KR20090044975A - Anthracene-based compound and organic light emitting device employing the same - Google Patents

Abstract

An anthracene-based compound having a substituent represented by Formula 1 or Formula 2 and an organic electroluminescent device using the same are provided.

[Formula 1]

[Formula 2]

In Formula 1 or Formula 2, R is hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1 ~ C20 alkyl group, substituted or unsubstituted C3 ~ C20 cycloalkyl group, substituted or unsubstituted C5 -C30 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2-C30 Is a heteroaryl group, L is a divalent linking group, substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene, l is an integer of 0 to 3.

Description

Anthracene-based compound and organic light emitting device using same

The present invention relates to an anthracene-based compound and an organic electroluminescent device using the same, and more particularly, an anthracene-based compound having a pyridinylquinoline-based or pyridinylisoquinoline-based substituent introduced therein, and formed using the same. An organic electroluminescent element provided with an organic film.

The organic electroluminescent device is an active light emitting display device using a phenomenon in which light is generated while electrons and holes are combined in an organic film when a current flows through a thin film of fluorescent or phosphorescent organic compound (hereinafter referred to as an organic film). It is possible, and the parts are simple, the manufacturing process is simple, and has the advantage of ensuring a wide viewing angle in high quality. In addition, video can be fully realized, high color purity can be realized, and low power consumption and low voltage can be driven to have electrical characteristics suitable for portable electronic devices.

Eastman Kodak Co. has developed a multi-layered organic electroluminescent device using an aluminum quinolinol complex layer and a triphenylamine derivative layer (US Pat. No. 4,885,211). As the low molecular weight is used in forming the organic light emitting layer, various light emission from the ultraviolet ray to the infrared ray region is possible. (US Pat. No. 5,151,629).

The light emitting device is a self-luminous device and has a wide viewing angle, excellent contrast, and fast response time. The light emitting device includes an inorganic light emitting device using an inorganic compound and an organic light emitting device using an organic compound (OLED) in the light emitting layer, and the organic light emitting device has higher luminance and driving than the inorganic light emitting device. Much research has been conducted in that the voltage and response speed characteristics are excellent and multicoloring is possible.

The organic light emitting device generally has a stacked structure of anode / organic light emitting layer / cathode, and includes anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode or anode / hole injection layer / hole transport layer / light emitting layer / hole It may also have various structures such as a blocking layer / electron transport layer / electron injection layer / cathode.

The material used for the organic light emitting device may be classified into a vacuum deposition material and a solution coating material according to the method of manufacturing an organic film. The vacuum evaporable material should have a vapor pressure of 10 ⁻⁶ torr or more under 500 ° C., and preferably a low molecular weight material having a molecular weight of 1200 or less. The solution coatable material is highly soluble in a solvent and must be able to be prepared as a solution, and mainly includes an aromatic or heterocyclic ring.

In the case of manufacturing the organic EL device using the vacuum deposition method, the manufacturing cost increases due to the use of a vacuum system, and when the shadow mask is used to manufacture the pixels for the color display, it is difficult to manufacture the high resolution pixels. On the other hand, solution coating methods such as inkjet printing, screen printing, and spin coating are easy to manufacture, inexpensive to manufacture, and have a relatively higher resolution than shadow masks.

On the other hand, when the organic light emitting device is driven or stored in a high temperature environment, there are problems such as a change in emission color, a decrease in luminous efficiency, an increase in driving voltage, and a short emission life. To solve these problems, it is necessary to develop a new electron transport material capable of lowering the driving voltage with a high glass transition temperature.

As the electron transporting material, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are widely used, and in recent years, active researches on electron transporting materials using phenanthroline or bipyridine compounds have been actively conducted. It's going on.

WO2007 / 026847 discloses a compound having a triazole ring structure linked to a substituted pyridinyl group, and Japanese Patent Laid-Open No. 15-123983 discloses a 1,10-phenanthroline-based compound, in which the compounds have higher electrons than conventional materials. It is intended to be applied to an organic electroluminescent device capable of low voltage drive and obtain a relatively high efficiency characteristics by using the transport characteristics.

An anthracene-based compound having a substituent represented by Formula 1 or Formula 2 is provided:

[Formula 1]

[Formula 2]

In Chemical Formula 1 or Chemical Formula 2

R is hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or Unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2-C30 heteroaryl group,

L is a divalent linking group, which is substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene,

l is 0, 1, 2 or 3.

A first electrode; Second electrode; And an organic electroluminescent device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film includes an anthracene-based compound as described above.

The compound according to an embodiment of the present invention is an anthracene-based compound into which a substituent represented by Formula 1 or Formula 2 below, that is, a pyridinylquinoline-based or pyridinylisoquinoline-based substituent is introduced.

[Formula 1]

[Formula 2]

In Chemical Formula 1 or Chemical Formula 2

R is hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or Unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2-C30 heteroaryl group,

L is a divalent linking group, which is substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene,

l is 0, 1, 2, or 3.

At this time, the method of determining the number of carbon positions of anthracene can be expressed as follows.

In the anthracene-based compound according to an embodiment of the present invention, the substituent represented by Formula 1 or Formula 2 may be substituted at one of 2, 3, 6, 7, 9, and 10 of anthracene.

Anthracene-based compound according to an embodiment of the present invention may be represented by the following formula (3):

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 3 to 6,

R ₁ to R ₁₇ are the same as or different from each other, and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2 C30 is a heteroaryl group,

Ar ₁ , Ar _2, and Ar ₃ are the same or differently substituted or unsubstituted C6 to C30 aryl groups, respectively.

L 'and L "are divalent linking groups, which may be substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene.

m and n are 0, 1, 2, or 3.

At this time, in Formula 1 to Formula 6, L, L 'and L "are the same or different from each other, it may be represented by any one of the following structural formula.

In the above structural formula, R` is the same or different from each other and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted A substituted C5 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted It is a substituted C2 ~ C 30 heteroaryl group.

In addition, in Chemical Formulas 3 to 6, Ar ₁ , Ar ₂ and Ar ₃ may be the same or different from each other, and may be represented by any one of the following structural formulas.

In the above structural formula, R` is the same or different from each other and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted A substituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group.

Among the terms of the substituent used in the present invention, the alkyl group is preferably a straight or branched alkyl group having 1 to 20 carbon atoms, more preferably a straight or branched alkyl group having 1 to 12 carbon atoms, and a straight chain having 1 to 6 carbon atoms. Or branched alkyl groups are most preferred. Examples of such unsubstituted alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, isoamyl, hexyl and the like.

By cycloalkyl group used in the present invention is meant a monovalent monocyclic system having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms.

The heterocycloalkyl group used in the present invention includes 1, 2 or 3 heteroatoms selected from N, O, P or S, and has 3 to 20, preferably 3 to 10 ring atoms having the remaining ring atoms of C, More preferably 3 to 6 monovalent monocyclic systems.

Among the terms of the substituents used in the present invention, an alkoxy group is preferably an oxygen-containing straight or branched alkoxy group each having an alkyl moiety of 1 to 20 carbon atoms. More preferred are alkoxy groups having 1 to 6 carbon atoms and most preferred are alkoxy groups having 1 to 3 carbon atoms. Examples of such alkoxy groups include methoxy, ethoxy, propoxy, butoxy, and t-butoxy. The alkoxy group may be further substituted with one or more halo atoms such as fluoro, chloro or bromo to provide a haloalkoxy group. Examples thereof include fluoromethoxy, chloromethoxy, trifluoromethoxy, trifluoroethoxy, fluoroethoxy, fluoropropoxy and the like.

In the terminology of a substituent used in the present invention, a heteroalkyl group is a heteroatom in the main chain of 1 to 20, preferably 1 to 12, more preferably 1 to 6 carbon atoms in the alkyl group, for example N, O, P , S and the like.

Among the terms of the substituents used in the present invention, an aryl group is used alone or in combination to mean a carbocycle aromatic system having 6 to 30 carbon atoms containing one or more rings, which rings may be attached or fused together in a pendant manner. The term aryl includes aromatic radicals such as phenyl, naphthyl, tetrahydronaphthyl, indane and biphenyl. More preferably phenyl.

In the term of the substituent used in the present invention, an arylalkyl group means that one or more hydrogen atoms of the alkyl group are substituted with the aryl group.

In the term of the substituent used in the present invention, the heteroaryl group contains 1, 2 or 3 heteroatoms selected from N, O, or S, and the remaining ring atoms are C to monovalent monocyclic monocyclic having 5 to 30 ring atoms. Or acyclic aromatic radicals. The term also refers to monovalent monocyclic or bicyclic aromatic radicals in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Representative examples include thienyl, benzothienyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, imidazolyl, furanyl, benzofuranyl, thiazolyl, isoxazolin, Benzisoxazolin, benzimidazolyl, triazolyl, pyrazolyl, pyrrolyl, indolyl, 2-pyridonyl, N-alkyl-2-pyridonyl, pyrazinyl, pyridazininyl, pyrimidinyl , Oxazoloyl and their corresponding N-oxides (eg pyridyl N-oxides, quinolinyl N-oxides), quaternary salts thereof, and the like.

In the above formulas, when an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, a cycloalkyl group and a heterocycloalkyl group are substituted, their substituents are -F; -Cl; -Br; -CN; -NO ₂ ; -OH; C1 to C20 alkyl group unsubstituted or substituted with -F, -Cl, -Br, -CN, -NO ₂ or -OH; C1-C20 alkoxy group unsubstituted or substituted with -F, -Cl, -Br, -CN, -NO ₂ or -OH; C6 to C30 aryl group which is unsubstituted or substituted with C1 to C20 alkyl group, C1 to C20 alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH; A C2 to C30 heteroaryl group unsubstituted or substituted with a C1 to C20 alkyl group, a C1 to C20 alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH; A C5 to C20 cycloalkyl group unsubstituted or substituted with a C1 to C20 alkyl group, a C1 to C20 alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH; Unsubstituted or substituted C1 to C20 alkyl group, C1 to 20 alkoxy group, C5 to C30 heterocycloalkyl group substituted with -F, -Cl, -Br, -CN, -NO ₂ or -OH and -N (G6) (G7) It may be one or more selected from the group consisting of a group represented by. In this case, G6 and G7 are each independently hydrogen; C1-C10 alkyl group; Or a C6 to C30 aryl group substituted with a C1 to C10 alkyl group.

More specifically, R ₁ to R ₁₇ are independently from each other, hydrogen, halogen, cyano group, hydroxyl group, C1 to C10 alkyl group, C1 to C10 alkoxy group, and from the group consisting of substituted or unsubstituted derivatives as follows: Can be selected: phenyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group, anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenyl group, fluorenyl group, Methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, ethyl- chrysenyl group, pisenyl group, peryllenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylle Neyl group, hexaphenyl group, hexasenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, fluorenyl group, pyrantrenyl group, ovarenyl group, carbazolyl group, thiophenyl group, indole Diary, Furinyl, Benzimidazolyl, Quinol Nyl group, benzothiophenyl group, parathiazinyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, imidazolinyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyri Dinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthrenyl group, thianthrenyl group, cyclopentyl group, cyclohexyl group, oxiranyl group, pyrrolidinyl group, pyrazolidinyl group, imidazolidinyl group , Piperidinyl group, piperazinyl group, morpholinyl group, di (C6 to C30 aryl) amino group, tri (C6 to C30 aryl) silyl group and derivatives thereof.

As used herein, the term "derivative" refers to a group in which one or more hydrogens of the groups listed above are substituted with a substituent as described above.

The anthracene-based compound according to an embodiment of the present invention has high thermal stability due to high solubility in a solvent when forming an organic layer, high glass transition temperature due to unlocalized electron distribution and rigid structure, and particularly pyridinylquinoline Substituents are introduced to show excellent electron injection and electron transportability, and thus, when applied to an organic EL device, low voltage driving is possible and high efficiency characteristics can be obtained.

The compound according to an embodiment of the present invention may be a compound represented by the following Chemical Formulas 7 to 50, but is not limited thereto.

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

 [Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

 [Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

[Formula 36]

[Formula 37]

[Formula 38]

[Formula 39]

[Formula 40]

[Formula 41]

[Formula 42]

[Formula 43]

[Formula 44]

[Formula 45]

[Formula 46]

[Formula 47]

[Formula 48]

[Formula 49]

[Formula 50]

Compounds according to one embodiment of the present invention can be synthesized using conventional synthetic methods, for a more detailed synthetic route of the compounds refer to the scheme of the following synthesis examples.

The organic electroluminescent device of the present invention,

A first electrode;

Second electrode; And

An organic electroluminescent device comprising an organic film interposed between the first electrode and the second electrode, characterized in that the organic film includes at least one anthracene-based compound having a substituent represented by the formula (1) or (2).

The anthracene-based compound according to an embodiment of the present invention is suitable for use in an organic film, particularly a light emitting layer, an electron injection layer, an electron transport layer or a hole blocking layer of an organic EL device. The light emitting layer of the organic electroluminescent device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.

According to the organic electroluminescent device according to an embodiment of the present invention, unlike the conventional organic electroluminescent device in which the stability of the organic film is poor when manufactured by the solution coating method, formation of a stable organic film with excellent solubility and thermal stability Possible compounds can be included to provide improved luminescent properties such as excellent drive voltage and color purity.

The structure of the organic electroluminescent device according to an embodiment of the present invention can be very diverse. That is, one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer and an electron injection layer may be further included between the first electrode and the second electrode.

More specifically, for specific examples of the organic electroluminescent device according to an embodiment of the present invention refer to Figures 1a, 1b and 1c. The organic electroluminescent device of FIG. 1A has a structure consisting of a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode, and the organic electroluminescent device of FIG. 1B includes a first electrode / hole It has a structure consisting of an injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode.

The organic film of the organic electroluminescent device according to an embodiment of the present invention may further include an organometallic complex.

The organometallic complex refers to a compound having an organic ligand and composed of only coordinating bonds with the metal.

At this time, the metal is an alkali metal (I) such as Li, Na, K, Rb, Cs; Alkaline earth metal (II) such as Mg, Ca, Sr, and Ba; Rare earth metals (III) such as Y, La, Ce, Pr, Nd, Sm, Eu, Er, and Yb.

In the organometallic complex, as ligands coordinated with these metals, β-diketones (eg, acetylacetone, 1,3-diphenyl-1,3-propanedione, 2,2,6,6- Tetramethyl-3,5-heptanedione, 1,1,1,2,2,3,3, -heptafluoro-7,7-dimethyl-4,6-octanedione, 1-phenyl-1,3- Butanedione, etc.), salicylaldehydes (e.g., salylaldehyde, diethylaminosaltyaldehyde, etc.), anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, ferric Reylene, Phthaloferylene, Naphthaloperylene, Perinone, Phthaloperinone, Naphthalopelinone, Diphenylbutadiene, Tetraphenylbutadiene, Coumarin, Oxadiazole, Aldazine, Bisbenzoxazolin, Bisstyryl And pyrazine, cyclopentadiene, quinoline, aminoquinoline, benzoquinoline, and the like.

The content of the organometallic complex is 0.01 to 90 parts by weight, preferably 0.1 to 60 parts by weight, based on 100 parts by weight of solids forming the organic film. In this case, when the content is less than 0.01 parts by weight, the emission efficiency is improved and electron injection is performed. If the effect is insufficient and more than 90 parts by weight, it is not preferable due to the deterioration of the electron transport characteristics.

In addition, the organic layer of the organic EL device according to an embodiment of the present invention may further include an ionic salt, that is, an inorganic ion salt, an organic ion salt or a metal ion salt.

In accordance with an embodiment of the present invention, the ionic salts included in the organic membrane are typically LiClO ₄ , LiPF ₆ , LiBF ₄ , LiN (CF ₃ SO ₂ ) ₂ , and lithium trifluoromethane trisulfonate. Inorganic salts containing Li cations such as sulfonate) and tetraethylammonium tetrafluoroborate (TEA-BF ₄ ), tetra-n-butylammonium tetrafluoroborate (Bu ₄ N-BF ₄ ), tetraalkyl, aryl or heteroaryl quarters Organic ammonium salts such as tetra-n-alkylammonium toluenesulfonate, tetra-n-alkylammonium tetrafluoroborate, tetra-n-alkyl ammonium tetraphenylborate, tetra-n-alkyl ammonium toluenesulfonate, tetraalkylammonium tetrafluoro borate, tetra-n-alkyl ammonium tetraphenylborate Polymeric salts such as ionic salts and polystyrenesulfonate (PSS) may be used.

In addition, the metal ion salt includes metals such as Al (III), Mn (II), Zr (IV), Ti (II), Hf (IV), Ta (V), Nb (III) and V (II). As the inorganic metal ion salt, hydrogen of the inorganic acid is substituted with a metal, and for example, halides (specifically, chloride, fluoride, bromide, iodide, etc.) are mentioned. Hydrogens of organic acids, alcohols and dialkylamides are substituted with metals, and specific examples include organic acid salts such as carboxylic acid and phenol, alcohol seeds and dialkylamide salts.

At this time, the carboxylic acid may be aliphatic or aromatic. The aliphatic carboxylic acid preferably has 1 to 24 carbon atoms, and may be saturated aliphatic carboxylic acid or unsaturated fatty acid carboxylic acid, or may have two or more carboxyl groups. Moreover, you may have substituents, such as an aryl group. Specific examples include aliphatic carboxylic acids such as acetic acid, propionic acid, octylcin, isooctyl acid, decanoic acid and lauryl acid; And polyvalent carboxylic acids such as di and tri, such as unsaturated aliphatic carboxylic acids such as oleic acid and ricinolic acid (such as licinorene), citric acid, malic acid, and oxalic acid. As aromatic carboxylic acid, the thing of 7-24 total carbons is preferable, It may have a substituent (alkyl group of 1-8 carbon atoms, a hydroxyl group), Specifically, benzoic acid, o- (t-butyl) benzoic acid, m- (t -Butyl) benzoic acid, salicylic acid, m- (hydroxy) benzoic acid, p- (hydroxy) benzoic acid), and the like. As the phenol, those having 6 to 46 carbon atoms in total are preferable, and a substituent (such as a linear or branched alkyl group having 1 to 8 carbon atoms or an aryl group such as a phenyl group) or a condensed ring (benzene ring which may have a substituted ring) Ring), or a monovalent phenol or a divalent or higher polyhydric phenol. Specifically, phenol, naphthol, 4-phenylphenol, 2, 2-bis (p-hydroxyphenyl) propane (bisphenol A), etc. are mentioned. As an alcohol which forms an alkoxide, it is preferable that it is C1-C10, A primary alcohol, such as ethyl alcohol, n-propyl alcohol, n-butyl alcohol; Secondary alcohols such as isopropyl alcohol and s-butyl alcohol; tertiary alcohols such as t-butyl alcohol; and the like. Moreover, a bivalent or more polyhydric alcohol may be sufficient, for example, ethylene glycol etc. are mentioned.

As dialkylamide, you may have a substituent and it is preferable that total carbon number is 2-24. Specifically, dimethylamide, diethylamide, N-methyl-N-ethylamide, etc. are mentioned.

However, the salts are merely examples that can be used as the ionic salt of the present invention, and various salts composed of cations and anions can be used in the present invention.

The content of the ionic salt may vary depending on the use, component, thickness, etc. of the EL layer to be manufactured, but is 0.01 to 50 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the solid content of the organic film. If the content of the ionic salt is less than 0.01 parts by weight, the effect of improving the luminous efficiency and reducing the operation start voltage of the organic electroluminescent device is insufficient, and if it exceeds 50 parts by weight, the operation of the device may be poor due to the excessive concentration of ions. not.

Hereinafter, a method of manufacturing an organic EL device according to an embodiment of the present invention will be described with reference to the organic EL device shown in FIG. 1A.

First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Herein, a substrate used in a conventional organic electroluminescent device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 mW / sec, and a film thickness are usually appropriately selected in the range of 10 mV to 5 m.

In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. The heat treatment temperature for removing the solvent after coating is preferably selected in a temperature range of about 80 ° C to 200 ° C.

The hole injection layer thickness may be about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. When the hole transport layer is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions vary depending on the compound used, and are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The hole transport layer thickness may be about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be degraded, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.

Next, the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like. When the light emitting layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa. This is because when the thickness of the light emitting layer is less than 100 kV, the light emission characteristic may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.

In the case of using the phosphorescent dopant in the light emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, a method such as vacuum deposition, spin coating, cast method, LB method, etc. is used on the hole transport layer. The hole blocking layer HBL may be formed. In the case of forming the hole blocking layer by vacuum deposition or spin coating, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer. The hole blocking layer material may be a compound having the above Chemical Formulas 3 to 6 as described above, and may be an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, a BCP, an aluminum complex, or the like.

Phenanthroline-containing organic compounds Imidazole-containing organic compounds

Triazole-containing organic compound

Oxadiazole-containing compound

   BAlq

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase.

Next, the electron transport layer (ETL) is formed using various methods such as vacuum deposition, spin coating, and casting. When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer. The electron transport layer material may be a compound having the above formulas (3) to (6) as described above as a function of stably transporting the electrons injected from the electron injection electrode (Cathode), an oxazole-based compound, isoxazole compound, Triazole-based compound, isothiazole-based compound, oxadiazole-based compound, thiadiazole-based compound, perylene-based compound, aluminum complex (e.g. Alq3 (tris (8-quinolinolato) Known materials such as tris (8-quinolinolato) -aluminum BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq'2OAc, 2 (Gaq'2)) and the like can also be used.

       Perylene-Based Compound

         Alq3 BAlq

       SAlq Almq3

  Gaq'2OPiv Gaq'2Oac

2 (Gaq'2)

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the material is not particularly limited.

As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from the range of conditions almost the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 50 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method. The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned. In addition, a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.

Hereinafter, the present invention will be described in more detail with reference to the following examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.

Example 1

1) Synthesis of 3- (5-Bromo-pyridin-3-yl) -quinoline [3- (5-Bromo-pyridin-3-yl) -quinoline]

1.11 g (4.7 mmol), 3- (4,4,5,5-tetramethyl- [1,3,5-Dibromo-pyridine) in a 100 ml round bottom flask under argon gas , 3,2] dioxaborolan-2-yl) -quinoline [3- (4,4,5,5-Tetramethyl- [1,3,2] dioxaborolan-2-yl) -quinoline] 1.0 g ( 3.92mmol), tetrakis (triphenylphosphine) palladium (0) 0.45g, 2M K2CO3 7.84ml, tetrabutylammonium bromide 1.26g were added, and 30ml and 15ml of THF and toluene were added and refluxed at 100 ° C for 16 hours. After confirming that the color of the solution turned dark brown, water was added and extracted with chloroform. The extracted organic layer was then dried over anhydrous magnesium sulfate, filtered, solvent removed, separated by silica gel column, 3- (5-bromo-pyridin-3-yl) -quinoline [3- (5-Bromo-pyridin- 3-yl) -quinoline] 1.1 g of a white solid was obtained, and measured by Atmospheric Pressure Chemical Ionization (APCI) method using LCMS (SHIMADZU, LCMS-IT-TOF), [M + H ] + = 285 was obtained as the main peak to confirm that it was the target compound.

2) Synthesis of Compound of Formula 9

0.61 g (2.15 mmol) of 3- (5-bromo-pyridin-3-yl) -quinoline, 2- (9,10-di-naphthalen-2-yl-anthracene-2 in a 100 ml round bottom flask under argon gas -Yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaborane [2- (9,10-Di-naphthalene-2-yl-anthracen-2-yl) -4, 4,5,5-tetramethyl- [1,3,2] dioxaborolane] 1.0 g (1.8 mmol), 3.6 ml of 1M K ₃ PO ₄ and 20 ml of dioxane were added and refluxed at 120 ° C. for 36 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO ₄ , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 1.1 g of the target compound in the solid state. As a result of the measurement using the APCI method using LCMS, [M + H] + = 635 was obtained to confirm that the target compound was obtained.

Example 2

1) Synthesis of 3- (6-Bromo-pyridin-3-yl) -quinoline [3- (5-Bromo-pyridin-3-yl) -quinoline]

1.11 g (4.7 mmol) 2,6-dibromo-pyridine, 3- (4,4,5,5-tetramethyll- [1,3,2] dioxabo, in a 100 ml round bottom flask under argon gas 1.0 g (3.92 mmol) of loran-2-yl) -quinoline, 0.45 g of tetrakis (triphenylphosphine) palladium (0), 7.84 ml of 2M K ₂ CO ₃ , 1.26 g of tetrabutylammonium bromide, and THF and toluene 30ml and 15ml were added and refluxed at 100 ° C. for 16 hours. After confirming that the color of the solution turned dark brown, water was added and extracted with chloroform. The extracted organic layer was then dried over anhydrous magnesium sulfate, filtered, solvent removed, and separated by silica gel column to obtain 0.8 g of a white solid of 3- (6-bromo-pyridin-2-yl) -quinoline, LCMS. As a result of checking by APCI method, [M + H] + = 285 was obtained, confirming that it was the target compound.

2) Synthesis of Compound of Formula 10

0.6 g (2.15 mmol) 3- (6-bromo-pyridin-2-yl) -quinoline, 2- (9,10-di-naphthalen-2-yl-anthracene-2 in a 100 ml round bottom flask under argon gas -Yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaboloran 1.0 g (1.8mmol), 1M K ₃ PO ₄ 3.6ml, 20ml dioxane and put at 120 ℃ 36 It was refluxed for hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO ₄ , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 0.9 g of the target compound in the solid state. The residue was measured by APCI method using LCMS. As a result, [M + H] + = 635 was obtained to confirm that the target compound was obtained.

Example 3

1) Synthesis of 3- (5-bromo-pyridin-2-yl) -quinoline

1.1 g (4.7 mmol) 2,5-dibromo-pyridine, 3- (4,4,5,5-tetramethyl- [1,3,2] dioxaboro in a 100 ml round bottom flask under argon gas Lan-2-yl) -quinoline 1.0 g (3.92 mmol), tetrakis (triphenylphosphine) palladium (0) 0.45g, 2M K ₂ CO ₃ 7.84 ml, tetrabutylammonium bromide 1.26g and THF and toluene 30ml and 15ml were added and refluxed at 100 ° C. for 16 hours. After confirming that the color of the solution turned dark brown, water was added and extracted with chloroform. The extracted organic layer was then dried over anhydrous magnesium sulfate, filtered, solvent removed, and separated by silica gel column to obtain 1.2 g of 3- (5-bromo-pyridin-2-yl) -quinoline white solid. As a result of checking by APCI method, [M + H] + = 285 was obtained, confirming that it was the target compound.

2) Synthesis of Compound of Formula 11

0.62 g (2.15 mmol) of 3- (5-bromo-pyridin-2-yl) -quinoline, 2- (9,10-di-naphthalen-2-yl-anthracene-2 in a 100 ml round bottom flask under argon gas -Yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaboloran 1.0 g (1.8mmol), 1M K ₃ PO ₄ 3.6ml, 20ml dioxane and put at 120 ℃ 36 It was refluxed for hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO ₄ , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 1.1 g of the target compound in the solid state. The residue was measured by APCI method using LCMS. As a result, [M + H] + = 635 was obtained. In FIG. 2A, thermal analysis (N ₂ atmosphere, temperature range: normal temperature to 600 ° C. (10 ° C.) using TGA (thermo gravimetric anaysis) and DSC (differential scanning calorimetry) / min) -TGA, 400 ℃ at room temperature Up to -DSC, pan type: Pt pan in disposable Al pan (TGA), disposable Al pan (DSC)), Td (℃) and Tg (℃) are 467 (℃) / 163 (degree. C.). The properties of TGA (thermo gravimetric anaysis) and DSC (differential scanning calorimetry) of the compound of Formula 11 prepared in Example 3 are shown in FIGS. 2B and 2C, respectively.

Example 4

1) Synthesis of 4- (5-bromo-pyridin-2-yl) -isoquinoline

In Example 1 1), 2,5-dibromo-pyridine instead of 3,5-dibromo-pyridine, 3- (4,4,5,5-tetramethyl- [1,3,2] 4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -isoquinoline is used instead of dioxaborolan-2-yl) -quinoline 4- (5-Bromo-pyridin-2-yl) -isoquinoline was synthesized using the same method except for the following method, which was measured by APCI method using LCMS. [M + H] + = 285 Was obtained, confirming that it was a target compound.

2) Synthesis of Compound of Formula 12

In Example 1 2) using 4- (5-bromo-pyridin-2-yl) -isoquinoline instead of 3- (5-bromo-pyridin-3-yl) -quinoline using the same method The compound of Chemical Formula 12 was synthesized, and the residue was examined by APCI method using LCMS. As a result, [M + H] + = 635 was confirmed to be the target compound.

Example 5

1) Synthesis of 4- (6-bromo-pyridin-2-yl) -isoquinoline

2,6-dibromo-pyridine instead of 3,5-dibromo-pyridine in 1) of Example 1, 3- (4,4,5,5-tetramethyl- [1,3,2] Use of 4- (4,4,5,5-tetra methyl- [1,3,2] dioxaborolan-2-yl) -isoquinoline instead of dioxaborolan-2-yl) -quinoline 4- (6-Bromo-pyridin-2-yl) -isoquinoline was synthesized using the same method except for the following method, which was measured by APCI method using LCMS. [M + H] + = 285 Was obtained, confirming that it was a target compound.

2) Synthesis of Compound of Formula 13

In Example 1 2) using 4- (6-bromo-pyridin-2-yl) -isoquinoline instead of 3- (5-bromo-pyridin-3-yl) -quinoline the same method was used The compound of Formula 13 was synthesized, and the resultant was examined by APCI method using LCMS. As a result, [M + H] + = 635 was obtained to confirm that the compound was the target compound.

Example 6

1) Synthesis of 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline

1.0 g (3.51 mmol) of 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline, 2.8 g (14 mmol) of 4-bromophenylboric acid in a 100 ml round bottom flask under argon gas, 0.4 g of tetrakis (triphenylphosphine) palladium (0), 7 ml of 2M K ₂ CO ₃ and 1.2 g of tetrabutylammonium bromide were added thereto, and 30 ml and 15 ml of THF and toluene were respectively added and refluxed at 100 ° C. for 12 hours. After completion of the reaction, water was added and extracted with chloroform. Then, the extracted organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and the residue was separated by a silica gel column to give 0.5 [4] white of 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline. A solid was obtained.

2) Synthesis of Compound of Formula 16

0.5 g (1.38 mmol), 2- (9,10-di-naphthalene-2, 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline, in a 100 ml round bottom flask under argon gas -Yl-anthracene-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaboloran 1.0 g (1.8mmol), 1M K3PO4 3.6ml, dioxane 20ml and 120 It was refluxed at 36 ° C. for 36 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO ₄ , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 0.67 g of the target compound in the solid state. The residue was measured by APCI method using LCMS. As a result, [M + H] + = 710 was obtained to confirm that the target compound was obtained.

Example  7: Synthesis of Compound of Formula 30

2- (9,10-di-naphthalen-2-yl-anthracen-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxabo in 2) of Example 4 Except using 4,4,5,5-tetramethyl-2- (10-naphthalen-2-yl-anthracene-9-yl)-[1,3,2] dioxaborolane instead of loran Then, the compound of Formula 30 was synthesized using the same method.

Example  8: Synthesis of Compound of Formula 32

2- (9,10-di-naphthalen-2-yl-anthracen-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxabolic in 2) of Example 3) Except using 4,4,5,5-tetramethyl-2- (10-naphthalen-2-yl-anthracene-9-yl)-[1,3,2] dioxaborolane instead of loran Then, the compound of Chemical Formula 32 was synthesized using the same method, and the result of having been measured by APCI method using LCMS, [M + H] + = 509 was obtained to confirm that the target compound.

Example  9: Synthesis of Compound of Formula 42

2- (9,10-di-naphthalen-2-yl-anthracen-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxabo in 2) of Example 6 Except using 4,4,5,5-tetramethyl-2- (10-naphthalen-2-yl-anthracene-9-yl)-[1,3,2] dioxaborolane instead of loran Then, using the same method to synthesize a compound of formula 42, and by LCCI using APCI method as a result, [M + H] + = 585 was obtained to confirm that the target compound.

[Formula 51]

[Formula 52]

[Formula 53]

[Formula 54]

Example 10 Fabrication and Evaluation of Organic Electroluminescent Device

The compound of Formula 9 prepared in Example 1 is an electron transport layer, the compound of Formula 51 is a hole injection layer, the compound of Formula 52 is a hole transport layer, the compound of Formula 53 and the compound of Formula 54 are respectively Using a host and a dopant, an organic light emitting device was manufactured having the following structure: ITO / Compound 51 (600 ') / Compound 52 (300') / Compound 53: Compound 54 (300 ') / Compound of formula 9 (250 ') / LiF (6') / Al (1500 ').

The anode was cut into 50 mm x 50 mm x 0.7 mm sized 15 Ω / cm ² (1000 Å) ITO glass substrate, sonicated for 15 minutes in acetone isopropyl alcohol and pure water, followed by UV ozone cleaning for 30 minutes. The compound of Formula 51 (hole injection layer) and the compound of Formula 52 (hole transport layer) were vacuum deposited on the substrate, and the compounds of Formula 53 and Formula 54 were vacuum deposited at a weight ratio of 100: 5 to form a light emitting layer. It was. Thereafter, the compound of Formula 9 was vacuum deposited to a thickness of 250 kPa on the emission layer to form an electron transport layer. LiF 6Å (electron injection layer) and Al 1500Å (cathode) were sequentially vacuum deposited on the electron transport layer to manufacture an organic light emitting device as shown in FIG. 1A. In this device, blue light emission of 20 mA / cm ² was obtained at a voltage of 6.1 V, and the luminous efficiency at this time and the half-life of 2000 nits are shown in Table 1.

Examples 11 to 18 Fabrication and Evaluation of Organic Electroluminescent Devices

In Example 10, an organic light emitting diode was manufactured according to the same method as Example 10 except for using the compounds prepared in Examples 2 to 9 instead of the compounds of formula 9 prepared in Example 1 as the electron transporting layer. Table 1 shows the driving voltage, luminous efficiency, and half-life at 2000 nits during constant current driving of 20 mA / cm ² in this device. In particular, the characteristics of the current density-voltage and the voltage-luminance of the organic EL device manufactured in Example 12 of the present invention are shown in FIGS. 3A and 3B, respectively.

Comparative Example 1: Fabrication and Evaluation of Organic Electroluminescent Device

In Example 10, an organic light emitting device was manufactured in the same manner as in Example 10, except that Alq3 was used instead of the compound of Formula 9 prepared in Example 1 as the electron transport layer. The luminous efficiency, luminous color, luminance and lifetime in this device are shown in Table 1. Table 1 shows the driving voltage, luminous efficiency, and half life at 2000 nits when driving the constant current at 20 mA / cm ² in this device.

material Driving voltage (V) Luminous Efficiency (cd / A) Luminance Half Life (hr) Example 10 Example 1 6.1 6.8 1330 Example 11 Example 2 5.7 7.2 1280 Example 12 Example 3 5.8 7.3 1400 Example 13 Example 4 5.8 7.2 1350 Example 14 Example 5 5.7 7.2 1300 Example 15 Example 6 6.2 6.6 1310 Example 16 Example 7 5.6 6.7 1200 Example 17 Example 8 5.5 6.7 1220 Example 18 Example 9 5.4 6.9 1290 Comparative Example 1 Alq3 6.6 6.7 1240

From the above examples, the compound according to the embodiment of the present invention has obtained a low driving voltage and high luminous efficiency, and from this result, the electron injection and electron mobility characteristics are much superior to the compound used as the electron transport layer in Comparative Example 1. I could see that. In addition, the compound according to an embodiment of the present invention was able to obtain excellent life characteristics in the organic electroluminescent device using the same due to the thermal stability due to the high glass transition temperature.

1A is a view schematically illustrating a structure of an organic EL device according to an embodiment of the present invention.

1B is a view schematically showing a structure of an organic EL device according to another embodiment of the present invention.

2A is a graph showing the results of LCMS of the compound prepared in Example 3 of the present invention.

Figure 2b is a graph showing the characteristics of the TGA (thermo gravimetric anaysis) of the compound prepared in Example 3 of the present invention.

Figure 2c is a graph showing the characteristics of the differential scanning calorimetry (DSC) of the compound prepared in Example 3 of the present invention.

3A is a graph showing the characteristics of current density-voltage of the organic EL device manufactured in Example 12 of the present invention.

3B is a graph showing characteristics of voltage-luminance of the organic EL device manufactured in Example 12 of the present invention.

Claims (11)

Anthracene-based compound having a substituent represented by the following formula (1) or (2): [Formula 1]

[Formula 2]

In Chemical Formula 1 or Chemical Formula 2, R is hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or Unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2-C30 heteroaryl group, L is a divalent linking group, which is substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene, l is an integer of 0-3. The anthracene-based compound according to claim 1, wherein the substituent represented by Formula 1 or Formula 2 is substituted at one of 2, 3, 6, 7, 9, and 10 of anthracene. The anthracene-based compound according to claim 1, wherein the compound is represented by the following Chemical Formulas 3 to 6. [Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 3 to 6, R ₁ to R ₁₇ are the same as or different from each other, and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2 C30 is a heteroaryl group, Ar ₁ , Ar _2, and Ar ₃ are the same or differently substituted or unsubstituted C6 to C30 aryl groups, respectively. L 'and L "are divalent linking groups, which may be substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene. m and n are integers of 0-3. The anthracene compound according to claim 3, wherein L 'and L "are the same as or different from each other, and are represented by any one of the following structural formulas:

In the above structural formula, R 'is the same or different from each other, and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted A substituted C5 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted It is a substituted C2 ~ C 30 heteroaryl group. The anthracene compound according to claim 3, wherein Ar ₁ , Ar ₂ and Ar ₃ are the same or different from each other, and are represented by any one of the following structural formulas:

In the above structural formula, R` is the same or different from each other and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted A substituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group. The anthracene-based compound of claim 1, wherein the anthracene-based compound having a substituent represented by Formula 1 or Formula 2 is one of the compounds represented by the following Formulas 7 to 50: [Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

[Formula 15]

[Formula 16]

 [Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

 [Formula 26]

[Formula 27]

[Formula 28]

[Formula 29]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

[Formula 36]

[Formula 37]

[Formula 38]

[Formula 39]

[Formula 40]

[Formula 41]

[Formula 42]

[Formula 43]

[Formula 44]

[Formula 45]

[Formula 46]

[Formula 47]

[Formula 48]

[Formula 49]

[Formula 50]

A first electrode; Second electrode; And An organic electroluminescent device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film comprises the compound of any one of claims 1 to 6. device. The organic electroluminescent device according to claim 7, wherein the organic film is a light emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer. The method of claim 7, further comprising at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer between the first electrode and the second electrode. An organic electroluminescent device, characterized in that. The organic electroluminescent device according to claim 7, wherein the organic film further comprises an organometallic complex. The organic electroluminescent device according to claim 7, wherein the organic film further comprises an ionic salt.

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