KR20190135250A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent luminous performance and thermal stability, and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the same in at least one organic material layer.

Description

Organic compound and organic electroluminescent device including the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to an organic electroluminescent device material, in particular an organic compound that can be used as a light emitting layer, more specifically a phosphorescent host material, and an organic electroluminescent device comprising the same.

Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose organic thin-film emission, followed by Tang in 1987. ) Is an organic electroluminescent device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

To date, NPB, BCP, Alq3, and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layer materials, and anthracene derivatives have been reported as emission layer materials. In particular, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3, and (acac) Ir (btp) 2, which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.

However, the conventional organic material is not a satisfactory level in terms of light emission characteristics and thermal stability, there was a limit to increase the low voltage characteristics and lifetime characteristics of the organic EL device. Therefore, the development of the organic material layer material which is excellent in performance is calculated | required.

The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent luminous ability and thermal stability.

Another object of the present invention is to provide an organic electroluminescent device including the aforementioned organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

R ₁ and R ₂ are the same as or different from each other, and each independently an alkyl group of C ₁ to C ₄₀ or an aryl group of C ₆ to C ₄₀ ,

R ₃ and R ₄ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group Is selected from;

a and b are each independently an integer of 0 to 4,

At least two of Ar ₁ , Ar ₂ and L has a moiety selected from the group represented by the following formula (2) and formula (3),

In Chemical Formula 2 or 3,

X is O or S,

Ar ₁ or Ar ₂ containing no moiety of Formula 2 is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ Alkynyl group of ˜C ₄₀ , cycloalkyl group of C ₃ ˜C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ˜ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ monoaryl phosphinyl group, C ₆ ~ C ₆₀ diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine A moiety represented by Formula 2 in the heteroaryl group is excluded;

A moiety of Formula 3 ratio (非) L comprising a single bond or, or C ₆ ~ C ₆₀ aryl group, and can be selected from 5 to 60 heteroaryl group nucleus atoms (provided that in the heteroaryl group Moieties represented by formula (3) are excluded),

The arylene group and the heteroarylene group of L and the alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups and alkyloxy groups of Ar ₁ to Ar ₂ and R ₁ to R ₄ , Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ ~ C ₄₀ , aryloxy group of C ₆ ~ C ₆₀ , alkylsilyl group of C ₁ ~ C ₄₀ , C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and C ₆ It may be substituted with one or more substituents selected from the group consisting of arylamine groups of ~ C ₆₀ , wherein when there are a plurality of the substituents, they may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising the above-described anode, cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is represented by the formula (1) It provides an organic electroluminescent device comprising a compound to be.

Since the compound according to the present invention has excellent luminous efficiency, it can be usefully applied as an organic material layer material of the organic electroluminescent device.

In addition, the organic electroluminescent device of the present invention including the compound in the organic material layer can be effectively applied to a full color display panel because the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.

Hereinafter, the present invention will be described in detail.

<New organic compound>

The novel organic compound according to the present invention has 4 fluorene (4-Fluorene) as a core, and a dibenzofuran / dibenzothiophene moiety and a heteroaromatic ring are bonded to the core and represented by Formula 1 It features.

Specifically, the compound represented by Chemical Formula 1 adopts 4-fluorene (four fluorene) having the highest triplet energy (T1) value among the existing fluorenes as a core, and at least two or more in the core. A dibenzo-based moiety and a triazine group, which is an electron withdrawing group (EWG), are bonded to each other. The high triplet energy can improve the luminous efficiency of the device by increasing the number of excitons contributing to the emission in the light emitting layer, and the durability and stability of the device can be improved to effectively increase the life of the device. In the present invention, by using the fluorene core at position 4 excellent in high T1 (triplet energy) and charge transport, electrons and holes can be easily transferred to greatly enhance the luminous efficiency.

In the present invention, the above-described fluorene core No. 4 is a dibenzo-based moiety having physicochemical properties of amphoteric properties for holes and electrons (eg, dibenzofuran (DBF) or dibenzothiophene (DBT)). It can be applied as a green phosphorescent material containing at least two and having excellent luminous efficiency through combination with triazine, a strong electron-withdrawing group (EWG). In addition, it is possible to drive a low voltage can exhibit the effect of increasing the life, and has excellent thermal stability, high glass transition temperature characteristics and uniform morphology (morphology) device characteristics.

In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent green n-type host and / or a phosphorescent red host, an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer life than a conventional light emitting host material is manufactured. In addition, it is possible to manufacture a full color display panel with improved efficiency and long life.

As described above, since the compound represented by Chemical Formula 1 has excellent light emission characteristics, the compound represented by Chemical Formula 1 may be used as any one material of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic layers of an organic EL device. Preferably, it can be used as a material of the light emitting layer of green phosphorescence and red phosphorescence, or an electron transport layer material. Accordingly, the compound represented by Formula 1 of the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (green, red, blue phosphorescent host material), electron transport layer / injection layer material, light emitting auxiliary layer material, It can be used as an electron transport auxiliary layer material, more preferably a light emitting layer material, an electron transport layer material, an electron transport auxiliary layer material. The organic electroluminescent device of the present invention including the compound of Formula 1 can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.

Compound represented by the formula (1) according to the invention is characterized in that the structure is bonded to the dibenzo-based moiety and triazine in the fluorene No. 4 position, at least two of the above-described dibenzo-based moieties are introduced do.

In Formula 1, R ₁ and R ₂ introduced to fluorene are the same as or different from each other, and each independently an alkyl group of C ₁ to C ₄₀ or an aryl group of C ₆ to C ₄₀ . As a preferable example, R ₁ and R ₂ may each independently be a methyl group or a phenyl group.

In addition, R ₃ and R ₄ are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C to each other ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono-aryl phosphonium blood group, C ₆ ~ C ₆₀ of the diaryl Phosphinicosuccinic consisting of groups and C ₆ ~ C ₆₀ aryl amine of the group of Can be selected from the group. Specifically, R ₃ and R ₄ are the same as or different from each other, and each independently composed of hydrogen, an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group having 5 to 60 nuclear atoms It is preferably selected from the group.

a and b are each independently an integer of 0-4. Here, when a is 0, R ₃ is hydrogen, and when a is 1 to 4, R ₃ may have the aforementioned substituents except hydrogen. Likewise, when b is 0, R ₄ is hydrogen, and when b is 1 to 4, R ₄ may have the aforementioned substituents except hydrogen.

In Formula 1 of the present invention, at least two of Ar ₁ , Ar _2, and L are dibenzo-based moieties selected from the group represented by Formula 2 and Formula 3, such as dibenzofuran-based (X = O) moiety. And / or dibenzothiophene (X = S) moieties. At least two dibenzo-based moieties may be the same or different from each other, and are not particularly limited.

The dibenzo-based moiety represented by Formula 2 and Formula 3 may be more specifically represented by the following structural formula.

On the other hand Ar ₁ or Ar ₂ containing no moiety of Formula 2 is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C Alkynyl group of ₂ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, C ₁ C ₆ -C ₄₀ alkyloxy group, C ₆ -C ₆₀ aryloxy group, C ₃ -C ₄₀ alkylsilyl group, C ₆ -C ₆₀ arylsilyl group, C ₁ -C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono-aryl phosphonium blood group, C ₆ ~ C ₆₀ diallyl Phosphinicosuccinic group and a C ₆ ~ C ₆₀ aryl group It may be selected from the group consisting of amine groups, except that the moiety represented by the formula (2) in the heteroaryl group. Specifically, Ar ₁ or Ar _{2 not} including the dibenzo-based moiety of formula (2) is preferably selected from the group consisting of C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl groups.

In addition, L containing no moiety of Formula 3 may be a linker of a conventional divalent group known in the art. For example, it may be selected from the group consisting of a single bond (eg, a direct bond) or a C ₆ ~ C ₆₀ arylene group and a hetero arylene group of 5 to 60 nuclear atoms, in the heteroarylene group The dibenzoic moiety represented by is excluded.

Specific examples of the L include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, a furinylene group, and a quinolinyl group And an ethylene group, a pyrrolyylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a pyridinylene group, a pyrimidinylene group, and the like. More specifically, it is preferable that L is a single bond, a phenylene group, or a biphenylene group.

In one embodiment of the present invention, L may be a single bond or a linker selected from the following structures.

The arylene group and the heteroarylene group of L and the alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups and alkyloxy groups of Ar ₁ to Ar ₂ and R ₁ to R ₄ , Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ ~ C ₄₀ , aryloxy group of C ₆ ~ C ₆₀ , alkylsilyl group of C ₁ ~ C ₄₀ , C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and C ₆ It may be substituted with one or more substituents selected from the group consisting of arylamine groups of ~ C ₆₀ , wherein when there are a plurality of the substituents, they may be the same or different from each other.

According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may be embodied in any one of the following Chemical Formulas 4 to 6.

In Chemical Formulas 4 to 6,

Ar ₁ , X and L are each as defined in Formula 1, and a plurality of X are the same or different from each other.

As a preferable example of the compound represented by any one of Formulas 4 to 6, a plurality of Xs may be the same or different from each other, and each may be O or S.

Ar ₁ may be selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group of 5 to 60 nuclear atoms, specifically, it is preferably a phenyl group or a biphenyl group.

L may be selected from the group consisting of a single bond (eg, a direct bond), an arylene group having ₆ to ₁₈ carbon atoms, and a heteroarylene group having 5 to 18 nuclear atoms, and specifically, it is a phenylene group or a biphenylene group. desirable.

The compounds represented by the above-described formulas (4) to (6) may be more specifically represented by the following formulas (4A) to (6A). However, it is not limited thereto.

[Formula 4A]

[Formula 5A]

[Formula 6A]

In Formulas 4A to 6A, Ar ₁ and L are as defined in Formula 1, respectively.

The compound represented by the formula (1) of the present invention described above may be more specific to the compounds exemplified below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.

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

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

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

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and in addition, a form may be included with a aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, linear, branched or cyclic structure It may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.

"Cycloalkyl" as used herein means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

By "heterocycloalkyl" is meant monovalent substituents derived from non-aromatic hydrocarbons having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

As used herein, the term “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

<Organic EL device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone or in combination of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 Compound. Specifically, the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, an electron transport auxiliary layer.

The light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, wherein the host material may include the compound of Formula 1 above. In addition, the light emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

When the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved. Specifically, the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of the light emitting layer having high efficiency.

The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a light emitting layer, more preferably a phosphorescent host May include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.

The organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.

The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1 above. have.

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

The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like.

In addition, the positive electrode material may use any positive electrode material known in the art without limitation. For example, metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

In addition, the negative electrode material may use any negative electrode material known in the art without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art can be used without limitation.

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

Preparation Example 1 2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolane

Step 1 Synthesis of 4-bromo-6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan

82.1 g (0.252 mol) of 4,6-dibromodibenzo [b, d] furan and 30 g (0.126 mol) of (9,9-dimethyl-9H-fluoren-4-yl) boronic acid 1.0 L of toluene, 200 mL of EtOH, H 200 mL of ₂ O was added. Next, 7.3 g (6.3 mmol) of Pd (PPh ₃ ) ₄ and 52.2 g (0.378 mol) of K ₂ CO ₃ were added, and the mixture was heated and refluxed at 120 ° C. for 3 hours. Then, the temperature was cooled to room temperature, 300 mL of purified water was added to the reaction solution to terminate the reaction, and then extracted with EA 1.5L and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain 34.3 g (yield 62%) of the title compound.

[LCMS]: 439

<Step 2> 2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3 Of 2-dioxaborolane

30.0 g (68.3 mmol) of 4-bromo-6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan synthesized in the above [Step 1] and 4,4,4 ′, 500 mL of dioxane was added to 20.8 g (82.0 mmol) of 4 ', 5,5,5', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane). Next, 2.9 g (3.5 mmol) of Pd (dppf) Cl ₂ and 20.1 g (205 mmol) of KOAc were added thereto, followed by heating to reflux for 3 hours at 130 ° C. Then, the reaction mixture was cooled to room temperature and 500 mL of an ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction, extracted with EA 1.0 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 21.0 g (yield 85%) of the title compound.

[LCMS]: 486

Preparation Example 2 2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolane

Step 1 Synthesis of 2-chloro-8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan

Except for using 2-bromo-8-chlorodibenzo [b, d] furan as a reaction, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain 21.5 g (yield 78%) of the title compound.

[LCMS]: 394

<Step 2> 2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 Of 2-dioxaborolane

20 g (50.7 mmol) of 2-chloro-8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan synthesized in the above [Step 1], 4,4,4 ′, 500 mL of dioxane was added to 15.5 g (60.9 mmol) of 4 ', 5,5,5', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane). Next, 2.1 g (2.6 mmol) of Pd (dppf) Cl _{2 and} 14.9 g (152 mmol) of XPhos 2.4g (5.1 mmol) KOAc were added thereto, followed by heating to reflux for 5 hours at 130 ° C. Then, the reaction mixture was cooled to room temperature and 500 mL of an ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction, extracted with EA 1.0 L, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 15.0 g (yield 61%) of the title compound.

[LCMS]: 486

Preparation Example 3 2- (6-chlorodibenzo [b, d] furan-2-yl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine Synthesis of

Step 1 Synthesis of 2- (6-chlorodibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Except that 2-bromo-6-chlorodibenzo [b, d] furan was used as a reaction product, the same procedure as in [Step 2] of Preparation Example 1 was performed, to obtain 17.4 g (yield 58%) of the title compound.

[LCMS]: 328

<Step 2> 2- (6-chlorodibenzo [b, d] furan-2-yl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine synthesis

2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine and 2- (6-chlorodibenzo [b, d] furan-2-yl as reactants ) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was subjected to the same procedure as in [Step 1] of Preparation Example 1 to yield 6.6 g of the target compound (yield 49%). Got.

[LCMS]: 523

Preparation Example 4 2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-1-yl) -4,4,5,5-tetramethyl-1, Synthesis of 3,2-dioxaborolane

<Step 1> Synthesis of 1-chloro-6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan

Except for using 6-bromo-1-chlorodibenzo [b, d] furan as a reaction, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain 25.8 g (yield 66%) of the title compound.

[LCMS]: 394

<Step 2> 2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-1-yl) -4,4,5,5-tetramethyl-1,3 Synthesis of, 2-dioxaborolane

[Step 2 of Preparation Example 2], except that 1-chloro-6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan of [Step 1] was used as a reactant. 19.5 g (yield 56%) of the title compound were obtained in the same manner as the].

[LCMS]: 486

Synthesis Example 1 Synthesis of Compound 1

2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 1 [Step of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine were used. 1] was carried out to obtain the title compound 8.7 g (yield 68%).

[LCMS]: 681

Synthesis Example 2 Synthesis of Compound 4

2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 1 [Step of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine were used. 1] was carried out to obtain the title compound 8.1 g (yield 62%).

[LCMS]: 681

Synthesis Example 3 Synthesis of Compound 6

2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 2 [Step of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine were used. 1] was carried out to obtain 5.4 g (yield 70%) of the title compound.

[LCMS]: 681

Synthesis Example 4 Synthesis of Compound 8

2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 2 [Step of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine were used. 1] was carried out to obtain the title compound 3.8 g (56% yield).

[LCMS]: 681

Synthesis Example 5 Synthesis of Compound 14

2- (6-chlorodibenzo [b, d] furan-2-yl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine 5.0 of Preparation Example 3 To g (9.6 mmol) and 3.0 g (12.5 mmol) of (9,9-dimethyl-9H-fluoren-4-yl) boronic acid were added 100 mL of toluene, 25 mL of EtOH, and 25 mL of H ₂ O. 0.11 g (0.5 mmol) of Pd (OAc) ₂ , 0.48 g (1.0 mmol) of XPhos, and 6.3 g (19.2 mmol) of Cs ₂ CO ₃ were added and heated to reflux at 120 ° C. for 5 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 1 L 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 2.9 g (yield 45%) of the title compound.

[LCMS]: 681

Synthesis Example 6 Synthesis of Compound 19

2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 1 , 2-dioxaborolane and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3,5-triazine Except for the use, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain 5.9 g (yield 70%) of the title compound.

[LCMS]: 757

Synthesis Example 7 Synthesis of Compound 24

2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 2 , 2-dioxaborolane and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] furan-1-yl) -1,3,5-triazine Except for the use, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain 9.2 g (yield 66%) of the title compound.

[LCMS]: 757

Synthesis Example 8 Synthesis of Compound 33

Reactants include 2-chloro-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine and 2- (3- (9,9-dimethyl-9H-fluoren-4 Except for using -yl) phenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain 9.2 g ( Yield 66%).

[LCMS]: 681

Synthesis Example 9 Synthesis of Compound 40

Reactants include 2-chloro-4,6-bis (dibenzo [b, d] furan-1-yl) -1,3,5-triazine and 2- (4- (9,9-dimethyl-9H-fluoren-4 Except for using -yl) phenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain the desired compound 7.0 g ( Yield 59%).

[LCMS]: 681

Synthesis Example 10 Synthesis of Compound 44

Reactants include 2-chloro-4,6-bis (dibenzo [b, d] furan-3-yl) -1,3,5-triazine and 2- (3 '-(9,9-dimethyl-9H-fluoren- [Step of Preparation Example 1], except that 4-yl)-[1,1'-biphenyl] -3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used. 1] was obtained to obtain 5.3 g (69% yield) of the title compound.

[LCMS]: 757

Synthesis Example 11 Synthesis of Compound 52

Reactants include 2-chloro-4,6-bis (dibenzo [b, d] furan-1-yl) -1,3,5-triazine and 2- (4 '-(9,9-dimethyl-9H-fluoren- [Step of Preparation Example 1], except that 4-yl)-[1,1'-biphenyl] -3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used. 1] was carried out to obtain 3.8 g (yield 65%) of the title compound.

[LCMS]: 757

Synthesis Example 12 Synthesis of Compound 56

2-chloro-4,6-bis (dibenzo [b, d] furan-2-yl) -1,3,5-triazine and 2- (3 ''-(9,9-dimethyl-9H-fluoren) as reactants Except for using 4-yl)-[1,1 ': 3', 1 ''-terphenyl] -3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane , 3.8 g (yield 65%) of the title compound was obtained by the same procedure as in [Step 1] of Preparation Example 1.

[LCMS]: 833

Synthesis Example 13 Synthesis of Compound 63

2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 1 [Step 1 of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4,6-bis (dibenzo [b, d] furan-3-yl) -1,3,5-triazine were used. 6.0 g (yield 51%) of the title compound were obtained by the same procedure as in the following].

[LCMS]: 771

Synthesis Example 14 Synthesis of Compound 66

2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 2 [Step 1 of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine were used. 4.8 g (yield 59%) of the title compound were obtained by the same procedure as in the following].

[LCMS]: 771

Synthesis Example 15 Synthesis of Compound 71

2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-1-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 4 [Step 1 of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4,6-bis (dibenzo [b, d] furan-3-yl) -1,3,5-triazine were used. 8.8 g (yield 71%) of the title compound were obtained in the same manner as the].

[LCMS]: 771

Synthesis Example 16 Synthesis of Compound 73

2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-1-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 4 [Step 1 of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4,6-bis (dibenzo [b, d] furan-1-yl) -1,3,5-triazine were used. 7.2 g (yield 55%) of the title compound were obtained by the same procedure as in the following].

[LCMS]: 771

Synthesis Example 17 Synthesis of Compound 79

2- (6- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-4-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 1 [Step of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine were used. 1] was carried out to obtain the target compound 5.5 g (yield 64%).

[LCMS]: 697

Synthesis Example 18 Synthesis of Compound 85

2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 2 [Step of Preparation Example 1], except that 2-dioxaborolane and 2-chloro-4- (dibenzo [b, d] thiophen-1-yl) -6-phenyl-1,3,5-triazine were used. 1] was carried out to obtain 2.9 g (yield 69%) of the title compound.

[LCMS]: 697

Synthesis Example 19 Synthesis of Compound 98

2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 2 , 2-dioxaborolane and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] thiophen-4-yl) -1,3,5-triazine Except for the use, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain 4.8 g (yield 66%) of the title compound.

[LCMS]: 773

Synthesis Example 20 Synthesis of Compound 101

2- (8- (9,9-dimethyl-9H-fluoren-4-yl) dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3 of Preparation Example 2 , 2-dioxaborolane and 2-([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] thiophen-1-yl) -1,3,5-triazine Except for the use, the same procedure as in [Step 1] of Preparation Example 1 was carried out to obtain 3.5 g (yield 62%) of the title compound.

[LCMS]: 773

Examples 1 to 20 Fabrication of Green Organic Electroluminescent Devices

Compounds 1, 4, 6, 8, 14, 19, 24, 33, 40, 44, 52, 56, 63, 66, 71, 73, 79, 85, 98, and 101 synthesized in the synthesis examples are commonly known. After purifying high purity sublimation by the method, a green organic EL device was manufactured according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / 90% of compound 1, 4, 6, 8, 14, 19, 24, 33, 40, 44, 52, on the prepared ITO transparent glass substrate (electrode) 56, 63, 66, 71, 73, 79, 85, 98, 101 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in order to produce a green organic electroluminescent device.

Comparative Example 1 Fabrication of Green Organic Electroluminescent Device

A green organic electroluminescent device of Comparative Examples 1 to 5 was prepared in the same manner as in Example 1, except that CBP and A, B, C, and D were used instead of Compound 1 as a light emitting host material.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP, BCP, Compounds A, B, C and D used in Examples 1 to 20 and Comparative Examples 1 to 5 are as follows.

[Evaluation Example 1]

For each of the green organic electroluminescent devices fabricated in Examples 1 to 20 and Comparative Examples 1 to 5, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured. Indicated.

Sample Host Driving voltage
(V) Luminous Peak
(nm) Current efficiency
(cd / A) Example 1 Compound 1 3.9 455 64.5 Example 2 Compound 4 3.8 457 62.5 Example 3 Compound 6 4.1 454 63.8 Example 4 Compound 8 4.2 454 58.2 Example 5 Compound 14 3.6 458 63.5 Example 6 Compound 19 3.5 457 60.9 Example 7 Compound 24 4.0 456 64.2 Example 8 Compound 33 3.9 455 63.0 Example 9 Compound 40 4.0 458 58.5 Example 10 Compound 44 3.8 457 63.1 Example 11 Compound 52 3.8 459 64.9 Example 12 Compound 56 3.6 459 62.4 Example 13 Compound 63 4.1 458 60.8 Example 14 Compound 66 4.5 454 59.5 Example 15 Compound 71 3.7 457 63.8 Example 16 Compound 73 4.1 457 65.5 Example 17 Compound 79 3.7 458 60.2 Example 18 Compound 85 3.8 458 58.9 Example 19 Compound 98 4.1 456 60.5 Example 20 Compound 101 4.2 457 60.4 Comparative Example 1 CBP 5.4 459 44.2 Comparative Example 2 A 4.9 459 52.4 Comparative Example 3 B 4.8 458 53.9 Comparative Example 4 C 5.0 459 51.0 Comparative Example 5 D 4.7 457 55.1

As shown in Table 1, the green organic EL device of Examples 1 to 20 to which the compound according to the present invention was applied as a material of the light emitting layer, Comparative Example 1 to which a conventional CBP was applied; And compared with the green organic electroluminescent element of Comparative Examples 2-5 which used compound A-D as a light emitting layer, it turned out that it is excellent in current efficiency and a drive voltage.

Particularly, in the present invention, the first fluorene (4-Fluorene) having the highest T1 (triplet energy) value is selected as the core, the first fluorene (1-Fluorene), the second fluorene (2-Fluorene) and In Comparative Examples 2 to 4 in which 3-fluoride was selected as the core, the low efficiency of T1 (triplet energy) was shown. In addition, molecular positional substitution of fluorene at position 4 has a low Ts (evaporation temperature), so that it can be variously expanded in designing a derivative compound represented by Formula 1 of the present invention and has excellent thermal stability. It can have

In addition, Comparative Example 5 has a structure containing a linker (linker) between the dibenzo-based moiety and a heterocyclic ring (eg triazine). As the linker is introduced in the above-described position, it is difficult to obtain high-efficiency characteristics by moving to a long wavelength band, and there are disadvantages in that high temperature derivatives are designed according to molecular weight increase during structural tuning. On the contrary, in embodiments including the compound represented by Chemical Formula 1 of the present invention, high efficiency characteristics may be obtained in a desired wavelength band by not including a linker at the aforementioned position.

Examples 21 to 29 Fabrication of Red Organic EL Devices

Compounds 14, 24, 33, 52, 66, 79, 85, 98, and 101 synthesized in Synthesis Example were subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was manufactured according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / 90% Compound 14, 24, 33, 52, 66, 79, 85, 98, 101 + 10% (piq) ₂ Ir (acac) on ITO transparent electrode thus prepared ) (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in order to fabricate an organic EL device. The structures of m-MTDATA, TCTA, and BCP used are as described in Example 1, and the structure of (piq) ₂ Ir (acac) is as follows.

[Comparative Examples 6 to 10]

A red organic electroluminescent device was manufactured in the same manner as in Example 21, except that CBP and A, B, C, and D were used instead of the compound 14 used as the light emitting host material in the formation of the light emitting layer in Example 21.

[Evaluation Example 2]

For the organic electroluminescent devices manufactured in Examples 21 to 29 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 21 Compound 14 3.6 518 23.7 Example 22 Compound 24 3.5 519 22.5 Example 23 Compound 33 4.0 518 19.5 Example 24 Compound 52 3.4 520 22.9 Example 25 Compound 66 3.7 518 21.8 Example 26 Compound 79 3.8 520 23.8 Example 27 Compound 85 3.5 518 21.9 Example 28 Compound 98 3.4 519 24.0 Example 29 Compound 101 3.7 520 22.5 Comparative Example 6 CBP 5.4 521 15.8 Comparative Example 7 A 4.8 520 17.7 Comparative Example 8 B 4.7 521 16.8 Comparative Example 9 C 4.7 521 16.3 Comparative Example 10 D 4.9 520 17.2

As shown in Table 2, in the red organic EL device of Examples 21 to 29 using the compound according to the present invention as a light emitting layer material, Comparative Example 6 using a conventional CBP; And compared with the red organic electroluminescent element of Comparative Examples 7-10 which used compound A-D as a light emitting layer, it was confirmed that it is excellent in efficiency and a driving voltage.

When looking at the results of the above-described evaluation examples 1 and 2, the compound represented by the formula (1) of the present invention, a comparative example compound containing 1-, 2- 3-fluorene (eg, compounds A ~ C); And a change in driving voltage, current efficiency, and lifetime characteristics of the device, respectively, compared to the case of applying a comparative compound including a linker between the dibenzoic moiety and the heterocyclic moiety (e.g. Compound D). It was found that the better performance.

Claims (11)

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

R ₁ and R ₂ are the same as or different from each other, and each independently an alkyl group of C ₁ to C ₄₀ or an aryl group of C ₆ to C ₄₀ ,
R ₃ and R ₄ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group Is selected from;
a and b are each independently an integer of 0 to 4,
At least two of Ar ₁ , Ar ₂ and L has a moiety selected from the group represented by the following formula (2) and formula (3),
[Formula 2]

[Formula 3]

In Chemical Formula 2 or 3,
X is O or S,
Ar ₁ or Ar ₂ containing no moiety of Formula 2 is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ Alkynyl group of ˜C ₄₀ , cycloalkyl group of C ₃ ˜C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ˜ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ monoaryl phosphinyl group, C ₆ ~ C ₆₀ diaryl phosphinyl group and C ₆ ~ C ₆₀ arylamine A moiety represented by Formula 2 in the heteroaryl group is excluded;
A moiety of Formula 3 ratio (非) L comprising a single bond or, or C ₆ ~ C ₆₀ aryl group, and can be selected from 5 to 60 heteroaryl group nucleus atoms (provided that in the heteroaryl group Moieties represented by formula (3) are excluded),
The arylene group and the heteroarylene group of L and the alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups and alkyloxy groups of Ar ₁ to Ar ₂ and R ₁ to R ₄ , Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro 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, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ ~ C ₄₀ , aryloxy group of C ₆ ~ C ₆₀ , alkylsilyl group of C ₁ ~ C ₄₀ , C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₆₀ group, and C ₆ It may be substituted with one or more substituents selected from the group consisting of arylamine groups of ~ C ₆₀ , wherein when there are a plurality of the substituents, they may be the same or different from each other. The method of claim 1,
Ar ₁ or Ar _{2 that} does not include the moiety represented by Formula 2 is a compound selected from the group consisting of C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms. The method of claim 1,
L including no moiety represented by Formula 3 is a linker selected from the following structural formulas.

The method of claim 1,
R ₁ and R ₂ are the same as or different from each other, and each independently a methyl group or a phenyl group. The method of claim 1,
The compound represented by Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 4 to 6.
[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 4 to 6,
Ar ₁ , X and L are each as defined in claim ₁ , and a plurality of Xs are the same or different from each other. The method of claim 5,
Compound represented by Formula 4 is selected from the following structural formula.

The method of claim 5,
Compound represented by Formula 5 is selected from the following structural formula.

The method of claim 5,
Compound represented by the formula (6) is selected from the following structural formula.

An organic material comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 8. EL device. The method of claim 9,
The organic material layer including the compound is selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer. The method of claim 10,
The light emitting layer includes a host and a dopant,
The host is an organic electroluminescent device comprising the compound of Formula 1.