTI ID = 0.0 > A-1 < / RTI > or A-2:

In the above Formulas A-1 to A-4,

* Means the part where the combination is made.

According to a preferred embodiment of the present invention, R ₆ is selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms,

The alkyl, aryl and heteroaryl groups of R ₆ are each independently substituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms , 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 ₆ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, A pyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinoxalinyl group, and a quinazolinyl group,

The above-mentioned R ₆ is preferably a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, The norbornyl group, the cinnolinyl group, the quinoxalinyl group and the quinazolinyl group are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, 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 ₆ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, A pyridinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinoxalinyl group, and a quinazolinyl group,

The above-mentioned R ₆ is preferably a methyl group, ethyl group, propyl group, butyl group, pentyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, naphthalenyl group, triazolopyridinyl group, quinolinyl group, The norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the norbornyl group, the phenanthryl group, Substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, They are the same or different from each other.

According to a preferred embodiment of the present invention, R ₆ may be a substituent represented by any of the following formulas (7) to (9):

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas (7) to (9)

* Denotes the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₈ );

o is an integer from 0 to 4;

R ₇ is a group 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, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, 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, an aryloxy group of a C ₆ ~ C ₆₀ of, C _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 arylphosphonyl group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination group adjacent to form a condensed ring, when the R ₇ a plurality individuals which are equal to each other Or different;

R ₈ is 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 arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination groups adjacent when forming a condensed ring, and individual said R ₈ is plural, they of Are the same or different from each other;

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 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, the substituent represented by the formula (7) 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 ~ for C ₆₀ aryl phosphazene group, it said shed some light 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;

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 or different;

Each of Z ₁ , Z ₃ and Z ₅ is the same as defined in the above formula (7).

According to a preferred embodiment of the present invention, the substituent represented by the formula (7) may be a substituent represented by any one of the following formulas (B-1) to (B-3)

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

* 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

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 ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms Selected;

The alkyl, aryl and heteroaryl groups of R ₉ and R ₁₀ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. 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, each of R ₉ and R ₁₀ may independently be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group,

The phenyl, biphenyl, pyridinyl, pyrimidinyl, triazinyl and naphthalenyl groups of R ₉ and R ₁₀ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heteroaryl group;

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 pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group, Preferably a phenyl group, a biphenyl group, and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₉ and R ₁₀ each independently represents a methyl group, an ethyl group, a butyl group, a propyl group, a pentyl group, 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, the substituent represented by Formula 8 may be a substituent represented by Formula 11:

(11)

In Formula 11,

* Denotes the part where the bond is made,

o, R < ₇ > and R < ₈ >

According to a preferred embodiment of the present invention, R ₈ is selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms;

The alkyl, aryl and heteroaryl groups of R ₈ are each independently substituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms , 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 ₈ may be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₈ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heteroaryl group.

According to a preferred embodiment of the present invention, R ₈ may be selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a naphthalenyl group, more preferably a phenyl group, A phenyl group and a pyridinyl group,

The phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, triazinyl group and naphthalenyl group of R ₈ each independently represents a group consisting of a methyl group, an ethyl group, a butyl group, a propanyl group, a pentyl group, , 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, the substituent represented by the formula (9) may be a substituent represented by the following formula (12)

[Chemical Formula 12]

In Formula 12,

* Denotes the part where the bond is made,

o and R < ₇ > are as defined in the above formula (9).

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 formula 1 of the present invention can be synthesized according to the general synthetic methods ( 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 injection layer 36 is a layer which is stacked on the electron transport layer 34 to facilitate injection of electrons from the cathode to ultimately improve power efficiency and is commonly used in the art . For example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, and BaO 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 .

In the present invention, the compound represented by the general formula (1) includes a spiroacridine-based moiety, has excellent electrochemical stability, has a high glass transition temperature and carrier transporting ability, The light emitting efficiency is increased. Further, the substituent of an electron-withdrawing group (EWG) is bonded to the moiety so that the electron mobility is particularly excellent, and the glass transition temperature and thermal stability are excellent.

In the present invention, since the compound represented by Formula 1 is excellent in electron transporting ability and light emitting property, the compound of Formula 1 can be used as a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, It can be used as a material.

Preferably used as a material of any one of a light emitting layer of green phosphorescence, an electron transporting layer and an electron transporting layer which is further laminated on the electron transporting layer. In addition, since the electron transporting layer has high triplet energy, it can exhibit excellent efficiency due to the triplet-triplet fusion (TTF) effect.

Further, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. The number of the excitons contributing to light emission in the light emitting layer can be increased to improve the light emitting efficiency of the device and the durability and stability of the device can be improved and the lifetime of the device can be efficiently increased. Most of the developed materials exhibit physical characteristics that can be driven at low voltage, thereby improving lifetime.

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.

Example

[ Preparation Example  1] Synthesis of Core 1

≪ Step 1 > 9- (4'- Chloro - [1,1'-biphenyl] -2-yl) -10,10-dimethyl-9,10- Dihydroanthracene -9-ol

To 50 g (0.19 mol) of 2-bromo-4'-chloro-1,1'-biphenyl was added 500 mL of THF. Next, the temperature of the reaction solution was lowered to -78 ° C, and 128 mL (0.21 mol) of a 1.6M solution of n-BuLi was slowly added dropwise to the reaction solution. After stirring for 1 hour at the same temperature, 45.7 g (0.21 mol) of 10,10-dimethyl anthracene-9 (10H) -one was dissolved in 500 mL of THF, slowly added to the reaction solution, stirred at the same temperature for 1 hour, Lt; / RTI > for 24 hours. Then, 500 mL of purified water was added to the reaction solution to terminate the reaction, followed by extraction with 2.0 L of EA and washing with distilled water. Then, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and then purified by silica gel column chromatography to obtain 52.2 g of the desired compound (yield: 68%).

^{1 H-NMR (in DMSO)} : δ 8.42 (d, 1H), 7.55 (t, 1H), 7.31 (m, 3H), 7.20 (m, 2H), 7.06 (m, 2H), 6.86 (d, 2H ), 6.68 (d, 1 H), 6.60 (d, 2H), 5.71 (s,

[LCMS]: 410

≪ Step 2 > Chloro -10,10-dimethyl-10H- Spiro [anthracene-9,9'-fluorene]  synthesis

To 46.0 g (0.11 mol) of 9- (4'-chloro- [1,1'-biphenyl] -2-yl) -10,10- 70 mL and 700 mL of AcOH were added. The reaction solution was heated to reflux at 100 ° C for 2 hours. After the reaction mixture was cooled to room temperature, 500 mL of purified water was added to the reaction mixture to terminate the reaction. The resulting solid was filtered under reduced pressure and dried under a warm air stream to obtain 43.1 g (yield: 98%) of the target compound.

_{^{1 H-NMR (in CDCl 3}} ): δ 7.78 (d, 1H), 7.73 (d, 1H), 7.60 (dd, 2H), 7.30 (m, 2H), 7.20 (dt, 2H), 7.14 (dt, 1H), 6.86 (m, 4H), 6.28 (dd, 2H), 1.92

[LCMS]: 392

[ Preparation Example  2] Synthesis of Core 2

≪ Step 1 > 9- (3'- Chloro - [1,1'-biphenyl] -2-yl) -10,10-dimethyl-9,10- Dihydroanthracene -9-ol

The same procedure as in Step 1 of [Preparation Example 1] was conducted to obtain 49.9 g (65%) of the target compound corresponding to the structural isomer of Core 1.

[LCMS]: 410

≪ Step 2 > 3'- Chloro -10,10-dimethyl-10H- Spiro [anthracene-9,9'-fluorene]  synthesis

The procedure of Step 2 of Preparation Example 1 was followed to obtain 28.6 g (60%) of the target compound corresponding to the structural isomer of Core 1.

[LCMS]: 392

[ Preparation Example  3] Synthesis of Core 3

≪ Step 1 > 9- (2'- Bromo - [1,1'-biphenyl] -2-yl) -10,10-dimethyl-9,10- Dihydroanthracene -9-ol

Except that 2,2'-dibromo-1,1'-biphenyl was used as the reactant The same procedure as in Step 1 of [Preparation Example 1] was conducted to obtain 42.3 g (58%) of the target compound corresponding to the structural isomer of Core 1.

[LCMS]: 455

≪ Step 2 > Bromo -10,10-dimethyl-10H- Spiro [anthracene-9,9'-fluorene]  synthesis

The same procedure as in Step 2 of [Preparation Example 1] was conducted to obtain 38.3 g (95%) of the target compound corresponding to the structural isomer of Core 1.

_{^{1 H-NMR (in CDCl 3}} ): δ 8.68 (d, 1H), 7.60 (d, 2H), 7.48 (d, 1H), 7.37 (t, 1H), 7.28 (m, 3H), 6.97 (t, 1H), 6.76 (m, 4H), 6.29 (d, 2H), 1.97

[LCMS]: 437

[ Preparation Example  4] Synthesis of Core 4

≪ Step 1 > 9- (4'- Chloro - [1,1'-biphenyl] -2-yl) -10,10-diphenyl-9,10- Dihydroanthracene -9-ol

To 50 g (0.19 mol) of 2-bromo-4'-chloro-1,1'-biphenyl was added 500 mL of THF. Next, the temperature of the reaction solution was lowered to -78 ° C, and 128 mL (0.21 mol) of a 1.6M solution of n-BuLi was slowly added dropwise to the reaction solution. After stirring at the same temperature for 1 hour, 45.7 g (0.21 mol) of 10,10-diphenylanthracene-9 (10H) -one was dissolved in 500 mL of THF, slowly added to the reaction solution, stirred at the same temperature for 1 hour, And further stirred at room temperature for 24 hours. Then, 500 mL of purified water was added to the reaction solution to terminate the reaction, followed by extraction with 2.0 L of EA and washing with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and then purified by silica gel column chromatography to obtain 62.0 g (yield 62%) of the target compound.

[LCMS]: 535

≪ Step 2 > Chloro -10,10-diphenyl-10H- Spiro [Anthracene-9,9'- Fluorene ] Synthesis of

To 62.0 g (0.12 mol) of 9- (4'-chloro- [1,1'-biphenyl] -2-yl) -10,10-diphenyl-9,10-dihydroanthracene- 90 mL of HCl and 900 mL of AcOH were added. The reaction solution was heated to reflux at 100 ° C for 2 hours. After the reaction mixture was cooled to room temperature, 500 mL of purified water was added to the reaction mixture to terminate the reaction. The resulting solid was filtered under reduced pressure and dried under a humid atmosphere to obtain 57.5 g of the target compound (yield: 96%).

[LCMS]: 517

[ Preparation Example  5] 4,4,5,5- Tetramethyl -2-( Spiro [ Fluorene -9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane

≪ Step 1 > 9- (3'- Chloro - [1,1'-biphenyl] -2-yl) -10,10-diphenyl-9,10- Dihydroanthracene -9-ol

The same procedure as in Step 1 of [Preparation Example 4] was conducted to obtain 66.0 g (66%) of the target compound corresponding to the structural isomer of Core 4.

[LCMS]: 535

≪ Step 2 > 3'- Chloro -10,10-diphenyl-10H- Spiro [Anthracene-9,9'- Fluorene ] Synthesis of

The procedure of Step 2 of Preparation Example 4 was followed to obtain 28.1 g (44%) of the target compound corresponding to the structural isomer of Core 4.

[LCMS]: 517

[ Preparation Example  6] Synthesis of Core 6

≪ Step 1 > 9- (2'- Bromo - [1,1'-biphenyl] -2-yl) -10,10-diphenyl-9,10- Dihydroanthracene -9-ol

Except that 2,2'-dibromo-1,1'-biphenyl was used as the reactant The same procedure as in Step 1 of [Preparation Example 4] was conducted to obtain 49.2 g (53%) of the target compound corresponding to the structural isomer of Core 4.

[LCMS]: 579

≪ Step 2 > Bromo -10,10-dimethyl-10H- Spiro [anthracene-9,9'-fluorene]  synthesis

The same procedure as in Step 2 of [Preparation Example 4] was conducted to obtain 43.7 g (92%) of the target compound corresponding to the structural isomer of Core 4.

[LCMS]: 561

[ Preparation Example  7] Synthesis of Core 7

≪ Step 1 > 9- (3- (4- Chlorophenyl ) Naphthalen-2-yl) -10,10-dimethyl-9,10- Dihydroanthracene -9-ol

Except that 2-bromo-3- (4-chlorophenyl) naphthalene was used as the reactant. The procedure of Step 1 of [Preparation Example 1] was repeated to obtain 42.1 g (58%) of the desired compound.

[LCMS]: 461

≪ Step 2 > Chloro -10,10-dimethyl-10H- Spiro [Anthracene-9,11'- benzo [b] fluorene ] Synthesis of

Except that 9- (3- (4-chlorophenyl) naphthalen-2-yl) -10,10-dimethyl-9,10-dihydroanthracene- The same procedure as in Step 2 of [Preparation Example 1] was conducted to obtain 38.3 g (95%) of the desired compound.

[LCMS]: 442

[ Preparation Example  8] Synthesis of Core 8

≪ Step 1 > 9- (3- (4- Chlorophenyl ) Naphthalen-2-yl) -10,10-dimethyl-9,10- Dihydroanthracene -9-ol

Except that 1- (2,6-dibromophenyl) naphthalene was used as a reactant The same procedure as in Step 1 of [Preparation Example 1] was conducted to obtain 34.9 g (50%) of the desired compound.

[LCMS]: 505

≪ Step 2 > Bromo -10,10-dimethyl-10H- Spiro [anthracene-9,7'-benzo [c] fluorene]  synthesis

Except that 9- (3-bromo-2- (naphthalen-1-yl) phenyl) -10,10-dimethyl-9,10-dihydroanthracene- The procedure of Step 2 of [Preparation Example 1] was repeated to obtain 23.9 g (73%) of the desired compound.

[LCMS]: 487

[ Preparation Example  9] 2- (10,10-dimethyl-10H- Spiro [Anthracene-9,9'- Fluorene ] -2'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

20.0 g (50.9 mmol) of 2'-chloro-10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] synthesized in Preparation Example 1 and 4,4,4 ' , Dioxane (500 mL) was added to 15.5 g (61.1 mmol) of 5,5,5 ', 5'-octamethyl-2,2' -bis (1,3,2-dioxaborolane). 2.1 g (2.6 mmol) of Pd (dppf) Cl ₂ , 2.4 g (5.1 mmol) of XPhos and 15.0 g (153 mmol) of KOAc were added, and the mixture was refluxed at 130 ° C for 8 hours. Then, the reaction solution was cooled to room temperature and 500 mL of ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction. The reaction solution was extracted with 1.0 L of EA and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and then purified by silica gel column chromatography to obtain 21.0 g (yield: 85%) of the desired compound.

_{^{1 H-NMR (in CDCl 3}} ): δ 7.92 (m, 3H), 7.60 (d, 2H), 7.34 (s, 1H), 7.30 (t, 1H), 7.18 (dt, 2H), 7.11 (t, 1H), 6.84 (m, 3H), 6.29 (dd, 2H), 1.92 (dd,

[LCMS]: 484

[ Preparation Example  10] 2- (10,10-dimethyl-10H- Spiro [Anthracene-9,9'- fluoren ] -3'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

10'-dimethyl-10H-spiro [anthracene-9,9'-fluorene] instead of 3'-chloro-10,10- ], The procedure of Preparation Example 9 was repeated to obtain 19.2 g of the desired compound (yield 78%).

[LCMS]: 484

[ Preparation Example  11] 2- (10,10-dimethyl-10H- Spiro [Anthracene-9,9'- Fluorene ] -4'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

15.0 g (34.3 mmol) of 4'-bromo-10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] synthesized in [Preparation Example 3] (500 mL) was added to 10.5 g (41.2 mmol) of 5,5,5 ', 5'-octamethyl-2,2' -bis (1,3,2-dioxaborolane). Next, 1.5 g (1.3 mmol) of Pd (dppf) Cl ₂ and 10.1 g (103 mmol) of KOAc were added and the mixture was heated to reflux at 130 ° C for 3 hours. Then, the reaction solution was cooled to room temperature and 500 mL of ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction. The reaction solution was extracted with 1.0 L of EA and washed with distilled water. Then, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and then purified by silica gel column chromatography to obtain 9.1 g (yield: 55%) of the target compound.

_{^{1 H-NMR (in CDCl 3}} ): δ 8.76 (d, 2H), 7.92 (dd, 1H), 7.58 (dd, 2H), 7.27 (dt, 1H), 7.09 (m, 4H), 6.93 (dd, 2H), 1.87 (dd, 6H), 1.48 (s, 12H)

[LCMS]: 484

[ Preparation Example  12] 2- (10,10-diphenyl-10H- Spiro [Anthracene-9,9'- Fluorene ] -2'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

The procedure of Preparation Example 9 was repeated except for using 2'-chloro-10,10-diphenyl-10H-spiro [anthracene-9,9'-fluorene] %).

[LCMS]: 608

[ Preparation Example  13] 2- (10,10-diphenyl-10H- Spiro [Anthracene-9,9'- Fluorene ] -3'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

The procedure of Preparation Example 9 was repeated except that 3'-chloro-10,10-diphenyl-10H-spiro [anthracene-9,9'-fluorene] was used to obtain 19.4 g (yield: 84% %).

[LCMS]: 608

[ Preparation Example  14] 2- (10,10-diphenyl-10H- Spiro [Anthracene-9,9'- Fluorene ] -4'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

The procedure of Preparation Example 11 was repeated except for using 4'-bromo-10,10-diphenyl-10H-spiro [anthracene-9,9'-fluorene] 52%).

[LCMS]: 608

[ Preparation Example  15] 2- (10,10-dimethyl-10H- Spiro [Anthracene-9,11'- Benzo [b] fluorene ] -2'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

The procedure of Preparation Example 9 was repeated except for using 2'-chloro-10,10-dimethyl-10H-spiro [anthracene-9,11'-benzo [b] fluorene] (Yield: 80%).

[LCMS]: 534

[ Preparation Example  16] 2- (10,10-dimethyl-10H- Spiro [Anthracene-9,7'- Benzo [c] fluorene ] -9'-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

The procedure of Preparation Example 11 was repeated except for using 11'-bromo-10,10-dimethyl-10H-spiro [anthracene-9,7'-benzo [c] fluorene] g (yield: 77%).

[LCMS]: 534

[ Synthetic example  1] Synthesis of Compound 1

To 100 ml of dioxane and 25 g of H ₂ O 25 were added to 8 g (16.6 mmol) of Preparation Example 9 synthesized above and 5.4 g (20.0 mmol) of 2-chloro-4,6-diphenyl- mL. _{Pd (PPh 3) 4 1.0 g} (0.9 mmol), K 2 CO 3 6.9 g After the addition of (49.8 mmol) was heated to reflux at 120 ℃ 6 hours. The reaction mixture was cooled to room temperature and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 1.0 L of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (6.4 g, yield 65%).

[LCMS]: 589

[ Synthetic example  2] Synthesis of Compound 4

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane was used in place of [(1, 1 ' -biphenyl-4-yl) -4-chloro-6-phenyl-1,3,5- 1], 7.8 g (yield 54%) of the desired compound was obtained.

^{1 H-NMR (in DMSO)} : δ 9.15 (d, 2H), 9.09 (dd, 2H), 8.61 (s, 1H), 8.33 (d, 2H), 8.26 (dd, 2H), 8.16 (dd, 2H ), 8.07 (m, 4H), 7.87 (t, 2H), 7.80 (d, IH), 7.73 (t, , 7.20 (d, 1 H), 6.59 (dd, 2H), 1.92 (d, 6H)

[LCMS]: 665

[ Synthetic example  3] Synthesis of Compound 5

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- The same procedure as in [Synthesis Example 1] was carried out except that dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine were used To obtain 5.6 g (yield: 48%) of the desired compound.

[LCMS]: 664

[ Synthetic example  4] Synthesis of Compound 8

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in the same manner as in [Synthesis Example 1] 6.0 g (yield: 55%) of a compound was obtained.

[LCMS]: 665

[ Synthetic example  5] Synthesis of Compound 9

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane and 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in place of [ 6.0 g (yield: 55%) of a compound was obtained.

^{1 H-NMR (in DMSO)} : δ 8.66 (m, 5H), 8.14 (d, 1H), 8.04 (d, 1H), 7.83 (d, 1H), 7.71 (m, 5H), 7.60 (m, 4H 2H), 6.17 (d, IH), 7.38 (t, IH), 7.19 (m, 3H), 7.13 , 1.90 (d, 6H)

 [LCMS]: 665

[ Synthetic example  6] Synthesis of Compound 14

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane (7.0 g, 14.5 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- (3- chlorophenyl) 200 mL of dioxane and 50 mL of H ₂ O were added to 6.7 g (16.0 mmol) of triazine. 0.18 g (0.8 mmol) of Pd (OAc) ₂ , 0.72 g (1.5 mmol) of XPhos and 9.5 g (29.0 mmol) of Cs ₂ CO ₃ were added and the mixture was refluxed at 120 ° C for 3 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of purified water. The mixture was extracted with 1 L of EA, and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain the desired compound (6.8 g, yield 63%).

[LCMS]: 741

[ Synthetic example  7] Synthesis of Compound 16

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- Except that dioxaborolane and 2 - ([1,1'-biphenyl] -4-yl) -4- (4-chlorophenyl) -6-phenyl-1,3,5-triazine were used The procedure of Synthesis Example 14 was repeated to give the desired compound (3.6 g, yield 66%).

[LCMS]: 741

[ Synthetic example  8] Synthesis of Compound 17

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- [Synthesis Example 14] Synthesis was carried out except that dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6- (4-chlorophenyl) (Yield: 58%) of the target compound.

[LCMS]: 740

[ Synthetic example  9] Synthesis of Compound 19

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxaborolan and 2- (4-chlorophenyl) -4-phenylquinazoline was used in place of 2-chloro-4-fluorobenzene in the same manner as in [Synthesis Example 14] to obtain 5.2 g of the desired compound (yield: 60%).

[LCMS]: 638

[ Synthetic example  10] Synthesis of Compound 22

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- Except that dioxaborolane and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Was subjected to the same procedure as in [Synthesis Example 14] to obtain the desired compound (8.0 g, yield 69%).

^{1 H-NMR (in DMSO)} : δ 8.87 (s, 1H), 8.71 (m, 5H), 7.87 (d, 1H), 7.82 (d, 1H), 7.71 (m, 2H), 7.64 (dd, 1H 2H), 6.34 (d, 2H), 7.56 (m, 10H), 7.42 (m, 2H) , 1.87 (d, 6H)

[LCMS]: 741

[ Synthetic example  11] Synthesis of Compound 24

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxabororane and 2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine Was subjected to the same procedure as in [Synthesis Example 14] to obtain the desired compound (6.4 g, yield 62%).

[LCMS]: 741

[ Synthetic example  12] Synthesis of Compound 31

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxabororane and 2 - ([1,1'-biphenyl] -4-yl) -4- (3'-chloro- [ Phenyl-1,3,5-triazine was used in place of the compound obtained in Synthesis Example 14, 3.5 g (yield: 57%) of the target compound was obtained.

[LCMS]: 818

[ Synthetic example  13] Synthesis of Compound 34

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6- (3'- Phenylpyrimidine, the procedure of Synthesis Example 14 was repeated to obtain the desired compound (4.4 g, yield 52%).

[LCMS]: 817

[ Synthetic example  14] Synthesis of Compound 41

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- -Dioxabororane and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -6,8-diphenyl- [1,2,4] triazolo [ -a] pyridine, the procedure of Synthesis Example 14 was repeated to obtain the desired compound (2.8 g, yield: 56%).

[LCMS]: 779

[ Synthetic example  15] Synthesis of Compound 44

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl- - dioxaborolane and 2- (3 "-chloro- [1,1 ': 3', 1" -terphenyl] -3-yl) -4,6-diphenyl- -Triazine was used to carry out the same procedure as in [Synthesis Example 14] to obtain the desired compound (3.3 g, yield 49%).

[LCMS]: 818

[ Synthetic example  16] Synthesis of Compound 52

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane was used in place of [(1, 1 ' -biphenyl-4-yl) -4-chloro-6-phenyl-1,3,5- 1], 5.3 g of the desired compound (yield: 63%) was obtained.

[LCMS]: 665

[ Synthetic example  17] Synthesis of Compound 56

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in the same manner as in [Synthesis Example 1] 4.4 g (yield 51%) of the compound was obtained.

[LCMS]: 665

[ Synthetic example  18] Synthesis of Compound 63

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl- [Synthesis Example 14] Synthesis was carried out except that dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6- (3- chlorophenyl) The target compound (5.0 g, yield: 37%) was obtained.

[LCMS]: 740

[ Synthetic example  19] Synthesis of Compound 79

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl- -Dioxabororane and 2 - ([1,1'-biphenyl] -4-yl) -4- (3'-chloro- [ Phenyl-1,3,5-triazine was used in place of the compound obtained in Synthesis Example 14 to give the desired compound (4.7 g, yield: 54%).

[LCMS]: 818

[ Synthetic example  20] Synthesis of Compound 86

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl- The same procedure as in [Synthesis Example 14] was conducted except that dioxaborolane and 2- (3'-chloro - [1,1'-biphenyl] -3-yl) -4-phenylquinazoline were used To obtain 6.9 g (yield 52%) of the desired compound.

[LCMS]: 714

[ Synthetic example  21] Synthesis of Compound 96

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane and 2-chloro-4,6-diphenyl-1,3,5-triazine were used in place of the target compound [ %).

[LCMS]: 589

[ Synthetic example  22] Synthesis of compound 99

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane was used in place of [(1, 1 ' -biphenyl-4-yl) -4-chloro-6-phenyl-1,3,5- 1], 2.5 g (yield 55%) of the desired compound was obtained.

[LCMS]: 665

[ Synthetic example  23] Synthesis of Compound 100

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl- The same procedure as in [Synthesis Example 1] was carried out except that dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine were used To obtain 3.6 g of the desired compound (yield 69%).

[LCMS]: 664

[ Synthetic example  24] Synthesis of Compound 102

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl- -Dioxaborolane and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used in the same manner as in [Synthesis Example 1] 6.5 g (yield 53%) of the compound was obtained.

[LCMS]: 665

[ Synthetic example  25] Synthesis of compound 109

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl- Except that dioxaborolane and 2 - ([1,1'-biphenyl] -4-yl) -4- (4-chlorophenyl) -6-phenyl-1,3,5-triazine were used The procedure of Synthesis Example 14 was followed to obtain 5.0 g of the desired compound (yield: 42%).

[LCMS]: 741

[ Synthetic example  26] Synthesis of Compound 110

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl- [Synthesis Example 14] Synthesis was carried out except that dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6- (3- chlorophenyl) The target compound (3.3 g, yield: 59%) was obtained.

[LCMS]: 740

[ Synthetic example  27] Synthesis of Compound 114

Preparation of 2- (10,10-dimethyl-10H-spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl- Except that dioxaborolane and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Was subjected to the same procedure as in [Synthesis Example 14] to obtain the desired compound (5.1 g, yield: 48%).

[LCMS]: 741

[ Synthetic example  28] Synthesis of Compound 123

Spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3,2- The procedure of Synthesis Example 1 was repeated except that 2-dioxaborolane and 2-chloro-4,6-diphenyl-1,3,5-triazine were used to obtain 6.5 g (yield: 40%).

[LCMS]: 713

[ Synthetic example  29] Synthesis of Compound 126

Spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3,2- Except that 2-dioxaborolane was used and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5- The procedure of Example 1] was repeated to obtain 5.2 g of the desired compound (yield: 55%).

[LCMS]: 789

[ Synthetic example  30] Synthesis of Compound 127

Spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was carried out except that 2-dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine were used To obtain 3.7 g of the desired compound (yield: 60%).

[LCMS]: 788

[ Synthetic example  31] Synthesis of Compound 130

Spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was carried out except that 2-dioxaborolane and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used 5.5 g (the yield: 62%) of the aimed compound was obtained.

[LCMS]: 789

[ Synthetic example  32] Synthesis of Compound 131

Spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was carried out except that 2-dioxaborolane and 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used 4.0 g (the yield: 58%) of the aimed compound was obtained.

[LCMS]: 789

[ Synthetic example  33] Synthesis of Compound 137

Spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3,2- Dioxaborolane and 2 - ([1,1'-biphenyl] -4-yl) -4- (4-chlorophenyl) -6-phenyl-1,3,5-triazine , 2.4 g (yield: 60%) of the target compound was obtained by carrying out the same processes as in [Synthesis Example 14].

[LCMS]: 866

[ Synthetic example  34] Synthesis of Compound 139

Spiro [anthracene-9,9'-fluorene] -2'-yl) -4,4,5,5-tetramethyl-1,3,2- [Synthesis Example 14 (2)] was repeated except for using 2-dioxaborolane and 4 - ([1,1'-biphenyl] -4-yl) -6- ], 3.8 g (yield 55%) of the desired compound was obtained.

[LCMS]: 865

[ Synthetic example  35] Synthesis of Compound 143

Spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was repeated but using 2-dioxaborolane and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the desired compound (3.0 g, 52%).

[LCMS]: 789

[ Synthetic example  36] Synthesis of Compound 145

Spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was repeated but using 2-dioxaborolane and 2-chloro-4-phenylquinazoline to obtain the desired compound (4.4 g, yield 51%).

[LCMS]: 686

[ Synthetic example  37] Synthesis of Compound 147

Spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was carried out except that 2-dioxaborolane and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used 5.5 g (the yield: 48%) of the desired compound was obtained.

[LCMS]: 789

[ Synthetic example  38] Synthesis of compound 154

Spiro [anthracene-9,9'-fluorene] -3'-yl) -4,4,5,5-tetramethyl-1,3,2- Dioxaborolane and 2 - ([1,1'-biphenyl] -4-yl) -4- (4-chlorophenyl) -6-phenyl-1,3,5-triazine , The same procedure as in [Synthesis Example 14] was conducted to obtain the desired compound (4.1 g, yield 50%).

[LCMS]: 866

[ Synthetic example  39] Synthesis of Compound 157

Spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was repeated but using 2-dioxaborolane and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the desired compound (4.6 g, 58%).

[LCMS]: 713

[ Synthetic example  40] Synthesis of Compound 165

Spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl-1,3,2- The same procedure as in [Synthesis Example 1] was carried out except that 2-dioxaborolane and 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine were used 6.7 g (yield 53%) of the desired compound was obtained.

[LCMS]: 789

[ Synthetic example  41] Synthesis of Compound 170

Spiro [anthracene-9,9'-fluorene] -4'-yl) -4,4,5,5-tetramethyl-1,3,2- Dioxaborolane and 2 - ([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-triazine , The same procedure as in [Synthesis Example 14] was conducted to obtain 6.0 g of the desired compound (yield: 56%).

[LCMS]: 866

[ Synthetic example  42] Synthesis of Compound 174

Preparation of 2-chloro-10,10-dimethyl-10H-spiro [anthracene-9,11'-benzo [b] fluorene] of Preparation Example 15 and 2-chloro-4,6- -Triazine was used in place of [alpha] -D-glucopyranoside in the same manner as in [Synthesis Example 1], 3.7 g (yield 43%) of the desired compound was obtained.

[LCMS]: 639

[ Synthetic example  43] Synthesis of Compound 177

Preparation of 2'-chloro-10,10-dimethyl-10H-spiro [anthracene-9,11'-benzo [b] fluorene] ) -4-chloro-6-phenyl-1,3,5-triazine was used in place of 4-chloro-6-phenyl-1,3,5-triazine in the same manner as in [Synthesis Example 1].

[LCMS]: 715

[ Synthetic example  44] Synthesis of Compound 178

Spiro [anthracene-9,11'-benzo [b] fluorene] of Preparation Example 15 and 4 - ([1,1'-biphenyl] -4- ) -6-chloro-2-phenylpyrimidine, the procedure of Synthesis Example 1 was repeated to obtain the desired compound (4.5 g, yield 52%).

[LCMS]: 714

[ Synthetic example  45] Synthesis of compound 180

Spiro [anthracene-9,11'-benzo [b] fluorene] of Preparation Example 15 and 2- (3-bromophenyl) -4,6-diphenyl -1,3,5-triazine was used in place of 2-chloro-4-methylpyridine, the objective compound (2.8 g, yield 40%) was obtained.

[LCMS]: 715

[ Synthetic example  46] Synthesis of Compound 181

Spiro [anthracene-9,11'-benzo [b] fluorene] of Preparation Example 15 and 2- (4-bromophenyl) -4,6-diphenyl -1,3,5-triazine was used in place of 1,3,5-triazine, the procedure of Synthesis Example 1 was repeated to obtain the desired compound (3.4 g, yield 45%).

[LCMS]: 715

[ Synthetic example  47] Synthesis of Compound 188

Preparation of 2'-chloro-10,10-dimethyl-10H-spiro [anthracene-9,11'-benzo [b] fluorene] ) Was obtained in the same manner as in [Synthesis Example 14], except that 4- (4-chlorophenyl) -6-phenyl-1,3,5- .

[LCMS]: 792

[ Synthetic example  48] Synthesis of Compound 189

Spiro [anthracene-9,11'-benzo [b] fluorene] of Preparation Example 15 and 4 - ([1,1'-biphenyl] -4- ) The title compound (3.5 g, yield 45%) was obtained in the same manner as in [Synthesis Example 14], except that 6- (4-chlorophenyl) -2-phenylpyrimidine was used.

[LCMS]: 791

[ Synthetic example  49] Synthesis of Compound 192

Preparation of 2'-chloro-10,10-dimethyl-10H-spiro [anthracene-9,11'-benzo [b] fluorene] of Preparation Example 15 and 2- (3'- ] -3-yl) -4,6-diphenyl-1,3,5-triazine was used in place of 4-bromobenzyl chloride to obtain 4.7 g (yield 58%) of the desired compound .

[LCMS]: 792

[ Example  1 to 21] green organic Field  Fabrication of light emitting device

The compounds 1, 8, 9, 14, 19, 22, 24, 31, 34, 41, 44, 56, 79, 102, 114, 123, 130, 147, 170, 180, After a high purity sublimation purification was performed by a known method, a green organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), washed with UV for 5 minutes and then coated with a vacuum evaporator The substrate was transferred.

9, 14, 19, 22, 24, 31, 34, 41, 44, and 44 of m-MTDATA (60 nm) / TCTA (80 nm) / 90% on an ITO transparent glass substrate (electrode) Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) of 56, 79, 102, 114, 123, 130, 147, / Al (200 nm) were laminated in this order to prepare a green organic electroluminescent device.

[ 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 Compound 1 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP used in Examples 1 to 21 and Comparative Example 1 are as follows.

[ Evaluation example  One]

The driving voltage, the current efficiency, and the light emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices manufactured in Examples 1 to 21 and Comparative Example 1, and the results are shown in the following Table 1 .

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 Compound 1 4.3 458 54.0 Example 2 Compound 8 3.6 457 59.5 Example 3 Compound 9 3.8 458 56.5 Example 4 Compound 14 3.8 459 55.2 Example 5 Compound 19 3.7 459 54.8 Example 6 Compound 22 3.7 457 60.5 Example 7 Compound 24 3.9 458 57.7 Example 8 Compound 31 3.9 459 58.6 Example 9 Compound 34 4.0 458 55.9 Example 10 Compound 41 3.8 457 58.5 Example 11 Compound 44 3.8 458 59.0 Example 12 Compound 56 3.6 458 60.0 Example 13 Compound 79 4.1 458 57.9 Example 14 Compound 102 3.8 459 58.3 Example 15 Compound 114 3.7 458 59.3 Example 16 Compound 123 4.1 458 57.0 Example 17 Compound 130 3.8 458 59.1 Example 18 Compound 147 3.9 458 58.0 Example 19 Compound 170 3.7 458 60.0 Example 20 Compound 180 3.6 457 58.8 Example 21 Compound 192 3.7 459 59.4 Comparative Example 1 CBP 5.5 459 44.2

As shown in Table 1, in the case where the compound of the present invention was applied to the material of the light emitting layer included in the organic material layer of the green organic electroluminescent device (Examples 1 to 21), compared with the case where the conventional CBP was applied (Comparative Example 1) The efficiency and the driving voltage are excellent.

[ Example  22 to 49] Blue organic Field  Fabrication of light emitting device

The compounds 1, 4, 5, 9, 16, 17, 52, 96, 99, 100, 102, 109, 110, 123, 126, 127, 131, 137, 139, 143, 154, 157, 165, 174, 177, 181, 188, and 189 were subjected to high purity sublimation purification by a conventionally known method, and blue organic electroluminescent devices were prepared as follows.

first. 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, 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) The substrate was transferred to a vacuum evaporator.

5 nm) / Compound 1, 4, 5, 9 (manufactured by Doosan Heavy Industries, Ltd.) on the ITO transparent electrode prepared above, , 16, 17, 52, 96, 99, 100, 102, 109, 110, 123, 126, 127, 131, 137, 139, 143, 154, 157, 165, 174, 177, 181, 188, Compound (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

A blue organic electroluminescent device was fabricated in the same manner as in Example 22 except that Alq ₃ was used instead of Compound 1 as the electron transport layer material.

[ Comparative Example  3] 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 Compound 1 was not used as an electron transport layer material.

The structures of NPB, AND and Alq3 used in Examples 22 to 49 and Comparative Examples 2 and 3 are as follows.

[ Evaluation example  2]

The driving voltage, current efficiency and emission wavelength at the current density of 10 mA / cm 2 were measured for the blue organic electroluminescent devices fabricated in each of Examples 22 to 49 and Comparative Examples 2 and 3. The results are shown in the following Table 1 Respectively.

Sample Electron transport layer Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 22 Compound 1 4.1 455 7.8 Example 23 Compound 4 3.6 451 8.8 Example 24 Compound 5 3.5 452 9.0 Example 25 Compound 9 3.4 452 8.9 Example 26 Compound 16 3.6 453 8.5 Example 27 Compound 17 3.5 451 8.8 Example 28 Compound 52 3.8 451 9.1 Example 29 Compound 96 3.4 453 8.6 Example 30 Compound 99 3.7 452 8.8 Example 31 Compound 100 3.6 451 9.1 Example 32 Compound 102 3.8 450 8.3 Example 33 Compound 109 3.4 452 8.8 Example 34 Compound 110 3.8 451 8.2 Example 35 Compound 123 4.0 455 8.5 Example 36 Compound 126 3.5 451 9.0 Example 37 Compound 127 3.6 451 9.2 Example 38 Compound 131 3.6 452 8.8 Example 39 Compound 137 3.7 452 8.5 Example 40 Compound 139 3.7 452 8.9 Example 41 Compound 143 3.8 451 8.6 Example 42 Compound 154 3.5 451 9.0 Example 43 Compound 157 3.6 452 8.7 Example 44 Compound 165 3.5 451 9.2 Example 45 Compound 174 3.3 452 8.8 Example 46 Compound 177 3.4 452 8.6 Example 47 Compound 181 3.5 452 8.7 Example 48 Compound 188 3.6 452 8.8 Example 49 Compound 189 3.5 452 9.0 Comparative Example 2 Alq ₃ 4.9 458 5.6 Comparative Example 3 - 4.8 460 6.2

As shown in Table 2, the blue organic electroluminescent devices (Examples 22 to 49) using the compound of the present invention as the electron transport layer (Comparative Examples 2 and ₃ ) used conventional Alq ₃ as the electron transport layer and the blue organic electroluminescent devices The organic EL device of the present invention exhibited excellent performance in terms of driving voltage, luminescent peak and current efficiency as compared with the blue organic electroluminescent device without the electron transport layer (Comparative Example 3).

[ Example  50 to 66] Blue organic Field  Fabrication of light emitting device

Compounds 8, 14, 22, 24, 31, 41, 56, 63, 79, 86, 102, 110, 114, 147, 170, 180, 192 synthesized in Synthesis Example were subjected to high purity sublimation purification Thereafter, a blue organic electroluminescent device was fabricated according to the following procedure.

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, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

NPN (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / compounds 8, 14, 22, 24, and 24 were formed on the ITO transparent electrode prepared as described above. Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) in order of 31, 41, 56, 63, 79, 86, 102, 110, 114, 147, Thereby preparing an organic electroluminescent device.

[ 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 50 except that Compound 8 was not used as an electron transporting auxiliary layer material and Alq ₃ , which is an electron transporting layer material, was deposited at 30 nm instead of 25 nm .

[ Evaluation example  3]

The driving voltage, the emission wavelength and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 50 to 66 and Comparative Example 4, respectively, and the results are shown in Table 3 below.

Sample Electron transporting auxiliary layer The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 50 Compound 8 3.6 455 9.1 Example 51 Compound 14 3.8 456 8.9 Example 52 Compound 22 3.4 455 9.2 Example 53 Compound 24 3.8 456 8.5 Example 54 Compound 31 3.7 455 8.8 Example 55 Compound 41 3.6 455 8.6 Example 56 Compound 56 3.5 454 9.0 Example 57 Compound 63 3.4 455 8.9 Example 58 Compound 79 3.6 454 8.2 Example 59 Compound 86 3.9 455 8.4 Example 60 Compound 102 3.5 455 9.2 Example 61 Compound 110 3.7 454 8.7 Example 62 Compound 114 3.4 454 9.1 Example 63 Compound 147 3.7 455 8.9 Example 64 Compound 170 3.9 454 9.0 Example 65 Compound 180 3.5 455 8.7 Example 66 Compound 192 3.6 455 8.9 Comparative Example 4 - 4.8 458 6.0

As shown in Table 3, the blue organic electroluminescent devices (Examples 50 to 66) using the compound of the present invention as the electron transporting auxiliary layer (Examples 50 to 66) were superior to the blue organic electroluminescent devices without the electron transporting auxiliary layer Current efficiency, emission peak, and driving voltage.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

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,
m and n are each independently an integer of 0 to 4;
Ring Q ₁ is C ₆ -C ₃₀ arene or heteroarylene having 5 to 30 nuclear atoms;
R ₁ and R ₂ 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
R ₃ to R ₅ is a nitro group, C ₁ ~ alkyl group of C _40, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ each independently represent a deuterium, a halogen, a cyano group, 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 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 ₃ to R ₅ in each case a plurality of individual, they are equal to each other, or Different;
Alkyl group of the R ₁ to R _5, 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 or different from each other;
Ar ₁ is a substituent represented by the following formula (2);
(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 direct bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nucleus atoms;
R ₆ is 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 arylphosphate 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;
Wherein L ₁ and the arylene group and a heteroarylene group, an alkyl group of the R ₆ of the L _2, 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, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphazene group of C _60, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ Arylsilyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Each of R ₁ and R ₂ is independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,
The alkyl, aryl and heteroaryl groups of R ₁ and R ₂ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein the ring Q ₁ is represented by any one of the following formulas (3) to (6):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 3 to 6,
The dotted line means a moiety in which the condensation is carried out in the above formula (1);
m and R < ₃ > are as defined in claim 1, respectively. The method according to claim 1,
Wherein L ₁ and L ₂ are each independently a direct bond or a linker selected from the group consisting of the following formulas A-1 to A-4:

In the above Formulas A-1 to A-4,
* Means the part where the combination is made. The method according to claim 1,
Wherein R ₆ is selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms,
The alkyl, aryl and heteroaryl groups of R ₆ are each independently substituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein R < ₆ > is a substituent represented by any one of the following formulas (7) to (9)
(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas (7) to (9)
* Denotes the part where the bond is made;
Z ₁ to Z ₅ are each independently N or C (R ₈ );
o is an integer from 0 to 4;
R ₇ is a group 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, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, 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, an aryloxy group of a C ₆ ~ C ₆₀ of, C _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 arylphosphonyl group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination group adjacent to form a condensed ring, when the R ₇ a plurality individuals which are equal to each other Or different;
R ₈ is 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 arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination groups adjacent when forming a condensed ring, and individual said R ₈ is plural, they of Are the same or different from each other;
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 And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 6,
Wherein the substituent represented by Formula 7 is a substituent represented by 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 ~ for C ₆₀ aryl phosphazene group, it said shed some light 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;
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 or different;
Each of Z ₁ , Z ₃ and Z ₅ is as defined in claim 6. The method according to claim 6,
Wherein the substituent represented by the formula (7) is a substituent represented by any one of the following formulas (B-1) to (B-3):

In the above Formulas B-1 to B-3,
* 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 ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
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. 8. The method of claim 7,
Each of R ₉ and R ₁₀ is independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms;
The alkyl, aryl and heteroaryl groups of R ₉ and R ₁₀ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 6,
Wherein the substituent represented by Formula 8 is a substituent represented by Formula 11:
(11)

In Formula 11,
* Denotes the part where the bond is made,
o, R < ₇ > and R < ₈ > are as defined in claim 6. 11. The method of claim 10,
Wherein R ₈ is selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms;
The alkyl, aryl and heteroaryl groups of R ₈ are each independently substituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they are the same as or different from each other. 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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