KR20140068637A - Anthracene derivatives compounds and organic electroluminescent devices comprising the same - Google Patents

Abstract

The present invention relates to a novel organic electroluminescent compound which is represented by the following [chemical formula 1] or [chemical formula 2]. The electroluminescent compound according to the present invention has high glass transition temperature, thereby having enhanced thermal stability; and can form an organic electroluminescent device having low driving voltage, high luminance, high color purity, and long-life when applying the same to the electroluminescent device.

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 exhibiting low-voltage driving, high luminance, high color purity and 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 have. In addition, an anthracene derivative containing benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like is also reported, but still has a problem that the long life, luminous efficiency and color purity are not satisfied at the same time.

Accordingly, the present invention has been made to solve the above-mentioned problems, and it is an object of the present invention to provide a novel organic electroluminescent compound having excellent luminous efficiency and long life.

Also, an organic electroluminescent device including such an organic electroluminescent compound and having excellent characteristics such as luminous efficiency, color purity, long life, and heat resistance is provided.

In order to solve the above problems, the present invention provides an organic electroluminescent compound of an anthracene derivative represented by the following formulas (1) to (2).

[Chemical Formula 1] < EMI ID =

In the above Chemical Formulas 1 to 2,

Wherein Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,

L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms (provided that when L is an anthrylene group),

X is oxygen (O), sulfur (S) or nitrogen (N)

Wherein R is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms.

The present invention also provides an organic electroluminescent device comprising an anode, a cathode opposed to the anode, and an organic layer interposed between the anode and the cathode, wherein the organic layer contains a plurality of compounds represented by Formulas 1 to 2 And at least one organic electroluminescent device.

Further, the present invention is characterized in that, in addition to various compounds represented by the above Chemical Formulas 1 to 2, the organic layer further includes at least one or more compounds represented by the following formulas (I) and (II) An organic electroluminescent device is provided.

(I) < RTI ID = 0.0 > (II)

Specific substituents of the above formulas (1) to (2), (I) and (II) will be described later.

When the organic electroluminescent compound according to the present invention is applied to an organic electroluminescent device, the device has excellent power efficiency and driving voltage characteristics, and at the same time has excellent long life, high color purity, high brightness and thermal stability.

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.

One aspect of the present invention relates to an organic electroluminescent compound represented by the following formulas (1) to (2).

[Chemical Formula 1] < EMI ID =

Wherein Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms (provided that when L is an anthrylene group), X is oxygen (O), sulfur (S) or nitrogen (N) And R is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms.

The present invention is characterized in that dihydrobenzofuran and dihydrobenzothiophene are contained in an anthracene derivative, thereby improving power efficiency and driving voltage characteristics compared with a device using a conventional anthracene derivative, and at the same time, Color purity, high luminance, and thermal stability are improved.

In the above Chemical Formulas 1 to 2, Ar may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and the aryl group having 6 to 60 carbon atoms may be a phenyl group, a 1-naphthyl group, a 2-naphthyl group, Naphthacene group, a 9-naphthacene group, a 1-pyrene group, a 3-phenanthryl group, A biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p- M-tolyl group, p-tolyl group, p-tolyl group, m-tolyl group, Methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4-t-butyl-p-terphenyl-4-yl group, fluorenyl group and the like.

Further, according to a preferred embodiment, it may be a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 9-phenanthryl group, a 2-biphenyl group, a 3-biphenyl group, May be a phenyl group, a 1-naphthyl group, a 2-naphthyl group, or a 9-phenanthryl group.

In the above Chemical Formulas 1 to 2, Ar may be a substituted or unsubstituted heteroaryl group containing N having 5 to 60 carbon atoms. According to a preferred embodiment, a pyridinyl group, a pyrimidinyl group, or a quinoline di Lt; / RTI >

A halogen atom, a hydroxyl group, a cyano group, a nitro group, an aryl group having 6 to 50 carbon atoms, a hetero atom, a carbon number having O, N or S, or a substituted or unsubstituted heteroaryl group in which Ar is a substituted aryl group or a substituted heteroaryl group; A cycloalkyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, And an arylthioxy group having 5 to 30 carbon atoms. According to a preferred embodiment, it may be further substituted with at least one member selected from the group consisting of hydrogen, deuterium, a halogen group, a hydroxyl group and a cyano group.

That is, in the present invention, an aryl group substituted with a substituent having excellent electron affinity or a heteroaryl group containing N is introduced into an anthracene 9 at an anthracene position in the above formulas (1) to (2) When the organic electroluminescent device is used in the organic electroluminescent device, it is possible to drive the device at a low voltage and improve the thermal stability.

Wherein L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and X is oxygen (O), sulfur (S) or nitrogen (N), provided that when L is an anthrylene group do.

According to a preferred embodiment, it may be a phenylene group, a biphenylene group, a terphenylene group, a quaterphenylene group, a naphthylene group, a phenanthrylene group, a chryshenylene group, a pyreneylene group, a perylenerene group, Preferably a phenylene group, a biphenylene group, or a naphthylene group.

An aryl group having 6 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms having O, N or S, a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, , An alkyloxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthioxy group having 1 to 30 carbon atoms, and an arylthioxy group having 5 to 30 carbon atoms, More preferably an aryl group having 6 to 50 carbon atoms or heteroaryl group having 3 to 50 carbon atoms having hetero atoms such as O, N or S, may be further substituted.

In the present invention, the term "substituted or unsubstituted" means a group selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, cyano, nitro, aryl, heteroaryl, cycloalkyl, alkyl, alkoxy, Substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen atom,

According to a preferred embodiment of the present invention, the above-mentioned formulas (1) to (2) may be organic electroluminescent compounds selected from the group consisting of the following formulas (3) to (126)

[Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7]

[Chemical Formula 11] [Chemical Formula 11] [Chemical Formula 12]

[Chemical Formula 13] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17]

[Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]

[Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46]

[Chemical Formula 48] [Chemical Formula 50] [Chemical Formula 51]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 60] [Chemical Formula 60]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 66]

[Formula 71] < EMI ID = 70.1 >

[Formula 75] [Formula 75] [Formula 75] [Formula 75]

[Formula 77] [Formula 79] [Formula 80] [Formula 81]

[Formula 86] < EMI ID = 86.0 >

[Chemical Formula 90] [Chemical Formula 90] [Chemical Formula 90]

[Formula 96] < EMI ID = 93.1 >

[Chemical Formula 100] [Chemical Formula 100] [Chemical Formula 98]

[Formula 10] < EMI ID = 102.1 >

[Formula 110] [Formula 110] [Formula 111] [Formula 111]

[Chemical Formula 112] [Chemical Formula 113]

[Formula 121] [Formula 120] [Formula 120] [Formula 121]

[Formula 124] [Formula 125] [Formula 126]

According to another aspect of the present invention, there is provided an organic electroluminescent device including at least one of compounds represented by Formulas 1 to 2, wherein the organic electroluminescent device includes 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 of various compounds represented by Formula 1.

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 Formulas 1 to 2 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 Formula 1 is used as a host compound in the light emitting layer, and various fluorescent or phosphorescent dopant materials are included therein to show characteristics such as luminous efficiency, color purity and long life .

According to a preferred embodiment, at least one or more dopant compounds represented by the following formulas (I) and (II) may be further included.

(I) < RTI ID = 0.0 > (II)

In the above formula (I)

A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms and is preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, picene, triphenylene, perylene, pentacene . At this time, A may be a compound represented by the following formulas (A1) to (A10).

[A1] [A2] [A3] [A4] [A5]

[A6] [A7] [A8] [A9] [A10]

B ₁ to B ₂ in the above [A3] are independently selected from the group consisting of hydrogen, a heavy hydrogen atom, 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 alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 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, (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a di (substituted or unsubstituted C1-C60 alkyl) amino group, Unsubstituted An aryl group having 6 to 60 carbon atoms) amino group, and each of B ₁ to B ₂ is the same or different from each other and can form a condensed ring with the adjacent groups.

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

Y ₁ to Y ₂ each independently represent 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 alkyl group having 1 to 24 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a cyano group, a halogen group, a substituted or unsubstituted carbon number of 6 A substituted or unsubstituted alkyl group having 1 to 40 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, boron, deuterium, Y ₁ to Y ₂ are the same or different from each other and can form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups adjacent to each other.

More specifically, each of X ₁ to X ₂ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalanylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthylene group, Substituted or unsubstituted phenanthrenes, substituted or unsubstituted phenanthrenes, substituted or unsubstituted phenanthrenes, substituted or unsubstituted phenanthrenes, substituted or unsubstituted phenanthrenes, substituted or unsubstituted phenanthrenes, A substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group , A substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, A substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted imidazolinylene group, a substituted or unsubstituted pyrazolylene group, A substituted or unsubstituted imidazopyrimidinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, A substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, A substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted sienolylene group, a substituted or unsubstituted indazolone group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinazolinylene group, A substituted or unsubstituted phenanthrene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted pyrene group, A substituted or unsubstituted thiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted inter A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted triazylene group, or a substituted or unsubstituted oxadiazolene group .

l and m are each an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (II)

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 cycloalkane may be fused. The substituted hydrogen may be substituted with deuterium or alkyl, and may be the same or different from each other.

Z is a single bond or _{- [C (R 5) (} R 6)] p - and wherein p is being from 1 to 3 integer, not less than p 2 2 or R ₅ and R ₆ are each the same or different,

R ₁ to R ₆ independently represent 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 alkylthio 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 carbon number 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 arylthio group having 1 to 60 carbon atoms (Substituted or unsubstituted C 6 -C 60 aryl) amino group, di (substituted or unsubstituted C 6 -C 60 alkyl) amino group, or a substituted or unsubstituted C 6 -C 60 arylamino group, An amino 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,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer of 1 to 4.

More specifically, R ₁ , R ₂ and R ₃ Are independently of each other 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 sulfonic acid group or a salt thereof, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted phenyl group, A substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted hepthalenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, Substituted or unsubstituted fluorenyl groups, substituted or unsubstituted phenanenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted anthryl groups, substituted or unsubstituted fluororanes A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted imidazolidinyl group, a substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted phthalazinyl group, A substituted or unsubstituted indazolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted sinolnirinyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted carbazolyl group , A substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted paranyl group, a substituted or unsubstituted chromenyl group, a substituted or unsubstituted furanyl group, A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted isoxazolyl group, , A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted oxadiazolyl group Emitter can be selected. In the present invention, Z in the formula (IV) may be a single bond.

The amine derivative substituent bonded to A and Z in the above formulas (I) and (II) may be any one selected from the group consisting of the following [substituents 1] to [Substituent 52], but is not limited thereto .

[Substituent 1] [Substituent 2] [Substituent 3] [Substituent 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 25] [Substituent 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 group 52]

In the above [substituents 1] to [52], R is the same or different from each other and is 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 alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group 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 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, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted (having 6 to 60 carbon atoms) amino group, a di (substituted) amino group having 1 to 60 carbon atoms, Or an unsubstituted aryl group having 6 to 60 carbon atoms) amino 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 Each of which may be substituted from 1 to 12, and each substituent may form a condensed ring with adjacent groups.

According to a preferred embodiment of the present invention, the organic electroluminescent device according to the present invention comprises a cathode, a cathode facing the anode, And at least one of various compounds represented by the following general formula (2).

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), m-MTDATA (4,4' -methylphenylph 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 examples. The following examples are given by way of illustration only and the present invention is not limited thereto.

Synthesis Example 1. Synthesis of Formula 3

1- (1) Intermediate 1-a was synthesized according to Reaction Scheme 1 below.

[Reaction Scheme 1]

1-a

Dibromophenol (10.2 g, 40 mmol), 1,2-dibromoethane (7.6 g, 40 mmol), sodium hydroxide (1.76 g, 44 mmol) and 60 mL of water were placed in a 250 mL round bottom flask The mixture was refluxed overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, washed with an aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, and extracted with ethyl acetate. The organic layer was separated from the organic layer and water, treated with magnesium sulfate, and then concentrated under reduced pressure. Purification by column chromatography gave Intermediate 1-a (10.0 g, 70%).

1- (2) Intermediate 1-b was synthesized according to Reaction Scheme 2 below.

[Reaction Scheme 2]

1-b

A 1 L round bottom flask 1-a (34.5 g, 96 mmol) was added, dissolved in 340 mL of THF and 80 mL of hexane, and then cooled to -78 ° C. 2.5 M normal butyl lithium (39 mL, 97.5 mmol) was added dropwise to the cooled reaction solution. After the dropwise addition, the mixture was stirred at the same temperature for 30 minutes and then heated to 0 占 폚. After completion of the reaction, 300 mL of water was added, and the mixture was stirred and extracted with ethyl acetate. The organic layer was separated, the water was removed with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 1-b. (15.0 g, 78%)

1- (3) According to Scheme 3, intermediate 1-c was synthesized:

[Reaction Scheme 3]

1-c

To a 300 mL round bottom flask was added 1-b (15 g, 75 mmol), bis (dipinacoleato) diboron (24.9 g, 98 mmol), PdCl2 (dppf) (1.2 g, 2 mmol), potassium acetate g, 226 mmol), 150 mL of toluene was added, and the mixture was refluxed overnight. After completion of the reaction, the reaction mixture was hot filtered and the filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 1-c (12.0 g, 64%).

1- (4) Intermediate 1-d was synthesized according to Scheme 4 below:

[Reaction Scheme 4]

1-d

To a 1 L round bottom flask reactor was added 1-bromo-4-iodobenzene (30.0 g, 106 mmol), 1-c (31.3 g, 0.127 mol), tetrakis (triphenylphosphine) palladium mol) and potassium carbonate (44.0 g, 0.318 mol) were placed, and 150 mL of toluene, 150 mL of dioxane and 60 mL of water were added. The temperature of the reactor was raised to 90 占 폚 and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 1-d (20.0 g, 68.5%).

1- (5) Compound (3) was synthesized according to Reaction Scheme 5 below.

[Reaction Scheme 5]

(3)

(10.0 g, 36 mmol), 10-phenylanthracene-9-boronic acid (13.0 g, 44 mmol) and tetrakis (triphenylphosphine) palladium (0.8 g, 1 mmol) were added to a 300 mL round- , Potassium carbonate (115.1 g, 109 mmol) were placed, and 50 mL of toluene, 50 mL of tetrahydrofuran, and 20 mL of water were added. The temperature of the reactor was raised to 110 < 0 > C and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature and 100 mL of methanol was added to crystallize. Filter the resulting solid and wipe it with water and acetone. A hot filter and recrystallization gave the formula 3 (8.0 g, yield 49%).

MS [M + 1]: 449

Synthesis Example 2. Synthesis of Compound (8)

2- (1) According to Reaction Scheme 6, intermediate 2-a was synthesized.

[Reaction Scheme 6]

2-a

Intermediate 2-a (21 g, 72%) was obtained using the same method except that 1-bromo-3-iodobenzene was used in place of 1-bromo-4-iodobenzene in Synthesis Example 1- (4) %).

2- (2) Synthesis of formula (8)

(8) was synthesized according to the following Reaction Scheme 7.

[Reaction Scheme 7]

8

(6.0 g, 52.6%) was obtained by using the same method except that Intermediate 2-a was used in place of Intermediate 1-d in Synthesis Example 1- (5).

MS [M + 1]: 449

Synthesis Example 3. Synthesis of Compound (13)

3- (1) According to the following Reaction Scheme 8, Intermediate 3-a was synthesized.

[Reaction Scheme 8]

3-a

1-Aminonaphthalene (200 g, 1.358 mol) and 800 mL of acetic acid were added to a 5 L round bottom flask reactor and the temperature of the reactor was cooled to 0 占 폚. Bromine was diluted in 1500 mL of acetic acid and added dropwise to the reactor. When dropwise addition was completed, the temperature was raised to 60 DEG C and stirred for 1 hour. When the reaction was completed, the temperature of the reactor was lowered to room temperature, and the resulting salt was filtered. The filtered salt was added to an aqueous solution of sodium hydroxide and stirred. The resulting solid was filtered and 3-a (200 g, 49%) was obtained by column chromatography.

3- (2) Intermediate 3-b was synthesized according to Reaction Scheme 9 below.

[Reaction Scheme 9]

3-b

3-a (45.0 g, 0.15 mol) and 650 mL of acetic acid were added to a 2 L round bottom flask reactor and cooled to 0 ° C. 112.5 mL of propionic acid was added to the reactor and stirred. Then, 12 g of sodium nitrate was added and stirred for 30 minutes. The reaction solution was poured into ice water at 0 ° C, and the resulting solid was filtered, and water was further added to the filtrate and stirred to produce a yellow precipitate. The resulting precipitate was filtered and dried to obtain Intermediate 3-b (17 g, yield 45.5% ).

3- (3) Intermediate 3-c was synthesized according to Reaction Scheme 10 below.

[Reaction Scheme 10]

3-c

3-b (14.3 g, 0.057 mol) was added to a 2 L round bottom flask reactor under a nitrogen stream and dissolved in 300 mL of ethanol. 0.7 g of sodium borohydride was added to the reactor and stirred for 12 hours. An aqueous hydrochloric acid solution containing 14 mL of water and 14 mL of hydrochloric acid was added dropwise to the reactor and stirred for 1 hour. When the reaction was completed, 10% aqueous sodium hydroxide solution was added to neutralize the solution. Upon completion of the neutralization, the mixture was extracted with methylene chloride and water, and the organic layer was distilled off under reduced pressure. Column chromatography and recrystallization gave intermediate 3-c (10.1 g yield 78%).

3- (4) According to the following reaction scheme 11, intermediate 3-d was synthesized.

[Reaction Scheme 11]

3-d

(10.0 g, 45 mmol), 10-phenylanthracene-9-boronic acid (16.0 g, 54 mmol), tetrakis (triphenylphosphine) palladium (0) , 1 mmol) and potassium carbonate (18.6 g, 134 mmol) were placed, and 50 mL of toluene, 50 mL of tetrahydrofuran and 20 mL of water were added. The temperature of the reactor was raised to 110 < 0 > C and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature and extracted with ethyl acetate. The organic layer was separated, concentrated under reduced pressure, and separated by column chromatography to obtain intermediate 3-d (11.5 g, yield 64.7%).

3- (5) According to Reaction Scheme 12, intermediate 3-e was synthesized.

[Reaction Scheme 12]

3-e

3-d (12.0 g, 0.030 mol) was added to a 300 mL round bottom flask reactor and dissolved in 200 mL of dichloromethane under a nitrogen stream. Pyridine (4.8 g, 0.061 mol) was added dropwise at room temperature, and the mixture was stirred at the same temperature for 30 minutes. After the temperature of the reactor was lowered to 0 ° C, trifluoromethanesulfonic acid hydride (11.10 g, 0.039 mol) was slowly added dropwise. When the dropping was completed, the temperature of the reactor was raised to room temperature and stirred for 1 hour. When the reaction was completed, 5 mL of 2.0 M hydrochloric acid was added. The mixture was extracted with dichloromethane and water, the organic layer was filtered through celite, and the filtrate was concentrated and recrystallized with hexane to obtain intermediate 3-e (13.0 g, 81.3%).

3- (6) Compound (13) was synthesized according to Reaction Scheme 13 below.

[Reaction Scheme 13]

Formula 13

(11.0 g, 0.021 mol), 3-e (6.1 g, 0.025 mol), tetrakis (triphenylphosphine) palladium (0) (0.31 g, 0.0006 mol), potassium Carbonate (5.75 g, 0.041 mol) was added, and toluene (77 mL), ethanol (33 mL) and water (22 mL) were added. The temperature of the reactor was raised to 90 < 0 > C and stirred for 5 hours. When the reaction was completed, the temperature of the reactor was lowered to room temperature and crystallized by adding 100 mL of methanol. The resulting solid was filtered, wiped with water and acetone, and subjected to hot filtration and recrystallization to obtain the compound (13). (5.30 g, 51.4%).

MS [M + 1]: 499

Synthesis Example 4. Synthesis of Compound (18)

4- (1) According to the following Reaction Scheme 14, Intermediate 4-a was synthesized.

[Reaction Scheme 14]

4-a

Intermediate 4-a (15 g, 72%) was obtained using the same method except that 4-bromonaphthol was used in place of 1-bromo-4-iodobenzene in Synthesis Example 1- (4).

4- (2) According to Reaction Scheme 15, Intermediate 4-b was synthesized.

[Reaction Scheme 15]

4-b

Intermediate 4-b was obtained using the same method except that Intermediate 4-a was used instead of Intermediate 3-d in Synthesis Example 3- (5). (17.8 g, 78.9%).

4- (3) According to Reaction Scheme 16 below, Formula 18 was synthesized.

[Reaction Scheme 16]

18

18 was obtained in the same manner as in Synthesis Example 3- (6) except that Intermediate 4-b was used instead of Intermediate 3-e and 10-Phenylanthracene-9-boronic acid was used instead of Intermediate 1-c . (4.5 g, 78.9%)

MS [M + 1]: 499

Synthesis Example 5. Synthesis of Compound (23)

5- (1) According to Reaction Scheme 17, Intermediate 5-a was synthesized.

[Reaction Scheme 17]

5-a

A 1 L round-bottom flask reactor was charged with 33 g of sodium hydroxide and 329 mL of water at room temperature to prepare a 2.5 M aqueous solution, which was then dissolved by adding 1,5-dihydroxynaphthalene (50 g, 0.312 mol). Dimethyl sulfate (43.3 g, 0.343 mol) was slowly added dropwise under the same conditions after the reaction solution of the reactor was bubbled with nitrogen. After completion of dropwise addition, the mixture is stirred for 30 minutes. After the reaction is completed, the reaction mixture is extracted with ethyl acetate and water. The organic layer is discarded, and 10M hydrochloric acid is added to the aqueous layer. Ethyl acetate is added to the fish sediment and extracted. The organic layer is subjected to distillation. Column chromatography afforded Intermediate 5-a (35 g, yield 64.8%).

5- (2) According to the following reaction scheme 18, intermediate 5-b was synthesized.

[Reaction Scheme 18]

5-b

Intermediate 5-b was obtained using the same method except that Intermediate 5-a was used instead of Intermediate 3-d in Synthesis Example 3- (5). (18.7 g, 78.9%).

5- (3) According to the following reaction scheme 19, intermediate 5-c was synthesized

[Reaction Scheme 19]

5-c

Intermediate 5-c was obtained using the same method except that Intermediate 5-b was used instead of Intermediate 3-e in Synthesis Example 3- (6). (20 g, 65.2%).

5- (4) According to Reaction Scheme 20, intermediate 5-d was synthesized

[Reaction Scheme 20]

5-d

Intermediate 5-c (50 g, 0.213 mol) was added to a 2 L round bottom flask reactor and dissolved in 600 mL of dichloromethane. The temperature of the reactor was cooled to -78 ° C and tribromoboron (53.17 g, 0.234 mol) was slowly added dropwise under a stream of nitrogen. When the addition was complete, the temperature of the reactor was raised to room temperature and stirred for 30 minutes. When the reaction was completed, a saturated aqueous sodium bicarbonate solution was slowly added dropwise and stirred for 1 hour. The mixture was extracted with dichloromethane and water, and the organic layer was concentrated under reduced pressure. Recrystallization was performed using dichloromethane and hexane to obtain intermediate 5-d. (40 g, 89%).

5- (5) According to Reaction Scheme 21, Intermediate 5-e was synthesized.

[Reaction Scheme 21]

5-e

Intermediate 5-e was obtained using the same method except that Intermediate 5-d was used instead of Intermediate 3-d in Synthesis Example 3- (5). (15 g, 78.9%).

5- (6) According to Reaction Scheme 22, a compound of Formula 23 was synthesized.

[Reaction Scheme 22]

Formula 23

(23) was obtained by using the same method as Intermediate 5-e instead of Intermediate 3-e in Synthesis Example 3- (6), but using 10-phenylanthracene-9-boronic acid instead of Intermediate 1-c . (5 g, 76.9%)

MS [M + 1]: 499

Synthesis Example 6. Synthesis of Compound (32)

6- (1) According to Reaction Scheme 23, Intermediate 6-a was synthesized.

[Reaction Scheme 23]

6-a

3-Bromophorophenol (30.0 g, 0.159 mol) was added to a 1 L round bottom flask, and sodium hydroxide (63.47 g, 1.587 mol) was dissolved in 500 mL of water. 2-Chloroacetic acid (16.5 g, 0.175 mol) was added dropwise to the reaction solution as 100 mL of water. The mixture was stirred at room temperature for 30 minutes and then refluxed for 1 hour and 30 minutes. After the reaction was completed, the reaction mixture was cooled to room temperature, acidified with 2 mol of hydrochloric acid to pH 1, and extracted with acetic acid. The organic layer was separated, water was removed with magnesium sulfate, and the filtrate was concentrated under reduced pressure to obtain Intermediate 6-a. (31.0 g, 79.1%).

6- (2) According to Reaction Scheme 24, intermediate 6-b was synthesized.

[Reaction Scheme 24]

6-b

6-a (24.5 g, 0.099 mol) and thionyl chloride (70 mL) were added to a 300 mL round bottom flask, and the mixture was stirred under reflux for 2 hours. The reaction solution was cooled to room temperature and then the solvent was removed under reduced pressure. After removal of the solvent, the remaining oil-like material was dissolved in 100 mL of 1,2-dichlorobenzene and aluminum trichloride (17.18 g, 0.128 mol) was added in four portions over 5 minutes. The reaction solution was stirred at 45 ° C for 1 hour and then cooled to room temperature. The cooled solution was poured into ice water and basified with 2 M aqueous sodium hydroxide solution. After extraction with diethyl ether, the aqueous layer was acidified again and extracted with ethyl acetate. The organic layer was dehydrated with magnesium sulfate and then concentrated under reduced pressure. Separation by column chromatography gave intermediate 6-b (16.0 g, 65.3%).

6- (3) According to Reaction Scheme 25, intermediate 6-c was synthesized.

[Reaction Scheme 25]

Intermediate 6-c

(16.0 g, 0.070 mol) and trifluoroacetic acid (192 mL) were added with triethylsilane (23.6 mL) for 4 h Lt; / RTI > After completion of the reaction, the reaction mixture was cooled to room temperature and water was added dropwise. After extraction with ethyl acetate and washing with an aqueous sodium chloride solution, the organic layer was separated, water was removed with magnesium sulfate, and the filtrate was concentrated under reduced pressure. Separation by column chromatography gave intermediate 6-c (13.2 g, 87.9%).

6- (4) According to Reaction Scheme 26, intermediate 6-d was synthesized.

[Reaction Scheme 26]

6-d

Intermediate 6-d was obtained (12 g, 65.9%) using the same method as Intermediate 6-c instead of Intermediate 1-b in Synthesis Example 1- (3).

6- (5) According to Reaction Scheme 27, Intermediate 6-e was synthesized.

[Reaction Scheme 27]

6-e

5-Amino-2-naphthol (24 g, 0.151 mol), sulfuric acid (48 mL) and acetic acid (72 mL) were placed in a 500 mL round bottom flask reactor and the temperature of the reactor was lowered to 0 ° C. At the same temperature, an aqueous solution of sodium nitrite (12.5 g, 0.181 mol) dissolved in 50 mL of water was slowly added dropwise, and the internal temperature of the reactor was maintained at 0-5 ° C. When the dropping was completed, the temperature of the reactor was raised to 5 캜 and stirred for 30 minutes. At the same temperature, 0.7 g of urea and 30 g of ice are added to the reactor to lower the temperature of the reactor. An aqueous solution of potassium iodide (75.1 g, 0.452 mol) dissolved in 100 mL of water was slowly added dropwise. When the addition was complete, the temperature was raised to room temperature and stirred overnight. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water, and the organic layer was distilled off under reduced pressure. Column chromatography and recrystallization gave intermediate 6-d (9.5 g, 25%).

6- (6) Intermediate 6-f was synthesized according to Scheme 28 below.

[Reaction Scheme 28]

6-f

Intermediate 6-f (16.2 g, 72%) was obtained using the same method except that Intermediate 6-c was used instead of Intermediate 3-c in Synthesis Example 3- (4).

6- (7) According to Reaction Scheme 29, intermediate 6-g was synthesized.

[Reaction Scheme 29]

6-g

Intermediate 6-g was obtained (12 g, 78%) using the same method except that Intermediate 6-f was used instead of Intermediate 3-d in Synthesis Example 3- (5).

6- (8) According to Reaction Scheme 30, Formula 32 was synthesized.

[Reaction Scheme 30]

(32)

(32 g) was obtained in the same manner as in the above Synthesis Example 3- (6) except that Intermediate 6-g was used instead of Intermediate 3-e, and Intermediate 6-d was used instead of Intermediate 1-c. %).

MS [M + 1]: 515

Synthesis Example 7. Synthesis of Compound (50)

7- (1) According to Reaction Scheme 31, intermediate 7-a was synthesized

[Reaction Scheme 31]

7-a

Aluminum trichloride (40.0 g, 0.310 mol) was added to a 2 L round bottom flask and purged with nitrogen for 10 minutes. 300 mL of benzene was added and the mixture was heated at 60 ° C for 2 hours. 4-Bromo-naphthol was dissolved in 300 mL of benzene and then slowly added dropwise. When the addition was completed, the mixture was stirred for 30 minutes. When the reaction was completed, the temperature of the reactor was lowered to room temperature and the reaction solution was slowly poured into 6M hydrochloric acid at 0 ° C. And the mixture was stirred at 0 ° C for 30 minutes. The solution in the reactor was extracted. The extracted organic layer was extracted three times with dichloromethane and water again. Again, it was extracted again with sodium bicarbonate, water and dichloromethane. The organic layer was subjected to vacuum distillation and column chromatography was used to obtain intermediate 7-a (16.4 g, 39.5%).

7- (2) According to Reaction Scheme 32, Intermediate 7-b was synthesized.

[Reaction Scheme 32]

7-b

The intermediate 7-a (16.4 g, 0.074 mol) was added to a 500 mL round bottom flask and dissolved in 160 mL of acetonitrile. The temperature of the reactor was maintained at 15 占 폚. N-Bromo-succiimide (14.47 g, 0.081 mol) was dissolved in 150 mL of acetonitrile and slowly added dropwise to the reactor and stirred for 2 hours. The insoluble solid was removed by silica gel filtration. The filtrate was filtered under reduced pressure and recrystallized with hexane. Intermediate 7-b was obtained. (20.4 g, 92%).

7- (3) According to Reaction Scheme 33, intermediate 7-c was synthesized.

[Reaction Scheme 33]

7-c

Intermediate 7-c was obtained in the same manner as Intermediate 7-b, except that Intermediate 6-d was used instead of Intermediate 7-b and Intermediate 1-c in place of 1-Bromo 4-Iodobenzene in Synthesis Example 1- (4) (15 g, 48%).

7- (4) According to the following reaction scheme 34, intermediate 7-d was synthesized.

[Reaction Scheme 34]

7-d

Intermediate 7-d was obtained using the same method except that Intermediate 7-c was used instead of Intermediate 3-d in Synthesis Example 3- (5). (10 g, 72.4%)

7- (5) According to Reaction Scheme 35, 50 was synthesized.

[Reaction Scheme 35]

50

Intermediate 7-d was obtained in the same manner as Intermediate 3-e in Synthesis Example 3- (6) except that 10- (2-naphthyl) anthracene 9-boronic acid was used instead of Intermediate 1-c (50). (5.5 g, 45%).

MS [M + 1]: 641

Synthesis Example 8. Synthesis of Compound (52)

8- (1) Compound (52) was synthesized according to Reaction Scheme 36 below.

[Reaction Scheme 36]

Formula 52

(52) was obtained using the same method except that 10- (2-naphthyl) anthracene 9-boronic acid was used in place of 10-phenylanthracene 9-boronic acid in Synthesis Example 1- (5) , 72.6%).

MS [M + 1]: 499

Synthesis Example 9. Synthesis of Formula 116

9- (1) Intermediate 9-a was synthesized according to Reaction Scheme 37 below.

[Reaction Scheme 37]

9-a

Intermediate 9-a (16.2 g, 78%) was obtained using the same method except for using beta-chloropropionic acid instead of 2-chromoacetic acid in Synthesis Example 6- (1).

9- (2) Intermediate 9-b was synthesized according to Scheme 38 below.

[Reaction Scheme 38]

9-b

Intermediate 9-b (15 g, 63%) was obtained using the same method except for using Intermediate 9-a instead of Intermediate 6-a in Synthesis Example 6- (2).

9- (3) Intermediate 9-c was synthesized according to Scheme 39 below.

[Reaction Scheme 39]

9-c

Intermediate 9-c (12 g, 60%) was obtained using the same method except for using Intermediate 9-b instead of Intermediate 6-b in Synthesis Example 6- (3).

9- (4) Intermediate 9-d was synthesized according to Reaction Scheme 40 below.

[Reaction Scheme 40]

9-d

Intermediate 9-d was obtained (10 g, 61.9%) in the same manner as in Synthesis Example 1- (3), except that Intermediate 9-c was used instead of Intermediate 1-b.

9- (5) Intermediate 9-e was synthesized according to Reaction Scheme 41 below.

[Reaction Scheme 41]

9-e

Except that Intermediate 9-d was used instead of Intermediate 7-b and Intermediate 1-c in place of 1-Bromo-4-iodobenzene in Synthesis Example 1- (4) (10 g, 49%).

9- (6) Intermediate 9-f was synthesized according to Reaction Scheme 42 below.

[Reaction Scheme 42]

9-f

Intermediate 9-f was obtained (12 g, 85.4%) using the same method as Intermediate 9-e instead of Intermediate 3-d in Synthesis Example 3- (5).

9- (7) 116 was synthesized according to Reaction Scheme 43 below.

[Reaction Scheme 43]

(116)

Except that Intermediate 9-f was used instead of Intermediate 3-e in Synthesis Example 3- (6), except that 10- (2-naphthyl) anthracene 9-boronic acid was used instead of Intermediate 1-c, 116 < / RTI > was obtained (5.5 g, 47%).

MS [M + 1]: 655

Synthesis Example 10. Synthesis of Formula 89

10- (1) Intermediate 10-a was synthesized according to Scheme 44 below.

[Reaction Scheme 44]

10-a

Except that 4-bromophenol was used instead of 3-bromophenol and beta-bromopropionic acid was used in place of 2-chloroacetic acid in Synthesis Example 6- (1), intermediate 10-a (20 g, 78%).

10- (2) Intermediate 10-b was synthesized according to Reaction Scheme 45 below.

[Reaction Scheme 45]

10-b

Intermediate 10-b (11 g, 60%) was obtained using the same method except that Intermediate 10-a was used in place of Intermediate 6-a in Synthesis Example 6- (2).

10- (3) Intermediate 10-c was synthesized according to Scheme 46 below.

[Reaction Scheme 46]

10-c

Intermediate 10-c (8 g, 72%) was obtained using the same method except that Intermediate 10-b was used instead of Intermediate 6-b in Synthesis Example 6- (3).

10- (4) Intermediate 10-d was synthesized according to Reaction Scheme 47 below.

[Reaction Scheme 47]

10-d

Intermediate 10-d was obtained (10 g, 63.9%), except that Intermediate 10-c was used instead of Intermediate 1-b in Synthesis Example 1- (3).

10- (5) Intermediate 10-e was synthesized according to Reaction Scheme 48 below.

[Reaction Scheme 48]

10-e

Except that 1-bromo-3-iodobenzene was used instead of 1-bromo-4-iodobenzene and Intermediate 10-d was used instead of Intermediate 1-c in Synthesis Example 1- (4) To obtain Intermediate 10-e (21 g, 72%).

(6) The compound of the formula 89 was synthesized according to the following reaction scheme 49.

[Reaction Scheme 49]

Formula 89

89 (4.0 g, 70.6%) was obtained using the same method except that Intermediate 10-e was used instead of Intermediate 1-d in Synthesis Example 1- (5).

MS [M + 1]: 463

Examples 1 to 10. 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 adjusted to have a pressure of 1 × 10 ^-6 torr. Then, an organic material was deposited on the ITO using DNTPD (700 Å), NPD (300 Å), organic electroluminescent compound + BD1 %) (300 Å), Alq ₃ (350 Å), LiF (5 Å) and Al (1,000 Å). The structure of BD1 is as follows.

[BD1]

Comparative Example

The organic light emitting diode device for the comparative example was fabricated in the same manner except that BH1 and BH2, which are generally used as a fluorescent host material, were used instead of the compound prepared by the invention in the device structure of the embodiment, and the structures of BH1 and BH2 Are as follows.

[BH1] [BH2]

division Host Dopant V Cd / ㎡ CIEx CIEy T97 (Hr) Comparative Example 1 BH1 BD1 4.8 730 0.14 0.12 23 Comparative Example 2 BH2 BD1 4.7 560 0.14 0.12 30 Example 1 3 BD1 3.8 787 0.14 0.13 145 Example 2 8 BD1 3.8 753 0.14 0.13 125 Example 3 13 BD1 3.8 747 0.14 0.14 163 Example 4 18 BD1 3.8 798 0.14 0.14 125 Example 5 23 BD1 3.7 781 0.14 0.13 110 Example 6 32 BD1 3.7 786 0.14 0.14 178 Example 7 50 BD1 3.9 776 0.14 0.14 110 Example 8 52 BD1 3.9 772 0.14 0.13 120 Example 9 116 BD1 3.7 808 0.14 0.14 153 Example 10 89 BD1 3.6 814 0.14 0.13 136

As shown in Table 1, the anthracene derivative according to the present invention contains dihydrobenzofuran or dihydrobenzothiophene through an arylene linking group. Therefore, the anthracene derivative of the present invention is superior in luminance and long life In the first embodiment.

In addition, as a result of examination by the present invention, the present inventors have found that, among many arylene linking groups, when a dihydrobenzothiophene or dihydrobenzothiophene is introduced into anthracene using a phenyl group or a 1-naphthyl group as a linking group, .

Further, when the anthracene derivative compound according to the present invention is used as a host and the pyrene derivative compound according to the present invention is used as a dopant and a light emitting layer material of an organic electroluminescent device, an organic electroluminescent device having more excellent luminous efficiency and long- Implementation is possible.

T97 means the time required for the luminance to be reduced to 97% of the initial luminance.

10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims (9)

An anthracene derivative represented by the following Chemical Formulas 1 to 2:
[Chemical Formula 1] < EMI ID =

In the above Chemical Formulas 1 to 2,
Wherein Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms,
L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms (provided that when L is an anthrylene group),
X is oxygen (O), sulfur (S) or nitrogen (N)
Wherein R is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms. The method according to claim 1,
Each of Ar 1 and R 2 is independently selected from the group consisting of hydrogen, deuterium, a halogen group, a hydroxy group, a cyano group, a nitro group, an aryl group having 6 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms having 0, A cycloalkyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthioxy group having 1 to 30 carbon atoms and an arylthioxy group having 5 to 30 carbon atoms Wherein the anthracene derivative is further substituted with one or more kinds of anthracene derivatives. The method according to claim 1,
Wherein L is an aryl group having 6 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms having 0, N or S as the hetero atom, a cycloalkyl group having 3 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, An aryloxy group having 6 to 30 carbon atoms, an alkylthioxy group having 1 to 30 carbon atoms, and an arylthioxy group having 5 to 30 carbon atoms. The method according to claim 1,
The anthracene derivative according to any one of claims 1 to 2, wherein the anthracene derivative is any one selected from the group consisting of the following formulas (3) to (126).
[Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7]

[Chemical Formula 11] [Chemical Formula 11] [Chemical Formula 12]

[Chemical Formula 13] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17]

[Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22]

[Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46]

[Chemical Formula 48] [Chemical Formula 50] [Chemical Formula 51]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 60] [Chemical Formula 60]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 66]

[Formula 71] < EMI ID = 70.1 >

[Formula 75] [Formula 75] [Formula 75] [Formula 75]

[Formula 77] [Formula 79] [Formula 80] [Formula 81]

[Formula 86] < EMI ID = 86.0 >

[Chemical Formula 90] [Chemical Formula 90] [Chemical Formula 90]

[Formula 96] < EMI ID = 93.1 >

[Chemical Formula 100] [Chemical Formula 100] [Chemical Formula 98]

[Formula 10] < EMI ID = 102.1 >

[Formula 110] [Formula 110] [Formula 111] [Formula 111]

[Chemical Formula 112] [Chemical Formula 113]

[Formula 121] [Formula 120] [Formula 120] [Formula 121]

[Formula 124] [Formula 125] [Formula 126]

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 4. 6. The method of claim 5,
Wherein the organic layer further comprises an amine compound represented by the following formula (I): < EMI ID =
(I)

In the above formula (I)
A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,
Y ₁ And Y ₂ are the same or different from each other 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 aryl group having 1 to 24 carbon atoms 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 aryloxy group having 6 to 24 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, boron, deuterium and hydrogen Y ₁ and Y ₂ may form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero linked to adjacent groups,
l and m are each an integer of 1 to 20, and n is an integer of 1 to 4. 6. The method of claim 5,
Wherein the organic layer further comprises an amine compound represented by the following formula II:
[Formula II]

In the above formula (II)
X is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
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, a plurality of C _y are the same or different from each other, and each cycloalkane has a fused form And when C _y is substituted cycloalkyl, it is substituted with at least one selected from deuterium and alkyl,
Z is a single bond or _{- [C (R 5) (} R 6)] p - and wherein p is being from 1 to 3 integer, not less than p 2 2 or R ₅ and R ₆ are each the same or different,
R ₁ to R ₆ independently represent 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 alkylthio 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 carbon number 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 arylthio group having 1 to 60 carbon atoms (Substituted or unsubstituted C 6 -C 60 aryl) amino group, di (substituted or unsubstituted C 6 -C 60 alkyl) amino group, or a substituted or unsubstituted C 6 -C 60 arylamino group, An amino 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, and boron,
a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer of 1 to 4. 8. The method according to claim 6 or 7,
Wherein the substituents of the amine derivatives respectively bonded to A and Z are any one selected from the group consisting of substituents 1 to 52 below.
[Substituent 1] [Substituent 2] [Substituent 3] [Substituent 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 25] [Substituent 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 group 52]

In the above [substituent groups 1] to [substituent group 52]
R is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, Or 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 alkoxy group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylthio 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 5 to 60 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 (alkyl) amino group having 1 to 60 carbon atoms, (Substituted or unsubstituted C1 to C60 alkyl) amino group, or a substituted or unsubstituted C6 to C60 aryl) amino group, a di (substituted or unsubstituted C6 to C60 aryl) amino 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, and boron, and is connected to adjacent substituents to form a condensed ring can do. 6. The method of claim 5,
Wherein the organic layer comprises one or more layers including a light emitting layer, and the organic layer further comprises at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.

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