KR20140064686A - Anthracene derivatives compounds and organic electroluminescent devices comprising the same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound presented by [chemical formula A]. The organic electroluminescent device comprising the organic electroluminescent compound presented by [chemical formula A] has an outstanding efficiency of light emitting and has excellent lifespan characteristics.

Description

TECHNICAL FIELD The present invention relates to an anthracene derivative compound and an organic electroluminescent device comprising the same,

The present invention relates to a novel organic electroluminescent compound, and more particularly, to an anthracene derivative compound having a high luminous efficiency and a long life, and an organic electroluminescent device including the same.

The organic electroluminescent device can not only form an element on a transparent substrate but also can operate at a low voltage of 10 V or less as compared with a plasma display panel (Plasma Display Panel) or an inorganic electroluminescence (EL) display, It has the advantage of excellent color and has three colors of green, blue, and red. It has recently become a subject of interest as a next generation display device.

However, in order for such an organic electroluminescent device to exhibit such characteristics, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are materials forming an organic layer in a device, However, until now, stable and efficient development of an organic layer material for an organic electroluminescence element has not been sufficiently developed yet. Therefore, there is a continuing demand for development of new materials having low-voltage driving, high efficiency and long life.

In particular, various compounds in which anthracene 9 and 10 are substituted with naphthyl groups, phenyl groups, and the like have been reported as blue light emitting materials, and a blue light emitting material in which various dopant compounds are added while hosting an anthracene derivative compound has also been reported However, it still has a problem that the long life, luminous efficiency, and color purity are not satisfied at the same time.

Japanese Patent Application Laid-Open No. 10-1068224 Patent Registration No. 10-1092006

Accordingly, it is an object of the present invention to provide a novel organic electroluminescent compound having high luminous efficiency and long life.

Further, it is an object of the present invention to provide an organic electroluminescent device including such an organic electroluminescent compound and having excellent luminous efficiency and lifetime.

In order to solve the above problems, the present invention provides an organic electroluminescent compound of an anthracene derivative represented by the following formula (A) as a novel organic electroluminescent compound.

(A)

Further, the present invention is an organic electroluminescent device comprising an anode, a cathode facing the anode, and an organic layer interposed between the anode and the cathode, wherein the organic layer contains at least one compound represented by the above formula (A) And an organic electroluminescent device.

In addition, the present invention relates to an organic electroluminescence device comprising at least one or more compounds represented by the following formulas (B) to (C) in addition to various compounds represented by the formula (1) Device.

[Chemical Formula B]

≪ RTI ID = 0.0 &

Specific substituents of the above-mentioned formulas (A), (B) and (C) will be described later.

The compound represented by the formula [A] according to the present invention is a fluorescent host compound used in an organic electroluminescent device, and has excellent lifetime characteristics and luminescent efficiency characteristics as compared with a conventional fluorescent host compound, An organic electroluminescent device can be provided.

1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention relates to an organic electroluminescent compound represented by the following formula [A], which can be used as a host in a light emitting layer of an organic electroluminescent device.

(A)

In the above formula (A)

A ₁ to A ₅ are the same as or different from each other and each independently selected from hydrogen, deuterium, and substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms.

According to a preferred embodiment of the present invention, A ₁ to A ₅ may be an alkyl group having 1 to 30 carbon atoms including deuterium or deuterium. Accordingly, the compound represented by the formula [A] according to the present invention is characterized in that the structure connected to the anthracene 9 position is a phenyl group substituted with a substituent including deuterium or deuterium, whereby the longevity property Can be implemented.

X is X ₁ to X ₇ , X ₁ to X ₇ and R ₁ to R ₇ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, A substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 1 -C 30 alkyl A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, A heteroaryl group having 2 to 50 carbon atoms having a ring or an unsubstituted heteroatom, O, N or S, a cyano group, a nitro group and a halogen group.

According to a preferred embodiment of the present invention, X ₁ to X ₇ and R ₁ to R ₇ may each be deuterium or a substituent containing deuterium. Accordingly, the compound represented by the formula [A] according to the present invention is characterized in that the structure to be connected to the anthracene 10-position is a 1-naphthyl group in which at least one of 2-naphthyl groups is substituted, -Naphthyl group is further characterized by having a substituent including deuterium or deuterium, whereby the lifetime characteristics of the luminescent compound can be realized.

The 1-naphthyl group and the 2-naphthyl group may be connected by a single bond or may further include a linking group therebetween, and the linking group L may be a single bond or a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, Substituted or unsubstituted C2-C60 Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- A substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. . n is an integer of 0 to 2, and when n is 2, plural Ls are the same or different from each other.

The anthracene derivative represented by the formula (A) according to the present invention is characterized in that the substituents A ₁ to A ₅ are each a substituent group containing deuterium or deuterium. Further, X ₁ to X ₇ and R ₁ to R _{7 are} also each a substituent group containing deuterium or deuterium, which can provide better long life characteristics than conventional anthracene derivative compounds.

In addition, the compound according to the present invention is characterized in that the 1-naphthyl group to which a substituted or unsubstituted 2-naphthyl group is bonded is bonded to the 10-position of anthracene linked with a phenyl group substituted or unsubstituted at the 9- , Whereby the molecule has appropriate crystallinity and the charge mobility of the host is controlled to increase the charge balance, and thus the luminous efficiency is remarkably improved.

More specifically, A ₁ to A ₅ , X ₁ to X ₇ , R ₁ to R _7, and L in the above 'substituted or unsubstituted' mean more substituted with one or more substituents, , A halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, An alkyl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms An amino group, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms May be further substituted with one or more substituents.

In consideration of the range of the alkyl or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 5 to 50 carbon atoms' and the like, And the number of carbon atoms of the aryl group having 5 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

An aryl group, which is a substituent used in the compound of the present invention, refers to an aromatic system composed of a hydrocarbon containing at least one ring, and when the aryl group has a substituent, it is fused with neighboring substituents to further form a ring .

Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl and the like. At least one hydrogen atom of the aryl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, , An amino group (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" are independently of each other an alkyl group having 1 to 10 carbon atoms, An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, An aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group, which is a substituent used in the compounds of the present invention, refers to a C 2 -C 24 ring aromatic system containing 1, 2 or 3 heteroatoms selected from N, O, P or S and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

The range of the anthracene derivative compound represented by the formula (A) according to the present invention is not limited thereby, but it may be any one compound represented by the following formulas (1) to (30) as a specific example .

[Formula 3] < EMI ID =

[Chemical Formula 4] < EMI ID =

[Chemical Formula 8] < EMI ID =

[Chemical Formula 11] [Chemical Formula 12]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 18] [Chemical Formula 18]

[Chemical Formula 20]

[Chemical Formula 22]

[Chemical Formula 25]

[Chemical Formula 30]

Another aspect of the present invention relates to an organic electroluminescent device comprising at least one of various compounds represented by the above formula (A), which is excellent in light emission characteristics and lifetime characteristics, wherein the organic electroluminescent device comprises an anode, And an organic layer interposed between the anode and the cathode, wherein the organic layer contains at least one of the compounds represented by the formula [A].

The organic layer may be a hole injecting layer, a hole transporting layer, a light emitting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer between the anode and the cathode.

According to a preferred embodiment, at least one of the compounds represented by Formula A may be included in the light emitting layer, and the thickness of the light emitting layer may be 50 to 2000 ANGSTROM.

In addition, the present invention is characterized in that at least one of various compounds represented by the formula (A) is used as a host compound in the light emitting layer, and various dopant materials are included therein to maximize characteristics such as luminous efficiency and long life . According to a preferred embodiment, at least one or more dopant compounds represented by the following formulas (B) to (C) may further be included.

[Chemical Formula B]

≪ RTI ID = 0.0 &

In the above formulas (B) to (C)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms And a heteroarylene group having 3 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S, may be used.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and examples thereof include an anthracene group such as an anthracene, a pyrene, a phenanthrene, an indenophenanthrene, a klycene, a naphthacene, a picene, a triphenylene, a perylene and a pentacene And more specifically, any one selected from the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

(A10)

In the above formula [A3]

Z ₁ to Z ₂ are independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkylthio having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted 6 to 60 carbon atom (s), a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group, (Alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, and a substituted or unsubstituted amino group having 6 to 60 carbon atoms, di (substituted or unsubstituted) 6 Is selected from aryl of paper 60) an amino group, and Z ₁ to Z ₂ each are the same or different from each other, may form a group and a condensed ring which are adjacent to each other.

X ₁ and X ₂ are the same or different and are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and X ₁ and X ₂ may be bonded to each other.

Y ₁ and Y ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted C1 to C24 alkyl group, a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen , And the Y ₁ To Y < ₂ > may form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero, each of which may be connected to each other or adjacent groups, and l and m are integers of 1 to 20, respectively.

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each is the same or different and each cycloalkane may be a fused form And the substituted hydrogen may be further substituted with deuterium or alkyl.

B Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, p is an integer of 1 to 3, and when p is 2 or more, two or more R ₅ and R ₆ may be the same or different have.

Wherein R ₁ , R ₂ , R _{3 ,} R ₅ and R ₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, Beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron.

a is an integer of 1 to 4, and when a is 2 or more, at least 2 of R ₃ may be the same or different, and a plurality of R ₃ may be fused, and n is an integer of 1 to 4.

The amine group bonded to A in the formulas (B) and (C) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3]

[Substituent group 4] [Substituent group 5] [Substituent group 6]

[Substituent group 7] [Substituent group 8] [Substituent group 9]

[Substituent group 10] [Substituent group 11] [Substituent group 12]

[Substituent group 13] [Substituent group 14] [Substituent group 15]

[Substituent group 16] [Substituent group 17] [Substituent group 18]

[Substituent group 19] [Substituent group 20] [Substituent group 21]

[Substituent group 22] [Substituent group 23] [Substituent group 24]

[Substituent group 25] [Substituent group 26] [Substituent group 27]

[Substituent group 28] [Substituent group 29] [Substituent group 30]

[Substituent group 31] [Substituent group 32] [Substituent group 33]

[Substituent group 34] [Substituent group 35] [Substituent group 36]

[Substituent group 37] [Substituent group 38] [Substituent group 39]

[Substituent group 40] [Substituent group 41] [Substituent group 42]

[Substituent group 43] [Substituent group 44] [Substituent group 45]

[Substituent group 46] [Substituent group 47] [Substituent group 48]

[Substituent group 49] [Substituent group 50] [Substituent group 51]

[Substituent 52]

In the above [substituent groups 1] to [substituent group 52]

R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, An aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, Up to 12 substituents may be substituted, and each substituent may form a condensed ring with adjacent groups.

According to a preferred embodiment, the organic electroluminescent device according to the present invention will be described in more detail. The organic electroluminescent device includes an anode, a cathode facing the anode, and a light emitting layer interposed between the anode and the cathode, ≪ RTI ID = 0.0 > and / or < / RTI >

Further, between the anode and the cathode, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer may be further included. The hole injection layer, the hole transport layer, the electron transport layer, Layer efficiently transports holes or electrons to the light emitting layer, thereby enhancing the probability of luminescent bonding in the light emitting polymer.

As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the light emitting layer. The hole transport layer An electron donor molecule having a low ionization potential is used as a material of the hole transport layer. In the electron donor molecule, a diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is often used .

In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenyl-amine) or m-MTDATA (4,4'4" -tris- (3-methylphenylphosphine enylamino) triphenylamine) and the like.

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, .

The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The organic electroluminescent device according to the present invention includes an anode 20, a hole transporting layer 40, an organic light emitting layer 50, an electron transporting layer 60, and a cathode (80), and if necessary, may further include a hole injection layer (30) and an electron injection layer (70). In addition, one or two intermediate layers may be further formed, Or an electron blocking layer may be further formed.

The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

According to another embodiment of the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

Synthetic example  [1]: Synthesis of [Formula 1]

Synthesis Example 1- (1): Synthesis of Intermediate 1-a

Intermediate 1-a

25 g (0.15 mole) of 8-amino-2-naphthol was added to 110 mL of acetic acid in a 1000 mL round bottom flask, and the temperature was cooled to 0 占 폚. 50 mL of sulfuric acid was added dropwise, and then an aqueous solution in which 19.5 g (0.28 mole) of sodium nitrite was dissolved in 130 mL of water was slowly added dropwise. After the dropwise addition, the temperature was raised to room temperature and stirred for 1 hour. After cooling to 0 ° C, 0.8 g of urea was added, and 91.1 g (0.55 mole) of potassium iodide was dissolved in 130 mL of water and slowly added dropwise. After the dropwise addition, the temperature was raised to room temperature and stirred for 24 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 500 mL of dichloromethane. The combined organic layers were concentrated under reduced pressure and column chromatography gave intermediate 1-a (20 g, 47%).

Synthesis Example 1- (2): Synthesis of Intermediate 1-b

Intermediate 1-b

L 10 4 400 9-bromo-anthracene-gu round bottom flask g (1.55 mole) and _{Pd (PPh 3) 4 35.99 g} (0.031 mole) of potassium carbonate and 430.7 g (3.11 mole) and phenylboronic acid 246.6 g (2.02 mole ), 2000 mL of toluene, 2000 mL of 1,4-dioxane, and 1000 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain intermediate 1-b (298 g, 75.3%).

Synthesis Example 1- (3): Synthesis of Intermediate 1-c

Intermediate 1-b Intermediate 1-c

298 g (1.17 moles) of Intermediate 1-b was added to a 10 L round bottom flask and 4000 mL of dichloromethane was added to dissolve. After cooling to 0 < 0 > C, 206 g (1.29 mole) of bromine was slowly added dropwise. After dropwise addition, the mixture was transferred to room temperature and stirred for 2 hours. After completion of the reaction, 1000 mL of an aqueous solution of sodium hydrogen carbonate was added and stirred for 30 minutes. The organic layer was separated, concentrated under reduced pressure, and recrystallized from dichloromethane and methanol to obtain intermediate 1-c (313 g, 80.3%).

Synthesis Example 1- (4): Intermediate 1-d Synthesis

Intermediate 1-c Intermediate 1-d

Add 280 g (0.84 mole) of Intermediate 1-c and 3000 mL of THF in a 10 L round bottom flask and keep at -78 ° C. 1.6 M n-BuLi 630 mL is slowly added dropwise and stirred for 2 hours, then B (OMe) ₃ is added dropwise at the same temperature. The temperature is raised to room temperature and stirred for 12 hours. The reaction is terminated and 2N HCl is added. The organic layer was separated, neutralized and recrystallized with toluene to give intermediate 1-d (228 g, 91%).

Synthesis Example 1- (5): Intermediate 1-e Synthesis

Intermediate 1-a Intermediate 1-d Intermediate 1-e

300 mL Intermediate To a round bottom flask was added 1-a 15 g (56 mmole ) and _{Pd (PPh 3) 4 3.2 g} (3 mmole) and potassium carbonate 19.2 g (0.13 mole) and intermediate 1-d 18.2 g (61 mmole ) of 90 mL of toluene, 90 mL of 1,4-dioxane and 45 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The combined organic layers were concentrated under reduced pressure and column chromatography gave intermediate 1-e (13 g, 60%).

Synthesis Example 1- (6): Intermediate 1-f Synthesis

Intermediate 1-e Intermediate 1-f

Add 10 g (25 mmole) of Intermediate 1-e to a 300 mL four-neck round bottom flask and dissolve in 100 mL of dichloromethane. When the reaction was dissolved, 2.59 g (32 mmole) of pyridine was added thereto, and the reaction was cooled to 0 ° C. 7.83 g (27 mmole) of (CF ₃ SO ₂ ) ₂ O was slowly added dropwise and the reaction was transferred to room temperature, stirred for 1 hour, and 100 mL of water was added. The organic layer was separated and concentrated under reduced pressure. Column chromatography gave Intermediate 1-f (9 g, 67.5%).

Synthesis Example 1- (7): Synthesis of Synthesis 1

Intermediate 1-f [Chemical Formula 1]

300 mL 4 gu intermediate 1-f 9 g (17 mmole ) in a round bottom flask was charged with _{Pd (PPh 3) 4 1 g} (0.001 mole) of potassium carbonate and 5.9 g (43 mmole) and 2-naphthyl boronic acid (2 2.9 g (17 mmole) of naphthyl boronic acid, 55 mL of toluene, 55 mL of 1,4-dioxane and 30 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and methanol to give 5 g (58%) of the compound of formula (1).

_{^{[1 H NMR (CDCl 3)}} : d 8.42 (Ar-H, d, 1H), d 8.14 (Ar-H, d, 1H), d 8.04 ~ 7.89 (Ar-H, m, 10H), d 7.79 ( (Ar-H, d, 1 H), d 7.59 (Ar-H, m, 2H), d 7.58-7.39

Synthetic example  [2]: Synthesis of [Formula 2]

Synthesis Example 2- (1): Synthesis of Intermediate 2-a

Intermediate 2-a

25 g (0.15 mole) of 5-amino-2-naphthol was added to 110 mL of acetic acid in a 1000 mL round bottom flask, and the temperature was cooled to 0 占 폚. 50 mL of sulfuric acid was added dropwise, and then an aqueous solution in which 19.5 g (0.28 mole) of sodium nitrite was dissolved in 130 mL of water was slowly added dropwise. After the dropwise addition, the temperature was raised to room temperature and stirred for 1 hour. After cooling to 0 ° C, 0.8 g of urea was added, and 91.1 g (0.55 mole) of potassium iodide was dissolved in 130 mL of water and slowly added dropwise. After the dropwise addition, the temperature was raised to room temperature and stirred for 24 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 500 mL of dichloromethane. The collected organic layer was concentrated under reduced pressure and column chromatography was used to obtain intermediate 2-a (18 g, 42.4%).

Synthesis Example 2- (2): Synthesis of Intermediate 2-b

Intermediate 2-b

5 L round bottom flask 4 gu 9-bromo-anthracene, 200 g (0.6 mole) and _{Pd (PPh 3) 4 34.71 g} (0.03 mole) of potassium carbonate and 165.91 g (1.2 mole) and phenylboronic acid (phenyl-d5- boronic acid (126.96 g, 0.66 mole), 1000 mL of toluene, 1000 mL of 1,4-dioxane and 500 mL of water were added and refluxed for 16 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain intermediate 2-b (112 g, 71.95%).

Synthesis Example 2- (3): Synthesis of Intermediate 2-c

Intermediate 2-b Intermediate 2-c

112 g (0.432 mole) of intermediate 2-b was placed in a 5 L four-neck round bottom flask and dissolved in 2000 mL of dichloromethane. Cool to 0 < 0 > C and slowly add 69.02 g (0.432 mole) of bromine. After dropwise addition, the mixture was transferred to room temperature and stirred for 2 hours. After completion of the reaction, 1000 mL of aqueous sodium hydrogencarbonate solution was added and stirred for 30 minutes. The organic layer was separated, concentrated under reduced pressure, and recrystallized from dichloromethane and methanol to obtain Intermediate 2-c (119.8 g, 82%).

Synthesis Example 2- (4): Synthesis of intermediate 2-d

Intermediate 2-c Intermediate 2-d

Add 119.8 g (0.0354 mole) of intermediate 2-c and 1200 mL of THF to a 3 L four-neck round bottom flask and keep at -78 ° C. 1.6 M n-BuLi 265 mL is slowly added dropwise and stirred for 2 hours, then B (OMe) ₃ is added dropwise at the same temperature. The temperature is raised to room temperature and stirred for 12 hours. The reaction is terminated and 2N HCl is added. The organic layer was separated and neutralized and recrystallized with toluene to give intermediate 2-d (76.2 g, 71%).

Synthesis Example 2- (5): Intermediate 2-e Synthesis

Intermediate 2-a Intermediate 2-d Intermediate 2-e

300 mL Intermediate To a round bottom flask was added 2-a 15 g (56 mmole ) and _{Pd (PPh 3) 4 3.2 g} (3 mmole) and potassium carbonate 19.2 g (0.13 mole) and intermediate 1-d 16.84 g (61 mmole ) of 70 mL of toluene, 70 mL of 1,4-dioxane and 45 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The collected organic layer was concentrated under reduced pressure and column chromatography was used to obtain intermediate 2-e (10.9 g, 49%).

Synthesis Example 2- (6): Intermediate 2-f Synthesis

Intermediate 2-e Intermediate 2-f

To a 300 mL four-neck round bottom flask was added 10.9 g (27 mmole) of Intermediate 2-e and dissolved in 100 mL of dichloromethane. When the reaction was dissolved, 2.59 g (32 mmole) of pyridine was added thereto, and the reaction was cooled to 0 ° C. 7.83 g (27 mmole) of (CF ₃ SO ₂ ) ₂ O was slowly added dropwise and the reaction was transferred to room temperature, stirred for 1 hour, and 100 mL of water was added. The organic layer was separated and concentrated under reduced pressure. Intermediate 2-e (10 g, 75%) was obtained by column chromatography.

Synthesis Example 2- (7): Synthesis of Compound (2)

Intermediate 2-f [Chemical Formula 2]

300 mL round bottom flask 4 gu intermediate 2-f 10 g (19 mmole ) and _{Pd (PPh 3) 4 1.1 g} (0.001 mole) of potassium carbonate and 6.5 g (47 mmole) and 2-naphthyl boronic acid (2 3.3 g (19 mmole) of naphthyl boronic acid, 60 mL of toluene, 60 mL of 1,4-dioxane and 30 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated, and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain 5.5 g (57.4%) of the compound of the formula (2).

_{^{[1 H NMR (CDCl 3)}} : d 8.42 (Ar-H, d, 1H), d 8.14 (Ar-H, d, 1H), d 8.04 ~ 7.91 (Ar-H, m, 10H), d 7.73 ( (Ar-H, d, 1 H), d 7.61-7.58 (Ar-H, m, 4H), 7.39

Synthetic example  [3] Synthesis of [Formula 3]

Synthesis Example 3- (1): Synthesis of Intermediate 3-a

Intermediate 3-a

To a 1000 mL round bottom flask was added 35 g (0.12 mole) of 1,5-dibromonaphthalene, 7.08 g (6 mmole) of Pd (PPh ₃ ) _4, 38.91 g (0.28 mole) of potassium carbonate, and 2-naphthylboronic acid -naphthyl boronic acid (2-naphthyl boronic acid), 210 mL of toluene, 210 mL of 1,4-dioxane and 100 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The combined organic layers were concentrated under reduced pressure and column chromatography was used to obtain intermediate 3-a (20 g, 50%).

Synthesis Example 3- (2): Synthesis of (3) Synthesis

Intermediate 3-a Intermediate 1-d < EMI ID =

300 mL 4 gu intermediate 3-a 10 g (3 mmole ) and _{Pd (PPh 3) 4 1.74 g} (2 mmole) and potassium carbonate 9.54 g (69 mmole) and intermediate 1-d 11.63 g To a round bottom flask (39 mmole ), 60 mL of toluene, 60 mL of 1,4-dioxane and 30 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated, and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain 8 g (52.6%) of the formula 3.

_{^{[1 H NMR (CDCl 3)}} : d 8.51 (Ar-H, d, 2H), d 8.42 (Ar-H, d, 2H), d 8.00 ~ 7.91 (Ar-H, m, 7H), d 7.73 ( (Ar-H, d, 1 H), d 7.61-7.39 (Ar-H, m,

Synthetic example  [4]: Synthesis of [Formula 4]

Synthesis Example 4- (1): Synthesis of Intermediate 4-a

Intermediate 4-a

1000 mL 1,4- dibromo-naphthalene 30 g (0.105 mole) to a round bottom flask was charged with _{Pd (PPh 3) 4 6.07 g} (5 mmole) and 33.35 g (0.24 mole) and 2-naphthyl boronic acid and potassium carbonate (2 -naphthyl boronic acid (2-naphthyl boronic acid), 180 mL of toluene, 180 mL of 1,4-dioxane and 90 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The collected organic layer was concentrated under reduced pressure and column chromatography was used to obtain intermediate 4-a (15 g, 42.9%).

Synthesis Example 4- (2): Synthesis 4 Synthesis

Intermediate 4-a Intermediate 2-d < EMI ID =

15 g (45 mmole) of intermediate 4-a, 2.6 g (2 mmole) of Pd (PPh ₃ ) _4, 14.31 g (0.104 mole) of potassium carbonate and 16.92 g (59 mmole) of intermediate 2-d in a 300 mL four- 90 mL of toluene, 90 mL of 1,4-dioxane and 45 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain 14 g (61.4%) of the compound of the formula (4).

_{^{[1 H NMR (CDCl 3)}} : d 8.55 (Ar-H, m, 2H), d 8.01 ~ 7.91 (Ar-H, m, 9H), d 7.73 (Ar-H, d, 1H), d 7.59 ~ (Ar-H, m, 4H) m / z: 511.23]

Synthetic example  [5]: Synthesis of [Formula 5]

Synthesis Example 5- (1): Synthesis of Intermediate 5-a

Intermediate 5-a

500 mL round-3-bromo-1-naphthol (3-bormo-1-naphthol ) in the bottom flask was charged 30g (0.13 mole) and _{Pd (PPh 3) 4 3.11g (} 3 mmole) of potassium carbonate and 37g (0.26 mole) and 24.3 g (0.14 mole) of 2-naphthyl boronic acid was added, 150 mL of toluene, 150 mL of 1,4-dioxane and 60 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The collected organic layer was concentrated under reduced pressure and recrystallized from toluene and methanol to obtain intermediate 5-a (16 g, 44%).

Synthesis Example 5- (2): Synthesis of Intermediate 5-b

Intermediate 5-b

Add 16 g (59 mmole) of intermediate 5-a to a 500 mL four-neck round bottom flask and dissolve in 160 mL of dichloromethane. When the reaction product melted, 6.1 g (77 mmole) of pyridine was added thereto, and the reaction product was cooled to 0 ° C. 18.4 g (65 mmole) of (CF ₃ SO ₂ ) ₂ O was slowly added dropwise, the reaction was transferred to room temperature, stirred for 1 hour, and 150 mL of water was added. The organic layer was separated and concentrated under reduced pressure. Intermediate 5-b (19.5 g, 81.9%) was obtained by column chromatography.

Synthesis Example 5- (3): Synthesis of Compound (5)

Intermediate 5-b Intermediate 1-d [Chemical Formula 5]

To a 300 mL four-neck round bottom flask was added 19 g (48 mmole) of Intermediate 5-b, 2.8 g (2 mmole) of Pd (PPh ₃ ) _4, 13.4 g (97 mmole) of potassium carbonate and 15.9 g ), 100 mL of toluene, 100 mL of 1,4-dioxane and 50 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain 15 g (61.1%) of the compound of the formula (5).

_{^{[1 H NMR (CDCl 3)}} : d 8.55 (Ar-H, d, 2H), d 8.08 ~ 7.85 (Ar-H, m, 9H), d 7.76 ~ 7.73 (Ar-H, m, 2H), d 7.59-7.39 (Ar-H, m, 14H), m / z: 506.2]

Synthetic example  [6] Synthesis of [Formula 6]

Synthesis Example 6- (1): Synthesis of Intermediate 6-a

Intermediate 6-a

30 g (0.16 mole) of 1,7-dimethoxynaphthalene was added to a 500 mL four-neck round bottom flask and 300 mL of acetonitrile was added to dissolve. After cooling to 0 ° C, 28.4 g (0.16 mole) of N-bromosuccinomide was dissolved in 60 mL of acetonitrile and slowly added dropwise. After dropwise addition, the mixture was transferred to room temperature and stirred for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, extracted with dichloromethane and water, and then recrystallized from dichloromethane and hexane to obtain intermediate 6-a (30 g, 70.5%).

Synthesis Example 6- (2): Synthesis of Intermediate 6-b

Intermediate 6-a Intermediate 6-b

30 g (0.11 mole) of intermediate 6-a was placed in a 1000 L four-neck round bottom flask and 300 mL of dichloromethane was added to dissolve. After cooling to -78 ° C, 56.4 g (0.23 mole) of boron tribromide was diluted in 30 mL of dichloromethane and slowly added dropwise. After dropwise addition, the mixture was transferred to room temperature and stirred for 6 hours. After completion of the reaction, 300 mL of aqueous sodium bicarbonate solution was added and stirred for 30 minutes. The organic layer was separated, concentrated under reduced pressure, and recrystallized from dichloromethane and hexane to obtain intermediate 6-b (25 g, 82.35%).

Synthesis Example 6- (3): Synthesis of Intermediate 6-c

Intermediate 6-b Intermediate 1-d Intermediate 6-c

25 g (0.105 mole) of intermediate 6-b, ₄ g (5 mmole) of Pd (PPh ₃ ) and 36.1 g (0.26 mole) of potassium carbonate and 34.3 g ), 150 mL of toluene, 150 mL of 1,4-dioxane and 75 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and heptane to obtain intermediate 6-c (20.7 g, 48%).

Synthesis Example 6- (4): Synthesis of Intermediate 6-d

Intermediate 6-c Intermediate 6-d

Add 20 g (48 mmole) of Intermediate 6-c to a 500 mL 4-neck round bottom flask and dissolve in 200 mL of dichloromethane. When the reaction product melted, 9.5 g (0.12 mole) of pyridine was added thereto, and the reaction product was cooled to 0 ° C. (0.13 mole) of (CF ₃ SO ₂ ) ₂ O was slowly added dropwise, and the reaction was transferred to room temperature, stirred for 1 hour, and 150 mL of water was added. The organic layer was separated and concentrated under reduced pressure. Intermediate 6-d (21.5 g, 65.5%) was obtained by column chromatography.

Synthesis Example 6- (5): Synthesis of Compound (6)

Intermediate 6-d [Chemical formula 6]

1 L 4 District ₄ Intermediate 6-d 21.5g (32 mmole) and Pd (PPh ₃₎ To a round bottom flask was added 3.7g (3 mmole) of potassium carbonate and 19.8g (0.14 mole) and 2-naphthyl boronic acid (2 (75 mmole) of naphthyl boronic acid, 150 mL of toluene, 150 mL of 1,4-dioxane and 75 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and heptane to obtain 13 g (64.7%) of the compound of the formula (6).

_{^{[1 H NMR (CDCl 3)}} : d 8.14 (Ar-H, d, 1H), d 8.01 ~ 7.89 (Ar-H, m, 14H), d 7.73 (Ar-H, m, 2H), d 7.59 ~ 7.39 (Ar-H, m, 15H), m / z: 632.25]

Synthetic example  [7]: Synthesis of [Formula 7]

Synthesis Example 7- (1): Synthesis of Intermediate 7-a

Intermediate 7-a

To a 500 mL round bottom flask was added 30 g (0.106 mole) of 1,3-iodobromobenzene, 6.13 g (5 mmole) of Pd (PPh ₃ ) _4, 29.31 g (0.212 mole) of potassium carbonate and 2-naphthylboronic acid 2-naphthyl boronic acid), 300 mL of toluene and 90 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The collected organic layer was concentrated under reduced pressure and column chromatography was used to obtain intermediate 7-a (15.9 g, 53%).

Synthesis Example 7- (2): Synthesis of Intermediate 7-b

Intermediate 7-a Intermediate 7-b

Add 15.9 g (0.056 mole) of Intermediate 7-a and 159 mL of THF to a 500 mL four-neck round bottom flask and keep at -78 ° C. Add 42 mL of 1.6 M n-BuLi dropwise and stir for 2 hours, then drop B (OMe) ₃ at the same temperature. The temperature is raised to room temperature and stirred for 12 hours. The reaction is terminated and 2N HCl is added. The organic layer was separated, neutralized and recrystallized with toluene to obtain intermediate 7-b (10.6 g, 76%).

Synthesis Example 7- (3): Synthesis of Compound (7)

Intermediate 2-c Intermediate 7-b [Chemical Formula 7]

Add 15 g (28 mmole) of intermediate 2-c, 1.6 g (1 mmole) of Pd (PPh ₃ ) _4, 9.8 g (71 mmole) of potassium carbonate and 7 g (28 mmole) of intermediate 7-b in a 300 mL four- 75 mL of toluene, 75 mL of 1,4-dioxane and 45 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated, and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and heptane to obtain 13 g (64.7%) of the formula 7.

_{^{[1 H NMR (CDCl 3)}} : d 8.42 (Ar-H, d, 1H), d 8.14 (Ar-H, d, 1H), d 8.04-7.89 (Ar-H, m, 10H), d 7.73- (Ar-H, m, 16H), m / z: 582.23], 7.70-7.70

Synthetic example  [8] Synthesis of [Formula 8]

Synthesis Example 8- (1): Synthesis of Intermediate 8-a

Intermediate 8-a

To a 500 mL round bottom flask was added 30 g (0.106 mole) of 1,4-iodobromobenzene, 6.13 g (5 mmole) of Pd (PPh ₃ ) _4, 29.31 g (0.212 mole) of potassium carbonate, and 2-naphthylboronic acid -naphthyl boronic acid), 300 mL of toluene and 90 mL of water were added, and the mixture was refluxed for 16 hours. The reaction was terminated and the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The collected organic layer was concentrated under reduced pressure and column chromatography was used to obtain intermediate 8-a (20 g, 66.6%).

Synthesis Example 8- (2): Synthesis of Intermediate 8-b

Intermediate 8-a Intermediate 8-b

Add 20 g (0.071 mole) of intermediate 8-a and 200 mL of THF to a 500 mL four-neck round bottom flask and keep at -78 ° C. 1.6 M n-BuLi 55.1 mL is slowly added dropwise and stirred for 2 hours, then B (OMe) ₃ is added dropwise at the same temperature. The temperature is raised to room temperature and stirred for 12 hours. The reaction is terminated and 2N HCl is added. The organic layer was separated and neutralized and recrystallized with toluene to obtain intermediate 8-b (12.3 g, 70.2%).

Synthesis Example 8- (3): Synthesis of Intermediate 8-c

Intermediate 1-d Intermediate 8-c

500 mL 4-neck round bottom flask intermediate 1-d 20.8g (0.07 mole) and _{Pd (PPh 3) 4 4g (} 3 mmole) of potassium carbonate and 19.3g (0.14 mole) and 1,4-bromo-naphthalene (1, 4-dibromonaphthalene), 100 mL of toluene, 100 mL of 1,4-dioxane and 60 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and heptane to obtain intermediate 8-c (17 g, 53%).

Synthesis Example 8- (4): Synthesis of

Intermediate 8-c Intermediate 8-b [Chemical Formula 8]

17 g (37 mmole) of Intermediate 8-c and 2.14 g (2 mmole) of Pd (PPh ₃ ) _4, 10.23 g (74 mmole) of potassium carbonate and 7 g (37 mmole) of Intermediate 8-b in a 300 mL four- 60 mL of toluene, 60 mL of 1,4-dioxane and 30 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and heptane to obtain 10.4 g (48.3%) of the compound of the formula (8).

_{^{[1 H NMR (CDCl 3)}} : d 8.55 (Ar-H, d, 2H), d 8.01 ~ 7.91 (Ar-H, m, 6H), d 7.73 (Ar-H, d, 1H), d 7.59 ~ (Ar-H, d, 4H) m / z: 582.23]

Synthetic example  [9] Synthesis of [Formula 9]

Synthesis Example 9- (1): Synthesis of Intermediate 9-a

Intermediate 3-a Intermediate 9-a

Add 14 g (0.042 mole) of intermediate 3-a and 140 mL of THF in a 500 mL four-neck round bottom flask and keep at -78 ° C. Add 31 mL of 1.6 M n-BuLi dropwise and stir for 2 hours, then drop B (OMe) ₃ at the same temperature. The temperature is raised to room temperature and stirred for 12 hours. The reaction is terminated and 2N HCl is added. The organic layer was separated, neutralized and recrystallized with toluene to obtain intermediate 9-a (8.3 g, 66.3%).

Synthesis Example 9- (2) Synthesis of

Intermediate 2-f Intermediate 9-a [Chemical Formula 9]

300 mL 4 gu Intermediate To a round bottom flask was added 2-f 11g (21 mmole) and _{Pd (PPh 3) 4 1.19g (} 1 mmole) of potassium carbonate and 5.7g (41 mmole) and the intermediate 9-a 6.15g (21 mmole) , 80 mL of toluene, 80 mL of 1,4-dioxane and 50 mL of water were added, and the mixture was refluxed for 12 hours. The reaction was terminated and the organic layer was separated, concentrated under reduced pressure, and recrystallized from toluene and heptane to obtain 6.4 g (49%) of the compound of the formula (9).

_{^{[1 H NMR (CDCl 3)}} : d 8.51 (Ar-H, d, 2H), d 8.42 (Ar-H, d, 3H), d 8.14 (Ar-H, d, 1H), d 8.04 ~ 7.89 ( (Ar-H, m, 4H), 7.73 (Ar-H, d, 1H), 7.61-7.58 637.28]

Example  1 to 8: Preparation of Organic Light Emitting Diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was allowed to have a pressure of 1 × 10 ^-6 torr, and then an organic material was deposited on the ITO using DNTPD (700 Å), α-NPD (300 Å) Chemical formulas 1 to 5 (examples 1 to 5)) and (7) to (9 (examples 6 to 8) as the one with the dopant of the agent was BD1 (3 wt%), a co-deposited (300 Å), Alq ₃ after (350 Å), LiF (5 Å) and Al (1,000 Å) in this order. The DNTPD, the structure of the α-NPB, Alq BD1 and ₃ are as follows.

[NTPD] [[alpha] -NPD]

[BD1] [Alq _3]

Comparative Example  1 to 2

(Comparative Example 1) and [Compound B] (Comparative Example 2) were used instead of the host compound prepared by the invention in the device structures of Examples 1 to 8, And the structure is as follows.

[Compound A] [Compound B]

The voltage, efficiency, luminance, color coordinates, and lifetime of the organic light emitting device manufactured according to Examples 1 to 8 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below.

division compound V cd / A EQE cd / ㎡ CIEx CIEy lambda max T97 (h) Comparative Example 1 Compound A 3.961 6.4 7.2 641.0 0.136 0.118 458 20.0 Comparative Example 2 Compound B 3.981 6.5 7.4 653.7 0.136 0.118 458 25.7 Example 1 Formula 1 3.728 7.5 8.5 747.9 0.133 0.124 459 56.1 Example 2 (2) 3.827 7.3 8.7 734.2 0.134 0.116 458 71.0 Example 3 (3) 3.802 7.5 8.4 750.5 0.133 0.126 460 69.7 Example 4 Formula 4 3.784 7.4 8.4 743.3 0.133 0.125 460 70.1 Example 5 Formula 5 3.843 7.3 8.9 730.2 0.135 0.112 458 50.4 Example 6 Formula 7 3.961 7.4 9.2 750.1 0.136 0.108 458 51.0 Example 7 8 3.981 7.5 9.4 761.0 0.136 0.108 458 59.1 Example 8 Formula 9 3.843 7.3 8.9 725.1 0.134 0.112 458 75.0

As shown in Table 1, the organic electroluminescent device comprising the organic electroluminescent compound having a specific structure according to the present invention has a higher luminous efficiency and a longer life time than the compound having the structure of [compound B] It can be used for devices.

Claims (11)

An anthracene derivative represented by the following formula (A):
(A)

In the above formula (A)
A ₁ to A ₅ are the same or different from each other and each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
X is X ₁ to X ₇ (* - means a connected position), and
X ₁ to X ₇ and R ₁ to R ₇ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms , A substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted hetero atom, O, N Is any one selected from a heteroaryl group having 2 to 50 having an S, a cyano group, a nitro group and a halogen group,
L is a single bond or a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C2-C6 heteroarylene group. ,
n is an integer of 0 to 2, and when n is 2, plural Ls are the same or different from each other. The method according to claim 1,
Wherein A ₁ to A _5, X ₁ to X _7, R ₁ to R ₇ and L are heavy hydrogen, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, An arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
Wherein X is X ₁ to X ₇ ≪ RTI ID = 0.0 > and / or < / RTI > The method according to claim 1,
Wherein each of A ₁ to A ₅ , X ₁ to X ₇ and R ₁ to R ₇ are the same or different and are each independently a substituent further substituted with deuterium or one or more deuterium atoms. The method according to claim 1,
The anthracene derivative according to claim 1, wherein the anthracene derivative is any one selected from the group consisting of the following formulas (2) to (30):

[Formula 3] < EMI ID =

[Chemical Formula 4] < EMI ID =

[Chemical Formula 8] < EMI ID =

[Chemical Formula 11] [Chemical Formula 12]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 18] [Chemical Formula 18]

[Chemical Formula 20]

[Chemical Formula 22]

[Chemical Formula 25]

[Chemical Formula 30] Anode; A cathode facing the anode; And an organic layer interposed between the anode and the cathode,
Wherein the organic layer comprises at least one or more anthracene derivatives according to any one of claims 1 to 5. The method according to claim 6,
Wherein the organic layer comprises at least one selected from the group consisting of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 8. The method of claim 7,
Wherein the organic layer interposed between the anode and the cathode is a light emitting layer, and the light emitting layer comprises a host and a dopant, and the anthracene derivative is used as a host. 9. The method of claim 8,
Wherein the dopant is a compound represented by the following formulas (B) to (C):
[Chemical Formula B]

≪ RTI ID = 0.0 &

In the above formulas (B) to (C)
A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms And a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms and having O, N or S as a hetero atom,
X ₁ and X ₂ are the same or different and are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, X ₁ and X ₂ may be bonded to each other,
Y ₁ and Y ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted C1 to C24 alkyl group, a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen , And the Y ₁ To Y < ₂ > may form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero, each of which may be bonded to each other or adjacent groups, l and m are each an integer of 1 to 20,
C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each is the same or different and each cycloalkane may be a fused form And the substituted hydrogen may be further substituted with deuterium or alkyl,
B Is a single bond or _{-C (R 5) (R 6} )] p - and wherein p is an integer from 1 to 3, and when p is 2 less than the two or more of R ₅ and R ₆ are the same or different from each other,
Wherein R ₁ , R ₂ , R _{3 ,} R ₅ and R ₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, Beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron,
a is an integer of 1 to 4, and when a is 2 or more, at least 2 of R ₃ may be the same or different, and a plurality of R ₃ may be fused, and n is an integer of 1 to 4. 8. The method of claim 7,
Wherein each of the organic layers is formed by a deposition process or a solution process. The method according to claim 6,
Wherein the organic electroluminescent device is used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel illumination device, and a monochromatic or white flexible illumination device.

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