WO2019054633A1 - Novel heterocyclic compound and organic light-emitting device using same - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light-emitting device using same.

Description

 Title of the Invention

 Novel heterocyclic compounds and organic light emitting devices using the same

TECHNICAL FIELD

Cross-reference with related application (s)

 This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0116818 dated September 12, 2017, and Korean Patent Application No. 10-2018-0087435 dated July 26, 2018, The entire contents of which are incorporated herein by reference.

 The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.

TECHNICAL BACKGROUND OF THE INVENTION

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, quick response time, and has been studied much because of its excellent luminance, driving voltage, and response speed characteristics. The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. The organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed, When the tone falls back to the ground state, the light is emitted. There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices. [Prior Art Document]

 [Patent Literature]

 (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

DISCLOSURE OF THE INVENTION

 [Problem to be solved]

 The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.

MEANS FOR SOLVING THE PROBLEMS

 The present invention provides a compound represented by the following formula (1).

 [Chemical Formula 1]

 In Formula 1,

Ri to R4 are each independently hydrogen; heavy hydrogen; halogen; Cyano, nitrile; Nitro; Amino; Substituted or unsubstituted d- ₆₀ alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d-60 alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C ₃ - ₆₀ cycloalkyl; Substituted or unsubstituted d-60 alkenyl; Substituted or unsubstituted C ₆ -C ₆₀ aryl; Substituted or unsubstituted C ₆ -C ₆₀ aryloxy; Substituted or unsubstituted C ₆ - ₆₀ arylamine; Or a substituted or unsubstituted C ₂ - ₆₀ heteroaryl containing at least one of O, N, Si and S,

 n and r are independently integers of from 0 to 8,

t and m are independently an integer of 0 to 4; The present invention also provides a display device comprising: a first electrode; The first electrode 12 is provided opposite to the first electrode 12 electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do. 【Effects of the Invention】

 The compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. In particular, the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, and light emitting material.

BRIEF DESCRIPTION OF THE DRAWINGS

 Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.

 2 is a sectional view of a light emitting device according to a first embodiment of the present invention which comprises a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a hole adjusting layer 7, a light emitting layer 8, an electron transporting layer 9, And shows an example of an organic light emitting device.

DETAILED DESCRIPTION OF THE INVENTION

 Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention. The present invention provides a compound represented by the above formula (1).

In the present specification, i and n means a bond connected to another substituent. As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aralkyl group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or N, 0 and S Or a heterocyclic group containing at least one atom of atoms, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure,

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula,

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto. In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine. In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, The number of carbon atoms is 1 to 10. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, n-butyl, n-butyl, 1-methylpentyl, N-heptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2, 2-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, But are not limited thereto. In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl and styrenyl groups. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Cyclopentyl, cyclopentyl, cyclopentyl, cyclopentyl, cyclopentyl, cyclopentyl, cyclopentyl, cyclopentyl, cyclopentyl, cyclohexyl, cyclohexyl, cyclohexyl, , 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group. In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Wherein the fluorenyl group is substituted

And the like. However, the present invention is not limited thereto. In the present specification, the heterocyclic group is a heterocyclic group containing at least one of 0, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazoyloxazol group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A benzooxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group, Thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited thereto. In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In this specification, the description of the aryl group described above, except that arylene is a bivalent Can be applied. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group. In the present specification, the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other. Preferably, the formula (1) may be any one selected from the compounds represented by the following formulas (1-1) to (1-4).

[Formula 1-3]

 In the above Formulas 1-1 to 1-4,

To L < ₆ > are each independently a direct bond; Substituted or unsubstituted C ₆ - ₆₀ arylene; Or C ₂ - ₆₀ heteroarylene containing at least one heteroatom selected from the group consisting of N, O, S and Si,

An to Ar ₄ each independently represent a substituted or unsubstituted C ₆ - ₆₀ aryl; Substituted or unsubstituted 0, N, C _2, including one or more of Si and S ring-or ₆₀ heteroaryl, or An to Ar ₄ may form a condensed ring by combining groups that are adjacent to each other. Preferably, A to Ar ₄ are each independently selected from the group consisting of Oso _{/: /} X1KI. ₈ S2

_// : _/ O ₈ SSMI _><i6 S _Z AV

_{/// O 8 SSMI><i6 S} Z A

R &lt; ₅ &gt; are each independently hydrogen; heavy hydrogen; halogen; Cyano, nitrile; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d-60 alkoxy; Substituted or unsubstituted d- ₆₀ haloalkoxy; Substituted or unsubstituted C ₃ - ₆₀ cycloalkyl; Substituted or unsubstituted d- ₆₀ alkenyl; Substituted or unsubstituted C ₆ - ₆₀ aryl; Substituted or unsubstituted C ₆ -C ₆₀ aryloxy; Or a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl containing one or more of O, N, Si and S; Preferably, each of L ₆ to L ₆ is independently selected from the group consisting of

Preferably, the compound represented by the formula (1) may be any one selected from the group consisting of _// : _/ O ₈ SSMI _><i6 S _Z AV

_{/// O 8 SSMI><i6 S} Z A

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

21

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ S2MI _><i6 S _Z AV

 _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

40 _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

55 _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

62 _{/// O 8 SSMI><i6 S} Z A

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

OAV _9i s0: _// 1 £ ₈ S2M.

The compound represented by the above formula (1-i) can be prepared, for example, by the following production method of Hwang Woong 1, and the compound represented by the formula (1-2) The above production method can be more specific in the production example to be described later.

[Hanwoong2]

In Paragraphs 1 and 2, L ₂ , L ₃ , A, and Ar ₂ are as defined in Formula 1 above. The compound represented by the formula (1) can be prepared by appropriately substituting the starting material according to the structure of the compound to be prepared with reference to the above-mentioned Hanwoongs 1 and 2. Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do. The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention includes a hole injection layer, a hole transport layer, A light-emitting layer, an electron transport layer, an electron injection layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers. The organic material layer may include a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, or a hole controlling layer, and the hole injecting layer, the hole transporting layer, the hole injecting and transporting layer, The hole-controlling layer includes the compound represented by the above formula (1). In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1). The organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1). Further, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound represented by the above formula (1). The organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1). In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, The compound to be displayed may be included in the light emitting layer. 2 is a schematic view of a light emitting device according to a first embodiment of the present invention which comprises a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a hole adjusting layer 7, a light emitting layer 8, an electron transporting layer 9, And shows an example of an organic light emitting device. In such a structure, the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the hole controlling layer, the light emitting layer, and the electron transporting layer. The organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1). In addition, when the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials. For example, the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. In this case, a metal oxide or a metal oxide having conductivity or a metal oxide thereof on the substrate may be formed by a PVDCphys i cal Vapor Deposition method such as a sputtering method or an e-beam evaporation method. Depositing an anode to form an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. In addition, the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spraying, coating, and the like, but is not limited thereto. In addition to such a method, a method of forming an organic material layer from a cathode material, The organic light emitting device can be manufactured by sequentially depositing the material (WO 2003/012890). However, the manufacturing method is not limited thereto. In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is a cathode. As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Ζη0: Α1 SN0 or _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline. The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnes, fox, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but the present invention is not limited thereto. The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (H0M0) of the hole injecting material be between the work function of the anode material and H0M0 of the surrounding organic layer. Specific examples of the hole injecting material include a metal porphyrin, a thiophene, an organic material of an arylamine series, an organic material of a quinacridone series, a quinacridone series organic material, a perylene perylene series organic matter, Anthraquinone, and conductive polymers such as polyaniline and polythiophene, but the present invention is not limited thereto. The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material. Is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly (P-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Lt; RTI ID = 0.0 &gt; A substituted or unsubstituted aryl group, an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto. The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include the M complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material with a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto. Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) Gallium, bis (2-methyl-8-quinolinato) (1-naphthalato) aluminum, bis (2- Methyl-8-quinolinato) (2-naphthalato) gallium, and the like. The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used. In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device. The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto. Production Example 1

9-phenanthreneol (22 g, 113.8 mmol) and 2-bromofluorene (58.9 g,

227.7 mmol) was added to 1,2-dichlorobenzene (300 ml), methanesulfonic acid (10 ml) was added, and the mixture was heated and stirred at 16 C for 24 hours. The temperature was lowered to room temperature and the reaction was terminated. The reaction mixture was extracted with chloroform and water, and then subjected to column chromatography with tetrahydrofuran and ethyl acetate to obtain the compound Al (48.7 g, yield 70%). MS [M + H] &lt; ⁺ &gt; = 612.54

The compound A2 was synthesized in the same manner as in the synthesis of Al except that 3-bromofluorene was used instead of 2-bromofluorene to prepare a compound A2. MS [M + H] ⁺ = 612.54

 Compound A3 was synthesized by the same method except for using 4-bromofluorene instead of 2-bromofluorene in the synthesis of A1 described above

MS [M + H] &lt; ⁺ &gt; = 612.54

Compound [A4] was synthesized in the same manner as in Synthesis of Al except that 2,6-bromofluorene was used instead of 2-bromofluorene. MS [M + H] ⁺ = 691.43

 A5

 Compound A5 was synthesized in the same manner as in the synthesis of A1 except that 3-bromo-9-hydroxy-phenanthrene and fluorene were used instead of 9-phenanthrene and 2-bromofluorene

MS [M + H] &lt; ⁺ &gt; = 691.43 Preparation 2

After adding Al (20 g, 32.7 mmol) and 4-chlorophenylboronic acid (5.57 g, 34.3 thigh 01) to 300 ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (150 ml) Phosphino palladium (793 mg, 2 mol%) was added thereto, followed by heating and stirring for 10 hours. After lowering the temperature to room temperature and terminating the reaction The aqueous potassium carbonate solution was removed and layered. After removing the solvent, the white solid was recrystallized from ethyl acetate to obtain 19.8 g of the compound BU (yield 90%).

MS [M + H] &lt; ⁺ &gt; = 644. 18

B2 was synthesized by the same method except that A2 was used instead of A1 in the synthesis of B1

MS [M + H] &lt; ⁺ &gt; = 644. 18

Except that A3 was used in place of &amp;alpha; in the synthesis of B1. To prepare B3

MS [M + H] &lt; ⁺ &gt; = 644. 18

B4 was synthesized in the same manner as B1 except that A3 was used instead of A1 and 2-chlorophenylboronic acid was used instead of 4-chlorophenylboronic acid

MS [M + H] &lt; ⁺ &gt; = 644. 18

The title compound was synthesized in the same manner as in the synthesis of B1 but using (4'-chloro- [1,1'-biphenyl] _-4- yl) boronic acid instead of 4-chlorophenylboronic acid

B5 was prepared MS [M + H] &lt; ⁺ &gt; = 720.28 Preparation 3

Al (15g, 23.27匪ol) and the die ([1,1 '-biphenyl] -4-yl) amine (7.6¾, 23.73mmol), _{sodium-t-side} appendix (3.13g, 32.58mol), the xylene The mixture was heated and stirred under reflux, and [bis (tri-t-butylphosphine)] palladium (238 mg, 2 mmol%) was added thereto. After lowering the temperature to room temperature and terminating the reaction, recrystallization was performed using tetrahydrofuran and ethyl acetate to prepare Compound 1 (16.25 g, 82%).

MS [M + H] &lt; ⁺ &gt; = 853.03

Except that 4- (dibenzo [b, d] furan-4-yl) -N-phenylaniline was used in place of di [(1,1 '-biphenyl] Were synthesized in the same manner to give Compound 2

MS [M + H] &lt; ⁺ &gt; = 867.03

(1, 1 '-biphenyl] -4-yl) - [1, 1' -biphenyl] 1, -biphenyl]) - 2-amine, the same procedure was repeated to produce Compound 3

MS [M + H] &lt; ⁺ &gt; = 853.03

Compound 3 was prepared by the same method except that A3 was used instead of A1 in the synthesis of Compound 1

MS [M + H] &lt; ⁺ &gt; = 853.03

In the synthesis of Compound 1 above, Instead, A3 was synthesized in the same manner except that 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine was used instead of di [(1,1'-biphenyl- To give Compound 5

MS [M + H] &lt; ⁺ &gt; = 826.02

Synthesis was conducted in the same manner as in the synthesis of the compound 1, except that B1 was used instead of A1 and N-phenylnaphthalen-1-amine was used instead of di [(1,1'-biphenyl] -4- 6 was prepared

MS [M + H] &lt; ⁺ &gt; = 827.01 Preparation Example 3-7: Synthesis of Compound 7

([1,1'-diphenyl] -4-yl) -9,9-diol ([1,1'-biphenyl] -Dimethyl-9H-fluorene-2-amine was used in place of the compound

MS [M + H] &lt; ⁺ &gt; = 969.21

In the synthesis of the above compound 1, B2 was used instead of A1, except that 9,9-dimethyl-phenyl-91 {- fluorene-2-amine was used instead of di [(1,1'-biphenyl] Were synthesized in the same manner as above to give Compound 8

MS [M + H] &lt; ⁺ &gt; = 893.11 Preparation Example 3-9: Synthesis of Compound 9

Except that B3 was used instead of A1 in the synthesis of the compound 1 and N-phenyldibenzo [b, d] thiophen-2-amine was used in place of di [(1,1'-biphenyl] Were synthesized in the same manner to give Compound 9

MS [M + H] &lt; ⁺ &gt; = 883.09

Except that B4 was used instead of A1 in the synthesis of the compound 1 and 9,9-dimethyl-phenyl-911-fluoren-2-amine was used in place of di [(1,1'-biphenyl] Were synthesized in the same manner to give Compound 10

MS [M + H] &lt; ⁺ &gt; = 893.11

Compound 11 was prepared by the same method as Compound 1 except that B5 was used instead of A1 and diphenylamine was used instead of di [(1,1 '-biphenyl] -4-yl) amine

MS [M + H] &lt; ⁺ &gt; = 853.05

Boronic acid (9.58 g, 33.35 mmol) was added to dioxane (300 ml), followed by addition of a 2M aqueous solution of potassium carbonate (150 ml) After the solution was cooled to room temperature, the reaction mixture was terminated, and then the aqueous solution of potassium carbonate was removed to separate the layers. After removing the solvent, Was recrystallized from tetrahydrofuran and ethyl acetate to give Compound 12 (18.75 g, yield 85%).

MS [M + H] &lt; ⁺ &gt; = 674.82 Preparation Example 3-13: Synthesis of Compound 13

D] furan-2-ylboronic acid was used in place of 4- (9H-carbazol-9-yl) phenyl) boronic acid in Synthesis of Compound 12 to obtain Compound 13 Gt;

MS [M + H] &lt; ⁺ &gt; = 599.70

(9.88 g, 43.88 mmol) and sodium-t-butyloxide (6.26 g, 65.16 mol) were added to xylene and heated and stirred Reflux and add [bis (tri-t-butylphosphine)] palladium (333 mg. After lowering the temperature to room temperature and terminating the reaction, the compound 14 was recrystallized using tetrahydrofuran and ethyl acetate to prepare Compound 14 (15.79 g, 75%).

MS [M + H] &lt; ⁺ &gt; = 980.28 Preparation Example 3-15: Synthesis of Compound 15

Phenyl] - [1,1'-biphenyl] -4-amine instead of 4-0 ^ 1 ^ -butyl) - phenylaniline was used in the synthesis of the compound 14 to obtain the compound 15 Was prepared

MS [M + H] &lt; ⁺ &gt; = 1020.26

 16 Compound 16 was prepared by the same method as the compound 14 except that N-phenyldibenzo [b, d] furan-4-amine was used in place of 4- (tert-butyl) Respectively.

MS [M + H] &lt; ⁺ &gt; = 1048.23 Preparation Example 3-17: Synthesis of Compound 17

Synthesis was carried out in the same manner as in the synthesis of the compound 14, except that A5 and N-phenyldibenzo [b, d] furan-4-amine were used instead of A4 and 4- (^ 61 -butyl) -1- Compound 17 was prepared.

MS [M + H] &lt; ⁺ &gt; = 1048.23 Example 1

 A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 A was immersed in distilled water containing a dispersant and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, it was repeated twice with distilled water and ultrasonic cleaned for 10 minutes. After washing with distilled water, isopropyl alcohol, acetone, and methane were ultrasonically washed and dried in the solvent order.

Hexanitrile hexaazatri phenylenes were thermally vacuum deposited to a thickness of 500 Å on the Πkey transparent electrode thus prepared to form a hole injection layer. Compound 1 synthesized in Preparation Example 3-1, which is a hole transporting material, was vacuum deposited on the hole injection layer to a thickness of 900 A to form a hole transport layer. Subsequently, HT2 was vacuum deposited on the hole transport layer to a thickness of 50 A Thereby forming a hole control layer. A host HI and a dopant D1 compound (25: 1) were vacuum deposited on the hole-transporting layer to a thickness of 300 A to form a light emitting layer. Thereafter, an E1 compound was vacuum deposited on the light emitting layer to a thickness of 300 A to form an electron transporting layer. Lithium fluoride (LiF) of 12 A thickness and aluminum of 2,000 A thickness were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device. In the above process, the deposition rate of the organic material was maintained at 1 A / sec, the lithium fluoride was 0.2 A / sec, and the aluminum was silver. Maintain a deposition rate of 3 7 A / sec

Hexa

EXAMPLES 2 AND 3 AND COMPARATIVE EXAMPLES 1 SIMILAR 3 Organic light emitting devices were prepared in the same manner as in Example 1 except that the compounds described in the following Table 1 were used instead of Compound 1 as the hole transporting layer. The current, (20 mA / cm ² ) was applied to the organic light emitting devices prepared in Examples 1 to 3 and Comparative Examples 1 to 3 to measure voltage, efficiency, color coordinates and lifetime.

[Table 1]

Example ⁴

 A glass substrate (corning 7059 glass) coated with a thin ITO (indium tin oxide) film with a thickness of 1,000 A was immersed in distilled water containing a dispersant and washed with ultrasonic waves. Detergent was manufactured by Fi Scher Co., And distilled water was used for Mi l l ipore Co. Distilled water, which was secondly filtered with a filter (Fi l ter) of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

A hexagonal nitrile hexaazatr iphenylene was deposited on the prepared ITO transparent electrode by thermal vacuum deposition to a thickness of 500A to form a hole injection layer. A hole transport layer was formed by vacuum evaporation of the following hole transport layer on the hole injection layer to a thickness of 900 A and then Compound 1 synthesized in Production Example 3-1 was vacuum deposited on the hole transport layer Thereby forming a hole control layer. The hole- A host HI and a dopant D1 compound (25: 1) were vacuum-deposited to a thickness of 300 A to form a light emitting layer. Then, the following E1 compound was vacuum-deposited on the light emitting layer to a thickness of 300 A to form an electron transporting layer. Lithium fluoride (LiF) having a thickness of 12A and aluminum having a thickness of 2,000A were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.

In the above procedure, the deposition rate of the organic material was maintained at 1 A / sec, the deposition rate of the lithium fluoride was 0.2 A / sec, and the deposition rate of aluminum was 3 to 7 A / sec.

Examples 5 to 16 and Comparative Examples 4 to 6 Organic light-emitting devices were prepared in the same manner as in Example 4, except that the compounds described in Table 2 were used instead of Compound 1 as the hole- . The current, 20 mA / cm ² , was applied to the organic light emitting devices prepared in Examples 4 to 16 and Comparative Examples 4 to 6 to measure voltage, efficiency, color coordinates and lifetime.

[Table 2]

According to Tables 1 and 2, the compound represented by the chemical formula according to the present invention can play a role of hole transport and hole control in an organic electronic device including an organic light emitting device, and the device according to the present invention has efficiency, And that it exhibits excellent properties in the case of the present invention. Example 17

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 A was immersed in distilled water dissolved in a dispersant and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. Distilled water After washing, ultrasonic washing was carried out in the order of isopropyl alcohol, acetone and methanol solvent, followed by drying.

 A hexagonal nitrile hexaazatri phenylenene was thermally vacuum deposited to a thickness of 500 Å on the Πkey transparent electrode thus prepared to form a hole injection layer. HT1 was vacuum deposited on the hole injection layer to form a hole transport layer, and then HT250A was vacuum deposited on the HTL to form a hole control layer. Then, host HI and compound 14 synthesized in Preparative Example 3-14 as a dopant were vacuum deposited on the hole control layer at a ratio of 25: 1 and a thickness of 300A to form a light emitting layer. The following E1 compound (300A) was vacuum-deposited on the light-emitting layer to form an electron transport layer. Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2,000 A were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.

In the above process, the deposition rate of organic material was maintained at a rate of 1 / sec, the deposition rate of lithium fluoride was 0.2 A / sec, and the deposition rate of aluminum was 3 to 7 A / sec.

 BD2 BD3

 Examples 18 to 20 and Comparative Examples 7 to 9

Was prepared in the same manner as in Example 17, except that the compound was used instead of the compound 14 as a dopant. The current, 20 mA / cm ² , was applied to the organic light emitting devices prepared in Examples 17 to 20 and Comparative Examples 7 to 9 to measure voltage, efficiency, color coordinates, and lifetime.

[Table 3]

According to the above Table 3, the compound represented by the formula according to the present invention can act as a blue dopant in an organic electronic device including an organic light emitting device, and the device according to the present invention has excellent characteristics in terms of efficiency, .

DESCRIPTION OF REFERENCE NUMERALS

 1: substrate 2:

 3: luminescent layer 4:

 A hundred

 5: hole injection layer 6: high

 7: Hole control layer 8: s

 9: Electron transport layer

Claims

Claims: 1. A compound represented by the following formula (1):

 [Chemical Formula 1]

[Rlln _{[R 2] r}

 In Formula 1,

Each R4 is independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; Cyano, nitrile; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d-60 alkoxy; Substituted or unsubstituted C5 haloalkoxy; Substituted or unsubstituted C ₃ - ₆₀ cycloalkyl; Substituted or unsubstituted d

60 alkenyl; Substituted or unsubstituted C ₆ -C ₆₀ aryl; Substituted or unsubstituted C ₆ -C ₆₀ aryloxy; Substituted or unsubstituted C ₆ - ₆₀ arylamine; Or a substituted or unsubstituted C ₂ - ₆₀ heteroaryl containing at least one of O, N, Si and S,

 n and r are independently integers of from 0 to 8,

 t and m are independently an integer of 0 to 4;

[Claim 2]

 The method according to claim 1,

Wherein at least one of R 4 to R 4 is C ₆ - ₆₀ arylamine.

[3]

 3. The method of claim 2,

 Wherein the compound represented by the formula (1) is any one selected from the compounds represented by the following formulas (1-1) to (1-4):

[Formula 1-1]

[Formula 1-4]

 In the above Formulas 1-1 to 1-4,

To L &lt; ₆ &gt; are each independently a direct bond; Substituted or unsubstituted C ₆ - ₆₀ arylene; Or C ₂ - ₆₀ heteroarylene containing at least one heteroatom selected from the group consisting of N, O, S and Si,

An to Ar ₄ each independently represent a substituted or unsubstituted C ₆ - ₆₀ aryl; Or C ₂ - ₆₀ heteroaryl containing at least one of substituted or unsubstituted O, N, Si and S, or A to Ar ₄ are bonded to adjacent groups to form a condensed ring.

Claim 4

 13. The method of claim 13,

An to Ar ₄ are each independently any one selected from the group consisting of:

SOT

S86800 / 8T0ZaM / X3d CC917S0 / 610Z OAV _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

R &lt; ₅ &gt; are each independently hydrogen; heavy hydrogen; halogen; Cyano, nitrile; Nitro; Substituted or unsubstituted d- ₆₀ alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d-60 alkoxy; Substituted or unsubstituted d- ₆₀ haloalkoxy; Substituted or unsubstituted C ₃ - ₆₀ cycloalkyl; Substituted or unsubstituted d- ₆₀ alkenyl; Substituted or unsubstituted C ₆ -C ₆₀ aryl; Substituted or unsubstituted C ₆ -C ₆₀ aryloxy; Or C ₂ - ₆₀ heteroaryl, including at least one of substituted or unsubstituted 0, N, Si and S;

[Claim 5]

 13. The method of claim 13,

To L &lt; ₆ &gt; are each independently a direct bond or a

[Claim 6]

 In Item 1,

The compound represented by the formula (1) is any one selected from the group consisting of the following compounds: _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

116

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ S2MI _><i6 S _Z AV

123 _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

127 _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

150 _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

S86800 / 8lOra¾ / X3d CC9t- £ 0 / 6I0i ΟΛΧ _// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

_// : _/ O ₈ SSMI _><i6 S _Z AV

7.

 A first electrode; A second electrode facing the first electrode; And at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound according to any one of claims 1 to 6 The organic light-emitting device.

8.

 8. The method of claim 7,

 The organic compound layer containing the compound may include a hole injection layer; A hole transport layer; A layer simultaneously injecting and transporting holes; A hole control layer; Or a light emitting layer.