KR101742436B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same. The compound according to the present invention can improve light-emitting efficiency, driving voltage, and lifespan of the organic electroluminescent device depending on being used in an organic layer of the organic electroluminescent device and preferably an electron transport layer or an electron transport auxiliary layer.

Description

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

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

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

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

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

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

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

However, conventional organic layer materials have advantages in terms of light emission characteristics, 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 an organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

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

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

[Chemical Formula 1]

In Formula 1,

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

o is an integer from 0 to 3;

Ar ₁ is selected from the group consisting of hydrogen, 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;

R ₁ to R ₄ 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 ₁ to R ₄ in each case a plurality of individual, they are equal to each other, or Different;

Alkyl group of the alkyl group of said Ar _1, aryl and heteroaryl groups, R ₁ to R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, group C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C of _An arylsilyl group having 1 to ₆₀ carbon atoms, and when they are substituted with a plurality of substituents, they may be the same or different;

L is a linker represented by the following formula (2);

Ar ₂ is a substituent represented by the following formula (3);

(2)

In Formula 2,

* Means the part where the bond is made;

(3)

In Formula 3,

* Denotes the part where the bond is made;

Each of Z ₁ to Z ₅ is independently N or C (R ₅ ), or at least one of Z ₁ to Z ₅ is N;

R ₅ 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 ₆ to C ₆₀ aryl, nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphospha group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting arylsilyl of C _60, the combined group and adjacent to which they are attached may form a condensed ring, a plurality of the said R ₅ individual They are the same or different from each other;

Alkyl groups of the 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 boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl 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 alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

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

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

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

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

"Aryl" in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. 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 phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

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

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

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

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

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

The compound represented by the formula (1) according to the present invention has excellent thermal stability, hole transportability, hole injection performance, electron transport and electron injection performance, and excellent phosphorescence property as a light emitting layer. .

In addition, when the novel compound represented by the general formula (1) of the present invention is used as a material of an electron transport layer or an electron transporting auxiliary layer, an organic electroluminescent device having an excellent light emitting performance, a low driving voltage, And further, a full color display panel in which performance and lifetime are greatly improved can be also manufactured.

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 organic compound according to the present invention can be used as an electron attracting agent such as a nitrogen-containing heterocycle (e.g., pyridine, pyrimidine, triazine, etc.) (EWG) is linked to the biphenyl linker. Specifically, it is a compound represented by the following formula (1):

[Chemical Formula 1]

In Formula 1,

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

o is an integer from 0 to 3;

Ar ₁ is selected from the group consisting of hydrogen, 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;

R ₁ to R ₄ 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 ₁ to R ₄ in each case a plurality of individual, they are equal to each other, or Different;

Alkyl group of the alkyl group of said Ar _1, aryl and heteroaryl groups, R ₁ to R _4, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl of the amine group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphazene group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, group C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C of _An arylsilyl group having 1 to ₆₀ carbon atoms, and when they are substituted with a plurality of substituents, they may be the same or different;

L is a linker represented by the following formula (2);

Ar ₂ is a substituent represented by the following formula (3);

(2)

In Formula 2,

* Means the part where the bond is made;

(3)

In Formula 3,

* Denotes the part where the bond is made;

Each of Z ₁ to Z ₅ is independently N or C (R ₅ ), or at least one of Z ₁ to Z ₅ is N;

R ₅ 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 ₆ to C ₆₀ aryl, nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group , C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphospha group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, the adjacent groups (e.g., phenylene group, R ₅ other adjacent) condensation in combination with And when a plurality of R < ₅ > s are present, they may be the same or different from each other;

Alkyl groups of the 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 boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl 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 alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

In the present invention, in the compound represented by the general formula (1), the moiety of spirobifluorenoxanthine or spiroacridine fluorene is basically excellent in electrochemical stability, has a high glass transition temperature and excellent carrier transporting ability , And particularly exhibits excellent electron mobility and blue luminescence efficiency. The materials represented by Formula 1 are structurally characteristic to be bonded with core core and EWG (electron withdrawing group), and have excellent electron mobility and excellent high glass transition temperature and thermal stability.

Therefore, the compound represented by the general formula (1) of the present invention is excellent in electron transporting ability and light emitting property. Therefore, the compound represented by the general formula (1) of the present invention is excellent in electron transporting ability and light emitting property, Layer material. ≪ RTI ID = 0.0 > A light-emitting layer; An electron transport layer; And an electron transporting layer further stacked on the electron transporting layer; , And more preferably, it can be used as a material for an electron transporting layer or an electron transporting layer.

In addition, since the compound represented by Formula 1 of the present invention has a high triplet energy, it can exhibit excellent efficiency due to a triplet-triplet fusion (TTF) effect, and most preferably, Can be used. In detail, the compound represented by Formula 1 can 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. Accordingly, 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, 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, the compound represented by Formula 1 may be represented by Formula 4 or 5:

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas (4) and (5)

L, R ₁ to R ₄ , Ar ₁ , Ar ₂ , l, m, n and o are as defined in the above formula (1).

The compound represented by the general formula (4) of the present invention has a substituent at the 2-position corresponding to the active-site of the fluorene-type core among the moieties of spiropyroxenethene or spiroacridine fluorene By linking, the physicochemical properties of the material to which the compound is applied can be stabilized, and high current efficiency and low driving voltage can be secured.

According to one embodiment, preferred according to the present invention, wherein Ar ₁ is hydrogen or C ₆ ~ C ₆₀ aryl may be an on the aryl group a halogen, a cyano group of Ar _1, C ₁ ~ C ₄₀ alkyl group and a C ₆ ~ C of An aryl group having 1 to ₆₀ carbon atoms, and when they are substituted with a plurality of substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a C ₆ to C ₂₀ aryl group, and the aryl group of Ar ₁ may be a C ₁ to C ₄₀ alkyl group or a C ₆ to C ₂₀ aryl group And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ may be a phenyl group or a biphenyl group.

According to a preferred embodiment of the present invention, L may be a linker represented by any one of the following formulas A-1 to A-6:

In the above Formulas A-1 to A-6,

* Means the part where the bond is made.

In the present invention, among the linkers represented by the above formulas A-1 to A-6, in particular, the linkers represented by A-2 to A-6 have a steric hindrance effect, A triplet-triplet fusion (TTF) effect due to an increase in the triplet energy value of the material can prevent the exciton from passing through the light emitting layer, and a synergistic effect of additional efficiency can be expected, May be any one of the linkers represented by any one of formulas (A-2) to (A-4).

According to a preferred embodiment of the present invention, Ar ₂ is a substituent represented by any one of the following formulas B-1 to B-9 in terms of current efficiency and driving voltage, but is not limited thereto:

In the above Formulas B-1 to B-9,

* Denotes the part where the bond is made;

p is an integer from 0 to 4;

q is an integer from 0 to 3;

r is an integer of 0 to 2

R ₆ represents a group selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, A C ₆ to C ₆₀ aryloxy group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C _A C ₆ to C ₆₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl 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 ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~, or selected from the group consisting arylsilyl of C _60, by combining together with the adjacent group (e. g., such as L or other R ₆₎ to form a condensed ring And when there are a plurality of R < ₆ > s, they are the same as or different from each other;

Alkyl group of the R _6, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, 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 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl 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 alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, each of p, q and r is independently an integer of 0 to 2, preferably 1 or 2.

According to a preferred embodiment of the present invention, R ₆ is selected from the group consisting of halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group and 5 to 60 nuclear heteroaryl groups Wherein the alkyl, aryl and heteroaryl groups of R ₆ are each independently substituted with one or more substituents selected from the group consisting of halogen, cyano, C ₁ to C ₄₀ alkyl and C ₆ to C ₆₀ aryl, And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₆ is a C ₆ to C ₂₀ aryl group, and the aryl group of R ₆ is at least one selected from the group consisting of halogen, cyano group and C ₆ to C ₂₀ aryl group When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, the R ₆ may be a phenyl group, a biphenyl group or a naphthalenyl group, and each of the phenyl group, biphenyl group and naphthalenyl group of R ₆ may be substituted with one kind selected from a fluorine group, And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a more preferred embodiment of the present invention, Ar ₁ is a phenyl group, L is a linker represented by the above formula (A-4), Ar ₂ is a triazinyl group substituted with at least one phenyl group, When used as a material for the electron transporting layer, high current efficiency and low voltage driving are possible but are not limited thereto.

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

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

2. Organic Field  Light emitting element

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

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

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI >

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

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

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

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

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

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

In the present invention, the spiropyroxenic acid or the spiroacridine fluorene moiety of the compound represented by the above formula (1) is basically excellent in electrochemical stability, has a high glass transition temperature and carrier transporting ability, The mobility is also excellent and the blue luminescence efficiency is enhanced. In addition, the materials represented by Formula 1 are structurally characteristic to be bonded to a core core and an electron-withdrawing group (EWG), and are particularly excellent in electron mobility and high in glass transition temperature and thermal stability. Therefore, the organic material layer containing the compound represented by Formula 1 is preferably a light emitting layer, an electron transporting layer, or an electron transporting layer, and more preferably an electron transporting layer or an electron transporting layer.

In the present invention, since the compound represented by Formula 1 has a high triplet energy, it can exhibit an excellent efficiency due to a triplet-triplet fusion (TTF) effect, and more preferably, Can be used. More specifically, in the present invention, the compound represented by Formula 1 can 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. Accordingly, 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, 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.

[ Preparation Example  One] Core  Synthesis of 1

<Step 1> 2- Bromo -9- (2- ( Diphenylamino ) Phenyl) -9H- Fluorene -9-ol

To 45 g (0.14 mol) of 2-bromo-N, N-diphenyl aniline was added 500 mL of THF. Next, the temperature of the reaction solution was lowered to -78 ° C, and 36.0 g (0.14 mol) of 2-bromo-9-fluorene was dissolved in 500 mL of THF, slowly added to the reaction solution and 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, and the mixture was extracted with 1.5 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 46.2 g of the desired compound (yield 66%).

[LCMS]: 504

&Lt; Step 2 > Bromo -10-phenyl-10H- Spiro [acridine-9,9'-fluorene]  synthesis

To 46.0 g (0.09 mol) of 2-bromo-9- (2- (diphenylamino) phenyl) -9H-fluoren-9-ol was added 460 mL of AcOH. 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, and the reaction was terminated. The resulting solid was filtered under reduced pressure and dried under a warm air stream to obtain the desired compound (38.1 g, yield 86%).

_{^{1 H-NMR (in CDCl 3}} ): δ 7.75 (d, 1H), 7.69 (t, 2H), 7.60 (d, 1H), 7.57 (m, 2H), 7.49 (m, 3H), 7.39 (m, 2H), 7.29 (dd, IH), 6.94 (t, 2H), 6.58 (t, 2H), 6.36

[LCMS]: 486

[ Preparation Example  2] Core  Synthesis of 2

&Lt; Step 1 > 3- Bromo -9- (2- ( Diphenylamino ) Phenyl) -9H- Fluorene -9-ol

The procedure of Step 1 of [Preparation Example 1] was repeated to obtain 20.5 g (79%) of the target compound corresponding to the structural isomer of Core 1.

[LCMS]: 504

&Lt; Step 2 > 3'- Bromo -10-phenyl-10H-spiro [acridine-9,9'- Fluorene ] Synthesis of

18.5 g (88%) of the desired compound corresponding to the structural isomer of Core 1 were obtained by carrying out the same procedure as in Step 2 of [Preparation Example 1].

_{^{1 H-NMR (in CDCl 3}} ): δ 7.92 (d, 1H), 7.70 (m, 3H), 7.56 (m, 1H), 7.47 (m, 2H), 7.35 (m, 3H), 7.27 (m, 2H), 6.90 (m, 2H), 6.55 (m, 2H), 6.34 (m, 4H)

[LCMS]: 486

[ Synthetic example  1] Synthesis of Compound 1

5.0 g (10.2 mmol) of 2'-bromo-10-phenyl-10H-spiro [acridine-9,9'-fluorene] and 2,4- 4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) - [1,1'-biphenyl] -3- g (10.2 mmol), dioxane (100 mL) and H ₂ O (20 mL) were added. _{Pd (PPh 3) 4 0.5 g} (0.5 mmol), K 2 CO 3 2.8 g After the addition of (20.4 mmol) was heated to reflux at 120 ℃ 3 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 80 mL of purified water. The mixture was extracted with 200 mL of EA and 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 (2.5 g, yield 38%).

^{1 H-NMR (in DMSO)} : δ 8.90 (s, 1H), 8.73 (m, 5H), 8.11 (d, 1H), 8.06 (m, 2H), 7.92 (dd, 2H), 7.71 (m, 7H 2H), 6.38 (d, 2H), 7.68 (t, 2H), 7.68 (m, 2H) , 6.22 (dd, 2H)

[LCMS]: 790

[ Synthetic example  2] Synthesis of Compound 3

2,4-diphenyl-6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2- yl) - [ ] -3-yl) pyrimidine was used in place of the compound obtained in Preparation Example 1, 4.2 g (yield 52%) of the target compound was obtained.

[LCMS]: 789

[ Synthetic example  3] Synthesis of Compound 4

2 - ([1,1'-biphenyl] -4-yl) -4-phenyl-6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxaboro- 2-yl) - [1,1'-biphenyl] -3-yl) -1,3,5-triazine, the procedure of Synthesis Example 1 was repeated to obtain 5.5 g Yield: 62%).

[LCMS]: 867

[ Synthetic example  4] Synthesis of Compound 5

4 - ([1,1'-biphenyl] -4-yl) -2-phenyl-6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxaboro Yl) - [1,1'-biphenyl] -3-yl) pyrimidine was used in place of 2-bromoaniline to obtain the title compound (5.1 g, yield: 58%).

[LCMS]: 866

 [ Synthetic example  5] Synthesis of Compound 8

Di ([1,1'-biphenyl] -4-yl) -6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-yl) - [1,1'-biphenyl] -3-yl) -1,3,5-triazine was used in place of 69%).

[LCMS]: 943

[ Synthetic example  6] Synthesis of Compound 14

(3'-bromo-10-phenyl-10H-spiro [acridine-9,9'-fluorene] of Preparation Example 2 and 2,4-diphenyl- Dioxabororane-2-yl) - [1,1'-biphenyl] -3-yl) -1,3,5-triazine , The target compound (5.9 g, yield: 73%) was obtained.

[LCMS]: 790

[ Synthetic example  7] Synthesis of Compound 16

Spiro [acridine-9,9'-fluorene] of Preparation Example 4 and 4,6-diphenyl-2- (3 '- (4,4,5- 5,5-tetramethyl-1,3,2-dioxabororane-2-yl) - [1,1'-biphenyl] -3-yl) pyrimidine was used instead of The same procedure was followed to obtain 5.2 g of the desired compound (yield: 64%).

[LCMS]: 789

[ Synthetic example  8] Synthesis of Compound 17

Preparation of 3'-bromo-10-phenyl-10H-spiro [acridine-9,9'-fluorene] and 2 - ([ 4-phenyl-6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2- yl) - [ -Yl) -1,3,5-triazine was used in place of 1,3,5-triazin-1-yl-1,3,5-triazine in the same manner as in Synthesis Example 1 to obtain 6.1 g of the desired compound (yield 69%).

[LCMS]: 867

[ Synthetic example  9] Synthesis of compound 18

Spiro [acridine-9,9'-fluorene] of Preparation Example 4 and 4 - ([1,1'-biphenyl] -4- 2-phenyl-6- (3 '- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2- yl) - [ -Yl) pyrimidine was used in place of 4-fluorobenzyl bromide, the target compound (4.7 g, yield 53%) was obtained.

[LCMS]: 866

[ Synthetic example  10] Synthesis of Compound 21

2,4-diphenyl-6- (4 '- (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2- yl) - [ ] -4-yl) -1,3,5-triazine was used in place of 1,3,5-triazine, the target compound (4.4 g, yield: 54%) was obtained.

[LCMS]: 790

[ Example  1 to 10] blue organic Field  Fabrication of light emitting device

Compounds 1, 3, 4, 5, 8, 14, 16, 17, 18, and 21 synthesized in Synthesis Example were subjected to high purity sublimation purification by a conventionally known method and then blue organic electroluminescent devices Respectively.

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.

DS-205 (hole transport layer) (Doosan Electronics 80 nm) / NPB (hole transporting auxiliary layer) (15 nm) / ADN + 5% DS-405 (light emitting layer) (anode) on the ITO transparent electrode Alq ₃ (electron transport layer) (25 nm) / LiF (electron transport layer) (5 nm) / compound 1, 3, 4, 5, 8, 14, 16, 17 or 18 (Injection layer) (1 nm) / Al (cathode) (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  1] Blue organic Field  Manufacturing 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 transporting auxiliary layer material and Alq ₃ , which is an electron transporting layer material, was deposited at 30 nm instead of 25 nm .

[ Comparative Example  2] Blue organic Field  Manufacturing 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 the electron transporting auxiliary layer material but the following Compound A was deposited.

[ Evaluation example  One]

The driving voltage, the emission wavelength and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 10 and Comparative Examples 1 and 2, .

Sample Electron transporting auxiliary layer The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 Compound 1 3.3 458 9.1 Example 2 Compound 3 3.4 456 8.5 Example 3 Compound 4 3.3 458 8.7 Example 4 Compound 5 3.6 455 9.0 Example 5 Compound 8 3.5 459 8.5 Example 6 Compound 14 3.9 458 8.0 Example 7 Compound 16 4.1 456 7.5 Example 8 Compound 17 4.2 456 7.9 Example 9 Compound 18 4.0 457 7.6 Example 10 Compound 21 4.3 456 7.0 Comparative Example 1 - 4.8 458 6.0 Comparative Example 2 Compound A 4.7 459 6.7

As shown in Table 1, the blue organic electroluminescent devices (Examples 1 to 10) using the compound of the present invention as the electron transporting auxiliary layer (Examples 1 to 10) were superior to the blue organic electroluminescent devices Current efficiency, emission peak, and driving voltage.

In addition, it can be seen that Examples 1 to 10 show higher current efficiency and lower driving voltage than Comparative Example 2 in which the compound A without a linker is used as an electron transporting auxiliary layer material. That is, when the biphenylene linker is present as in the compound of the present invention, the bandgap is widened due to the LUMO level increase of the material, and the current efficiency and the driving voltage can be lowered when the electron transporting layer is applied to the electron transporting layer.

Further, in the presence of a steric hindrance in the biphenylene linker as in Examples 1 to 9, the current efficiency can be further improved and the driving voltage can be further reduced. As in the case of Examples 1 to 5, the spirobifluoren- The current efficiency is higher than that in the case where the substituent is connected to the position 2 of the fluorene type core in the moiety of the cycloheptadiene fluorocarbene and the substituent is connected to the other position (Examples 6 to 9), and the driving voltage is lower Which is a more desirable form.

[ Evaluation example  2]

EQE of the following compounds A, B and Compound 1 were measured to compare the energy difference according to the linker as the material for the electron transporting layer, and the results are shown in Table 2 below.

Gaussian Experimental value EQE (%) HOMO (eV) LUMO (eV) Eg (eV) HOMO (eV) LUMO (eV) Eg (eV) Compound A 4.98 1.83 3.14 5.59 2.27 3.32 10.8 Compound B 4.95 1.80 3.15 5.58 2.06 3.52 12.6 Compound 1 4.96 1.81 3.15 5.55 1.91 3.64 14.1

As shown in Table 2, it can be seen that Compound 1 of the present invention has a much higher EQE value than Compound A or B. As in the present invention, when the biphenyl linker has a higher level of LUMO than that of Compound A or B, the bandgap becomes wider and the bandgap is wider than the HOMO and LUMO levels of the luminescent layer to the electron transport layer It can be seen that the EQE is increased by effectively blocking the hole.

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

Claims (14)

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

In Formula 1,
l, m, n and o are each independently 0 or 1;
Ar ₁ is a C ₆ to C ₆₀ aryl group;
R ₁ to R ₄ are each independently a C ₁ to C ₄₀ alkyl group or a C ₆ to C ₆₀ aryl group;
The aryl group of said Ar _1, R ₁ to R ₄ alkyl groups and aryl groups each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ 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 ~ C ₄₀ alkylsilyl group, C ₁ ~ alkyl boron C ₄₀ of the group, C ₆ ~ C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one substituent at least one selected from an aryl silyl group the group consisting of the C ₆₀ of the And when they are unsubstituted or substituted with a plurality of substituents, they are the same or different from each other;
L is a linker represented by the following formula (2);
Ar ₂ is a substituent represented by the following formula (3);
(2)

In Formula 2,
* Means the part where the bond is made;
(3)

In Formula 3,
* Denotes the part where the bond is made;
Each of Z ₁ to Z ₅ is independently N or C (R ₅ ), or at least one of Z ₁ to Z ₅ is N;
R ₅ is selected from the group consisting of hydrogen, 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 a plurality of R _{5 s} are the same, ;
The alkyl, aryl and heteroaryl groups of R ₅ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl , C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ of the alkyloxy group, an arylamine group of C ₆ ~ C ₆₀ , C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C ₆₀ , C ₆ ~ C ₆₀ aryl phosphazene group, substituted with one substituent at least one selected from the group consisting of C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ with an aryl silyl group of C ₆₀ or is unsubstituted, 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 represented by the following formula 4 or 5:
[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas (4) and (5)
L, R ₁ to R ₄ , Ar ₁ , Ar ₂ , l, m, n and o are each as defined in claim 1. The method according to claim 1,
Wherein L is a linker represented by any one of the following formulas A-1 to A-6:

In the above Formulas A-1 to A-6,
* Means the part where the bond is made. The method of claim 3,
And L is a linker represented by any one of formulas A-2 to A-6. The method according to claim 1,
Wherein Ar &lt; ₂ &gt; is a substituent represented by any one of the following formulas (B-1) to (B-9)

In the above Formulas B-1 to B-9,
* Denotes the part where the bond is made;
p is an integer from 0 to 4;
q is an integer from 0 to 3;
r is an integer of 0 to 2
R ₆ is a C ₁ to C ₄₀ alkyl group or a C ₆ to C ₆₀ aryl group, and when a plurality of R _{6 s} are present, they are the same or different;
The R ₆ groups and aryl groups are each independently selected from deuterium, halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C of ₆ ~ C ₆₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a _{C 6 ~ C 60, C 6} ~ C substituted with at least ₆₀ of the aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group, and the group consisting of C ₆ ~ with an aryl silyl group of C ₆₀ of the selected one more substituents or being unsubstituted, a plurality of substituents When they are substituted, they are the same as or different from each other. 6. The method of claim 5,
Each of p, q and r is independently an integer of 0 to 2. [ 6. The method of claim 5,
Wherein R ₆ is C ₁ ~ alkyl of C ₄₀ or C ₆ ~ C ₆₀ aryl group and the said R ₆ alkyl groups and aryl groups each independently represent a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group and a C ₆ ~ C of An aryl group having 1 to ₆₀ carbon atoms, and when they are substituted with a plurality of substituents, they are the same as or different from each other. 6. The method of claim 5,
Wherein R ₆ is a C ₆ to C ₂₀ aryl group, and the aryl group of R ₆ is substituted or unsubstituted with at least one substituent selected from the group consisting of halogen, cyano group and C ₆ to C ₂₀ aryl group, When they are substituted with a substituent, they are the same as or different from each other. The method according to claim 1,
Wherein said compound is an electron transporting layer of an organic electroluminescent device. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds:

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). 12. The method of claim 11,
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. 12. The method of claim 11,
Wherein the organic compound layer containing the compound is selected from the group consisting of a light emitting layer, an electron transport layer, and an electron transporting auxiliary layer. 14. The method of claim 13,
Wherein the organic compound layer containing the compound is an electron transporting auxiliary layer.

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